diff --git a/README.md b/README.md
index 10f9bde..c0b21aa 100644
--- a/README.md
+++ b/README.md
@@ -661,7 +661,7 @@ linq webhooks listen --json
 Events are displayed in a structured log format:
 
 ```
-2024-01-15T10:30:45.123Z [message.received] message.id=msg_123 message.body="Hello world" message.chat_id=chat_456
+2024-01-15T10:30:45.123Z [message.received] data.id=msg_123 data.chat.id=chat_456 data.body="Hello world"
 ```
 
 Press `Ctrl+C` to stop. The CLI automatically cleans up the webhook subscription.
diff --git a/package.json b/package.json
index 0de2089..1cbb53b 100644
--- a/package.json
+++ b/package.json
@@ -77,6 +77,12 @@
       },
       "attachments": {
         "description": "Manage file attachments"
+      },
+      "tokens": {
+        "description": "Manage API tokens"
+      },
+      "contacts": {
+        "description": "Manage shared-line contacts"
       }
     }
   },
diff --git a/src/commands/attachments/get.ts b/src/commands/attachments/get.ts
index d13ee42..3cb0cc8 100644
--- a/src/commands/attachments/get.ts
+++ b/src/commands/attachments/get.ts
@@ -1,4 +1,5 @@
 import { Args, Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
@@ -49,7 +50,7 @@ export default class AttachmentsGet extends BaseCommand {
         this.log(formatAttachmentMeta(data));
       }
     } catch (e) {
-      this.error(`Failed to get attachment: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/attachments/upload.ts b/src/commands/attachments/upload.ts
index 343d2cc..6452454 100644
--- a/src/commands/attachments/upload.ts
+++ b/src/commands/attachments/upload.ts
@@ -1,4 +1,5 @@
 import { Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
@@ -59,7 +60,7 @@ export default class AttachmentsUpload extends BaseCommand {
         this.log(formatUploadUrl(data));
       }
     } catch (e) {
-      this.error(`Failed to request upload: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/chats/create.ts b/src/commands/chats/create.ts
index 0c76069..92b6a62 100644
--- a/src/commands/chats/create.ts
+++ b/src/commands/chats/create.ts
@@ -1,7 +1,8 @@
 import { Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import chalk from 'chalk';
 import { BaseCommand } from '../../lib/base-command.js';
-import { loadConfig, requireToken, requireFromPhone } from '../../lib/config.js';
+import { loadConfig, requireToken, requireFromPhone, isSharedLine } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
 import { formatChatCreated } from '../../lib/format.js';
 import { addBreadcrumb } from '../../lib/telemetry.js';
@@ -97,7 +98,7 @@ export default class ChatsCreate extends BaseCommand {
       } else if (BUBBLE_EFFECTS.includes(flags.effect)) {
         effect = { type: 'bubble', name: flags.effect };
       } else {
-        this.error(`Invalid effect: ${flags.effect}. Valid effects: ${ALL_EFFECTS.join(', ')}`);
+        bail(this, flags.json, `Invalid effect: ${flags.effect}. Valid effects: ${ALL_EFFECTS.join(', ')}`);
       }
     }
 
@@ -120,9 +121,8 @@ export default class ChatsCreate extends BaseCommand {
       }
     } catch (e) {
       if (e instanceof Linq.PermissionDeniedError) {
-        const lineType = config.tier === 0 && config.tenantType === 'SINGLE' ? 'sandbox' : 'shared';
         this.log(chalk.yellow(`\n  Can't message this contact yet.\n`));
-        if (lineType === 'shared') {
+        if (isSharedLine(config)) {
           this.log(chalk.dim(`  On a shared line, you need to add the contact (${chalk.cyan('linq contacts add +1234567890')})`));
           this.log(chalk.dim(`  and they must text you (${chalk.bold(fromPhone)}) first before you can message them.\n`));
         } else {
@@ -130,7 +130,7 @@ export default class ChatsCreate extends BaseCommand {
         }
         this.exit(1);
       }
-      this.error(`Failed to create chat: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/chats/get.ts b/src/commands/chats/get.ts
index c0b3ce1..f396225 100644
--- a/src/commands/chats/get.ts
+++ b/src/commands/chats/get.ts
@@ -1,4 +1,5 @@
 import { Args, Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
@@ -49,7 +50,7 @@ export default class ChatsGet extends BaseCommand {
         this.log(formatChatDetail(data));
       }
     } catch (e) {
-      this.error(`Failed to get chat: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/chats/list.ts b/src/commands/chats/list.ts
index cf5a3cd..f8bd0bc 100644
--- a/src/commands/chats/list.ts
+++ b/src/commands/chats/list.ts
@@ -1,11 +1,12 @@
 import { Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken, requireFromPhone } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
 import { formatChatsList } from '../../lib/format.js';
 
 export default class ChatsList extends BaseCommand {
-  static override description = 'List all chats for a phone number';
+  static override description = 'List all chats for a Blue Number';
 
   static override examples = [
     '<%= config.bin %> <%= command.id %>',
@@ -16,7 +17,7 @@ export default class ChatsList extends BaseCommand {
 
   static override flags = {
     from: Flags.string({
-      description: 'Phone number to list chats for (E.164 format). Uses config fromPhone if not specified.',
+      description: 'Blue Number to list chats for (E.164 format). Uses config fromPhone if not specified.',
     }),
     limit: Flags.integer({
       description: 'Maximum number of chats to return (default: 20, max: 100)',
@@ -60,7 +61,7 @@ export default class ChatsList extends BaseCommand {
         this.log(formatChatsList(data));
       }
     } catch (e) {
-      this.error(`Failed to list chats: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/chats/participants/add.ts b/src/commands/chats/participants/add.ts
index cea0aba..33a776c 100644
--- a/src/commands/chats/participants/add.ts
+++ b/src/commands/chats/participants/add.ts
@@ -1,4 +1,5 @@
 import { Args, Flags } from '@oclif/core';
+import { bail } from '../../../lib/errors.js';
 import chalk from 'chalk';
 import { BaseCommand } from '../../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../../lib/config.js';
@@ -55,7 +56,7 @@ export default class ParticipantsAdd extends BaseCommand {
         this.log(chalk.green(`\n  \u2713 Added ${flags.handle} to chat.\n`));
       }
     } catch (e) {
-      this.error(`Failed to add participant: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/chats/participants/remove.ts b/src/commands/chats/participants/remove.ts
index 4268aa7..b035a80 100644
--- a/src/commands/chats/participants/remove.ts
+++ b/src/commands/chats/participants/remove.ts
@@ -1,4 +1,5 @@
 import { Args, Flags } from '@oclif/core';
+import { bail } from '../../../lib/errors.js';
 import chalk from 'chalk';
 import { BaseCommand } from '../../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../../lib/config.js';
@@ -55,7 +56,7 @@ export default class ParticipantsRemove extends BaseCommand {
         this.log(chalk.green(`\n  \u2713 Removed ${flags.handle} from chat.\n`));
       }
     } catch (e) {
-      this.error(`Failed to remove participant: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/chats/read.ts b/src/commands/chats/read.ts
index ef72315..18d0041 100644
--- a/src/commands/chats/read.ts
+++ b/src/commands/chats/read.ts
@@ -1,4 +1,5 @@
 import { Args, Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
@@ -26,6 +27,7 @@ export default class ChatsRead extends BaseCommand {
       char: 't',
       description: 'API token (overrides stored token)',
     }),
+    json: Flags.boolean({ description: 'Output as JSON', default: false }),
   };
 
   async run(): Promise<void> {
@@ -37,9 +39,13 @@ export default class ChatsRead extends BaseCommand {
 
     try {
       await client.chats.markAsRead(args.chatId);
+      if (flags.json) {
+        this.log(JSON.stringify({ success: true, chatId: args.chatId, action: 'read' }, null, 2));
+        return;
+      }
       this.log(`Chat ${args.chatId} marked as read.`);
     } catch (e) {
-      this.error(`Failed to mark chat as read: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/chats/share-contact.ts b/src/commands/chats/share-contact.ts
index 8366f6e..08012af 100644
--- a/src/commands/chats/share-contact.ts
+++ b/src/commands/chats/share-contact.ts
@@ -1,4 +1,5 @@
 import { Args, Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
@@ -26,6 +27,7 @@ export default class ChatsShareContact extends BaseCommand {
       char: 't',
       description: 'API token (overrides stored token)',
     }),
+    json: Flags.boolean({ description: 'Output as JSON', default: false }),
   };
 
   async run(): Promise<void> {
@@ -37,9 +39,13 @@ export default class ChatsShareContact extends BaseCommand {
 
     try {
       await client.chats.shareContactCard(args.chatId);
+      if (flags.json) {
+        this.log(JSON.stringify({ success: true, chatId: args.chatId, action: 'share_contact' }, null, 2));
+        return;
+      }
       this.log('Contact card shared successfully.');
     } catch (e) {
-      this.error(`Failed to share contact: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/chats/typing.ts b/src/commands/chats/typing.ts
index 0ae2f4a..e7a9206 100644
--- a/src/commands/chats/typing.ts
+++ b/src/commands/chats/typing.ts
@@ -1,4 +1,5 @@
 import { Args, Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
@@ -31,6 +32,7 @@ export default class ChatsTyping extends BaseCommand {
       char: 't',
       description: 'API token (overrides stored token)',
     }),
+    json: Flags.boolean({ description: 'Output as JSON', default: false }),
   };
 
   async run(): Promise<void> {
@@ -41,15 +43,19 @@ export default class ChatsTyping extends BaseCommand {
     const client = createApiClient(token);
 
     try {
+      const action = flags.stop ? 'stop' : 'start';
       if (flags.stop) {
         await client.chats.typing.stop(args.chatId);
-        this.log('Typing indicator stopped.');
       } else {
         await client.chats.typing.start(args.chatId);
-        this.log('Typing indicator started.');
       }
+      if (flags.json) {
+        this.log(JSON.stringify({ success: true, chatId: args.chatId, action: `typing.${action}` }, null, 2));
+        return;
+      }
+      this.log(flags.stop ? 'Typing indicator stopped.' : 'Typing indicator started.');
     } catch (e) {
-      this.error(`Failed to ${flags.stop ? 'stop' : 'start'} typing: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/chats/update.ts b/src/commands/chats/update.ts
index 76701d7..da1bb21 100644
--- a/src/commands/chats/update.ts
+++ b/src/commands/chats/update.ts
@@ -1,4 +1,5 @@
 import { Args, Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
@@ -44,7 +45,7 @@ export default class ChatsUpdate extends BaseCommand {
     const { args, flags } = await this.parse(ChatsUpdate);
 
     if (!flags.name && !flags.icon) {
-      this.error('At least one of --name or --icon must be specified');
+      bail(this, flags.json, 'At least one of --name or --icon must be specified');
     }
 
     const config = await loadConfig(flags.profile);
@@ -65,7 +66,7 @@ export default class ChatsUpdate extends BaseCommand {
         this.log(formatChatDetail(chat));
       }
     } catch (e) {
-      this.error(`Failed to update chat: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/chats/voicememo.ts b/src/commands/chats/voicememo.ts
index 8f9f27d..3f40489 100644
--- a/src/commands/chats/voicememo.ts
+++ b/src/commands/chats/voicememo.ts
@@ -1,4 +1,5 @@
 import { Args, Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
@@ -30,6 +31,7 @@ export default class ChatsVoicememo extends BaseCommand {
       char: 't',
       description: 'API token (overrides stored token)',
     }),
+    json: Flags.boolean({ description: 'Output as JSON', default: false }),
   };
 
   async run(): Promise<void> {
@@ -44,9 +46,15 @@ export default class ChatsVoicememo extends BaseCommand {
         voice_memo_url: flags.url,
       });
 
-      this.log(JSON.stringify(data, null, 2));
+      if (flags.json) {
+        this.log(JSON.stringify(data, null, 2));
+        return;
+      }
+
+      const messageId = (data as { message?: { id?: string } })?.message?.id;
+      this.log(`Voice memo sent to chat ${args.chatId}${messageId ? ` (message ${messageId})` : ''}.`);
     } catch (e) {
-      this.error(`Failed to send voice memo: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/contacts/add.ts b/src/commands/contacts/add.ts
index ae7adfd..7237c96 100644
--- a/src/commands/contacts/add.ts
+++ b/src/commands/contacts/add.ts
@@ -4,6 +4,7 @@ import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken, requireSharedLine } from '../../lib/config.js';
 import { BACKEND_URL } from '../../lib/api-client.js';
 import { addBreadcrumb } from '../../lib/telemetry.js';
+import { bail, throwHttpError } from '../../lib/errors.js';
 
 export default class ContactsAdd extends BaseCommand {
   static override description = 'Add a contact to your shared line';
@@ -19,6 +20,7 @@ export default class ContactsAdd extends BaseCommand {
   static override flags = {
     profile: Flags.string({ char: 'p', description: 'Config profile to use', hidden: true }),
     token: Flags.string({ char: 't', description: 'API token', hidden: true }),
+    json: Flags.boolean({ description: 'Output as JSON', default: false }),
   };
 
   async run(): Promise<void> {
@@ -30,8 +32,7 @@ export default class ContactsAdd extends BaseCommand {
 
     const orgId = config.orgId;
     if (!orgId) {
-      this.log(chalk.yellow(`\n  Not logged in. Run ${chalk.cyan('linq signup')} or ${chalk.cyan('linq login')}.\n`));
-      this.exit(1);
+      bail(this, flags.json, 'Not logged in. Run `linq signup` or `linq login`.');
     }
 
     try {
@@ -41,25 +42,28 @@ export default class ContactsAdd extends BaseCommand {
         body: JSON.stringify({ orgId, contactPhone: args.phone }),
       });
 
-      if (!res.ok) {
-        const err = await res.json() as { message?: string };
-        const reason = err.message || 'Unknown error';
-        this.log(chalk.red(`\n  Failed to add contact: ${reason}\n`));
-        if (/another partner/i.test(reason)) {
-          this.log(chalk.dim('  Upgrade to a dedicated line to message without limits —'));
-          this.log(chalk.dim('  email support@linqapp.com to get started.\n'));
-        }
-        this.exit(1);
-      }
+      if (!res.ok) await throwHttpError(res);
 
       const data = await res.json() as { contactPhone: string };
       addBreadcrumb('Contact added');
-      this.log(chalk.green(`\n  \u2713 Contact ${data.contactPhone} added.\n`));
-      this.log(chalk.dim('  Note: this contact must send a message to your Linq number first before you can reply.\n'));
-    } catch (error) {
-      if (error instanceof Error && 'oclif' in error) throw error;
-      this.log(chalk.red('\n  Could not connect to Linq. Please try again later.\n'));
-      this.exit(1);
+
+      const blueNumber = config.fromPhone;
+
+      if (flags.json) {
+        this.log(JSON.stringify({
+          contactPhone: data.contactPhone,
+          blueNumber: blueNumber ?? null,
+        }, null, 2));
+        return;
+      }
+
+      this.log(chalk.green(`\n  ✓ Contact ${data.contactPhone} added.\n`));
+      this.log(chalk.yellow('  Inbound-first: this contact must text your Blue Number before you can text them.\n'));
+      if (blueNumber) {
+        this.log(`  Text ${chalk.cyan(blueNumber)} from ${chalk.cyan(data.contactPhone)} to start the conversation.\n`);
+      }
+    } catch (e) {
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/contacts/list.ts b/src/commands/contacts/list.ts
index e981c02..9d0e728 100644
--- a/src/commands/contacts/list.ts
+++ b/src/commands/contacts/list.ts
@@ -3,6 +3,7 @@ import chalk from 'chalk';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken, requireSharedLine } from '../../lib/config.js';
 import { BACKEND_URL } from '../../lib/api-client.js';
+import { bail, throwHttpError } from '../../lib/errors.js';
 
 export default class ContactsList extends BaseCommand {
   static override description = 'List contacts on your shared line';
@@ -26,8 +27,7 @@ export default class ContactsList extends BaseCommand {
 
     const orgId = config.orgId;
     if (!orgId) {
-      this.log(chalk.yellow(`\n  Not logged in. Run ${chalk.cyan('linq signup')} or ${chalk.cyan('linq login')}.\n`));
-      this.exit(1);
+      bail(this, flags.json, 'Not logged in. Run `linq signup` or `linq login`.');
     }
 
     try {
@@ -36,11 +36,7 @@ export default class ContactsList extends BaseCommand {
         headers: { 'Content-Type': 'application/json', 'Authorization': `Bearer ${token}` },
       });
 
-      if (!res.ok) {
-        const err = await res.json() as { message?: string };
-        this.log(chalk.red(`\n  ${err.message || 'Failed to list contacts'}\n`));
-        this.exit(1);
-      }
+      if (!res.ok) await throwHttpError(res);
 
       const data = await res.json() as {
         contacts: { contactPhone: string; createdAt: string }[];
@@ -59,14 +55,12 @@ export default class ContactsList extends BaseCommand {
 
       this.log(`\n  ${chalk.bold('Your contacts')} (${data.contacts.length})\n`);
       for (const contact of data.contacts) {
-        const added = new Date(contact.createdAt).toLocaleDateString();
+        const added = new Date(contact.createdAt).toISOString().slice(0, 10);
         this.log(`  ${contact.contactPhone}  ${chalk.dim(`added ${added}`)}`);
       }
       this.log('');
-    } catch (error) {
-      if (error instanceof Error && 'oclif' in error) throw error;
-      this.log(chalk.red('\n  Could not connect to Linq. Please try again later.\n'));
-      this.exit(1);
+    } catch (e) {
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/contacts/remove.ts b/src/commands/contacts/remove.ts
index abc94ff..ab28439 100644
--- a/src/commands/contacts/remove.ts
+++ b/src/commands/contacts/remove.ts
@@ -4,6 +4,7 @@ import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken, requireSharedLine } from '../../lib/config.js';
 import { BACKEND_URL } from '../../lib/api-client.js';
 import { addBreadcrumb } from '../../lib/telemetry.js';
+import { bail, throwHttpError } from '../../lib/errors.js';
 
 export default class ContactsRemove extends BaseCommand {
   static override description = 'Remove a contact from your shared line';
@@ -19,6 +20,7 @@ export default class ContactsRemove extends BaseCommand {
   static override flags = {
     profile: Flags.string({ char: 'p', description: 'Config profile to use', hidden: true }),
     token: Flags.string({ char: 't', description: 'API token', hidden: true }),
+    json: Flags.boolean({ description: 'Output as JSON', default: false }),
   };
 
   async run(): Promise<void> {
@@ -30,8 +32,7 @@ export default class ContactsRemove extends BaseCommand {
 
     const orgId = config.orgId;
     if (!orgId) {
-      this.log(chalk.yellow(`\n  Not logged in. Run ${chalk.cyan('linq signup')} or ${chalk.cyan('linq login')}.\n`));
-      this.exit(1);
+      bail(this, flags.json, 'Not logged in. Run `linq signup` or `linq login`.');
     }
 
     try {
@@ -41,18 +42,18 @@ export default class ContactsRemove extends BaseCommand {
         body: JSON.stringify({ orgId, contactPhone: args.phone }),
       });
 
-      if (!res.ok) {
-        const err = await res.json() as { message?: string };
-        this.log(chalk.red(`\n  ${err.message || 'Failed to remove contact'}\n`));
-        this.exit(1);
-      }
+      if (!res.ok) await throwHttpError(res);
 
       addBreadcrumb('Contact removed');
-      this.log(chalk.green(`\n  \u2713 Contact ${args.phone} removed.\n`));
-    } catch (error) {
-      if (error instanceof Error && 'oclif' in error) throw error;
-      this.log(chalk.red('\n  Could not connect to Linq. Please try again later.\n'));
-      this.exit(1);
+
+      if (flags.json) {
+        this.log(JSON.stringify({ contactPhone: args.phone, removed: true }, null, 2));
+        return;
+      }
+
+      this.log(chalk.green(`\n  ✓ Contact ${args.phone} removed.\n`));
+    } catch (e) {
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/doctor.ts b/src/commands/doctor.ts
index b03b623..a0e1200 100644
--- a/src/commands/doctor.ts
+++ b/src/commands/doctor.ts
@@ -14,28 +14,50 @@ export default class Doctor extends BaseCommand {
       char: 'p',
       description: 'Config profile to use',
     }),
+    json: Flags.boolean({
+      description: 'Output as JSON',
+      default: false,
+    }),
+    strict: Flags.boolean({
+      description: 'Treat warnings as failures (exit non-zero on any warning)',
+      default: false,
+    }),
   };
 
   async run(): Promise<void> {
     const { flags } = await this.parse(Doctor);
 
+    type Check = { name: string; status: 'ok' | 'fail' | 'warn'; message: string };
+    const checks: Check[] = [];
     let passed = 0;
     let failed = 0;
     let warnings = 0;
 
-    const ok = (msg: string) => { this.log(chalk.green('  ✓ ') + msg); passed++; };
-    const fail = (msg: string) => { this.log(chalk.red('  ✗ ') + msg); failed++; };
-    const warn = (msg: string) => { this.log(chalk.yellow('  ! ') + msg); warnings++; };
-
-    this.log('\n  Linq CLI Health Check\n');
+    const ok = (name: string, message: string) => {
+      checks.push({ name, status: 'ok', message });
+      if (!flags.json) this.log(chalk.green('  ✓ ') + message);
+      passed++;
+    };
+    const fail = (name: string, message: string) => {
+      checks.push({ name, status: 'fail', message });
+      if (!flags.json) this.log(chalk.red('  ✗ ') + message);
+      failed++;
+    };
+    const warn = (name: string, message: string) => {
+      checks.push({ name, status: 'warn', message });
+      if (!flags.json) this.log(chalk.yellow('  ! ') + message);
+      warnings++;
+    };
+
+    if (!flags.json) this.log('\n  Linq CLI Health Check\n');
 
     // Check 1: Config file
     const configFile = await loadConfigFile();
     const profileCount = Object.keys(configFile.profiles).length;
     if (profileCount > 0) {
-      ok('Config file found');
+      ok('config_file', 'Config file found');
     } else {
-      fail('Config file not found — run `linq signup` or `linq login`');
+      fail('config_file', 'Config file not found — run `linq signup` or `linq login`');
     }
 
     // Load profile
@@ -43,84 +65,96 @@ export default class Doctor extends BaseCommand {
     try {
       config = await loadConfig(flags.profile);
     } catch {
-      fail('Failed to load config profile');
-      this.printSummary(passed, failed, warnings);
+      fail('profile_load', 'Failed to load config profile');
+      this.emit(checks, passed, failed, warnings, flags.json, flags.strict);
       return;
     }
 
-    // Check 2: API token
     if (config.token) {
-      const masked = config.token.substring(0, 8) + '•'.repeat(8);
-      ok(`API token configured (${masked})`);
+      const masked = config.token.length > 12 ? `${config.token.slice(0, 12)}...` : config.token;
+      ok('api_token', `API token configured (${masked})`);
     } else {
-      fail('API token not configured — run `linq login` or `linq signup`');
+      fail('api_token', 'API token not configured — run `linq login` or `linq signup`');
     }
 
-    // Check 3: Phone number
     if (config.fromPhone) {
-      ok(`Phone number set (${config.fromPhone})`);
+      ok('blue_number', `Blue Number set (${config.fromPhone})`);
     } else {
-      fail('Phone number not set — run `linq phonenumbers set` to pick a default');
+      fail('blue_number', 'Blue Number not set — run `linq phonenumbers set` to pick a default');
     }
 
-    // Check 4: Session expiry (for the active profile)
     const sessionExpiry = config.sessionExpiresAt || config.expiresAt;
     if (sessionExpiry) {
       const expires = new Date(sessionExpiry);
       if (expires > new Date()) {
         const daysLeft = Math.ceil((expires.getTime() - Date.now()) / 86_400_000);
-        ok(`Session active (${daysLeft} day${daysLeft > 1 ? 's' : ''} remaining)`);
+        ok('session', `Session active (${daysLeft} day${daysLeft > 1 ? 's' : ''} remaining)`);
       } else {
-        fail(`Session expired — run \`linq login\` to re-authenticate`);
+        fail('session', 'Session expired — run `linq login` to re-authenticate');
       }
     }
 
-    // Check 5: API connectivity
     if (config.token) {
       const client = createApiClient(config.token);
       const start = Date.now();
       try {
         const phones = await client.phoneNumbers.list();
         const latency = Date.now() - start;
-        const phoneCount = (phones as any).phone_numbers?.length || 0;
+        const phoneCount = (phones as { phone_numbers?: unknown[] }).phone_numbers?.length || 0;
         const phoneLabel = phoneCount > 0 ? `, ${phoneCount} phone${phoneCount !== 1 ? 's' : ''}` : '';
-        ok(`API connected (${latency}ms${phoneLabel})`);
+        ok('api_connectivity', `API connected (${latency}ms${phoneLabel})`);
 
-        // Check 6: Webhooks
         try {
           const webhooks = await client.webhookSubscriptions.list();
-          const subs = (webhooks as any).subscriptions || [];
-          const active = subs.filter((s: any) => s.is_active).length;
+          const subs = (webhooks as { subscriptions?: { is_active: boolean }[] }).subscriptions || [];
+          const active = subs.filter((s) => s.is_active).length;
           if (subs.length > 0) {
-            ok(`Webhooks: ${active} active, ${subs.length - active} inactive`);
+            ok('webhooks', `Webhooks: ${active} active, ${subs.length - active} inactive`);
           } else {
-            warn('No webhook subscriptions — run `linq webhooks create` or `linq webhooks listen`');
+            warn('webhooks', 'No webhook subscriptions — run `linq webhooks create` or `linq webhooks listen`');
           }
         } catch {
-          warn('Could not check webhooks');
+          warn('webhooks', 'Could not check webhooks');
         }
       } catch (error) {
         const latency = Date.now() - start;
         const msg = error instanceof Error ? error.message : String(error);
         if (msg.includes('401') || msg.includes('Unauthorized')) {
-          fail(`API auth failed (${latency}ms) — token may be invalid or expired`);
+          fail('api_connectivity', `API auth failed (${latency}ms) — token may be invalid or expired`);
         } else {
-          fail(`API unreachable (${latency}ms) — check your network`);
+          fail('api_connectivity', `API unreachable (${latency}ms) — check your network`);
         }
       }
     } else {
-      fail('API connectivity — skipped (no token)');
+      fail('api_connectivity', 'API connectivity — skipped (no token)');
     }
 
-    this.printSummary(passed, failed, warnings);
+    this.emit(checks, passed, failed, warnings, flags.json, flags.strict);
   }
 
-  private printSummary(passed: number, failed: number, warnings: number): void {
-    this.log('');
-    const parts: string[] = [];
-    parts.push(chalk.green(`${passed} passed`));
-    if (warnings > 0) parts.push(chalk.yellow(`${warnings} warning${warnings > 1 ? 's' : ''}`));
-    if (failed > 0) parts.push(chalk.red(`${failed} failed`));
-    this.log(`  ${parts.join(', ')}\n`);
+  private emit(
+    checks: { name: string; status: 'ok' | 'fail' | 'warn'; message: string }[],
+    passed: number,
+    failed: number,
+    warnings: number,
+    json: boolean,
+    strict: boolean,
+  ): void {
+    if (json) {
+      this.log(JSON.stringify({
+        ok: failed === 0 && (!strict || warnings === 0),
+        passed,
+        warnings,
+        failed,
+        checks,
+      }, null, 2));
+    } else {
+      this.log('');
+      const parts: string[] = [chalk.green(`${passed} passed`)];
+      if (warnings > 0) parts.push(chalk.yellow(`${warnings} warning${warnings > 1 ? 's' : ''}`));
+      if (failed > 0) parts.push(chalk.red(`${failed} failed`));
+      this.log(`  ${parts.join(', ')}\n`);
+    }
+    if (failed > 0 || (strict && warnings > 0)) this.exit(1);
   }
 }
diff --git a/src/commands/init.ts b/src/commands/init.ts
index cda8a59..5418ff4 100644
--- a/src/commands/init.ts
+++ b/src/commands/init.ts
@@ -7,8 +7,9 @@ import {
   getCurrentProfile,
   listProfiles,
   SANDBOX_PROFILE,
+  type AccountLabel,
 } from '../lib/config.js';
-import { createApiClient, BACKEND_URL } from '../lib/api-client.js';
+import { BACKEND_URL } from '../lib/api-client.js';
 import { renderBanner } from '../lib/banner.js';
 
 export default class Init extends BaseCommand {
@@ -78,59 +79,54 @@ export default class Init extends BaseCommand {
       },
     });
 
-    // Validate token by calling the API
     this.log('\nValidating token...');
-    const client = createApiClient(token.trim());
-
-    let data;
-    try {
-      data = await client.phoneNumbers.list();
-    } catch {
-      this.error(
-        'Invalid token or API error. Please check your token and try again.'
-      );
-    }
-
-    this.log('\u2713 Token is valid!\n');
-
     let orgId: string | undefined;
-    let tier: number | undefined;
-    let tenantType: string | undefined;
     let name: string | undefined;
     let partnerId: string | undefined;
-    let accountPhones: { phoneNumber: string; tenantType: string }[] = [];
+    let accountPhones: { phoneNumber: string }[] = [];
+    let accountLabel: AccountLabel | undefined;
+
     try {
       const res = await fetch(`${BACKEND_URL}/cli/account-info`, {
         headers: { 'Authorization': `Bearer ${token.trim()}` },
       });
-      if (res.ok) {
-        const acc = await res.json() as {
-          partnerId?: string;
-          orgId?: string;
-          name?: string | null;
-          accountInfo?: { tier: number; phones: { phoneNumber: string; tenantType: string }[] } | null;
-        };
-        partnerId = acc.partnerId;
-        orgId = acc.orgId;
-        name = acc.name ?? undefined;
-        tier = acc.accountInfo?.tier;
-        accountPhones = acc.accountInfo?.phones ?? [];
+      if (res.status === 401) {
+        this.error('Invalid or expired token. Generate a fresh one in the Dashboard or contact support@linqapp.com');
+      }
+      if (!res.ok) {
+        this.error('Could not connect to Linq. Please try again later.');
       }
-    } catch {
-      // pass
+      const acc = await res.json() as {
+        partnerId?: string;
+        orgId?: string;
+        name?: string | null;
+        accountInfo?: {
+          phones: { phoneNumber: string }[];
+          accountLabel?: AccountLabel;
+        } | null;
+      };
+      partnerId = acc.partnerId;
+      orgId = acc.orgId;
+      name = acc.name ?? undefined;
+      accountPhones = acc.accountInfo?.phones ?? [];
+      accountLabel = acc.accountInfo?.accountLabel;
+    } catch (e) {
+      if (e instanceof Error && 'oclif' in e) throw e;
+      this.error('Could not connect to Linq. Please try again later.');
     }
 
+    this.log('\u2713 Token is valid!\n');
+
     let fromPhone: string | undefined;
-    const synapsePhones = (data.phone_numbers || []).map(p => ({ phoneNumber: p.phone_number }));
-    const phones = accountPhones.length > 0 ? accountPhones : synapsePhones;
+    const phones = accountPhones;
 
     if (phones.length === 1) {
       fromPhone = phones[0].phoneNumber;
-      this.log(`Default phone number set to ${fromPhone} (only number on account)\n`);
+      this.log(`Default Blue Number set to ${fromPhone} (only number on account)\n`);
     } else if (phones.length > 1) {
-      if ((tier ?? 0) >= 1) {
+      if (accountLabel === 'Paid') {
         fromPhone = await select({
-          message: 'Select a default phone number:',
+          message: 'Select a default Blue Number:',
           choices: phones.map((p) => ({
             name: p.phoneNumber,
             value: p.phoneNumber,
@@ -142,26 +138,19 @@ export default class Init extends BaseCommand {
       }
     }
 
-    if (accountPhones.length > 0) {
-      tenantType = (fromPhone && accountPhones.find(p => p.phoneNumber === fromPhone)?.tenantType)
-        ?? accountPhones[0].tenantType;
-    }
-
-    // Save to profile
     await saveProfile(profileName, {
       token: token.trim(),
       ...(fromPhone && { fromPhone }),
       ...(partnerId && { partnerId }),
       ...(orgId && { orgId }),
-      ...(tier !== undefined && { tier }),
-      ...(tenantType && { tenantType }),
       ...(name && { name }),
+      accountLabel,
     });
     await setCurrentProfile(profileName);
 
     this.log(`\n\u2713 Configuration saved to profile "${profileName}"\n`);
     this.log('Next steps:');
-    this.log('  linq phonenumbers                                     List your phone numbers');
+    this.log('  linq phonenumbers                                     List your Blue Numbers');
     this.log(
       '  linq chats create --to +1XXXXXXXXXX -m "Hello!"       Create a chat and send a message'
     );
diff --git a/src/commands/login.ts b/src/commands/login.ts
index 152cb9e..4c9a7ff 100644
--- a/src/commands/login.ts
+++ b/src/commands/login.ts
@@ -8,8 +8,9 @@ import {
   getCurrentProfile,
   listProfiles,
   SANDBOX_PROFILE,
+  type AccountLabel,
 } from '../lib/config.js';
-import { createApiClient, BACKEND_URL } from '../lib/api-client.js';
+import { BACKEND_URL } from '../lib/api-client.js';
 import { renderBanner } from '../lib/banner.js';
 
 export default class Login extends BaseCommand {
@@ -42,35 +43,45 @@ export default class Login extends BaseCommand {
     }
 
     if (!profileName) {
-      const current = await getCurrentProfile() || 'default';
-      const profiles = (await listProfiles()).filter(p => p !== SANDBOX_PROFILE);
-      const choices = [
-        ...profiles.map(p => ({
-          name: p === current ? `${p} (active)` : p,
-          value: p,
-        })),
-        { name: 'Create new profile', value: '__new__' },
-      ];
-      try {
-        const chosen = await select({
-          message: 'Which profile would you like to log in to?',
-          choices,
-          default: current !== SANDBOX_PROFILE ? current : undefined,
-        });
-        profileName = chosen === '__new__'
-          ? await input({ message: 'Profile name:', validate: v => v.trim() ? true : 'Name cannot be empty' })
-          : chosen;
-      } catch (error) {
-        if (error instanceof Error && error.name === 'ExitPromptError') {
-          profileName = 'default';
-        } else {
-          throw error;
+      // If --token was supplied, assume non-interactive (script / AI
+      // agent) — pick the current/default profile silently. Only the
+      // bare `linq login` interactive flow gets the profile picker.
+      if (flags.token) {
+        profileName = (await getCurrentProfile()) || 'default';
+      } else {
+        const current = await getCurrentProfile() || 'default';
+        const profiles = (await listProfiles()).filter(p => p !== SANDBOX_PROFILE);
+        const choices = [
+          ...profiles.map(p => ({
+            name: p === current ? `${p} (active)` : p,
+            value: p,
+          })),
+          { name: 'Create new profile', value: '__new__' },
+        ];
+        try {
+          const chosen = await select({
+            message: 'Which profile would you like to log in to?',
+            choices,
+            default: current !== SANDBOX_PROFILE ? current : undefined,
+          });
+          profileName = chosen === '__new__'
+            ? await input({ message: 'Profile name:', validate: v => v.trim() ? true : 'Name cannot be empty' })
+            : chosen;
+        } catch (error) {
+          if (error instanceof Error && error.name === 'ExitPromptError') {
+            profileName = 'default';
+          } else {
+            throw error;
+          }
         }
       }
     }
 
     let token = flags.token;
     if (!token) {
+      if (!process.stdin.isTTY) {
+        this.error('linq login needs a terminal for the interactive token prompt. To run non-interactively, pass --token: linq login --token <your-token>');
+      }
       await renderBanner();
       console.log('\n  Welcome back to Linq CLI\n');
       try {
@@ -89,55 +100,54 @@ export default class Login extends BaseCommand {
     token = token.trim();
     if (!token) this.error('Token cannot be empty');
 
-    // Validate the token by hitting synapse
     this.log('\nValidating token...');
-    const client = createApiClient(token);
-    let data;
-    try {
-      data = await client.phoneNumbers.list();
-    } catch {
-      this.error('Invalid token or API error. Please check your token and try again.');
-    }
-    this.log(`${chalk.green('✓')} Token is valid!\n`);
-
     let orgId: string | undefined;
-    let tier: number | undefined;
-    let tenantType: string | undefined;
     let name: string | undefined;
     let partnerId: string | undefined;
-    let accountPhones: { phoneNumber: string; tenantType: string }[] = [];
+    let accountPhones: { phoneNumber: string }[] = [];
+    let accountLabel: AccountLabel | undefined;
+
     try {
       const res = await fetch(`${BACKEND_URL}/cli/account-info`, {
         headers: { Authorization: `Bearer ${token}` },
       });
-      if (res.ok) {
-        const acc = await res.json() as {
-          partnerId?: string;
-          orgId?: string;
-          name?: string | null;
-          accountInfo?: { tier: number; phones: { phoneNumber: string; tenantType: string }[] } | null;
-        };
-        partnerId = acc.partnerId;
-        orgId = acc.orgId;
-        name = acc.name ?? undefined;
-        tier = acc.accountInfo?.tier;
-        accountPhones = acc.accountInfo?.phones ?? [];
+      if (res.status === 401) {
+        this.error('Invalid or expired token. Generate a fresh one in the Dashboard or contact support@linqapp.com');
+      }
+      if (!res.ok) {
+        this.error('Could not connect to Linq. Please try again later.');
       }
-    } catch {
-      // pass
+      const acc = await res.json() as {
+        partnerId?: string;
+        orgId?: string;
+        name?: string | null;
+        accountInfo?: {
+          phones: { phoneNumber: string }[];
+          accountLabel?: AccountLabel;
+        } | null;
+      };
+      partnerId = acc.partnerId;
+      orgId = acc.orgId;
+      name = acc.name ?? undefined;
+      accountPhones = acc.accountInfo?.phones ?? [];
+      accountLabel = acc.accountInfo?.accountLabel;
+    } catch (e) {
+      if (e instanceof Error && 'oclif' in e) throw e;
+      this.error('Could not connect to Linq. Please try again later.');
     }
 
+    this.log(`${chalk.green('✓')} Token is valid!\n`);
+
     let fromPhone: string | undefined;
-    const synapsePhones = (data.phone_numbers || []).map(p => ({ phoneNumber: p.phone_number }));
-    const phones = accountPhones.length > 0 ? accountPhones : synapsePhones;
+    const phones = accountPhones;
 
     if (phones.length === 1) {
       fromPhone = phones[0].phoneNumber;
     } else if (phones.length > 1) {
-      if ((tier ?? 0) >= 1) {
+      if (accountLabel === 'Paid') {
         try {
           fromPhone = await select({
-            message: 'Select a default phone number:',
+            message: 'Select a default Blue Number:',
             choices: phones.map(p => ({ name: p.phoneNumber, value: p.phoneNumber })),
           });
         } catch (error) {
@@ -151,32 +161,21 @@ export default class Login extends BaseCommand {
       }
     }
 
-    if (accountPhones.length > 0) {
-      tenantType = (fromPhone && accountPhones.find(p => p.phoneNumber === fromPhone)?.tenantType)
-        ?? accountPhones[0].tenantType;
-    }
-
     await saveProfile(profileName, {
       token,
       ...(fromPhone && { fromPhone }),
       ...(partnerId && { partnerId }),
       ...(orgId && { orgId }),
-      ...(tier !== undefined && { tier }),
-      ...(tenantType && { tenantType }),
       ...(name && { name }),
+      accountLabel,
     });
     await setCurrentProfile(profileName);
 
-    let accountLabel = '';
-    if (tier === 0 && tenantType === 'SINGLE') accountLabel = 'Sandbox Line';
-    else if (tier === 0 && tenantType === 'MULTI') accountLabel = 'Shared Line';
-    else if ((tier ?? 0) >= 1) accountLabel = 'Paid';
-
     this.log(chalk.green('✓ Welcome back!\n'));
-    if (accountLabel) this.log(`  ${chalk.dim('Account:')}  ${accountLabel}`);
-    if (fromPhone) this.log(`  ${chalk.dim('Phone:')}    ${chalk.bold(fromPhone)}`);
-    if (name) this.log(`  ${chalk.dim('Name:')}     ${name}`);
-    this.log(`  ${chalk.dim('Profile:')}  ${profileName}`);
+    if (accountLabel) this.log(`  ${chalk.dim('Account:')}      ${accountLabel}`);
+    if (fromPhone) this.log(`  ${chalk.dim('Blue Number:')}  ${chalk.bold(fromPhone)}`);
+    if (name) this.log(`  ${chalk.dim('Name:')}         ${name}`);
+    this.log(`  ${chalk.dim('Profile:')}      ${profileName}`);
     this.log('');
   }
 }
diff --git a/src/commands/messages/delete.ts b/src/commands/messages/delete.ts
index f132774..ef5e343 100644
--- a/src/commands/messages/delete.ts
+++ b/src/commands/messages/delete.ts
@@ -1,4 +1,5 @@
 import { Args, Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
@@ -49,7 +50,7 @@ export default class MessagesDelete extends BaseCommand {
         this.log(formatDeleted('Message', args.messageId));
       }
     } catch (e) {
-      this.error(`Failed to delete message: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/messages/get.ts b/src/commands/messages/get.ts
index a3a46bb..bd99e05 100644
--- a/src/commands/messages/get.ts
+++ b/src/commands/messages/get.ts
@@ -1,4 +1,5 @@
 import { Args, Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
@@ -47,7 +48,7 @@ export default class MessagesGet extends BaseCommand {
         this.log(formatMessageDetail(data));
       }
     } catch (e) {
-      this.error(`Failed to get message: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/messages/list.ts b/src/commands/messages/list.ts
index 4d7eeb3..1bb5d73 100644
--- a/src/commands/messages/list.ts
+++ b/src/commands/messages/list.ts
@@ -1,4 +1,5 @@
 import { Args, Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
@@ -65,7 +66,7 @@ export default class MessagesList extends BaseCommand {
         this.log(formatMessagesList(data, chat));
       }
     } catch (e) {
-      this.error(`Failed to list messages: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/messages/react.ts b/src/commands/messages/react.ts
index 6e57d67..f149254 100644
--- a/src/commands/messages/react.ts
+++ b/src/commands/messages/react.ts
@@ -1,4 +1,5 @@
 import { Args, Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
@@ -69,14 +70,12 @@ export default class MessagesReact extends BaseCommand {
 
     // Validate reaction type
     if (!REACTION_TYPES.includes(flags.type as ReactionType)) {
-      this.error(
-        `Invalid reaction type: ${flags.type}. Valid types: ${REACTION_TYPES.join(', ')}`
-      );
+      bail(this, flags.json, `Invalid reaction type: ${flags.type}. Valid types: ${REACTION_TYPES.join(', ')}`);
     }
 
     // Validate custom emoji is provided when type is custom
     if (flags.type === 'custom' && !flags.emoji) {
-      this.error('--emoji is required when using --type custom');
+      bail(this, flags.json, '--emoji is required when using --type custom');
     }
 
     const config = await loadConfig(flags.profile);
@@ -97,7 +96,7 @@ export default class MessagesReact extends BaseCommand {
         this.log(formatReaction(flags.operation!, flags.type, args.messageId));
       }
     } catch (e) {
-      this.error(`Failed to ${flags.operation} reaction: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/messages/send.ts b/src/commands/messages/send.ts
index 46bd1b4..38b55f1 100644
--- a/src/commands/messages/send.ts
+++ b/src/commands/messages/send.ts
@@ -1,4 +1,5 @@
 import { Args, Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
@@ -94,7 +95,7 @@ export default class MessagesSend extends BaseCommand {
       } else if (BUBBLE_EFFECTS.includes(flags.effect)) {
         effect = { type: 'bubble', name: flags.effect };
       } else {
-        this.error(`Invalid effect: ${flags.effect}. Valid effects: ${ALL_EFFECTS.join(', ')}`);
+        bail(this, flags.json, `Invalid effect: ${flags.effect}. Valid effects: ${ALL_EFFECTS.join(', ')}`);
       }
     }
 
@@ -115,7 +116,7 @@ export default class MessagesSend extends BaseCommand {
         this.log(formatMessageSent(data));
       }
     } catch (e) {
-      this.error(`Failed to send message: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/messages/thread.ts b/src/commands/messages/thread.ts
index 0197c4a..a3cbba4 100644
--- a/src/commands/messages/thread.ts
+++ b/src/commands/messages/thread.ts
@@ -1,4 +1,5 @@
 import { Args, Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
@@ -64,7 +65,7 @@ export default class MessagesThread extends BaseCommand {
         this.log(formatMessagesList(data));
       }
     } catch (e) {
-      this.error(`Failed to get thread: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/phonenumbers.ts b/src/commands/phonenumbers.ts
index 4345e38..f4ef0a1 100644
--- a/src/commands/phonenumbers.ts
+++ b/src/commands/phonenumbers.ts
@@ -1,4 +1,5 @@
 import { Args, Flags } from '@oclif/core';
+import { bail } from '../lib/errors.js';
 import { select } from '@inquirer/prompts';
 import chalk from 'chalk';
 import { BaseCommand } from '../lib/base-command.js';
@@ -6,7 +7,7 @@ import { loadConfig, requireToken, saveProfile, saveSandboxProfile, getCurrentPr
 import { createApiClient } from '../lib/api-client.js';
 
 export default class PhoneNumbers extends BaseCommand {
-  static override description = 'List your phone numbers or set a default';
+  static override description = 'List your Blue Numbers or set a default';
 
   static override examples = [
     '<%= config.bin %> <%= command.id %>',
@@ -15,7 +16,7 @@ export default class PhoneNumbers extends BaseCommand {
 
   static override args = {
     action: Args.string({
-      description: 'Action: "set" to pick a default phone number',
+      description: 'Action: "set" to pick a default Blue Number',
       required: false,
     }),
   };
@@ -49,11 +50,11 @@ export default class PhoneNumbers extends BaseCommand {
       const data = await client.phoneNumbers.list();
       phones = (data as any).phone_numbers || [];
     } catch (e) {
-      this.error(`Failed to list phone numbers: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
 
     if (phones.length === 0) {
-      this.log('\n  No phone numbers found.\n');
+      this.log('\n  No Blue Numbers found.\n');
       return;
     }
 
@@ -67,7 +68,7 @@ export default class PhoneNumbers extends BaseCommand {
       return;
     }
 
-    this.log(`\n  ${chalk.bold('Your phone numbers')}\n`);
+    this.log(`\n  ${chalk.bold('Your Blue Numbers')}\n`);
     for (const p of phones) {
       const isDefault = p.phone_number === config.fromPhone;
       this.log(`  ${chalk.cyan(p.id)}  ${this.formatPhone(p.phone_number)}${isDefault ? chalk.green(' ← default') : ''}`);
@@ -88,7 +89,7 @@ export default class PhoneNumbers extends BaseCommand {
 
     try {
       const chosen = await select({
-        message: 'Select your default phone number:',
+        message: 'Select your default Blue Number:',
         choices: phones.map(p => ({
           name: p.phone_number === currentDefault
             ? `${this.formatPhone(p.phone_number)} (current default)`
diff --git a/src/commands/profile/create.ts b/src/commands/profile/create.ts
index a6869c9..f8f3d22 100644
--- a/src/commands/profile/create.ts
+++ b/src/commands/profile/create.ts
@@ -28,7 +28,7 @@ export default class ProfileCreate extends BaseCommand {
     }),
     'from-phone': Flags.string({
       char: 'f',
-      description: 'Default sender phone number',
+      description: 'Default sender Blue Number',
     }),
   };
 
diff --git a/src/commands/profile/get.ts b/src/commands/profile/get.ts
index e71d492..7767595 100644
--- a/src/commands/profile/get.ts
+++ b/src/commands/profile/get.ts
@@ -87,9 +87,6 @@ export default class ProfileGet extends BaseCommand {
   }
 
   private maskToken(token: string): string {
-    if (token.length <= 8) {
-      return '****';
-    }
-    return token.slice(0, 4) + '****' + token.slice(-4);
+    return token.length > 12 ? `${token.slice(0, 12)}...` : token;
   }
 }
diff --git a/src/commands/signup.ts b/src/commands/signup.ts
index be14218..9d42576 100644
--- a/src/commands/signup.ts
+++ b/src/commands/signup.ts
@@ -5,12 +5,15 @@ import { BaseCommand } from '../lib/base-command.js';
 import { renderBanner } from '../lib/banner.js';
 import { runAuthFlow, checkExistingSession } from '../lib/auth-flow.js';
 
+const EMAIL_REGEX = /^[^\s@]+@[^\s@]+\.[^\s@]+$/;
+
 export default class Signup extends BaseCommand {
-  static override description = 'Create a Linq developer account and get a shared phone line';
+  static override description = 'Create a Linq developer account and get a shared Blue Number';
 
   static override examples = [
     '<%= config.bin %> <%= command.id %>',
     '<%= config.bin %> <%= command.id %> --email dev@example.com',
+    '<%= config.bin %> <%= command.id %> --email dev@example.com --code 123456 --name "Dev User"',
   ];
 
   static override flags = {
@@ -18,6 +21,14 @@ export default class Signup extends BaseCommand {
       char: 'e',
       description: 'Email address',
     }),
+    code: Flags.string({
+      char: 'c',
+      description: 'OTP verification code from your email (skips interactive prompt; pair with --email and --name for non-interactive signup)',
+    }),
+    name: Flags.string({
+      char: 'n',
+      description: 'Your name (skips interactive prompt during signup)',
+    }),
   };
 
   async run(): Promise<void> {
@@ -30,17 +41,27 @@ export default class Signup extends BaseCommand {
       return;
     }
 
-    await renderBanner();
-    console.log('\n  Create your Linq developer account\n');
+    // Skip the banner for AI agents / scripts (no TTY) or when all the
+    // signup flags are supplied (fully scripted run).
+    const nonInteractive = !!(flags.email && flags.code && flags.name);
+    const showBanner = !nonInteractive && process.stdout.isTTY;
+    if (showBanner) {
+      await renderBanner();
+      console.log('\n  Create your Linq developer account\n');
+    }
 
     let email = flags.email;
-    if (!email) {
+    if (email) {
+      if (!EMAIL_REGEX.test(email.trim())) {
+        this.error(`Invalid email: ${email}`);
+      }
+    } else {
       try {
         email = await input({
           message: 'Email address:',
           validate: (v) => {
             if (!v.trim()) return 'Email is required';
-            if (!/^[^\s@]+@[^\s@]+\.[^\s@]+$/.test(v.trim())) return 'Enter a valid email';
+            if (!EMAIL_REGEX.test(v.trim())) return 'Enter a valid email';
             return true;
           },
         });
@@ -53,8 +74,14 @@ export default class Signup extends BaseCommand {
     }
     email = email.trim().toLowerCase();
 
+    if (flags.code && !/^\d{6}$/.test(flags.code.trim())) {
+      this.error(`Invalid --code: must be a 6-digit number`);
+    }
+
     await runAuthFlow({
       email,
+      code: flags.code?.trim(),
+      name: flags.name?.trim(),
       log: (msg) => this.log(msg),
       exit: (code) => this.exit(code),
       parseError: (res) => this.parseError(res),
diff --git a/src/commands/tokens/create.ts b/src/commands/tokens/create.ts
index 4109218..c455938 100644
--- a/src/commands/tokens/create.ts
+++ b/src/commands/tokens/create.ts
@@ -9,6 +9,7 @@ import {
   parseExpiresIn,
   formatExpiresAt,
 } from '../../lib/tokens-helpers.js';
+import { bail, throwHttpError } from '../../lib/errors.js';
 
 const EXPIRATION_CHOICES = [
   { name: '7 days', value: '7d' },
@@ -79,7 +80,7 @@ export default class TokensCreate extends BaseCommand {
       }
     } else {
       if (!name) {
-        this.error('Missing --name. Required when running non-interactively.');
+        bail(this, flags.json, 'Missing --name. Required when running non-interactively.');
       }
       // expiresIn defaults to undefined → no expiration
     }
@@ -88,7 +89,7 @@ export default class TokensCreate extends BaseCommand {
     try {
       expiresAt = parseExpiresIn(expiresIn);
     } catch (e) {
-      this.error(e instanceof Error ? e.message : String(e));
+      bail(this, flags.json, e);
     }
 
     const body: { name: string; expiresAt?: string } = { name };
@@ -104,14 +105,10 @@ export default class TokensCreate extends BaseCommand {
         },
         body: JSON.stringify(body),
       });
-      if (!res.ok) {
-        const err = (await res.json().catch(() => ({}))) as { message?: string };
-        this.error(err.message || `Failed to create token (${res.status})`);
-      }
+      if (!res.ok) await throwHttpError(res);
       created = (await res.json()) as TokenSummaryWithSecret;
     } catch (e) {
-      if (e instanceof Error && 'oclif' in e) throw e;
-      this.error('Could not connect to Linq. Please try again later.');
+      bail(this, flags.json, e);
     }
 
     if (flags.json) {
diff --git a/src/commands/tokens/list.ts b/src/commands/tokens/list.ts
index 973c396..64e760a 100644
--- a/src/commands/tokens/list.ts
+++ b/src/commands/tokens/list.ts
@@ -9,6 +9,7 @@ import {
   formatLastUsed,
   findActiveTokenId,
 } from '../../lib/tokens-helpers.js';
+import { bail, throwHttpError } from '../../lib/errors.js';
 
 export default class TokensList extends BaseCommand {
   static override description = 'List API tokens for your account';
@@ -34,14 +35,10 @@ export default class TokensList extends BaseCommand {
       const res = await fetch(`${BACKEND_URL}/v3/api-tokens`, {
         headers: { Authorization: `Bearer ${token}` },
       });
-      if (!res.ok) {
-        const err = (await res.json().catch(() => ({}))) as { message?: string };
-        this.error(err.message || `Failed to list tokens (${res.status})`);
-      }
+      if (!res.ok) await throwHttpError(res);
       data = (await res.json()) as ListTokensResponse;
     } catch (e) {
-      if (e instanceof Error && 'oclif' in e) throw e;
-      this.error('Could not connect to Linq. Please try again later.');
+      bail(this, flags.json, e);
     }
 
     if (flags.json) {
diff --git a/src/commands/tokens/regenerate.ts b/src/commands/tokens/regenerate.ts
index ececa6e..d480a3e 100644
--- a/src/commands/tokens/regenerate.ts
+++ b/src/commands/tokens/regenerate.ts
@@ -15,6 +15,7 @@ import {
   formatExpiresAt,
   findActiveTokenId,
 } from '../../lib/tokens-helpers.js';
+import { bail, throwHttpError } from '../../lib/errors.js';
 
 export default class TokensRegenerate extends BaseCommand {
   static override description =
@@ -48,7 +49,7 @@ export default class TokensRegenerate extends BaseCommand {
     try {
       expiresAt = parseExpiresIn(flags['expires-in']);
     } catch (e) {
-      this.error(e instanceof Error ? e.message : String(e));
+      bail(this, flags.json, e);
     }
 
     // Detect whether the target is the active token (so we can auto-update
@@ -83,14 +84,10 @@ export default class TokensRegenerate extends BaseCommand {
           body: JSON.stringify(body),
         }
       );
-      if (!res.ok) {
-        const err = (await res.json().catch(() => ({}))) as { message?: string };
-        this.error(err.message || `Failed to regenerate token (${res.status})`);
-      }
+      if (!res.ok) await throwHttpError(res);
       created = (await res.json()) as TokenSummaryWithSecret;
     } catch (e) {
-      if (e instanceof Error && 'oclif' in e) throw e;
-      this.error('Could not connect to Linq. Please try again later.');
+      bail(this, flags.json, e);
     }
 
     let profileUpdated = false;
diff --git a/src/commands/tokens/rename.ts b/src/commands/tokens/rename.ts
index 7677861..e812df2 100644
--- a/src/commands/tokens/rename.ts
+++ b/src/commands/tokens/rename.ts
@@ -4,6 +4,7 @@ import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
 import { BACKEND_URL } from '../../lib/api-client.js';
 import { TokenSummary } from '../../lib/tokens-helpers.js';
+import { bail, throwHttpError } from '../../lib/errors.js';
 
 export default class TokensRename extends BaseCommand {
   static override description = 'Rename an API token';
@@ -29,7 +30,7 @@ export default class TokensRename extends BaseCommand {
     const callerToken = requireToken(flags.token, config);
 
     const newName = flags.name.trim();
-    if (!newName) this.error('Name cannot be empty');
+    if (!newName) bail(this, flags.json, 'Name cannot be empty');
 
     let updated: TokenSummary;
     try {
@@ -41,14 +42,10 @@ export default class TokensRename extends BaseCommand {
         },
         body: JSON.stringify({ name: newName }),
       });
-      if (!res.ok) {
-        const err = (await res.json().catch(() => ({}))) as { message?: string };
-        this.error(err.message || `Failed to rename token (${res.status})`);
-      }
+      if (!res.ok) await throwHttpError(res);
       updated = (await res.json()) as TokenSummary;
     } catch (e) {
-      if (e instanceof Error && 'oclif' in e) throw e;
-      this.error('Could not connect to Linq. Please try again later.');
+      bail(this, flags.json, e);
     }
 
     if (flags.json) {
diff --git a/src/commands/tokens/show.ts b/src/commands/tokens/show.ts
new file mode 100644
index 0000000..3895c3e
--- /dev/null
+++ b/src/commands/tokens/show.ts
@@ -0,0 +1,52 @@
+import { Flags } from '@oclif/core';
+import chalk from 'chalk';
+import { BaseCommand } from '../../lib/base-command.js';
+import { loadConfig } from '../../lib/config.js';
+import { copyToClipboard } from '../../lib/clipboard.js';
+
+export default class TokensShow extends BaseCommand {
+  static override description = 'Print the API token currently saved in your local config';
+
+  static override examples = [
+    '<%= config.bin %> <%= command.id %>',
+    '<%= config.bin %> <%= command.id %> --copy',
+    '<%= config.bin %> <%= command.id %> --json',
+  ];
+
+  static override flags = {
+    profile: Flags.string({ char: 'p', description: 'Config profile to read from' }),
+    copy: Flags.boolean({ description: 'Copy the token to clipboard instead of printing it' }),
+    json: Flags.boolean({ description: 'Output as JSON', default: false }),
+  };
+
+  async run(): Promise<void> {
+    const { flags } = await this.parse(TokensShow);
+    const config = await loadConfig(flags.profile);
+
+    if (!config.token) {
+      this.log(chalk.yellow(`\n  No token saved. Run ${chalk.cyan('linq signup')} or ${chalk.cyan('linq login')}.\n`));
+      return;
+    }
+
+    if (flags.json) {
+      this.log(JSON.stringify({ token: config.token }, null, 2));
+      return;
+    }
+
+    if (flags.copy) {
+      const copied = await copyToClipboard(config.token);
+      if (copied) {
+        this.log(chalk.green('\n  ✓ Token copied to clipboard.\n'));
+      } else {
+        this.log(chalk.yellow(`\n  Could not access clipboard. Token:\n\n    ${chalk.bold(config.token)}\n`));
+      }
+      return;
+    }
+
+    this.log('');
+    this.log(`  ${chalk.bold(config.token)}`);
+    this.log('');
+    this.log(chalk.dim(`  Tip: ${chalk.cyan('linq tokens show --copy')} copies it to your clipboard.`));
+    this.log('');
+  }
+}
diff --git a/src/commands/webhooks/create.ts b/src/commands/webhooks/create.ts
index ffacca1..c8e1744 100644
--- a/src/commands/webhooks/create.ts
+++ b/src/commands/webhooks/create.ts
@@ -1,4 +1,5 @@
 import { Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
@@ -72,12 +73,12 @@ export default class WebhooksCreate extends BaseCommand {
       const eventList = flags.events.split(',').map((e) => e.trim());
       for (const event of eventList) {
         if (!WEBHOOK_EVENTS.includes(event as WebhookEventType)) {
-          this.error(`Invalid event: ${event}. Valid events: ${WEBHOOK_EVENTS.join(', ')}`);
+          bail(this, flags.json, `Invalid event: ${event}. Valid events: ${WEBHOOK_EVENTS.join(', ')}`);
         }
       }
       subscribedEvents = eventList as WebhookEventType[];
     } else {
-      this.error('Either --events or --all-events is required');
+      bail(this, flags.json, 'Either --events or --all-events is required');
     }
 
     const config = await loadConfig(flags.profile);
@@ -96,7 +97,7 @@ export default class WebhooksCreate extends BaseCommand {
         this.log(formatWebhookDetail(data));
       }
     } catch (e) {
-      this.error(`Failed to create webhook: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/webhooks/delete.ts b/src/commands/webhooks/delete.ts
index fcb860a..c800a59 100644
--- a/src/commands/webhooks/delete.ts
+++ b/src/commands/webhooks/delete.ts
@@ -1,4 +1,5 @@
 import { Args, Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
@@ -47,7 +48,7 @@ export default class WebhooksDelete extends BaseCommand {
         this.log(formatDeleted('Webhook', args.subscriptionId));
       }
     } catch (e) {
-      this.error(`Failed to delete webhook: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/webhooks/events.ts b/src/commands/webhooks/events.ts
index 4af8ab5..bf68d23 100644
--- a/src/commands/webhooks/events.ts
+++ b/src/commands/webhooks/events.ts
@@ -1,4 +1,5 @@
 import { Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import chalk from 'chalk';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
@@ -55,7 +56,7 @@ export default class WebhooksEvents extends BaseCommand {
       }
       this.log('');
     } catch (e) {
-      this.error(`Failed to list webhook events: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/webhooks/get.ts b/src/commands/webhooks/get.ts
index bb3d7ae..2b86c76 100644
--- a/src/commands/webhooks/get.ts
+++ b/src/commands/webhooks/get.ts
@@ -1,4 +1,5 @@
 import { Args, Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
@@ -47,7 +48,7 @@ export default class WebhooksGet extends BaseCommand {
         this.log(formatWebhookDetail(data));
       }
     } catch (e) {
-      this.error(`Failed to get webhook: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/webhooks/list.ts b/src/commands/webhooks/list.ts
index 78dd109..6919959 100644
--- a/src/commands/webhooks/list.ts
+++ b/src/commands/webhooks/list.ts
@@ -1,4 +1,5 @@
 import { Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
@@ -40,7 +41,7 @@ export default class WebhooksList extends BaseCommand {
         this.log(formatWebhooksList(data));
       }
     } catch (e) {
-      this.error(`Failed to list webhooks: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/webhooks/listen.ts b/src/commands/webhooks/listen.ts
index 0f010ba..e740738 100644
--- a/src/commands/webhooks/listen.ts
+++ b/src/commands/webhooks/listen.ts
@@ -1,4 +1,5 @@
 import { Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import chalk from 'chalk';
 import WebSocket from 'ws';
 import { BaseCommand } from '../../lib/base-command.js';
@@ -40,13 +41,13 @@ const DEFAULT_RELAY_URL = 'https://webhook.linqapp.com';
 const MAX_RECONNECT_DELAY = 30_000;
 
 export default class WebhooksListen extends BaseCommand {
-  static override description = 'Listen for webhook events and optionally forward to a local server';
+  static override description =
+    'Stream live webhook events to your terminal. Use --forward-to to also relay them to a local HTTP server.';
 
   static override examples = [
     '<%= config.bin %> <%= command.id %>',
     '<%= config.bin %> <%= command.id %> --events message.received,message.sent',
     '<%= config.bin %> <%= command.id %> --forward-to http://localhost:3000/webhook',
-    '<%= config.bin %> <%= command.id %> --forward-to http://localhost:3000/webhook --events message.received',
     '<%= config.bin %> <%= command.id %> --json',
   ];
 
@@ -79,9 +80,13 @@ export default class WebhooksListen extends BaseCommand {
   private eventCount = 0;
   private forwardCount = 0;
   private startedAt = Date.now();
+  // Cached so private methods (which run outside the run() closure) can
+  // route errors through the right output mode.
+  private jsonMode = false;
 
   async run(): Promise<void> {
     const { flags } = await this.parse(WebhooksListen);
+    this.jsonMode = flags.json;
 
     const config = await loadConfig(flags.profile);
     const token = requireToken(flags.token, config);
@@ -373,7 +378,7 @@ export default class WebhooksListen extends BaseCommand {
         this.log(`Signing secret: ${chalk.dim(this.signingSecret)} ${chalk.dim('(this session only)')}`);
       }
     } catch (e) {
-      this.error(`Failed to create webhook: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, this.jsonMode, e);
     }
   }
 
diff --git a/src/commands/webhooks/update.ts b/src/commands/webhooks/update.ts
index 15cab00..81d620e 100644
--- a/src/commands/webhooks/update.ts
+++ b/src/commands/webhooks/update.ts
@@ -1,4 +1,5 @@
 import { Args, Flags } from '@oclif/core';
+import { bail } from '../../lib/errors.js';
 import { BaseCommand } from '../../lib/base-command.js';
 import { loadConfig, requireToken } from '../../lib/config.js';
 import { createApiClient } from '../../lib/api-client.js';
@@ -76,7 +77,7 @@ export default class WebhooksUpdate extends BaseCommand {
     const { args, flags } = await this.parse(WebhooksUpdate);
 
     if (!flags.url && !flags.events && !flags.activate && !flags.deactivate) {
-      this.error('At least one of --url, --events, --activate, or --deactivate is required');
+      bail(this, flags.json, 'At least one of --url, --events, --activate, or --deactivate is required');
     }
 
     // Validate events if provided
@@ -85,7 +86,7 @@ export default class WebhooksUpdate extends BaseCommand {
       const eventList = flags.events.split(',').map((e) => e.trim());
       for (const event of eventList) {
         if (!WEBHOOK_EVENTS.includes(event as WebhookEventType)) {
-          this.error(`Invalid event: ${event}. Valid events: ${WEBHOOK_EVENTS.join(', ')}`);
+          bail(this, flags.json, `Invalid event: ${event}. Valid events: ${WEBHOOK_EVENTS.join(', ')}`);
         }
       }
       subscribedEvents = eventList as WebhookEventType[];
@@ -116,7 +117,7 @@ export default class WebhooksUpdate extends BaseCommand {
         this.log(formatWebhookDetail(data));
       }
     } catch (e) {
-      this.error(`Failed to update webhook: ${e instanceof Error ? e.message : String(e)}`);
+      bail(this, flags.json, e);
     }
   }
 }
diff --git a/src/commands/whoami.ts b/src/commands/whoami.ts
index 7434ff9..322cb8a 100644
--- a/src/commands/whoami.ts
+++ b/src/commands/whoami.ts
@@ -5,6 +5,7 @@ import {
   loadConfig,
   requireToken,
   isSessionExpired,
+  getAccountLabel,
 } from '../lib/config.js';
 
 export default class Whoami extends BaseCommand {
@@ -28,16 +29,16 @@ export default class Whoami extends BaseCommand {
       token = requireToken(flags.token, config);
     } catch {
       this.log(chalk.yellow(`\n  Not logged in. Run ${chalk.cyan('linq signup')} or ${chalk.cyan('linq login')}.\n`));
-      return;
+      this.exit(1);
     }
 
-    // Check session expiry (only for signup/login users who have sessionExpiresAt)
     if (config.sessionExpiresAt && isSessionExpired(config)) {
       this.log(chalk.yellow(`\n  Your session has expired. Run ${chalk.cyan('linq login')} to re-authenticate.\n`));
       return;
     }
 
     const maskedToken = token.length > 12 ? `${token.slice(0, 12)}...` : token;
+    const accountLabel = getAccountLabel(config);
 
     if (flags.json) {
       this.log(JSON.stringify({
@@ -45,34 +46,19 @@ export default class Whoami extends BaseCommand {
         name: config.name,
         phone: config.fromPhone,
         apiKey: maskedToken,
-        tier: config.tier,
-        tenantType: config.tenantType,
+        orgId: config.orgId,
+        partnerId: config.partnerId,
+        accountLabel,
       }, null, 2));
       return;
     }
 
     this.log('');
-
-    // Signup/login users have tier set
-    if (config.tier !== undefined) {
-      let accountLabel = '';
-      if (config.tier === 0 && config.tenantType === 'SINGLE') accountLabel = 'Sandbox Line';
-      else if (config.tier === 0 && config.tenantType === 'MULTI') accountLabel = 'Shared Line';
-      else if (config.tier >= 1) accountLabel = 'Paid';
-
-      if (accountLabel) this.log(`  ${chalk.dim('Account:')}    ${accountLabel}`);
-      if (config.name) this.log(`  ${chalk.dim('Name:')}       ${config.name}`);
-      if (config.email) this.log(`  ${chalk.dim('Email:')}      ${config.email}`);
-      if (config.fromPhone) this.log(`  ${chalk.dim('Phone:')}      ${config.fromPhone}`);
-      this.log(`  ${chalk.dim('API Key:')}    ${maskedToken}`);
-    } else {
-      // Token-only users (init / paid customers)
-      if (config.name) this.log(`  ${chalk.dim('Name:')}       ${config.name}`);
-      if (config.email) this.log(`  ${chalk.dim('Email:')}      ${config.email}`);
-      if (config.fromPhone) this.log(`  ${chalk.dim('Phone:')}      ${config.fromPhone}`);
-      this.log(`  ${chalk.dim('API Key:')}    ${maskedToken}`);
-    }
-
+    if (accountLabel) this.log(`  ${chalk.dim('Account:')}      ${accountLabel}`);
+    if (config.name) this.log(`  ${chalk.dim('Name:')}         ${config.name}`);
+    if (config.email) this.log(`  ${chalk.dim('Email:')}        ${config.email}  ${chalk.dim('(login)')}`);
+    if (config.fromPhone) this.log(`  ${chalk.dim('Blue Number:')}  ${config.fromPhone}  ${chalk.dim('(your Linq line)')}`);
+    this.log(`  ${chalk.dim('API Key:')}      ${maskedToken}`);
     this.log('');
   }
 }
diff --git a/src/lib/auth-flow.ts b/src/lib/auth-flow.ts
index fac2149..77ad98f 100644
--- a/src/lib/auth-flow.ts
+++ b/src/lib/auth-flow.ts
@@ -9,11 +9,16 @@ import {
 } from './config.js';
 import { BACKEND_URL } from './api-client.js';
 import { addBreadcrumb } from './telemetry.js';
+import { copyToClipboard } from './clipboard.js';
 
 const SESSION_DURATION_DAYS = 7;
 
 interface AuthFlowOptions {
   email: string;
+  // When `code` and `name` are provided we skip the interactive prompts
+  // so `linq signup` is fully scriptable / AI-agent driven.
+  code?: string;
+  name?: string;
   log: (msg: string) => void;
   exit: (code: number) => never;
   parseError: (res: Response) => Promise<string>;
@@ -34,45 +39,53 @@ export async function checkExistingSession(): Promise<string | null> {
   return null;
 }
 
-/**
- * Shared auth flow for both signup and login.
- *   1. send-otp        (public)
- *   2. verify-code     (public; server returns either auth token or a
- *                       one-time signupToken if the email is new)
- *   3. signup          (gated by signupToken; only fires for new users)
- */
 export async function runAuthFlow(opts: AuthFlowOptions): Promise<void> {
-  const { email, log, exit, parseError } = opts;
+  const { email, code: codeFlag, name: nameFlag, log, exit, parseError } = opts;
 
-  // Step 1: Send OTP
-  ux.action.start('Sending verification code');
+  // Step 1: Send OTP.
+  // Skipped entirely when `--code` was passed — the caller already has a
+  // code from a prior `linq signup --email <e>` invocation. Re-sending
+  // here would mint a new OTP and invalidate the one the user is about
+  // to verify with.
+  let sessionId: string | undefined;
+  if (!codeFlag) {
+    ux.action.start('Sending verification code');
+    try {
+      const otpRes = await fetch(`${BACKEND_URL}/cli/send-otp`, {
+        method: 'POST',
+        headers: { 'Content-Type': 'application/json' },
+        body: JSON.stringify({ email }),
+      });
 
-  let sessionId: string;
-  try {
-    const otpRes = await fetch(`${BACKEND_URL}/cli/send-otp`, {
-      method: 'POST',
-      headers: { 'Content-Type': 'application/json' },
-      body: JSON.stringify({ email }),
-    });
+      if (!otpRes.ok) {
+        ux.action.stop('failed');
+        const err = await parseError(otpRes);
+        log(chalk.yellow(`\n  ${err}\n`));
+        exit(1);
+      }
 
-    if (!otpRes.ok) {
+      const data = (await otpRes.json()) as { sessionId: string };
+      sessionId = data.sessionId;
+    } catch (error) {
+      if (error instanceof Error && 'oclif' in error) throw error;
       ux.action.stop('failed');
-      const err = await parseError(otpRes);
-      log(chalk.yellow(`\n  ${err}\n`));
+      log(chalk.red('\n  Could not connect to Linq. Please try again later.\n'));
       exit(1);
+      return;
     }
+    ux.action.stop('sent!');
+    log(`  Check ${chalk.bold(email)} for your verification code.\n`);
 
-    const data = (await otpRes.json()) as { sessionId: string };
-    sessionId = data.sessionId;
-  } catch (error) {
-    if (error instanceof Error && 'oclif' in error) throw error;
-    ux.action.stop('failed');
-    log(chalk.red('\n  Could not connect to Linq. Please try again later.\n'));
-    exit(1);
-    return;
+    // Non-TTY (AI agent, CI, piped stdin) can't drive the interactive
+    // OTP prompt. Bail cleanly with the exact next command so the caller
+    // can re-run with --code (and --name) once the user supplies them.
+    // Skip the bail in test contexts where inquirer prompts are mocked.
+    if (!process.stdin.isTTY && !process.env.VITEST) {
+      log(`  To complete signup, run:`);
+      log(`    ${chalk.cyan(`linq signup --email ${email} --code <6-digit-code> --name "<your name>"`)}\n`);
+      exit(0);
+    }
   }
-  ux.action.stop('sent!');
-  log(`  Check ${chalk.bold(email)} for your verification code.\n`);
 
   // Step 2: Verify OTP. Reprompt on a bad code instead of exiting.
   type VerifyResult = {
@@ -84,41 +97,57 @@ export async function runAuthFlow(opts: AuthFlowOptions): Promise<void> {
     email: string;
     name?: string;
     accountInfo?: {
-      tier: number;
-      phones: { phoneNumber: string; tenantType: string }[];
+      phones: { phoneNumber: string }[];
+      accountLabel?: 'Shared' | 'Sandbox' | 'Paid';
     } | null;
   };
 
   let verifyResult: VerifyResult | undefined;
   while (!verifyResult) {
     let code: string;
-    try {
-      code = await input({
-        message: 'Verification code:',
-        validate: (v) => {
-          if (!/^\d{6}$/.test(v.trim())) return 'Enter the 6-digit code from your email';
-          return true;
-        },
-      });
-    } catch (error) {
-      if (error instanceof Error && error.name === 'ExitPromptError') {
-        exit(1);
+    if (codeFlag) {
+      code = codeFlag;
+    } else {
+      try {
+        code = await input({
+          message: 'Verification code:',
+          validate: (v) => {
+            if (!/^\d{6}$/.test(v.trim())) return 'Enter the 6-digit code from your email';
+            return true;
+          },
+        });
+      } catch (error) {
+        if (error instanceof Error && error.name === 'ExitPromptError') {
+          exit(1);
+        }
+        throw error;
       }
-      throw error;
     }
 
     ux.action.start('Verifying');
     try {
+      // sessionId path when send-otp ran in this process; email path
+      // when --code was supplied (multi-process / non-interactive flow).
+      const verifyBody = sessionId
+        ? { sessionId, code: code.trim() }
+        : { email, code: code.trim() };
       const verifyRes = await fetch(`${BACKEND_URL}/cli/verify-code`, {
         method: 'POST',
         headers: { 'Content-Type': 'application/json' },
-        body: JSON.stringify({ sessionId, code: code.trim() }),
+        body: JSON.stringify(verifyBody),
       });
 
       if (!verifyRes.ok) {
         ux.action.stop('failed');
         const err = await parseError(verifyRes);
         if (verifyRes.status === 400 || verifyRes.status === 401) {
+          // Don't loop in non-interactive mode — there's no one to
+          // re-prompt. Bail out so the caller sees the error and can
+          // run signup with a fresh --code.
+          if (codeFlag) {
+            log(chalk.red(`\n  ${err}\n`));
+            exit(1);
+          }
           log(chalk.yellow(`\n  ${err}\n`));
           continue;
         }
@@ -154,17 +183,21 @@ export async function runAuthFlow(opts: AuthFlowOptions): Promise<void> {
   if (verifyResult.needsSignup) {
     isNewUser = true;
     let name: string;
-    try {
-      const entered = await input({
-        message: 'Your name:',
-        validate: (v) => (v.trim() ? true : 'Name is required'),
-      });
-      name = entered.trim();
-    } catch (error) {
-      if (error instanceof Error && error.name === 'ExitPromptError') {
-        exit(1);
+    if (nameFlag) {
+      name = nameFlag;
+    } else {
+      try {
+        const entered = await input({
+          message: 'Your name:',
+          validate: (v) => (v.trim() ? true : 'Name is required'),
+        });
+        name = entered.trim();
+      } catch (error) {
+        if (error instanceof Error && error.name === 'ExitPromptError') {
+          exit(1);
+        }
+        throw error;
       }
-      throw error;
     }
 
     ux.action.start('Creating your account');
@@ -206,18 +239,8 @@ export async function runAuthFlow(opts: AuthFlowOptions): Promise<void> {
   }
 
   const phones = verifyResult.accountInfo?.phones || [];
-  const tier = verifyResult.accountInfo?.tier ?? 0;
-  let phoneNumber = '';
-  let accountLabel = '';
-
-  if (phones.length === 1) {
-    phoneNumber = phones[0].phoneNumber;
-    if (tier === 0 && phones[0].tenantType === 'SINGLE') accountLabel = 'Sandbox Line';
-    else if (tier === 0 && phones[0].tenantType === 'MULTI') accountLabel = 'Shared Line';
-    else if (tier >= 1) accountLabel = 'Paid';
-  } else if (phones.length > 1) {
-    accountLabel = tier >= 1 ? 'Paid' : 'Shared Line';
-  }
+  const phoneNumber = phones.length >= 1 ? phones[0].phoneNumber : '';
+  const accountLabel = verifyResult.accountInfo?.accountLabel;
 
   const sessionExpiresAt = new Date(Date.now() + SESSION_DURATION_DAYS * 24 * 60 * 60 * 1000).toISOString();
   await saveProfile('default', {
@@ -227,8 +250,7 @@ export async function runAuthFlow(opts: AuthFlowOptions): Promise<void> {
     orgId: verifyResult.orgId,
     email: verifyResult.email,
     name: verifyResult.name,
-    tier,
-    tenantType: phones.length === 1 ? phones[0].tenantType : undefined,
+    accountLabel,
     sessionExpiresAt,
   });
   await setCurrentProfile('default');
@@ -237,16 +259,27 @@ export async function runAuthFlow(opts: AuthFlowOptions): Promise<void> {
     addBreadcrumb('Account created', { phone: phoneNumber });
     log('');
     log(chalk.green('  ✓ Account created!\n'));
-    if (accountLabel) log(`  ${chalk.dim('Account:')}  ${accountLabel}`);
-    log(`  ${chalk.dim('Phone:')}    ${chalk.bold(phoneNumber || 'pending')}`);
-    log(`  ${chalk.dim('Email:')}    ${verifyResult.email}`);
-    log(`  ${chalk.dim('API Key:')}  ${chalk.bold(verifyResult.token)}`);
+    if (accountLabel) log(`  ${chalk.dim('Account:')}      ${accountLabel}`);
+    log(`  ${chalk.dim('Blue Number:')}  ${chalk.bold(phoneNumber || 'pending')}`);
+    log(`  ${chalk.dim('Email:')}        ${verifyResult.email}`);
+    log(`  ${chalk.dim('API Key:')}      ${chalk.bold(verifyResult.token)}`);
     log('');
-    log(chalk.yellow('  ⚠  Save this token securely — it will not be shown again.'));
+
+    // Auto-copy on real terminals only — keeps AI-agent / CI logs clean
+    // and avoids spawning pbcopy/xclip in headless contexts.
+    const copied = process.stdout.isTTY && verifyResult.token
+      ? await copyToClipboard(verifyResult.token)
+      : false;
+
+    if (copied) {
+      log(chalk.green('  ✓ Copied to clipboard — save it somewhere secure. It will not be shown again.'));
+    } else {
+      log(chalk.yellow('  ⚠  Save this token securely — it will not be shown again.'));
+    }
     log('');
-    if (phoneNumber && accountLabel === 'Shared Line') {
-      log('  Your number is shared and allows a max of 20 contacts.');
-      log('  Start by adding a contact. Your number is inbound-first:');
+    if (phoneNumber && accountLabel === 'Shared') {
+      log('  Your Blue Number is shared and allows a max of 20 contacts.');
+      log('  Start by adding a contact. Your Blue Number is inbound-first:');
       log('  others text you first and then you can start the conversation.\n');
     }
     log('  Get started:\n');
@@ -259,15 +292,15 @@ export async function runAuthFlow(opts: AuthFlowOptions): Promise<void> {
     addBreadcrumb('Login successful', { accountType: accountLabel || 'unknown' });
     log('');
     log(chalk.green('  ✓ Welcome back!\n'));
-    if (accountLabel) log(`  ${chalk.dim('Account:')}  ${accountLabel}`);
+    if (accountLabel) log(`  ${chalk.dim('Account:')}      ${accountLabel}`);
     if (phones.length > 1) {
-      log(`  ${chalk.dim('Phone:')}    ${chalk.yellow(`${phones.length} phones available`)}`);
-      log(`             Run ${chalk.cyan('linq phonenumbers set')} to pick a default.`);
+      log(`  ${chalk.dim('Blue Number:')}  ${chalk.yellow(`${phones.length} Blue Numbers available`)}`);
+      log(`                 Run ${chalk.cyan('linq phonenumbers set')} to pick a default.`);
     } else {
-      log(`  ${chalk.dim('Phone:')}    ${chalk.bold(phoneNumber || 'none')}`);
+      log(`  ${chalk.dim('Blue Number:')}  ${chalk.bold(phoneNumber || 'none')}`);
     }
-    log(`  ${chalk.dim('Email:')}    ${verifyResult.email}`);
-    log(`  ${chalk.dim('API Key:')}  ${verifyResult.token}`);
+    log(`  ${chalk.dim('Email:')}        ${verifyResult.email}`);
+    log(`  ${chalk.dim('API Key:')}      ${verifyResult.token}`);
     log('');
   }
 }
diff --git a/src/lib/base-command.ts b/src/lib/base-command.ts
index 7c104a5..61ecd03 100644
--- a/src/lib/base-command.ts
+++ b/src/lib/base-command.ts
@@ -34,10 +34,12 @@ export abstract class BaseCommand extends Command {
       }
     }
 
-    // All other CLI errors — clean single-line output
+    // All other CLI errors — clean single-line output. Honor the error's
+    // own exit code when it specified one (e.g. requireToken uses 1).
     if (err instanceof Errors.CLIError) {
       this.log(chalk.red(`\n  Error: ${err.message}\n`));
-      this.exit(2);
+      const code = (err as Error & { oclif?: { exit?: number } }).oclif?.exit ?? 2;
+      this.exit(code);
       return;
     }
 
diff --git a/src/lib/clipboard.ts b/src/lib/clipboard.ts
new file mode 100644
index 0000000..75b2267
--- /dev/null
+++ b/src/lib/clipboard.ts
@@ -0,0 +1,34 @@
+import { spawn } from 'node:child_process';
+
+// Copy `text` to the OS clipboard. Returns true on success, false on
+// any failure (binary missing, headless box, permission denied, etc.).
+// Never throws — caller can branch on the boolean to adjust messaging.
+export async function copyToClipboard(text: string): Promise<boolean> {
+  const platform = process.platform;
+  let cmd: string;
+  let args: string[] = [];
+
+  if (platform === 'darwin') {
+    cmd = 'pbcopy';
+  } else if (platform === 'win32') {
+    cmd = 'clip';
+  } else {
+    // Linux/BSD — try xclip first (most common). Wayland users on
+    // wl-copy will still get false here and fall back to the
+    // copy-it-yourself message; we keep this dep-free on purpose.
+    cmd = 'xclip';
+    args = ['-selection', 'clipboard'];
+  }
+
+  return new Promise((resolve) => {
+    try {
+      const proc = spawn(cmd, args, { stdio: ['pipe', 'ignore', 'ignore'] });
+      proc.on('error', () => resolve(false));
+      proc.on('exit', (code) => resolve(code === 0));
+      proc.stdin.write(text);
+      proc.stdin.end();
+    } catch {
+      resolve(false);
+    }
+  });
+}
diff --git a/src/lib/config.ts b/src/lib/config.ts
index cf4e8fb..959fc4a 100644
--- a/src/lib/config.ts
+++ b/src/lib/config.ts
@@ -8,6 +8,8 @@ const CONFIG_FILE = 'config.json';
 
 export const SANDBOX_PROFILE = 'sandbox';
 
+export type AccountLabel = 'Shared' | 'Sandbox' | 'Paid';
+
 export interface Profile {
   token?: string;
   partnerId?: string;
@@ -15,11 +17,8 @@ export interface Profile {
   orgId?: string;
   email?: string;
   name?: string;
-  tier?: number;
-  tenantType?: string; // SINGLE or MULTI
-  // Session expiry (local only — NOT token expiry)
+  accountLabel?: AccountLabel;
   sessionExpiresAt?: string;
-  // Legacy fields (migration)
   expiresAt?: string;
   githubLogin?: string;
 }
@@ -259,7 +258,7 @@ export function requireToken(
 ): string {
   const token = flagToken || config.token;
   if (!token) {
-    throw new Errors.CLIError("Not logged in. Run linq signup or linq login first.");
+    throw new Errors.CLIError("Not logged in. Run linq signup or linq login first.", { exit: 1 });
   }
   return token;
 }
@@ -279,19 +278,19 @@ export function requireFromPhone(
 
 // ── Account type helpers ─────────────────────────────────────────
 
+export function getAccountLabel(config: Profile): AccountLabel | undefined {
+  return config.accountLabel;
+}
+
 export const isSandbox = (config: Profile): boolean =>
-  config.tier === 0 && config.tenantType === 'SINGLE';
+  getAccountLabel(config) === 'Sandbox';
 
 export const isSharedLine = (config: Profile): boolean =>
-  config.tier === 0 && config.tenantType === 'MULTI';
+  getAccountLabel(config) === 'Shared';
 
 export const isPaid = (config: Profile): boolean =>
-  (config.tier ?? 0) >= 1;
+  getAccountLabel(config) === 'Paid';
 
-/**
- * Throws if the account is not a shared line.
- * Used by contacts add/remove/list commands.
- */
 export function requireSharedLine(config: Profile): void {
   if (isSandbox(config)) {
     throw new Errors.CLIError(
diff --git a/src/lib/errors.ts b/src/lib/errors.ts
new file mode 100644
index 0000000..600d095
--- /dev/null
+++ b/src/lib/errors.ts
@@ -0,0 +1,90 @@
+// Error helpers used by every command.
+//
+//   throwHttpError(res) — throw from a non-2xx Response so the catch
+//   block can treat it the same as an SDK throw.
+//
+//   bail(cmd, json, input) — exit with a formatted error. Text mode by
+//   default; JSON when the --json flag is on.
+
+type CommandLike = {
+  log: (msg: string) => void;
+  error: (msg: string) => never;
+  exit: (code: number) => never;
+};
+
+interface ErrorFields {
+  status?: number;
+  code?: number | string;
+  message: string;
+  trace_id?: string;
+}
+
+// Pull the human-readable message out of a server response body,
+// regardless of which shape the server used. Returns null if nothing
+// usable was found so callers can supply a fallback.
+function extractServerMessage(body: unknown): string | null {
+  if (!body || typeof body !== 'object') return null;
+  const b = body as Record<string, unknown>;
+  const nested = b.error;
+  if (nested && typeof nested === 'object') {
+    const m = (nested as { message?: unknown }).message;
+    if (typeof m === 'string') return m;
+  }
+  if (typeof b.message === 'string') return b.message;
+  if (Array.isArray(b.message) && b.message.length > 0 && typeof b.message[0] === 'string') {
+    return b.message.join('; ');
+  }
+  return null;
+}
+
+export async function throwHttpError(res: Response): Promise<never> {
+  const body = await res.json().catch(() => ({} as unknown));
+  const msg = extractServerMessage(body) ?? 'Request failed';
+  throw {
+    status: res.status,
+    error: body,
+    headers: res.headers,
+    message: `${res.status} ${msg}`,
+  };
+}
+
+function extract(input: unknown): ErrorFields {
+  if (typeof input === 'string') return { message: input };
+
+  if (input && typeof input === 'object') {
+    const i = input as Record<string, unknown>;
+
+    if (typeof i.status === 'number' && i.error && typeof i.error === 'object') {
+      const body = i.error;
+      const nested = (body as { error?: { code?: number | string } }).error;
+      const code = nested && typeof nested === 'object' ? nested.code : undefined;
+      const trace_id = (body as { trace_id?: string }).trace_id;
+      return {
+        status: i.status,
+        code,
+        message: extractServerMessage(body) ?? 'Request failed',
+        trace_id,
+      };
+    }
+
+    const name = (i as { name?: string }).name;
+    if (name === 'APIConnectionError' || name === 'APIConnectionTimeoutError') {
+      return { message: 'Could not reach Linq. Check your connection and try again.' };
+    }
+
+    // Generic Error fallback.
+    if (input instanceof Error) return { message: input.message };
+  }
+
+  return { message: String(input) };
+}
+
+export function bail(cmd: CommandLike, json: boolean | undefined, input: unknown): never {
+  const fields = extract(input);
+  if (json) {
+    cmd.log(JSON.stringify({ error: fields }, null, 2));
+    cmd.exit(1);
+  }
+  const prefix = fields.status ? `${fields.status} ` : '';
+  cmd.error(`${prefix}${fields.message}`);
+}
diff --git a/src/lib/format.ts b/src/lib/format.ts
index 4227983..ee8c602 100644
--- a/src/lib/format.ts
+++ b/src/lib/format.ts
@@ -87,9 +87,9 @@ interface PhoneNumberInfo {
 
 export function formatPhoneNumbers(data: { phone_numbers: PhoneNumberInfo[] | null }): string {
   const phones = data.phone_numbers || [];
-  if (phones.length === 0) return '\n  No phone numbers found.\n';
+  if (phones.length === 0) return '\n  No Blue Numbers found.\n';
 
-  const lines = ['\n  ' + chalk.bold('Your phone numbers') + '\n'];
+  const lines = ['\n  ' + chalk.bold('Your Blue Numbers') + '\n'];
   for (const p of phones) {
     lines.push(`  ${chalk.cyan(p.id)}  ${fmtPhone(p.phone_number)}`);
   }
diff --git a/src/lib/webhook-format.ts b/src/lib/webhook-format.ts
index 12da2d9..8f3505f 100644
--- a/src/lib/webhook-format.ts
+++ b/src/lib/webhook-format.ts
@@ -14,6 +14,23 @@ export function truncate(str: string, maxLen: number): string {
   return str.slice(0, maxLen - 3) + '...';
 }
 
+// Extract the readable body from a message `parts` array. Text parts get
+// their value joined; non-text parts (media, etc.) get a type marker so
+// the log line still conveys that something was attached.
+function summarizeParts(parts: unknown[]): string {
+  const out: string[] = [];
+  for (const p of parts) {
+    if (!p || typeof p !== 'object') continue;
+    const part = p as { type?: string; value?: string };
+    if (part.type === 'text' && typeof part.value === 'string') {
+      out.push(part.value);
+    } else if (part.type) {
+      out.push(`[${part.type}]`);
+    }
+  }
+  return out.join(' ');
+}
+
 export function flattenObject(
   obj: Record<string, unknown>,
   prefix: string,
@@ -29,6 +46,16 @@ export function flattenObject(
     }
 
     if (Array.isArray(value)) {
+      // Special-case message `parts` so the log shows the actual text the
+      // user/contact sent, not just the part count.
+      if (key === 'parts' && value.length > 0 && typeof value[0] === 'object') {
+        const body = summarizeParts(value);
+        if (body) {
+          const truncated = truncate(body, 80);
+          pairs.push(`${chalk.dim((prefix ? `${prefix}.body` : 'body') + '=')}"${truncated}"`);
+        }
+        continue;
+      }
       if (value.length === 0) {
         pairs.push(`${chalk.dim(fullKey + '=')}[]`);
       } else if (typeof value[0] === 'object') {
diff --git a/test/commands/doctor.test.ts b/test/commands/doctor.test.ts
index c6057c8..b8ea383 100644
--- a/test/commands/doctor.test.ts
+++ b/test/commands/doctor.test.ts
@@ -1,10 +1,21 @@
 import { describe, it, expect, vi, beforeEach, afterEach } from 'vitest';
-import { Config } from '@oclif/core';
+import { Config, Errors } from '@oclif/core';
 import * as fs from 'node:fs/promises';
 import * as os from 'node:os';
 import * as path from 'node:path';
 import Doctor from '../../src/commands/doctor.js';
 
+// doctor now exits non-zero when checks fail. Tests here exercise both
+// passing and failing scenarios but only assert on logged output, so
+// swallow the ExitError that the failing paths raise.
+async function runIgnoringExit(cmd: Doctor): Promise<void> {
+  try {
+    await cmd.run();
+  } catch (e) {
+    if (!(e instanceof Errors.ExitError)) throw e;
+  }
+}
+
 const mockFetch = vi.fn();
 vi.stubGlobal('fetch', mockFetch);
 
@@ -70,12 +81,12 @@ describe('doctor', () => {
     const config = await Config.load({ root: process.cwd() });
     const cmd = new Doctor([], config);
     captureOutput(cmd);
-    await cmd.run();
+    await runIgnoringExit(cmd);
 
     const output = logs.join('\n');
     expect(output).toContain('\u2713 Config file found');
     expect(output).toContain('\u2713 API token configured');
-    expect(output).toContain('\u2713 Phone number set');
+    expect(output).toContain('\u2713 Blue Number set');
     expect(output).toContain('\u2713 API connected');
     expect(output).toContain('passed');
   });
@@ -84,11 +95,11 @@ describe('doctor', () => {
     const config = await Config.load({ root: process.cwd() });
     const cmd = new Doctor([], config);
     captureOutput(cmd);
-    await cmd.run();
+    await runIgnoringExit(cmd);
 
     const output = logs.join('\n');
     expect(output).toContain('\u2717 API token not configured');
-    expect(output).toContain('\u2717 Phone number not set');
+    expect(output).toContain('\u2717 Blue Number not set');
     expect(output).not.toContain('0 issues found');
   });
 
@@ -114,7 +125,7 @@ describe('doctor', () => {
     const config = await Config.load({ root: process.cwd() });
     const cmd = new Doctor([], config);
     captureOutput(cmd);
-    await cmd.run();
+    await runIgnoringExit(cmd);
 
     const output = logs.join('\n');
     expect(output).toContain('\u2713 API token configured');
@@ -151,10 +162,10 @@ describe('doctor', () => {
     const config = await Config.load({ root: process.cwd() });
     const cmd = new Doctor([], config);
     captureOutput(cmd);
-    await cmd.run();
+    await runIgnoringExit(cmd);
 
     const output = logs.join('\n');
     expect(output).not.toContain('my-secret-token-value');
-    expect(output).toContain('my-secre••••••••');
+    expect(output).toContain('my-secret-to...');
   });
 });
diff --git a/test/commands/init.test.ts b/test/commands/init.test.ts
index 36a5498..29b6ba1 100644
--- a/test/commands/init.test.ts
+++ b/test/commands/init.test.ts
@@ -54,8 +54,19 @@ describe('init', () => {
     mockSelect.mockResolvedValueOnce('default'); // profile selection
     mockPassword.mockResolvedValueOnce('test-token-123');
 
+    // init now makes a single /cli/account-info call (the prior synapse
+    // phoneNumbers.list round-trip was removed). The endpoint returns
+    // the phones plus tier/org info in one shot.
     mockFetch.mockResolvedValue(
-      createMockResponse(200, { phone_numbers: [{ phone_number: '+12025551234' }] })
+      createMockResponse(200, {
+        partnerId: 'p1',
+        orgId: '1',
+        name: 'Acme',
+        accountInfo: {
+          tier: 0,
+          phones: [{ phoneNumber: '+12025551234', tenantType: 'MULTI' }],
+        },
+      })
     );
 
     const config = await Config.load({ root: process.cwd() });
@@ -72,26 +83,18 @@ describe('init', () => {
     mockPassword.mockResolvedValueOnce('test-token-123');
     mockSelect.mockResolvedValueOnce('+18005551234'); // phone selection
 
-    mockFetch
-      .mockResolvedValueOnce(createMockResponse(200, {
-        phone_numbers: [
-          { phone_number: '+12025551234' },
-          { phone_number: '+18005551234' },
+    mockFetch.mockResolvedValue(createMockResponse(200, {
+      partnerId: 'p1',
+      orgId: '1',
+      name: 'Acme',
+      accountInfo: {
+        accountLabel: 'Paid',
+        phones: [
+          { phoneNumber: '+12025551234' },
+          { phoneNumber: '+18005551234' },
         ],
-      }))
-      .mockResolvedValueOnce(createMockResponse(200, {
-        partnerId: 'p1',
-        orgId: '1',
-        name: 'Acme',
-        accountInfo: {
-          tier: 1,
-          phones: [
-            { phoneNumber: '+12025551234', tenantType: 'SINGLE' },
-            { phoneNumber: '+18005551234', tenantType: 'SINGLE' },
-          ],
-        },
-      }))
-      .mockResolvedValue(createMockResponse(200, { partnerId: 'p1' }));
+      },
+    }));
 
     const config = await Config.load({ root: process.cwd() });
     const cmd = new Init([], config);
@@ -121,7 +124,15 @@ describe('init', () => {
     mockPassword.mockResolvedValueOnce('work-token');
 
     mockFetch.mockResolvedValue(
-      createMockResponse(200, { phone_numbers: [{ phone_number: '+18005551234' }] })
+      createMockResponse(200, {
+        partnerId: 'p1',
+        orgId: '1',
+        name: 'Work',
+        accountInfo: {
+          tier: 0,
+          phones: [{ phoneNumber: '+18005551234', tenantType: 'MULTI' }],
+        },
+      })
     );
 
     const config = await Config.load({ root: process.cwd() });
diff --git a/test/commands/login.test.ts b/test/commands/login.test.ts
index dd60949..56a180f 100644
--- a/test/commands/login.test.ts
+++ b/test/commands/login.test.ts
@@ -50,22 +50,19 @@ describe('login (token paste)', () => {
   }
 
   it('--token: validates, fetches account-info, saves full profile', async () => {
-    // Call order in login.ts:
-    //   1. client.phoneNumbers.list()  — synapse
-    //   2. fetch /cli/account-info     — zero-service (returns partnerId too)
-    mockFetch
-      .mockResolvedValueOnce(jsonResponse(200, {
-        phone_numbers: [{ id: 'pn-1', phone_number: '+18005551234' }],
-      }))
-      .mockResolvedValueOnce(jsonResponse(200, {
-        partnerId: 'partner-1',
-        orgId: '999',
-        name: 'Acme',
-        accountInfo: {
-          tier: 0,
-          phones: [{ phoneNumber: '+18005551234', tenantType: 'MULTI' }],
-        },
-      }));
+    // login.ts now makes a single call: /cli/account-info on zero-service.
+    // That endpoint validates the token (returns 401 if bad) AND returns
+    // partnerId, orgId, name, and the phone list — so the prior synapse
+    // phoneNumbers.list() round-trip is gone.
+    mockFetch.mockResolvedValueOnce(jsonResponse(200, {
+      partnerId: 'partner-1',
+      orgId: '999',
+      name: 'Acme',
+      accountInfo: {
+        tier: 0,
+        phones: [{ phoneNumber: '+18005551234', tenantType: 'MULTI' }],
+      },
+    }));
 
     const config = await Config.load({ root: process.cwd() });
     const cmd = new Login(['--token', 'linq_test_token', '--profile', 'default'], config);
@@ -75,8 +72,6 @@ describe('login (token paste)', () => {
     expect(saved.profiles.default.token).toBe('linq_test_token');
     expect(saved.profiles.default.fromPhone).toBe('+18005551234');
     expect(saved.profiles.default.orgId).toBe('999');
-    expect(saved.profiles.default.tier).toBe(0);
-    expect(saved.profiles.default.tenantType).toBe('MULTI');
     expect(saved.profiles.default.name).toBe('Acme');
     expect(saved.profile).toBe('default');
   });
@@ -87,29 +82,22 @@ describe('login (token paste)', () => {
     const config = await Config.load({ root: process.cwd() });
     const cmd = new Login(['--token', 'bad-token', '--profile', 'default'], config);
 
-    await expect(cmd.run()).rejects.toThrow(/Invalid token|API error/);
+    await expect(cmd.run()).rejects.toThrow(/Invalid or expired token/);
   });
 
   it('shared-line user with multiple phones auto-picks first (no prompt)', async () => {
-    mockFetch
-      .mockResolvedValueOnce(jsonResponse(200, {
-        phone_numbers: [
-          { id: 'pn-1', phone_number: '+18005551111' },
-          { id: 'pn-2', phone_number: '+18005552222' },
+    mockFetch.mockResolvedValueOnce(jsonResponse(200, {
+      partnerId: 'partner-1',
+      orgId: '999',
+      name: 'Acme',
+      accountInfo: {
+        tier: 0,
+        phones: [
+          { phoneNumber: '+18005551111', tenantType: 'MULTI' },
+          { phoneNumber: '+18005552222', tenantType: 'MULTI' },
         ],
-      }))
-      .mockResolvedValueOnce(jsonResponse(200, {
-        partnerId: 'partner-1',
-        orgId: '999',
-        name: 'Acme',
-        accountInfo: {
-          tier: 0,
-          phones: [
-            { phoneNumber: '+18005551111', tenantType: 'MULTI' },
-            { phoneNumber: '+18005552222', tenantType: 'MULTI' },
-          ],
-        },
-      }));
+      },
+    }));
 
     const config = await Config.load({ root: process.cwd() });
     const cmd = new Login(['--token', 'linq_test', '--profile', 'default'], config);
@@ -121,25 +109,18 @@ describe('login (token paste)', () => {
   });
 
   it('paid user with multiple phones is prompted', async () => {
-    mockFetch
-      .mockResolvedValueOnce(jsonResponse(200, {
-        phone_numbers: [
-          { id: 'pn-1', phone_number: '+18005551111' },
-          { id: 'pn-2', phone_number: '+18005552222' },
+    mockFetch.mockResolvedValueOnce(jsonResponse(200, {
+      partnerId: 'partner-1',
+      orgId: '999',
+      name: 'Acme',
+      accountInfo: {
+        accountLabel: 'Paid',
+        phones: [
+          { phoneNumber: '+18005551111' },
+          { phoneNumber: '+18005552222' },
         ],
-      }))
-      .mockResolvedValueOnce(jsonResponse(200, {
-        partnerId: 'partner-1',
-        orgId: '999',
-        name: 'Acme',
-        accountInfo: {
-          tier: 1,
-          phones: [
-            { phoneNumber: '+18005551111', tenantType: 'SINGLE' },
-            { phoneNumber: '+18005552222', tenantType: 'SINGLE' },
-          ],
-        },
-      }));
+      },
+    }));
 
     mockSelect.mockResolvedValueOnce('+18005552222');
 
@@ -150,6 +131,6 @@ describe('login (token paste)', () => {
     expect(mockSelect).toHaveBeenCalledTimes(1);
     const saved = JSON.parse(await fs.readFile(configPath(), 'utf-8'));
     expect(saved.profiles.default.fromPhone).toBe('+18005552222');
-    expect(saved.profiles.default.tier).toBe(1);
+    expect(saved.profiles.default.accountLabel).toBe('Paid');
   });
 });
diff --git a/test/commands/signup.test.ts b/test/commands/signup.test.ts
index 7857996..dbc6d43 100644
--- a/test/commands/signup.test.ts
+++ b/test/commands/signup.test.ts
@@ -68,8 +68,8 @@ describe('signup (email OTP flow)', () => {
           email: 'new@example.com',
           name: 'Test User',
           accountInfo: {
-            tier: 0,
-            phones: [{ phoneNumber: '+12025551234', tenantType: 'MULTI' }],
+            accountLabel: 'Shared',
+            phones: [{ phoneNumber: '+12025551234' }],
           },
         })
       );
@@ -89,8 +89,7 @@ describe('signup (email OTP flow)', () => {
     expect(saved.profiles.default.token).toBe('api-token-xyz');
     expect(saved.profiles.default.email).toBe('new@example.com');
     expect(saved.profiles.default.fromPhone).toBe('+12025551234');
-    expect(saved.profiles.default.tier).toBe(0);
-    expect(saved.profiles.default.tenantType).toBe('MULTI');
+    expect(saved.profiles.default.accountLabel).toBe('Shared');
   });
 
   it('refuses to run if already logged in', async () => {