diff --git a/apps/sim/app/api/files/view/[id]/route.ts b/apps/sim/app/api/files/view/[id]/route.ts
index 681d00f4430..e9d68b86821 100644
--- a/apps/sim/app/api/files/view/[id]/route.ts
+++ b/apps/sim/app/api/files/view/[id]/route.ts
@@ -5,7 +5,7 @@ import { fileViewContract } from '@/lib/api/contracts/storage-transfer'
 import { parseRequest } from '@/lib/api/server'
 import { checkSessionOrInternalAuth } from '@/lib/auth/hybrid'
 import { withRouteHandler } from '@/lib/core/utils/with-route-handler'
-import { USE_BLOB_STORAGE } from '@/lib/uploads/config'
+import { type StorageContext, USE_BLOB_STORAGE } from '@/lib/uploads/config'
 import { getFileMetadataById } from '@/lib/uploads/server/metadata'
 import { verifyFileAccess } from '@/app/api/files/authorization'
 
@@ -29,16 +29,44 @@ export const GET = withRouteHandler(
       return NextResponse.json({ error: 'Not found' }, { status: 404 })
     }
 
-    const hasAccess = await verifyFileAccess(record.key, authResult.userId)
+    // Authorize before disclosing anything about the file. Pass the record's own context so access is
+    // resolved from the DB row (workspace and mothership both map to workspace membership) rather than
+    // re-inferred from the key, and deny with 404 so a caller without access cannot distinguish a
+    // file's existence or context from a missing id.
+    const hasAccess = await verifyFileAccess(
+      record.key,
+      authResult.userId,
+      undefined,
+      record.context as StorageContext | 'general'
+    )
     if (!hasAccess) {
       logger.warn('Unauthorized file view attempt', { id, userId: authResult.userId })
-      return NextResponse.json({ error: 'Forbidden' }, { status: 403 })
+      return NextResponse.json({ error: 'Not found' }, { status: 404 })
+    }
+
+    // Only workspace-scoped files are embeddable/viewable here. Other contexts (e.g. chat-scoped
+    // `mothership` uploads) are not durable workspace artifacts; now that the caller is known to have
+    // access, reject with a legible 422 so the embed fails cleanly and the file agent can self-correct.
+    if (record.context !== 'workspace') {
+      logger.warn('Rejected non-workspace file view', { id, context: record.context })
+      return NextResponse.json(
+        {
+          error: `File ${id} has context "${record.context}" and is not embeddable. Only workspace files can be viewed via /api/files/view. Save it into the workspace and reference the workspace copy.`,
+        },
+        { status: 422 }
+      )
     }
 
     const storagePrefix = USE_BLOB_STORAGE ? 'blob' : 's3'
     const servePath = `/api/files/serve/${storagePrefix}/${encodeURIComponent(record.key)}`
     logger.info('Redirecting file view to serve path', { id, servePath })
 
-    return NextResponse.redirect(new URL(servePath, request.url), { status: 302 })
+    // Emit a relative Location so the browser resolves it against the public origin it requested.
+    // `NextResponse.redirect(new URL(servePath, request.url))` bakes in the host from `request.url`,
+    // which behind the load balancer is the internal pod host (e.g. ip-10-0-x.ec2.internal:3000) —
+    // unreachable from the browser, so embedded <img src="/api/files/view/<id>"> loads fail. A
+    // relative Location resolves against the original public URL (matching how the Files tab fetches
+    // serve URLs directly).
+    return new NextResponse(null, { status: 302, headers: { Location: servePath } })
   }
 )
diff --git a/apps/sim/lib/copilot/tools/server/files/edit-content.ts b/apps/sim/lib/copilot/tools/server/files/edit-content.ts
index a84cea989d4..ffc12f6721e 100644
--- a/apps/sim/lib/copilot/tools/server/files/edit-content.ts
+++ b/apps/sim/lib/copilot/tools/server/files/edit-content.ts
@@ -8,6 +8,7 @@ import {
 import { isE2BDocEnabled } from '@/lib/core/config/env-flags'
 import { updateWorkspaceFileContent } from '@/lib/uploads/contexts/workspace/workspace-file-manager'
 import { getE2BDocFormat } from './doc-compile'
+import { buildEmbeddedImageRefWarning } from './embedded-image-refs'
 import { consumeLatestFileIntent } from './file-intent-store'
 import { compileDocForWrite, getDocumentFormatInfo, inferContentType } from './workspace-file'
 
@@ -250,9 +251,13 @@ export const editContentServerTool: BaseServerTool<EditContentArgs, EditContentR
         userId: context.userId,
       })
 
+      // Flag any `/api/files/view/<id>` embeds the model just authored that won't render/export
+      // (non-workspace or missing), so it can self-correct on the next step.
+      const embedWarning = await buildEmbeddedImageRefWarning(content, workspaceId)
+
       return {
         success: true,
-        message: `File "${fileRecord.name}" ${verb} successfully (${fileBuffer.length} bytes)`,
+        message: `File "${fileRecord.name}" ${verb} successfully (${fileBuffer.length} bytes)${embedWarning}`,
         data: {
           id: intent.fileId,
           name: fileRecord.name,
diff --git a/apps/sim/lib/copilot/tools/server/files/embedded-image-refs.ts b/apps/sim/lib/copilot/tools/server/files/embedded-image-refs.ts
new file mode 100644
index 00000000000..fb7a0eb5967
--- /dev/null
+++ b/apps/sim/lib/copilot/tools/server/files/embedded-image-refs.ts
@@ -0,0 +1,51 @@
+import { getFileMetadataById } from '@/lib/uploads/server/metadata'
+
+/** The canonical embed form the file agent writes for workspace images: `/api/files/view/<fileId>`. */
+const VIEW_EMBED_RE = /\/api\/files\/view\/([A-Za-z0-9_-]+)/g
+
+/**
+ * Returns the ids of `/api/files/view/<id>` image embeds in `content` that will not render or survive a
+ * workspace export. An embed is valid only when its id resolves to a workspace file in this same
+ * workspace — the only thing the view route serves and an export can bundle. Every other case (missing,
+ * archived, a different workspace, or a non-`workspace` upload such as a chat-scoped `mothership` file)
+ * is flagged by id alone, without disclosing the referenced file's real context or owning workspace, so
+ * the result can't be used to probe files outside this workspace. Best-effort and never throws, so a
+ * content write is never blocked by this validation.
+ */
+export async function findUnembeddableImageRefs(
+  content: string,
+  workspaceId: string
+): Promise<string[]> {
+  const ids = new Set<string>()
+  for (const match of content.matchAll(VIEW_EMBED_RE)) ids.add(match[1])
+  if (ids.size === 0) return []
+
+  const checked = await Promise.all(
+    [...ids].map(async (id): Promise<string | null> => {
+      try {
+        const record = await getFileMetadataById(id)
+        const embeddable = record?.context === 'workspace' && record.workspaceId === workspaceId
+        return embeddable ? null : id
+      } catch {
+        return null
+      }
+    })
+  )
+
+  return checked.filter((id): id is string => id !== null)
+}
+
+/**
+ * Builds an actionable suffix appended to a successful file-write tool result so the model can
+ * self-correct: only workspace files in this workspace embed, so any other reference must be re-saved
+ * into the workspace and re-referenced by the workspace file's id. Empty when there is nothing to flag.
+ */
+export async function buildEmbeddedImageRefWarning(
+  content: string,
+  workspaceId: string
+): Promise<string> {
+  const ids = await findUnembeddableImageRefs(content, workspaceId)
+  if (ids.length === 0) return ''
+  const list = ids.map((id) => `/api/files/view/${id}`).join('; ')
+  return ` Warning: embedded image(s) will not render or export because they are not workspace files in this workspace — ${list}. Save each image as a workspace file (under files/) and reference it via /api/files/view/<workspace-file-id>.`
+}
diff --git a/apps/sim/lib/copilot/tools/server/files/workspace-file.ts b/apps/sim/lib/copilot/tools/server/files/workspace-file.ts
index a490441d4cc..7ed7fb69dd2 100644
--- a/apps/sim/lib/copilot/tools/server/files/workspace-file.ts
+++ b/apps/sim/lib/copilot/tools/server/files/workspace-file.ts
@@ -34,6 +34,7 @@ import {
   getE2BDocFormat,
   PPTXGENJS_SOURCE_MIME,
 } from './doc-compile'
+import { buildEmbeddedImageRefWarning } from './embedded-image-refs'
 import { storeFileIntent } from './file-intent-store'
 
 const logger = createLogger('WorkspaceFileServerTool')
@@ -398,9 +399,11 @@ export const workspaceFileServerTool: BaseServerTool<WorkspaceFileArgs, Workspac
             userId: context.userId,
           })
 
+          const embedWarning = await buildEmbeddedImageRefWarning(content, workspaceId)
+
           return {
             success: true,
-            message: `File "${fileName}" created successfully (${fileBuffer.length} bytes)`,
+            message: `File "${fileName}" created successfully (${fileBuffer.length} bytes)${embedWarning}`,
             data: {
               id: result.id,
               name: result.name,