From c02306291ca0793ed093e9936db82ebd1540fe4a Mon Sep 17 00:00:00 2001
From: Benjamin Borbe <benjamin.borbe@gmail.com>
Date: Thu, 2 Jul 2026 19:56:03 +0200
Subject: [PATCH] 159-work-on-headless-non-interactive

---
 CHANGELOG.md                                               | 4 ++++
 pkg/ops/workon.go                                          | 5 ++++-
 pkg/ops/workon_test.go                                     | 7 +++++++
 .../159-work-on-headless-non-interactive.md                | 7 ++++++-
 4 files changed, 21 insertions(+), 2 deletions(-)
 rename prompts/{in-progress => completed}/159-work-on-headless-non-interactive.md (94%)

diff --git a/CHANGELOG.md b/CHANGELOG.md
index 02a438a..e1a2969 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,9 @@
 # Changelog
 
+## Unreleased
+
+- fix(workon): append `--non-interactive` to the headless `claude --print` bootstrap prompt in `handleClaudeSession` to prevent the 5-minute hang when `work-on` command needs input that cannot be answered headlessly
+
 All notable changes to this project will be documented in this file.
 
 Please choose versions by [Semantic Versioning](http://semver.org/).
diff --git a/pkg/ops/workon.go b/pkg/ops/workon.go
index 03be09a..694b6f0 100644
--- a/pkg/ops/workon.go
+++ b/pkg/ops/workon.go
@@ -188,7 +188,10 @@ func (w *workOnOperation) handleClaudeSession(
 	if w.starter == nil {
 		return "", ErrStarterUnavailable
 	}
-	prompt := fmt.Sprintf(`%s "%s"`, vault.GetWorkOnCommand(), task.FilePath)
+	// The bootstrap always runs headless `claude --print`, which cannot answer
+	// AskUserQuestion; --non-interactive tells the work-on command to take safe
+	// defaults instead of prompting (prevents the 5m headless hang).
+	prompt := fmt.Sprintf(`%s "%s" --non-interactive`, vault.GetWorkOnCommand(), task.FilePath)
 	slog.Info("starting claude session", "task", task.Name)
 	sessionID, err := w.starter.StartSession(ctx, prompt, vaultPath, task.Name)
 	if err != nil {
diff --git a/pkg/ops/workon_test.go b/pkg/ops/workon_test.go
index 75930ed..c86b6ad 100644
--- a/pkg/ops/workon_test.go
+++ b/pkg/ops/workon_test.go
@@ -194,6 +194,13 @@ var _ = Describe("WorkOnOperation", func() {
 			_, prompt, _, _ := mockStarter.StartSessionArgsForCall(0)
 			Expect(prompt).To(MatchRegexp(`^/custom-cmd "`))
 		})
+
+		It("appends --non-interactive to the bootstrap prompt", func() {
+			Expect(mockStarter.StartSessionCallCount()).To(Equal(1))
+			_, prompt, _, _ := mockStarter.StartSessionArgsForCall(0)
+			Expect(prompt).To(MatchRegexp(` --non-interactive$`))
+			Expect(prompt).To(MatchRegexp(`/path/to/vault/tasks/my-task\.md`))
+		})
 	})
 
 	Context("when starter is nil and task has no cached session ID", func() {
diff --git a/prompts/in-progress/159-work-on-headless-non-interactive.md b/prompts/completed/159-work-on-headless-non-interactive.md
similarity index 94%
rename from prompts/in-progress/159-work-on-headless-non-interactive.md
rename to prompts/completed/159-work-on-headless-non-interactive.md
index 1d5bced..db93640 100644
--- a/prompts/in-progress/159-work-on-headless-non-interactive.md
+++ b/prompts/completed/159-work-on-headless-non-interactive.md
@@ -1,7 +1,12 @@
 ---
-status: approved
+status: completed
+summary: Appended `--non-interactive` to the headless bootstrap prompt in `handleClaudeSession` and added unit test verifying the flag is present and the task file path is preserved
+execution_id: vault-cli-exec-159-work-on-headless-non-interactive
+dark-factory-version: v0.191.0
 created: "2026-07-02T18:15:00Z"
 queued: "2026-07-02T17:51:16Z"
+started: "2026-07-02T17:54:37Z"
+completed: "2026-07-02T17:56:03Z"
 ---
 
 <summary>