diff --git a/COMMAND_STREAM_ISSUE.md b/COMMAND_STREAM_ISSUE.md
new file mode 100644
index 0000000..a574fea
--- /dev/null
+++ b/COMMAND_STREAM_ISSUE.md
@@ -0,0 +1,63 @@
+# Command-Stream JSON Quoting Issue Tracking
+
+## Issue Summary
+The `claude-profiles.mjs` script cannot use command-stream for macOS keychain storage commands due to automatic quote wrapping that corrupts JSON data.
+
+## Affected Code Location
+- **File**: `claude-profiles.mjs`
+- **Line**: 387-391 (commented out code)
+- **Function**: `setKeychainCredentials()`
+
+## Problem Description
+Command-stream's `$` template function automatically wraps interpolated values in single quotes, which corrupts JSON strings:
+
+```javascript
+// ❌ Current issue (line 387-391 in claude-profiles.mjs)
+const result = await $`security add-generic-password -U -a $USER -s "Claude Code-credentials" -w "${escapedJson}"`;
+// Results in: '{"claudeAiOauth":{...}}'  ← Invalid JSON with wrapping quotes
+// Expected:   {"claudeAiOauth":{...}}   ← Valid JSON
+```
+
+## Current Workaround
+Using Node.js `execSync` instead (lines 372-376):
+```javascript
+const command = `security add-generic-password -U -a $USER -s "Claude Code-credentials" -w "${escapedJson}"`;
+execSync(command, { shell: true, stdio: isVerbose ? 'inherit' : 'ignore' });
+```
+
+## Upstream Issue Tracking
+- **Repository**: https://github.com/link-foundation/command-stream
+- **Issue #39**: JSON strings with quotes cause escaping issues
+- **Issue #45**: Automatic quote addition in interpolation causes issues
+- **Status**: OPEN (as of 2025-09-10)
+- **Our Comment**: https://github.com/link-foundation/command-stream/issues/39#issuecomment-3275976359
+
+## Monitoring for Fix
+To check if the issue has been resolved:
+
+1. **Check issue status**: Visit issue #39 and #45 on the command-stream repository
+2. **Test with reproduction script**: Run `examples/command-stream-json-issue-reproduction.mjs`
+3. **Check for new releases**: Monitor https://www.npmjs.com/package/command-stream for versions > 0.7.0
+
+## How to Update When Fixed
+When the issue is resolved:
+
+1. Uncomment the command-stream code (lines 387-391)
+2. Remove or comment the execSync workaround (lines 372-376) 
+3. Test with various JSON payloads to ensure reliability
+4. Update the version constraint in the use() call if needed
+
+## Testing the Fix
+Use the reproduction script to verify the fix:
+```bash
+node examples/command-stream-json-issue-reproduction.mjs
+```
+
+Expected output after fix:
+- JSON should not be wrapped in extra single quotes
+- Command output should show valid JSON format
+- No escaping issues with nested quotes
+
+## Related Files
+- `claude-profiles.mjs` - Main script with the affected code
+- `examples/command-stream-json-issue-reproduction.mjs` - Test reproduction script
\ No newline at end of file
diff --git a/claude-profiles.mjs b/claude-profiles.mjs
index de3d92a..b1bd31b 100755
--- a/claude-profiles.mjs
+++ b/claude-profiles.mjs
@@ -384,6 +384,10 @@ async function setKeychainCredentials(credentials) {
        * 
        * This makes the JSON invalid and Claude Code cannot parse it.
        * 
+       * ISSUE REPORTED: https://github.com/link-foundation/command-stream/issues/39
+       * MONITORING: Run `node examples/check-command-stream-fix.mjs` to check for fix
+       * DOCUMENTATION: See COMMAND_STREAM_ISSUE.md for full details
+       * 
        * const result = await $`security add-generic-password -U -a $USER -s "Claude Code-credentials" -w "${escapedJson}"`.run({
        *   capture: true,
        *   mirror: false
diff --git a/examples/check-command-stream-fix.mjs b/examples/check-command-stream-fix.mjs
new file mode 100644
index 0000000..446868b
--- /dev/null
+++ b/examples/check-command-stream-fix.mjs
@@ -0,0 +1,82 @@
+#!/usr/bin/env node
+// Script to check if command-stream JSON quoting issue has been fixed
+// Run this periodically to monitor for fix availability
+
+import { execSync } from 'child_process';
+
+console.log('🔍 Checking command-stream JSON quoting issue status...\n');
+
+// Check if we can load command-stream
+let commandStreamVersion;
+try {
+  const { use } = eval(
+    await fetch('https://unpkg.com/use-m/use.js').then(r => r.text())
+  );
+  const [{ $ }] = await Promise.all([
+    use('command-stream@latest') // Use latest to check for fixes
+  ]);
+  
+  // Try to get version info
+  try {
+    const versionInfo = execSync('npm view command-stream version', { 
+      encoding: 'utf8', 
+      stdio: 'pipe' 
+    }).trim();
+    commandStreamVersion = versionInfo;
+    console.log(`📦 Command-stream version: ${commandStreamVersion}`);
+  } catch (e) {
+    console.log('📦 Command-stream loaded (version unknown)');
+  }
+
+  // Test the JSON quoting issue
+  const testJson = '{"test": "value with \\"quotes\\""}';
+  const result = await $`echo "JSON: ${testJson}"`.run({
+    capture: true,
+    mirror: false
+  });
+  
+  const output = result.stdout.trim();
+  const extractedJson = output.replace('JSON: ', '');
+  
+  console.log('\n🧪 Test Results:');
+  console.log('Input JSON :', testJson);
+  console.log('Output     :', extractedJson);
+  
+  // Check if JSON is properly handled (not wrapped in extra quotes)
+  let isFixed = false;
+  try {
+    // If it's properly handled, we should be able to parse it
+    const parsed = JSON.parse(extractedJson);
+    if (parsed && typeof parsed === 'object') {
+      isFixed = true;
+      console.log('✅ FIXED: JSON is properly handled without extra quoting!');
+      console.log('🎉 You can now update claude-profiles.mjs to use command-stream');
+    }
+  } catch (parseError) {
+    console.log('❌ NOT FIXED: JSON is still corrupted by extra quoting');
+    console.log('   Expected:', testJson);  
+    console.log('   Got     :', extractedJson);
+  }
+  
+  // Additional checks
+  console.log('\n📊 Status:');
+  if (isFixed) {
+    console.log('🟢 Issue Status: RESOLVED');
+    console.log('🔧 Action Needed: Update claude-profiles.mjs to use command-stream');
+    console.log('📝 Update Instructions: See COMMAND_STREAM_ISSUE.md');
+  } else {
+    console.log('🔴 Issue Status: NOT YET RESOLVED');
+    console.log('⏳ Action Needed: Continue monitoring for fix');
+    console.log('🔗 Track: https://github.com/link-foundation/command-stream/issues/39');
+  }
+  
+} catch (error) {
+  console.error('❌ Error testing command-stream:', error.message);
+  console.log('\n💡 This might indicate:');
+  console.log('   - Network connectivity issues');
+  console.log('   - Command-stream package issues');
+  console.log('   - Breaking changes in the library');
+}
+
+console.log('\n📅 Last checked:', new Date().toISOString());
+console.log('🔄 Run this script periodically to monitor for fixes');
\ No newline at end of file
diff --git a/examples/command-stream-json-issue-reproduction.mjs b/examples/command-stream-json-issue-reproduction.mjs
new file mode 100644
index 0000000..1fb80b5
--- /dev/null
+++ b/examples/command-stream-json-issue-reproduction.mjs
@@ -0,0 +1,57 @@
+#!/usr/bin/env node
+// Minimal reproduction of command-stream JSON quoting issue affecting claude-profiles.mjs
+
+// This is the same import used in claude-profiles.mjs
+const { use } = eval(
+  await fetch('https://unpkg.com/use-m/use.js').then(r => r.text())
+);
+const [{ $ }] = await Promise.all([
+  use('command-stream@0.7.0')
+]);
+
+// Sample credentials data similar to what claude-profiles.mjs handles
+const credentials = {
+  claudeAiOauth: {
+    accessToken: "sample_access_token_123",
+    refreshToken: "sample_refresh_token_456",
+    name: "Test User",
+    description: "User with \"quotes\" and 'apostrophes'"
+  }
+};
+
+console.log('Testing command-stream JSON interpolation issue...\n');
+
+const jsonStr = JSON.stringify(credentials);
+const escapedJson = jsonStr.replace(/"/g, '\\"'); // Escape quotes like in claude-profiles.mjs
+
+console.log('Original JSON:', jsonStr);
+console.log('Escaped JSON:', escapedJson);
+
+try {
+  // This is the exact command that fails in claude-profiles.mjs line 387
+  console.log('\nTesting command-stream $ interpolation:');
+  const result = await $`echo "JSON would be: ${escapedJson}"`.run({
+    capture: true,
+    mirror: false
+  });
+  
+  console.log('Command output:', result.stdout);
+  console.log('Expected: JSON with proper double quotes');
+  console.log('Actual: JSON wrapped in single quotes (invalid for parsing)');
+  
+  // Show the difference
+  console.log('\nActual behavior:');
+  console.log('command-stream wraps the entire JSON in single quotes:');
+  console.log("'", result.stdout.trim().replace('JSON would be: ', ''), "'");
+  
+  console.log('\nExpected behavior:');  
+  console.log('JSON should remain as valid JSON without extra quoting:');
+  console.log(jsonStr);
+  
+} catch (error) {
+  console.error('Command failed:', error.message);
+}
+
+console.log('\nThis issue prevents claude-profiles.mjs from using command-stream');
+console.log('for the keychain storage command at line 387.');
+console.log('The workaround is using Node.js execSync instead.');
\ No newline at end of file