diff --git a/CHANGELOG.md b/CHANGELOG.md
index 72879cf..b39e51e 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -6,6 +6,16 @@ the image workflows publish (plus `latest` from every push to `main`).
 
 ## [Unreleased]
 
+### Fixed
+
+- **Untrusted-workspace wedge on headless runs.** Phase 4's tmux-path deletion also
+  removed the only call to `claude_config.ensure_onboarded`, so agent working dirs —
+  every fresh worktree — were never pre-trusted in `~/.claude.json` and headless
+  `claude -p` runs wedged or refused on the trust dialog with nobody at a TTY. Spawn
+  and resume now re-seed onboarding + per-directory trust before every launch (resume
+  included, so a cross-worker resume landing in a container that has never seen the
+  working dir is covered). 2 regression tests.
+
 ### Added — mobile app feature parity
 
 The iOS app (`app/`) catches up with everything the backend and web dashboard gained
diff --git a/src/handler/control/spawn.py b/src/handler/control/spawn.py
index eaa50d0..a2e158d 100644
--- a/src/handler/control/spawn.py
+++ b/src/handler/control/spawn.py
@@ -15,6 +15,7 @@ from ..config import get_settings
 from ..db import repository as repo
 from ..db.engine import connection
 from . import (
+    claude_config,
     claude_gen,
     credentials,
     forge,
@@ -160,6 +161,11 @@ def spawn(
     # half also feeds pi-harness agents (their settings.json points at the same dir).
     # Scoped to the project's owner: shared rows plus theirs, nobody else's.
     claude_gen.apply(working_dir, visible_to=project.get("owner_user_id"))
+    # Mark onboarding complete and trust this working dir in ~/.claude.json before
+    # claude boots: a fresh worktree is a brand-new path, and an untrusted workspace
+    # wedges/refuses a headless run with nobody at a TTY to accept the dialog. (The
+    # old tmux launch path did this; it was lost when phase 4 deleted that path.)
+    claude_config.ensure_onboarded(working_dir)
     env, harness = _agent_env(project, agent, token, role=role, mise_init=mise_init)
 
     # Verify the pinned forge version, if one is configured. Non-fatal: a version drift
@@ -286,6 +292,9 @@ def resume(agent: dict, answer: str, worker_id: str | None = None) -> tuple[bool
     working_dir = agent["working_dir"]
     settings_path = settings_gen.write_settings(working_dir)
     claude_gen.apply(working_dir, visible_to=project.get("owner_user_id"))
+    # Cross-worker resume may land in a container whose ~/.claude.json has never seen
+    # this working dir — re-seed trust exactly as spawn does.
+    claude_config.ensure_onboarded(working_dir)
     try:
         token = None
         with connection() as conn:
diff --git a/tests/test_control_spawn.py b/tests/test_control_spawn.py
index 4500b88..629274a 100644
--- a/tests/test_control_spawn.py
+++ b/tests/test_control_spawn.py
@@ -181,3 +181,38 @@ def test_resume_refused_while_run_live(env, fake_launch):
     ok, detail = spawn.resume(agent, "answer")
     assert ok is False
     assert "live run" in detail
+
+
+def test_spawn_trusts_working_dir_in_claude_json(env, fake_launch):
+    """The launch must pre-trust the agent's working dir in ~/.claude.json — an
+    untrusted workspace wedges a headless run on the trust dialog with nobody at a
+    TTY (regression: the call was lost when phase 4 deleted the tmux launch path)."""
+    root = env["tmp"] / "proj"
+    _write_mise(root, with_test=True)
+    _register_project(root)
+
+    spawn.spawn("proj", "api", task="build the thing")
+
+    cfg = json.loads((env["tmp"] / ".claude.json").read_text())
+    assert cfg["hasCompletedOnboarding"] is True
+    entry = cfg["projects"][str(root)]
+    assert entry["hasTrustDialogAccepted"] is True
+
+
+def test_resume_trusts_working_dir_in_claude_json(env, fake_launch):
+    """Cross-worker resume may run in a container that has never seen this working
+    dir; resume must re-seed trust exactly as spawn does."""
+    root = env["tmp"] / "proj"
+    _write_mise(root, with_test=True)
+    _register_project(root)
+    spawn.spawn("proj", "api", task="do it")
+    with get_engine().begin() as conn:
+        agent = repo.get_agent_by_name(conn, "proj", "api")
+        repo.finish_run(conn, repo.get_latest_run(conn, agent["id"])["id"], "completed")
+    (env["tmp"] / ".claude.json").unlink()  # a "fresh container": no config at all
+
+    ok, _ = spawn.resume(agent, "use Postgres")
+
+    assert ok is True
+    cfg = json.loads((env["tmp"] / ".claude.json").read_text())
+    assert cfg["projects"][str(root)]["hasTrustDialogAccepted"] is True