diff --git a/apps/cloud/src/auth/context.ts b/apps/cloud/src/auth/context.ts
index e76272592..bfd3ea25c 100644
--- a/apps/cloud/src/auth/context.ts
+++ b/apps/cloud/src/auth/context.ts
@@ -27,3 +27,16 @@ export class UserStoreService extends Context.Service<UserStoreService, UserStor
     Effect.map(DbService.asEffect(), ({ db }) => makeService(makeUserStore(db))),
   );
 }
+
+/**
+ * A FRESH `UserStoreService` layer (new layer value per call). `UserStoreService.Live`
+ * captures its `db` at build time; when a long-lived runtime's shared memo map
+ * memoizes that const layer once, it pins the first request's postgres socket and
+ * reuses it on later requests — illegal under Cloudflare's per-request I/O. Build
+ * this (over a fresh `DbService` layer) anywhere a service is constructed once but
+ * invoked across many requests (the MCP org-authorization seam). See [[makeDbLayer]].
+ */
+export const makeUserStoreLayer = (): Layer.Layer<UserStoreService, never, DbService> =>
+  Layer.effect(UserStoreService)(
+    Effect.map(DbService.asEffect(), ({ db }) => makeService(makeUserStore(db))),
+  );
diff --git a/apps/cloud/src/db/db.ts b/apps/cloud/src/db/db.ts
index 5610e4b2d..219beaf38 100644
--- a/apps/cloud/src/db/db.ts
+++ b/apps/cloud/src/db/db.ts
@@ -93,3 +93,18 @@ export class DbService extends Context.Service<DbService, DbServiceShape>()(
     Effect.acquireRelease(Effect.sync(makePostgresResource), (resource) => resource.close()),
   );
 }
+
+/**
+ * A FRESH `DbService` layer (a new layer value on every call). Provide this
+ * — rather than the shared `DbService.Live` — anywhere a service is built ONCE
+ * by the facade but invoked across many Workers requests (e.g. the MCP
+ * org-authorization seam). A single shared `DbService.Live` opens its postgres
+ * socket on the first request and reuses it on later ones, which Cloudflare
+ * forbids ("Cannot perform I/O on behalf of a different request"). A distinct
+ * layer value per call gets its own request-scoped socket, acquired and
+ * released within that request.
+ */
+export const makeDbLayer = (): Layer.Layer<DbService> =>
+  Layer.effect(DbService)(
+    Effect.acquireRelease(Effect.sync(makePostgresResource), (resource) => resource.close()),
+  );
diff --git a/apps/cloud/src/mcp/auth.ts b/apps/cloud/src/mcp/auth.ts
index 79a6e7d33..c6efb0eb4 100644
--- a/apps/cloud/src/mcp/auth.ts
+++ b/apps/cloud/src/mcp/auth.ts
@@ -16,9 +16,9 @@ import { createCachedRemoteJWKSet } from "../auth/jwks-cache";
 import { ApiKeyService } from "../auth/api-keys";
 import { BEARER_PREFIX } from "../auth/bearer";
 import { authorizeOrganization } from "../auth/organization";
-import { UserStoreService } from "../auth/context";
+import { makeUserStoreLayer } from "../auth/context";
 import { CoreSharedServices } from "../auth/workos";
-import { DbService } from "../db/db";
+import { makeDbLayer } from "../db/db";
 import { bearerChallenge } from "./responses";
 import { McpJwtVerificationError, verifyWorkOSMcpAccessToken, type VerifiedToken } from "./jwt";
 
@@ -150,15 +150,25 @@ const verifyJwt = (token: string) =>
     audience: WORKOS_CLIENT_ID,
   });
 
-const DbLive = DbService.Live;
-const UserStoreLive = UserStoreService.Live.pipe(Layer.provide(DbLive));
-const McpOrganizationAuthServices = Layer.mergeAll(DbLive, UserStoreLive, CoreSharedServices);
+// Built FRESH per `authorize` call. `McpOrganizationAuthLive` is constructed
+// once by the facade but `authorize` runs on every MCP request; a shared
+// `DbService.Live` would open its postgres socket on the first request and
+// illegally reuse it on later ones ("Cannot perform I/O on behalf of a
+// different request"), failing the org lookup on every follow-up — the
+// "connected · tools fetch failed" symptom. A fresh DB + UserStore layer per
+// call gives each request its own request-scoped socket. `CoreSharedServices`
+// (WorkOS, no per-request socket) stays shared.
+const makeMcpOrganizationAuthServices = () => {
+  const dbLive = makeDbLayer();
+  const userStoreLive = makeUserStoreLayer().pipe(Layer.provide(dbLive));
+  return Layer.mergeAll(dbLive, userStoreLive, CoreSharedServices);
+};
 
 export const McpOrganizationAuthLive = Layer.succeed(McpOrganizationAuth)({
   authorize: (accountId, organizationId) =>
     authorizeOrganization(accountId, organizationId).pipe(
       Effect.map((org) => org !== null),
-      Effect.provide(McpOrganizationAuthServices),
+      Effect.provide(makeMcpOrganizationAuthServices()),
     ),
 });