diff --git a/server/src/__tests__/issues-goal-context-routes.test.ts b/server/src/__tests__/issues-goal-context-routes.test.ts
index 25ce2042..db2bdbc4 100644
--- a/server/src/__tests__/issues-goal-context-routes.test.ts
+++ b/server/src/__tests__/issues-goal-context-routes.test.ts
@@ -10,6 +10,7 @@ const mockIssueService = vi.hoisted(() => ({
   findMentionedProjectIds: vi.fn(),
   getCommentCursor: vi.fn(),
   getComment: vi.fn(),
+  listAttachments: vi.fn(),
 }));
 
 const mockProjectService = vi.hoisted(() => ({
@@ -129,6 +130,7 @@ describe("issue goal context routes", () => {
       latestCommentAt: null,
     });
     mockIssueService.getComment.mockResolvedValue(null);
+    mockIssueService.listAttachments.mockResolvedValue([]);
     mockProjectService.getById.mockResolvedValue({
       id: legacyProjectLinkedIssue.projectId,
       companyId: "company-1",
@@ -197,5 +199,6 @@ describe("issue goal context routes", () => {
       }),
     );
     expect(mockGoalService.getDefaultCompanyGoal).not.toHaveBeenCalled();
+    expect(res.body.attachments).toEqual([]);
   });
 });
diff --git a/server/src/routes/issues.ts b/server/src/routes/issues.ts
index 2898feae..0c334ee7 100644
--- a/server/src/routes/issues.ts
+++ b/server/src/routes/issues.ts
@@ -482,11 +482,12 @@ export function issueRoutes(
         ? req.query.wakeCommentId.trim()
         : null;
 
-    const [{ project, goal }, ancestors, commentCursor, wakeComment] = await Promise.all([
+    const [{ project, goal }, ancestors, commentCursor, wakeComment, attachments] = await Promise.all([
       resolveIssueProjectAndGoal(issue),
       svc.getAncestors(issue.id),
       svc.getCommentCursor(issue.id),
       wakeCommentId ? svc.getComment(wakeCommentId) : null,
+      svc.listAttachments(issue.id),
     ]);
 
     res.json({
@@ -533,6 +534,14 @@ export function issueRoutes(
         wakeComment && wakeComment.issueId === issue.id
           ? wakeComment
           : null,
+      attachments: attachments.map((a) => ({
+        id: a.id,
+        filename: a.originalFilename,
+        contentType: a.contentType,
+        byteSize: a.byteSize,
+        contentPath: withContentPath(a).contentPath,
+        createdAt: a.createdAt,
+      })),
     });
   });