Expose trusted cloud import errors

server/src/__tests__/error-handler.test.ts

@@ -37,6 +37,31 @@ describe("errorHandler", () => {
     expect(res.__errorContext?.error?.message).toBe("boom");
   });
 
+  it("exposes raw 500 messages for trusted Cloud tenant imports", () => {
+    const req = {
+      ...makeReq(),
+      method: "POST",
+      originalUrl: "/api/companies/import",
+      actor: {
+        type: "board",
+        userId: "cloud-user",
+        source: "cloud_tenant",
+      },
+    } as unknown as Request;
+    const res = makeRes() as any;
+    const next = vi.fn() as unknown as NextFunction;
+    const err = new Error("portable file references missing upload id");
+
+    errorHandler(err, req, res, next);
+
+    expect(res.status).toHaveBeenCalledWith(500);
+    expect(res.json).toHaveBeenCalledWith({
+      error: "Internal server error",
+      message: "portable file references missing upload id",
+    });
+    expect(res.err).toBe(err);
+  });
+
   it("attaches HttpError instances for 500 responses", () => {
     const req = makeReq();
     const res = makeRes() as any;

server/src/middleware/error-handler.ts

@@ -74,5 +74,14 @@ export function errorHandler(
   const tc = getTelemetryClient();
   if (tc) trackErrorHandlerCrash(tc, { errorCode: rootError.name });
 
-  res.status(500).json({ error: "Internal server error" });
+  res.status(500).json({
+    error: "Internal server error",
+    ...(shouldExposeTrustedCloudTenantImportError(req) ? { message: rootError.message } : {}),
+  });
+}
+
+function shouldExposeTrustedCloudTenantImportError(req: Request) {
+  return req.actor?.source === "cloud_tenant"
+    && req.method === "POST"
+    && req.originalUrl.split("?")[0] === "/api/companies/import";
 }