diff --git a/e2e/scenarios/toolkits-mcp.test.ts b/e2e/scenarios/toolkits-mcp.test.ts
index bd0b91229a..b84eed1e15 100644
--- a/e2e/scenarios/toolkits-mcp.test.ts
+++ b/e2e/scenarios/toolkits-mcp.test.ts
@@ -584,6 +584,73 @@ scenario(
   }),
 );
 
+scenario(
+  "Toolkits · a broad approve policy applies over a narrower connection grant",
+  { timeout: 240_000 },
+  Effect.gen(function* () {
+    const target = yield* Target;
+    const mcp = yield* Mcp;
+    const { client: makeClient } = yield* Api;
+    const identity = yield* target.newIdentity();
+    const client = yield* makeClient(api, identity);
+
+    const toolkitName = unique("broad-approve-kit");
+    const createdPattern = `${unique("broad-approved-policy")}.*`;
+
+    yield* Effect.gen(function* () {
+      const toolkit = yield* client.toolkits.create({
+        payload: { owner: "org", name: toolkitName },
+      });
+      yield* client.toolkits.createConnection({
+        params: { toolkitId: toolkit.id },
+        payload: { pattern: "executor.coreTools.policies.create" },
+      });
+      yield* client.toolkits.createPolicy({
+        params: { toolkitId: toolkit.id },
+        payload: { pattern: "executor.coreTools.*", action: "approve" },
+      });
+
+      const session = mcp.session(identity, {
+        url: toolkitUrl(target.baseUrl, toolkit.slug),
+      });
+      const result = yield* session.call("execute", {
+        code: createPolicyCode({ pattern: createdPattern, action: "block" }),
+      });
+
+      expect(result.text, "the broad approve policy does not pause execution").not.toContain(
+        "Execution paused",
+      );
+      expect(result.ok, `the approved tool succeeds: ${result.text}`).toBe(true);
+      const policies = yield* client.policies.list();
+      expect(
+        policies.map((policy) => `${policy.owner} ${policy.pattern} ${policy.action}`),
+        "the approved tool reaches its side effect",
+      ).toContain(`user ${createdPattern} block`);
+    }).pipe(
+      Effect.ensuring(
+        Effect.gen(function* () {
+          const listed = yield* client.toolkits.list();
+          yield* Effect.forEach(
+            listed.toolkits.filter((toolkit) => toolkit.name === toolkitName),
+            (toolkit) => client.toolkits.remove({ params: { toolkitId: toolkit.id } }),
+            { discard: true },
+          );
+          const policies = yield* client.policies.list();
+          yield* Effect.forEach(
+            policies.filter((policy) => policy.pattern === createdPattern),
+            (policy) =>
+              client.policies.remove({
+                params: { policyId: policy.id },
+                payload: { owner: policy.owner },
+              }),
+            { discard: true },
+          );
+        }).pipe(Effect.ignore),
+      ),
+    );
+  }),
+);
+
 scenario(
   "Toolkits · the provider catalog hides integrations the toolkit grants no tools",
   { timeout: 240_000 },
diff --git a/packages/plugins/toolkits/src/server.test.ts b/packages/plugins/toolkits/src/server.test.ts
index 53d0d53cbd..bab67eb0e9 100644
--- a/packages/plugins/toolkits/src/server.test.ts
+++ b/packages/plugins/toolkits/src/server.test.ts
@@ -165,4 +165,38 @@ describe("toolkitsPlugin", () => {
       ).toContain("executor.coreTools.* approve");
     }),
   );
+
+  it.effect("applies a broad approve policy over a narrower connection", () =>
+    Effect.gen(function* () {
+      const executor = yield* makeTestExecutor({
+        plugins: [toolkitsPlugin()] as const,
+      });
+
+      const toolkit = yield* executor.toolkits.create({
+        owner: "org",
+        name: "Docs Kit",
+      });
+      yield* executor.toolkits.createConnection(toolkit.id, {
+        pattern: "google_docs.org.main.*",
+      });
+      yield* executor.toolkits.createPolicy(toolkit.id, {
+        pattern: "google_docs.org.*",
+        action: "approve",
+      });
+
+      const result = yield* executor.toolkits.resolvePolicyForSlug(
+        toolkit.slug,
+        "google_docs.org.main.documents.update",
+        true,
+      );
+      expect(result.action).toBe("approve");
+      expect(result.source).toBe("user");
+
+      const rules = yield* executor.toolkits.policyRulesForSlug(toolkit.slug);
+      expect(
+        rules.map((rule) => `${rule.pattern} ${rule.action}`),
+        "policy listing agrees with toolkit enforcement",
+      ).toContain("google_docs.org.* approve");
+    }),
+  );
 });
diff --git a/packages/plugins/toolkits/src/server.ts b/packages/plugins/toolkits/src/server.ts
index 0b70e33575..7dacc3e456 100644
--- a/packages/plugins/toolkits/src/server.ts
+++ b/packages/plugins/toolkits/src/server.ts
@@ -181,11 +181,12 @@ const legacyConnectionPolicyIds = (
   policies: readonly ToolkitPolicyRecord[],
   connections: readonly ToolkitConnectionRecord[],
 ): ReadonlySet<string> => {
-  const connectionPatterns = new Set(connections.map((connection) => connection.pattern));
   return new Set(
     policies
       .filter(
-        (policy) => isLegacyConnectionPolicy(policy) && !connectionPatterns.has(policy.pattern),
+        (policy) =>
+          isLegacyConnectionPolicy(policy) &&
+          !connections.some((connection) => matchPattern(policy.pattern, connection.pattern)),
       )
       .map((policy) => policy.id),
   );