From e6598d304135f6e2b42873921249e7b6c7c631c2 Mon Sep 17 00:00:00 2001
From: Siddharth Ganesan <siddharthganesan@gmail.com>
Date: Thu, 6 Aug 2026 17:29:45 -0700
Subject: [PATCH] fix(mship): fix image handling

---
 apps/sim/lib/copilot/chat/payload.test.ts | 51 +++++++++++++++++------
 apps/sim/lib/copilot/chat/payload.ts      | 12 ++++--
 bun.lock                                  |  1 -
 3 files changed, 47 insertions(+), 17 deletions(-)

diff --git a/apps/sim/lib/copilot/chat/payload.test.ts b/apps/sim/lib/copilot/chat/payload.test.ts
index 92e77ffb63a..2f061cf8592 100644
--- a/apps/sim/lib/copilot/chat/payload.test.ts
+++ b/apps/sim/lib/copilot/chat/payload.test.ts
@@ -374,19 +374,46 @@ describe('buildCopilotRequestPayload', () => {
       ])
     })
 
-    it('fails the request when an authorized attachment cannot be prepared', async () => {
+    it('isolates a failed attachment and still prepares valid siblings', async () => {
       const cause = new Error('provenance sidecar unavailable')
-      mockTrackChatUpload.mockRejectedValueOnce(cause)
-
-      await expect(
-        buildCopilotRequestPayload(
-          { ...attachmentParams, userPermission: 'write' },
-          { selectedModel: 'claude-opus-4-8' }
-        )
-      ).rejects.toMatchObject({
-        message: 'Failed to prepare attached file "payroll.xlsx" for Copilot. Please try again.',
-        cause,
-      })
+      mockTrackChatUpload
+        .mockRejectedValueOnce(cause)
+        .mockResolvedValueOnce({ displayName: 'photo.png' })
+
+      const payload = await buildCopilotRequestPayload(
+        {
+          ...attachmentParams,
+          userPermission: 'write',
+          fileAttachments: [
+            ...attachmentParams.fileAttachments,
+            {
+              id: 'a2',
+              key: 'workspace/ws-1/1731000000001-ab12cd35-photo.png',
+              filename: 'photo.png',
+              media_type: 'image/png',
+              size: 10,
+            },
+          ],
+        },
+        { selectedModel: 'claude-opus-4-8' }
+      )
+
+      expect(mockTrackChatUpload).toHaveBeenCalledTimes(2)
+      expect(payload.context).toEqual([
+        {
+          type: 'uploaded_file',
+          content:
+            'File "payroll.xlsx" could not be prepared for Copilot and was omitted. Other attached files remain available.',
+        },
+        {
+          type: 'uploaded_file',
+          content: [
+            'File "photo.png" (image/png, 10 bytes) uploaded.',
+            'Read with: read("uploads/photo.png")',
+            'To save permanently: materialize_file(fileName: "photo.png")',
+          ].join('\n'),
+        },
+      ])
     })
   })
 
diff --git a/apps/sim/lib/copilot/chat/payload.ts b/apps/sim/lib/copilot/chat/payload.ts
index 7c9988ddac4..ef1ea48d159 100644
--- a/apps/sim/lib/copilot/chat/payload.ts
+++ b/apps/sim/lib/copilot/chat/payload.ts
@@ -401,10 +401,14 @@ export async function buildCopilotRequestPayload(
           chatId,
           error: cause.message,
         })
-        throw new Error(
-          `Failed to prepare attached file "${filename}" for Copilot. Please try again.`,
-          { cause }
-        )
+        // Isolate failures by entry. Aborting here discarded every valid
+        // sibling attachment in the request, even ones already tracked. Give
+        // the model a local marker for this file and continue preparing the
+        // rest of the batch.
+        uploadContexts.push({
+          type: 'uploaded_file',
+          content: `File "${filename}" could not be prepared for Copilot and was omitted. Other attached files remain available.`,
+        })
       }
     }
   }
diff --git a/bun.lock b/bun.lock
index 0132ebcfa12..f3070e48480 100644
--- a/bun.lock
+++ b/bun.lock
@@ -1,6 +1,5 @@
 {
   "lockfileVersion": 1,
-  "configVersion": 0,
   "workspaces": {
     "": {
       "name": "simstudio",