hookd: 🐛 Wait for uv to resolve the release before installing

CHANGELOG.md

@@ -138,6 +138,12 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
   `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.
+- **Self-updates wait until uv can resolve the new version.** PyPI index lag made the
+  12.88.0 update fail with `No solution found` after publishing succeeded.
+  `capt-hookd package-install` now probes uv every 5 seconds for up to 10 minutes before
+  installing, honoring uv's configured indexes and local wheelhouses. A tool env already
+  installed for this build skips the wait, and `capt-hook helper install` names it in its
+  progress line.
 - **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}: up to 15 minutes while uv installs the tool env, "
-        "then up to 3 minutes to restart the host...",
+        f"Landing Captain Hook {cellar}: up to 10 minutes while the package index catches up, "
+        "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

@@ -351,7 +351,10 @@ func packageInstallCommand(args []string, stderr io.Writer) int {
 	if len(args) != 0 {
 		return 2
 	}
-	err := installPackage(installProductToolEnv, applyPackagedApplication, packageToolEnvTimeout, packageLifecycleTimeout)
+	err := awaitProductRelease()
+	if err == nil {
+		err = installPackage(installProductToolEnv, applyPackagedApplication, packageToolEnvTimeout, packageLifecycleTimeout)
+	}
 	if err != nil {
 		fmt.Fprintln(stderr, err)
 		return 1

internal/hookd/toolrelease.go

@@ -0,0 +1,62 @@
+package hookd
+
+import (
+	"bytes"
+	"context"
+	"errors"
+	"fmt"
+	"os/exec"
+	"strings"
+	"time"
+)
+
+const (
+	productDist        = "capt-hook"
+	releaseWaitTimeout = 10 * time.Minute
+	releasePollEvery   = 5 * time.Second
+)
+
+func awaitProductRelease() error {
+	if _, err := installedPython(); err == nil {
+		return nil
+	}
+	ctx, cancel := context.WithTimeout(context.Background(), releaseWaitTimeout)
+	defer cancel()
+	if err := awaitResolvable(ctx, "uv", productDist, Build); err != nil {
+		return fmt.Errorf("captain package: wait for capt-hook %s to resolve: %w", Build, err)
+	}
+	return nil
+}
+
+// awaitResolvable holds until uv resolves dist==version from the sources it
+// installs from: PyPI lists a fresh upload minutes after publish succeeds, and
+// until then uv tool install fails with "No solution found".
+func awaitResolvable(ctx context.Context, uv, dist, version string) error {
+	poll := time.NewTicker(releasePollEvery)
+	defer poll.Stop()
+	reason := "no probe finished"
+	for ctx.Err() == nil {
+		cmd := exec.CommandContext(
+			ctx, uv, "pip", "compile", "--no-deps", "--refresh-package", dist, "--quiet", "--no-header", "-",
+		)
+		cmd.Stdin = strings.NewReader(dist + "==" + version + "\n")
+		var stderr bytes.Buffer
+		cmd.Stderr = &stderr
+		err := cmd.Run()
+		if err == nil {
+			return nil
+		}
+		if ctx.Err() != nil {
+			break
+		}
+		if exit := (*exec.ExitError)(nil); !errors.As(err, &exit) {
+			return err
+		}
+		reason = strings.TrimSpace(stderr.String())
+		select {
+		case <-ctx.Done():
+		case <-poll.C:
+		}
+	}
+	return fmt.Errorf("uv cannot resolve %s==%s: %s: %w", dist, version, reason, ctx.Err())
+}

internal/hookd/toolrelease_test.go

@@ -0,0 +1,68 @@
+package hookd
+
+import (
+	"context"
+	"fmt"
+	"os"
+	"path/filepath"
+	"strings"
+	"testing"
+	"time"
+)
+
+func fakeUV(t *testing.T, failures int) (uv, requests string) {
+	t.Helper()
+	dir := t.TempDir()
+	requests = filepath.Join(dir, "requests")
+	uv = filepath.Join(dir, "uv")
+	script := fmt.Sprintf(`#!/bin/sh
+cat >> %[1]q
+echo "$@" >> %[1]q
+if [ "$(grep -c '^pip compile' %[1]q)" -le %[2]d ]; then
+  echo "No solution found when resolving dependencies" >&2
+  exit 1
+fi
+`, requests, failures)
+	if err := os.WriteFile(uv, []byte(script), 0o700); err != nil { //nolint:gosec // a fake uv must be executable
+		t.Fatal(err)
+	}
+	return uv, requests
+}
+
+func TestAwaitResolvableHoldsUntilUVResolvesTheVersion(t *testing.T) {
+	t.Parallel()
+	uv, requests := fakeUV(t, 1)
+	if err := awaitResolvable(t.Context(), uv, productDist, "12.88.0"); err != nil {
+		t.Fatalf("awaitResolvable = %v, want nil once uv resolves 12.88.0", err)
+	}
+	got, err := os.ReadFile(requests)
+	if err != nil {
+		t.Fatal(err)
+	}
+	probe := "capt-hook==12.88.0\npip compile --no-deps --refresh-package capt-hook --quiet --no-header -\n"
+	if string(got) != probe+probe {
+		t.Fatalf("uv saw %q, want two resolution probes", got)
+	}
+}
+
+func TestAwaitResolvableGivesUpAtItsDeadlineNamingTheVersion(t *testing.T) {
+	t.Parallel()
+	uv, _ := fakeUV(t, 9)
+	ctx, cancel := context.WithTimeout(t.Context(), 3*time.Second)
+	defer cancel()
+	err := awaitResolvable(ctx, uv, productDist, "12.88.0")
+	if err == nil || !strings.Contains(err.Error(), "uv cannot resolve capt-hook==12.88.0: No solution found") {
+		t.Fatalf("awaitResolvable = %v, want the unresolved version named", err)
+	}
+}
+
+func TestAwaitResolvableFailsAtOnceWithoutUV(t *testing.T) {
+	t.Parallel()
+	ctx, cancel := context.WithTimeout(t.Context(), time.Minute)
+	defer cancel()
+	start := time.Now()
+	err := awaitResolvable(ctx, filepath.Join(t.TempDir(), "uv"), productDist, "12.88.0")
+	if err == nil || time.Since(start) > releasePollEvery {
+		t.Fatalf("awaitResolvable without uv = %v after %v, want an immediate failure", err, time.Since(start))
+	}
+}