diff --git a/server/src/__tests__/connection-management.integration.test.ts b/server/src/__tests__/connection-management.integration.test.ts
index cd08b7b7daa..0af35c18f6d 100644
--- a/server/src/__tests__/connection-management.integration.test.ts
+++ b/server/src/__tests__/connection-management.integration.test.ts
@@ -650,7 +650,8 @@ describe("connection management with production default agents", () => {
       const [beforeRotation] = await server.db.select().from(toolConnections).where(eq(toolConnections.id, created.body.connectionId));
       for (const token of [f.key.token, f.jwt]) {
         const rotation = await f.request("POST", `/chat-endpoints/${created.body.id}/setup-secret`, {}, token);
-        expect(rotation, JSON.stringify(rotation)).toMatchObject({ status: 200, body: { status: "needs_user_action", endpointId: created.body.id } });
+        expect(rotation, JSON.stringify(rotation)).toMatchObject({ status: 200, body: { status: "needs_user_action", endpointId: created.body.id,
+          requiredUserAction: { kind: "enter_credentials", userId: f.userId } } });
         expect(rotation.body).not.toHaveProperty("webhookSecret");
       }
       const [afterRotation] = await server.db.select().from(toolConnections).where(eq(toolConnections.id, created.body.connectionId));
diff --git a/server/src/__tests__/openapi-routes.test.ts b/server/src/__tests__/openapi-routes.test.ts
index b67d31593ca..0023aa7642b 100644
--- a/server/src/__tests__/openapi-routes.test.ts
+++ b/server/src/__tests__/openapi-routes.test.ts
@@ -788,6 +788,10 @@ describe("openapi routes", () => {
 
     const setupSecret =
       spec.paths["/api/chat-endpoints/{endpointId}/setup-secret"].post;
+    const secretHandoff = setupSecret.responses["200"].content["application/json"].schema;
+    expect(secretHandoff.properties.requiredUserAction.properties.kind.enum).toEqual(["enter_credentials"]);
+    expect(secretHandoff.properties).not.toHaveProperty("webhookSecret");
+    expect(setupSecret.description).toContain("without rotating or reading");
     expect(
       setupSecret.responses["201"].content["application/json"].schema,
     ).toMatchObject({
diff --git a/server/src/routes/chat-channels.ts b/server/src/routes/chat-channels.ts
index 2eec96346c0..be396452f1c 100644
--- a/server/src/routes/chat-channels.ts
+++ b/server/src/routes/chat-channels.ts
@@ -30,6 +30,7 @@ import {
   resolveChatPublicationSchema,
   updateChatEndpointSchema,
   type ChatProvider,
+  type ConnectionRequiredUserAction,
 } from "@paperclipai/shared";
 import { validate } from "../middleware/validate.js";
 import {
@@ -103,7 +104,7 @@ export function chatChannelRoutes(db: Db, options: ChatChannelRouteOptions) {
   const access = accessService(db);
   const github = githubChatManagementService(db, options.fetch);
 
-  async function setupHandoff(req: ExpressRequest, reason: string) {
+  async function setupHandoff(req: ExpressRequest, reason: string, kind: ConnectionRequiredUserAction["kind"] = "authenticate") {
     const endpoint = await service.get(endpointId(req));
     const [company] = await db.select({ prefix: companies.issuePrefix }).from(companies).where(eq(companies.id, endpoint.companyId));
     const interactionId = req.actor.type === "agent" && req.actor.runId && endpoint.assignedAgentId === req.actor.agentId
@@ -112,7 +113,7 @@ export function chatChannelRoutes(db: Db, options: ChatChannelRouteOptions) {
       : null;
     return { status: "needs_user_action", interactionId, endpointId: endpoint.id, connectionId: endpoint.connectionId,
       ...requiredConnectionUserAction(req, { type: "chat_endpoint", id: endpoint.id, companyId: endpoint.companyId },
-        `/${encodeURIComponent(company!.prefix)}/apps/chat/connect?${new URLSearchParams({ provider: endpoint.provider, resume: endpoint.id })}`, reason),
+        `/${encodeURIComponent(company!.prefix)}/apps/chat/connect?${new URLSearchParams({ provider: endpoint.provider, resume: endpoint.id })}`, reason, kind),
     };
   }
 
@@ -430,7 +431,7 @@ export function chatChannelRoutes(db: Db, options: ChatChannelRouteOptions) {
     if (!(await assertEndpointManagementAccess(req, res))) return;
     res.set("Cache-Control", "no-store");
     if (req.actor.type === "agent") {
-      res.json(await setupHandoff(req, "The responsible user must rotate and enter the webhook signing secret in GitHub."));
+      res.json(await setupHandoff(req, "The responsible user must rotate and enter the webhook signing secret in GitHub.", "enter_credentials"));
       return;
     }
     res
diff --git a/server/src/routes/openapi.ts b/server/src/routes/openapi.ts
index 08b081dfc6b..3abede41608 100644
--- a/server/src/routes/openapi.ts
+++ b/server/src/routes/openapi.ts
@@ -2566,9 +2566,23 @@ registry.registerPath({
   tags: ["chat-channels"],
   summary: "Generate a GitHub webhook secret",
   description:
-    "Generates and vaults a new GitHub webhook secret. The plaintext value is returned exactly once for entry in GitHub; normal endpoint reads expose only whether one is configured. Regeneration immediately rotates the server-side value.",
+    "Authorized agents receive a saved human setup handoff without rotating or reading the signing secret. A human session generates and vaults a new secret, returned exactly once for entry in GitHub. Normal endpoint reads expose only whether one is configured. Human regeneration immediately rotates the server-side value.",
   request: { params: z.object({ endpointId: z.string().uuid() }) },
   responses: {
+    200: r.ok(z.object({
+      status: z.literal("needs_user_action"),
+      interactionId: z.string().uuid().nullable(),
+      endpointId: z.string().uuid(),
+      connectionId: z.string().uuid(),
+      requiredUserAction: z.object({
+        kind: z.literal("enter_credentials"),
+        userId: z.string(),
+        resource: z.object({ type: z.literal("chat_endpoint"), id: z.string().uuid(), companyId: z.string().uuid() }),
+        setupPath: z.string(),
+        reason: z.string(),
+        continuation: z.string(),
+      }),
+    })),
     201: r.ok(chatEndpointSetupSecretResponseSchema),
     401: r.unauthorized,
     403: r.forbidden,