hookd: 🐛 Give package-install's tool-env download its own budget

CHANGELOG.md

@@ -132,6 +132,12 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
   install, the deploy, and the host ping. Brew's output and `package-install`'s stderr
   appear live, and each failure written to the update log is also printed. The final
   error gives the update log's path. The background updater still captures output.
+- **`capt-hookd package-install` converges on a slow link.** Installing the capt-hook
+  tool env shared the command's 3-minute lifecycle budget, so on a slow connection the
+  89 MiB `claude-agent-sdk` wheel download outlasted it, the context SIGKILLed
+  `uv tool install`, and the host stayed on its previous build. The tool env now gets
+  its own 15-minute budget, and the 3-minute budget starts once it is in place, still
+  bounding quiesce, supersede, activation, and the broker ping.
 - **The session guard lets agents quit apps that host no session.** `osascript` that
   quits a named application was blocked for every app, including Slack. The guard now
   blocks only terminals, editors, Orca, Captain Hook, tmux, and any app whose process

captain_hook/desktop/cli.py

@@ -36,8 +36,8 @@ def install() -> None:
         brew(["reinstall", "--formula", FORMULA], stream=True)
     cellar = cellar_version()
     click.echo(
-        f"Landing Captain Hook {cellar} and restarting the host. "
-        "This can take up to about 3 minutes while uv installs the tool env...",
+        f"Landing Captain Hook {cellar}: up to 15 minutes while uv installs the tool env, "
+        "then up to 3 minutes to restart the host...",
         err=True,
     )
     if (host := deploy(cellar, stream=True)) is None:

internal/hookd/command.go

@@ -27,6 +27,11 @@ const (
 	// them. A budget that cannot hold that drain fails on exactly the machine
 	// the command exists to repair.
 	packageLifecycleTimeout = 3 * time.Minute
+
+	// packageToolEnvTimeout bounds installing this build's capt-hook tool env
+	// ahead of the install lifecycle. Nothing is disrupted yet, and its wheels
+	// outlast packageLifecycleTimeout on a slow link.
+	packageToolEnvTimeout = 15 * time.Minute
 )
 
 // Main executes one capt-hookd client or host command and returns its exit code.
@@ -346,15 +351,25 @@ func packageInstallCommand(args []string, stderr io.Writer) int {
 	if len(args) != 0 {
 		return 2
 	}
-	ctx, cancel := context.WithTimeout(context.Background(), packageLifecycleTimeout)
-	defer cancel()
-	if err := applyPackagedApplication(ctx); err != nil {
+	err := installPackage(installProductToolEnv, applyPackagedApplication, packageToolEnvTimeout, packageLifecycleTimeout)
+	if err != nil {
 		fmt.Fprintln(stderr, err)
 		return 1
 	}
 	return 0
 }
 
+func installPackage(toolEnv, apply func(context.Context) error, toolEnvTimeout, lifecycleTimeout time.Duration) error {
+	toolEnvCtx, cancel := context.WithTimeout(context.Background(), toolEnvTimeout)
+	defer cancel()
+	if err := toolEnv(toolEnvCtx); err != nil {
+		return err
+	}
+	ctx, cancel := context.WithTimeout(context.Background(), lifecycleTimeout)
+	defer cancel()
+	return apply(ctx)
+}
+
 func packageUninstallCommand(args []string, stderr io.Writer) int {
 	if len(args) != 0 {
 		return 2

internal/hookd/command_test.go

@@ -349,6 +349,45 @@ func TestVersionReportsExactSchemaAndBuild(t *testing.T) {
 	}
 }
 
+func TestPackageInstallStartsTheLifecycleBudgetAfterASlowToolEnv(t *testing.T) {
+	t.Parallel()
+	const toolEnvTimeout, lifecycleTimeout = 10 * time.Second, 100 * time.Millisecond
+	var lifecycleBudget time.Duration
+	err := installPackage(
+		func(ctx context.Context) error {
+			select {
+			case <-ctx.Done():
+				return fmt.Errorf("the tool env was cancelled: %v", ctx.Err())
+			case <-time.After(3 * lifecycleTimeout):
+				return nil
+			}
+		},
+		func(ctx context.Context) error {
+			deadline, ok := ctx.Deadline()
+			if !ok {
+				return errors.New("the lifecycle ran without a deadline")
+			}
+			lifecycleBudget = time.Until(deadline)
+			select {
+			case <-ctx.Done():
+				return ctx.Err()
+			case <-time.After(toolEnvTimeout):
+				return errors.New("the lifecycle outlived its budget")
+			}
+		},
+		toolEnvTimeout, lifecycleTimeout,
+	)
+	if !errors.Is(err, context.DeadlineExceeded) {
+		t.Fatalf("installPackage = %v, want the lifecycle budget to expire", err)
+	}
+	if lifecycleBudget <= 0 || lifecycleBudget > lifecycleTimeout {
+		t.Fatalf(
+			"lifecycle started with %v left, want a fresh %v budget after the tool env",
+			lifecycleBudget, lifecycleTimeout,
+		)
+	}
+}
+
 func TestRunSpellsTheRequestFromThePayload(t *testing.T) {
 	cwd := "/payload/cwd"
 	payload := `{"session_id":"abc","cwd":"` + cwd + `"}`

internal/hookd/deployment_darwin.go

@@ -11,7 +11,6 @@ import (
 	"time"
 
 	"github.com/yasyf/daemonkit"
-	"github.com/yasyf/daemonkit/artifact"
 	"github.com/yasyf/daemonkit/deploy"
 	"github.com/yasyf/daemonkit/launchd"
 )
@@ -141,13 +140,6 @@ func openDeployment(appPath string) (*deploy.Deployment, error) {
 }
 
 func applyPackagedApplication(ctx context.Context) error {
-	store, err := artifact.DefaultStore()
-	if err != nil {
-		return err
-	}
-	if _, err := store.Resolve(ctx, productToolDescriptor()); err != nil {
-		return fmt.Errorf("captain package: install the capt-hook %s tool env: %w", Build, err)
-	}
 	source, err := packagedApplicationPath()
 	if err != nil {
 		return err

internal/hookd/deployment_darwin_test.go

@@ -67,9 +67,9 @@ func TestPackageInstallAbortsBeforeTheAppWhenTheToolEnvFails(t *testing.T) {
 	t.Setenv("HOME", home)
 	t.Setenv("DAEMONKIT_HOME", home)
 	t.Setenv("PATH", t.TempDir())
-	err = applyPackagedApplication(t.Context())
+	err = installPackage(installProductToolEnv, applyPackagedApplication, packageToolEnvTimeout, packageLifecycleTimeout)
 	if err == nil || !strings.Contains(err.Error(), "install the capt-hook "+Build+" tool env") {
-		t.Fatalf("applyPackagedApplication without uv = %v, want the tool env failure", err)
+		t.Fatalf("installPackage without uv = %v, want the tool env failure", err)
 	}
 	if _, err := os.Lstat(filepath.Join(home, "Applications")); !errors.Is(err, os.ErrNotExist) {
 		t.Fatalf("package-install touched ~/Applications after the tool env failed: %v", err)

internal/hookd/deployment_linux.go

@@ -10,7 +10,6 @@ import (
 	"path/filepath"
 
 	"github.com/yasyf/daemonkit"
-	"github.com/yasyf/daemonkit/artifact"
 	"github.com/yasyf/daemonkit/durable"
 	"github.com/yasyf/daemonkit/supervise"
 )
@@ -61,13 +60,6 @@ func (p installedPaths) lock(ctx context.Context, name string) (*durable.Lock, e
 }
 
 func applyPackagedApplication(ctx context.Context) error {
-	store, err := artifact.DefaultStore()
-	if err != nil {
-		return err
-	}
-	if _, err := store.Resolve(ctx, productToolDescriptor()); err != nil {
-		return fmt.Errorf("captain package: install the capt-hook %s tool env: %w", Build, err)
-	}
 	source, err := canonicalExecutable()
 	if err != nil {
 		return err

internal/hookd/deployment_linux_test.go

@@ -13,9 +13,9 @@ func TestPackageInstallAbortsBeforeTheHostWhenTheToolEnvFails(t *testing.T) {
 	t.Setenv("HOME", home)
 	t.Setenv("DAEMONKIT_HOME", home)
 	t.Setenv("PATH", t.TempDir())
-	err := applyPackagedApplication(t.Context())
+	err := installPackage(installProductToolEnv, applyPackagedApplication, packageToolEnvTimeout, packageLifecycleTimeout)
 	if err == nil || !strings.Contains(err.Error(), "install the capt-hook "+Build+" tool env") {
-		t.Fatalf("applyPackagedApplication without uv = %v, want the tool env failure", err)
+		t.Fatalf("installPackage without uv = %v, want the tool env failure", err)
 	}
 	if _, err := os.Lstat(filepath.Join(home, ".local")); !errors.Is(err, os.ErrNotExist) {
 		t.Fatalf("package-install touched ~/.local after the tool env failed: %v", err)

internal/hookd/manager.go

@@ -1021,6 +1021,17 @@ func productToolDescriptor() *artifact.Descriptor {
 	}
 }
 
+func installProductToolEnv(ctx context.Context) error {
+	store, err := artifact.DefaultStore()
+	if err != nil {
+		return err
+	}
+	if _, err := store.Resolve(ctx, productToolDescriptor()); err != nil {
+		return fmt.Errorf("captain package: install the capt-hook %s tool env: %w", Build, err)
+	}
+	return nil
+}
+
 func installedPython() (string, error) {
 	store, err := artifact.DefaultStore()
 	if err != nil {