diff --git a/apps/server/src/cloud/bootService.test.ts b/apps/server/src/cloud/bootService.test.ts
index 814d470cad410..33b95e7bc9d5e 100644
--- a/apps/server/src/cloud/bootService.test.ts
+++ b/apps/server/src/cloud/bootService.test.ts
@@ -120,11 +120,18 @@ const makeHarness = Effect.fn("test.make_boot_service_harness")(function* (
     linger: string;
     enabled: boolean;
     active: boolean;
+    // launchd can load a bootstrapped job yet leave its RunAtLoad spawn pending.
+    bootstrapSpawns: boolean;
+    launchdLoaded: boolean;
+    launchdRunning: boolean;
   } = {
     failCommand: undefined,
     linger: "yes",
     enabled: true,
     active: true,
+    bootstrapSpawns: true,
+    launchdLoaded: false,
+    launchdRunning: false,
   };
   const runner = ProcessRunner.ProcessRunner.of({
     run: Effect.fn("test.run_boot_service_command")(function* (
@@ -134,13 +141,27 @@ const makeHarness = Effect.fn("test.make_boot_service_harness")(function* (
       commands.push(command);
       invocations.push(input);
       timeouts.set(command, input.timeout);
-      const failed = command === control.failCommand;
+      const launchdVerb = input.command === "launchctl" ? input.args[0] : undefined;
+      // launchd rejects bootstrap of a loaded job and kickstart of an unloaded one.
+      const failed =
+        command === control.failCommand ||
+        (launchdVerb === "bootstrap" && control.launchdLoaded) ||
+        (launchdVerb === "kickstart" && !control.launchdLoaded);
       if (!failed && command === "loginctl enable-linger --no-ask-password 501")
         control.linger = "yes";
       if (!failed && command === "systemctl --user enable t3code.service") control.enabled = true;
       if (!failed && command === "systemctl --user restart t3code.service") control.active = true;
       // A timed-out stop may still stop the service.
       if (command === "systemctl --user stop t3code.service") control.active = false;
+      if (launchdVerb === "bootout") {
+        control.launchdRunning = false;
+        if (!failed) control.launchdLoaded = false;
+      }
+      if (!failed && launchdVerb === "bootstrap") {
+        control.launchdLoaded = true;
+        control.launchdRunning = control.bootstrapSpawns;
+      }
+      if (!failed && launchdVerb === "kickstart") control.launchdRunning = true;
       if (
         control.stateAfterStop !== undefined &&
         (command === "systemctl --user stop t3code.service" ||
@@ -497,6 +518,7 @@ it.layer(NodeServices.layer)("boot service install", (it) => {
             : [
                 "launchctl bootout --wait gui/501/com.t3tools.t3code.service",
                 `launchctl bootstrap gui/501 ${plan.unitPath}`,
+                "launchctl kickstart gui/501/com.t3tools.t3code.service",
               ],
         );
       }),
@@ -951,6 +973,7 @@ it.layer(NodeServices.layer)("boot service install", (it) => {
     Effect.gen(function* () {
       const { service, control } = yield* makeHarness("darwin");
       yield* service.install();
+      control.launchdLoaded = false;
       control.failCommand = "launchctl bootout --wait gui/501/com.t3tools.t3code.service";
 
       yield* service.install();
@@ -983,4 +1006,25 @@ it.layer(NodeServices.layer)("boot service install", (it) => {
       expect((yield* service.status).current).toBe(true);
     }),
   );
+
+  // regression: #29522
+  it.effect.each(["install", "withStopped after a failed stop"] as const)(
+    "runs a launch agent that launchd leaves pending after bootstrap via %s",
+    (operation) =>
+      Effect.gen(function* () {
+        const { service, control } = yield* makeHarness("darwin");
+        yield* service.install();
+        control.bootstrapSpawns = false;
+
+        if (operation === "install") {
+          yield* service.install();
+        } else {
+          // The bootout timed out with the job still loaded, so recovery's bootstrap is rejected.
+          control.failCommand = "launchctl bootout --wait gui/501/com.t3tools.t3code.service";
+          yield* service.withStopped(Effect.void).pipe(Effect.flip);
+        }
+
+        expect(control.launchdRunning, "launch agent is loaded but not running").toBe(true);
+      }),
+  );
 });
diff --git a/apps/server/src/cloud/bootService.ts b/apps/server/src/cloud/bootService.ts
index 88d477974ae0a..8da8dc10d88d6 100644
--- a/apps/server/src/cloud/bootService.ts
+++ b/apps/server/src/cloud/bootService.ts
@@ -296,7 +296,7 @@ function launchdManager(input: {
   );
   const domainTarget = `gui/${input.uid}`;
   const serviceTarget = `${domainTarget}/${BOOT_SERVICE_LAUNCHD_LABEL}`;
-  // Unloaded jobs may reject bootout/enable. Bootstrap starts RunAtLoad/KeepAlive jobs; kickstart would restart them.
+  // Unloaded jobs may reject bootout/enable. Bootstrap can leave RunAtLoad jobs pending; plain kickstart starts them.
   return {
     kind: "launchd",
     unitPath,
@@ -328,12 +328,25 @@ function launchdManager(input: {
         command: "launchctl",
         args: ["bootstrap", domainTarget, unitPath],
       },
+      {
+        step: "starting the launch agent",
+        command: "launchctl",
+        args: ["kickstart", serviceTarget],
+      },
     ],
+    // A failed stop can leave the job loaded, so bootstrap may be rejected; kickstart still
+    // starts it, and fails on its own when bootstrap left nothing loaded.
     restart: [
       {
         step: "restarting the service after a failed update",
         command: "launchctl",
         args: ["bootstrap", domainTarget, unitPath],
+        optional: true,
+      },
+      {
+        step: "starting the launch agent after a failed update",
+        command: "launchctl",
+        args: ["kickstart", serviceTarget],
       },
     ],
     // Persisted launchctl disable overrides would block reinstall.