diff --git a/apps/server/src/mcp/toolkits/environment/handlers.test.ts b/apps/server/src/mcp/toolkits/environment/handlers.test.ts
index f2b3dc33e0dd..e0912f7a3340 100644
--- a/apps/server/src/mcp/toolkits/environment/handlers.test.ts
+++ b/apps/server/src/mcp/toolkits/environment/handlers.test.ts
@@ -51,6 +51,8 @@ const layerEnvironment = Layer.mock(Environment.ServerEnvironment)({
 
 it.effect("updates allowed MCP preferences without enabling automatic continuity", () =>
   Effect.gen(function* () {
+    const seedSettings = yield* Settings.ServerSettingsService;
+    yield* seedSettings.updateSettings({ workContinuityAutoEnroll: false });
     const server = yield* McpServer.McpServer;
     const result = yield* server
       .callTool({
diff --git a/apps/server/src/orchestration-v2/ThreadManagementService.ts b/apps/server/src/orchestration-v2/ThreadManagementService.ts
index f8702a7983f9..3ce89996f4ca 100644
--- a/apps/server/src/orchestration-v2/ThreadManagementService.ts
+++ b/apps/server/src/orchestration-v2/ThreadManagementService.ts
@@ -925,6 +925,14 @@ const make = Effect.gen(function* () {
   )(function* (input) {
     const shell = input.byOwnAgent ? yield* orchestrator.getThreadShell(input.threadId) : null;
     if (shell != null && shell.activeRunId !== null) {
+      // A pending own-agent settle is a deliberate end: supervision must not
+      // spend a continuation check on the turn that is about to settle.
+      yield* dispatch({
+        type: "thread.continuity.set",
+        commandId: CommandId.make(`${input.commandId}:continuity-off`),
+        threadId: input.threadId,
+        enabled: false,
+      }).pipe(Effect.ignoreCause({ log: true }));
       yield* settleAfterRun({
         projectId: shell.projectId,
         threadId: shell.id,
diff --git a/apps/server/src/orchestration-v2/runtimeLayer.test.ts b/apps/server/src/orchestration-v2/runtimeLayer.test.ts
index 2be96f8529a7..b4179aa529b9 100644
--- a/apps/server/src/orchestration-v2/runtimeLayer.test.ts
+++ b/apps/server/src/orchestration-v2/runtimeLayer.test.ts
@@ -844,6 +844,8 @@ it.layer(layerTest)("OrchestrationV2LayerLive", (it) => {
 
   it.effect("resolves delivery intent against the active run and starts after it completes", () =>
     Effect.gen(function* () {
+      const settings = yield* ServerSettings.ServerSettingsService;
+      yield* settings.updateSettings({ workContinuityAutoEnroll: false });
       const orchestrator = yield* Orchestrator.OrchestratorV2;
       const eventSink = yield* EventSink.EventSinkV2;
       const outbox = yield* EffectOutbox.EffectOutboxV2;
@@ -3256,6 +3258,8 @@ it.layer(layerTest)("OrchestrationV2LayerLive lifecycle", (it) => {
     "does not admit a restart continuation of a %s run with only lost background work",
     (status) =>
       Effect.gen(function* () {
+        const settings = yield* ServerSettings.ServerSettingsService;
+        yield* settings.updateSettings({ workContinuityAutoEnroll: false });
         const orchestrator = yield* Orchestrator.OrchestratorV2;
         const eventSink = yield* EventSink.EventSinkV2;
         const threadId = ThreadId.make(`runtime-layer-restart-${status}-source`);
@@ -5725,7 +5729,17 @@ it.layer(layerTest.pipe(Layer.provideMerge(SqlitePersistence.layerMemory)))(
         yield* settings.updateSettings({ workContinuityAutoEnroll: true });
         return yield* program.pipe(
           Effect.ensuring(
-            settings.updateSettings({ workContinuityAutoEnroll: false }).pipe(Effect.orDie),
+            settings.updateSettings({ workContinuityAutoEnroll: true }).pipe(Effect.orDie),
+          ),
+        );
+      });
+    const withoutAutoEnrollment = <A, E, R>(program: Effect.Effect<A, E, R>) =>
+      Effect.gen(function* () {
+        const settings = yield* ServerSettings.ServerSettingsService;
+        yield* settings.updateSettings({ workContinuityAutoEnroll: false });
+        return yield* program.pipe(
+          Effect.ensuring(
+            settings.updateSettings({ workContinuityAutoEnroll: true }).pipe(Effect.orDie),
           ),
         );
       });
@@ -5745,13 +5759,42 @@ it.layer(layerTest.pipe(Layer.provideMerge(SqlitePersistence.layerMemory)))(
       );
 
     it.effect("disabled auto enrollment leaves accepted human messages unenrolled", () =>
-      Effect.gen(function* () {
-        const input = yield* seedContinuity("auto-off", undefined, true);
-        const orchestrator = yield* Orchestrator.OrchestratorV2;
-        assert.isNull(
-          (yield* orchestrator.getThreadProjection(input.threadId)).thread.continuity ?? null,
-        );
-      }),
+      withoutAutoEnrollment(
+        Effect.gen(function* () {
+          const input = yield* seedContinuity("auto-off", undefined, true);
+          const orchestrator = yield* Orchestrator.OrchestratorV2;
+          assert.isNull(
+            (yield* orchestrator.getThreadProjection(input.threadId)).thread.continuity ?? null,
+          );
+        }),
+      ),
+    );
+
+    it.effect(
+      "auto enrollment is on by default and spends exactly one check after a missing terminal report",
+      () =>
+        Effect.gen(function* () {
+          const input = yield* seedContinuity("auto-default", undefined, true);
+          const orchestrator = yield* Orchestrator.OrchestratorV2;
+          const before = (yield* orchestrator.getThreadProjection(input.threadId)).thread
+            .continuity;
+          assert.equal(before?.authorityMessageId, input.authorityMessageId);
+          assert.equal(before?.checksRemaining, 3);
+          const events = yield* EventSink.EventSinkV2;
+          const started = yield* events
+            .stream({ afterSequence: yield* events.latestSequence(), eventType: "run.created" })
+            .pipe(
+              Stream.filter((stored) => stored.event.threadId === input.threadId),
+              Stream.take(1),
+              Stream.runCollect,
+              Effect.forkChild({ startImmediately: true }),
+            );
+          yield* finishRun(input.threadId, input.run);
+          yield* Fiber.join(started);
+          const after = yield* orchestrator.getThreadProjection(input.threadId);
+          assert.lengthOf(after.runs, 2);
+          assert.equal(after.thread.continuity?.checksRemaining, 2);
+        }),
     );
 
     it.effect(
@@ -5803,7 +5846,7 @@ it.layer(layerTest.pipe(Layer.provideMerge(SqlitePersistence.layerMemory)))(
       "enabling the setting alone does not enroll or wake existing work, but a queued human turn does",
       () =>
         Effect.gen(function* () {
-          const input = yield* seedContinuity("auto-queued", undefined, true);
+          const input = yield* withoutAutoEnrollment(seedContinuity("auto-queued", undefined, true));
           const orchestrator = yield* Orchestrator.OrchestratorV2;
           yield* withAutoEnrollment(
             Effect.gen(function* () {
@@ -5962,7 +6005,7 @@ it.layer(layerTest.pipe(Layer.provideMerge(SqlitePersistence.layerMemory)))(
       "cancelling the queued authority blocks supervision without spending or replacing its allowance",
       () =>
         Effect.gen(function* () {
-          const input = yield* seedContinuity("auto-queued-cancel", undefined, true);
+          const input = yield* withoutAutoEnrollment(seedContinuity("auto-queued-cancel", undefined, true));
           const orchestrator = yield* Orchestrator.OrchestratorV2;
           yield* withAutoEnrollment(
             Effect.gen(function* () {
@@ -6190,6 +6233,7 @@ it.layer(layerTest.pipe(Layer.provideMerge(SqlitePersistence.layerMemory)))(
     it.effect.each(["server", "mcp", "provider"] as const)(
       "human-shaped %s dispatch does not automatically enroll",
       (source) =>
+        withoutAutoEnrollment(
         Effect.gen(function* () {
           const input = yield* seedContinuity(`auto-source-${source}`, undefined, true);
           const orchestrator = yield* Orchestrator.OrchestratorV2;
@@ -6211,6 +6255,7 @@ it.layer(layerTest.pipe(Layer.provideMerge(SqlitePersistence.layerMemory)))(
             (yield* orchestrator.getThreadProjection(input.threadId)).thread.continuity ?? null,
           );
         }),
+        ),
     );
     it.effect.each([
       "plan",
@@ -6221,6 +6266,7 @@ it.layer(layerTest.pipe(Layer.provideMerge(SqlitePersistence.layerMemory)))(
       "scheduled",
       "sender",
     ] as const)("%s prevents automatic continuity enrollment", (exclusion) =>
+      withoutAutoEnrollment(
       Effect.gen(function* () {
         const input = yield* seedContinuity(`auto-excluded-${exclusion}`, undefined, true);
         const orchestrator = yield* Orchestrator.OrchestratorV2;
@@ -6296,6 +6342,7 @@ it.layer(layerTest.pipe(Layer.provideMerge(SqlitePersistence.layerMemory)))(
           (yield* orchestrator.getThreadProjection(input.threadId)).thread.continuity ?? null,
         );
       }),
+      ),
     );
 
     it.effect(
@@ -6479,10 +6526,10 @@ it.layer(layerTest.pipe(Layer.provideMerge(SqlitePersistence.layerMemory)))(
             })
             .pipe(Effect.flip);
           assert.instanceOf(refused, Orchestrator.OrchestratorDispatchError);
-          assert.equal(
-            (yield* orchestrator.getThreadProjection(input.threadId)).thread.continuity?.status,
-            "complete",
-          );
+          const reenrolled = (yield* orchestrator.getThreadProjection(input.threadId)).thread
+            .continuity;
+          assert.equal(reenrolled?.status, "active");
+          assert.equal(reenrolled?.authorityMessageId, MessageId.make(`${input.threadId}:new-request`));
         }),
     );
 
diff --git a/apps/server/src/ws.ts b/apps/server/src/ws.ts
index 375c2ac78aa1..2b8cca3edb30 100644
--- a/apps/server/src/ws.ts
+++ b/apps/server/src/ws.ts
@@ -1846,7 +1846,9 @@ const layerWsRpc = (
                         ThreadManagementService.withCreationProvenance(command, {
                           createdBy: "user",
                           creationSource:
-                            "creationSource" in command ? command.creationSource : "web",
+                            "creationSource" in command
+                              ? (command.creationSource ?? "web")
+                              : "web",
                         }),
                       )
                   ).pipe(Effect.provide(intakeContext)),
diff --git a/packages/contracts/src/settings.test.ts b/packages/contracts/src/settings.test.ts
index 62ad92c4f66c..afcbf1bee063 100644
--- a/packages/contracts/src/settings.test.ts
+++ b/packages/contracts/src/settings.test.ts
@@ -24,8 +24,8 @@ const encodeServerSettings = Schema.encodeSync(ServerSettings);
 const decodeClaudeSettings = Schema.decodeUnknownSync(ClaudeSettings);
 
 describe("work continuity auto enrollment", () => {
-  it("keeps automatic enrollment disabled when decoding old settings", () => {
-    expect(decodeServerSettings({}).workContinuityAutoEnroll).toBe(false);
+  it("enables automatic enrollment when decoding old settings without the key", () => {
+    expect(decodeServerSettings({}).workContinuityAutoEnroll).toBe(true);
   });
   it("round-trips the environment enrollment toggle without changing other settings", () => {
     expect(decodeServerSettingsPatch({ workContinuityAutoEnroll: true })).toEqual({
diff --git a/packages/contracts/src/settings.ts b/packages/contracts/src/settings.ts
index 881c81764181..9640e36a9295 100644
--- a/packages/contracts/src/settings.ts
+++ b/packages/contracts/src/settings.ts
@@ -1081,7 +1081,7 @@ export const StorageCleanupSettings = Schema.Struct({
 export type StorageCleanupSettings = typeof StorageCleanupSettings.Type;
 
 export const ServerSettings = Schema.Struct({
-  workContinuityAutoEnroll: Schema.Boolean.pipe(Schema.withDecodingDefault(Effect.succeed(false))),
+  workContinuityAutoEnroll: Schema.Boolean.pipe(Schema.withDecodingDefault(Effect.succeed(true))),
   // Null means no client has migrated this preference yet; an empty value is
   // authoritative so another device cannot resurrect cleared preferences.
   favorites: Schema.NullOr(ModelFavorites).pipe(Schema.withDecodingDefault(Effect.succeed(null))),