feat(state): clean up per-bottle state on session end (except capability-block)

Previously every bottle launch left ~/.claude-bottle/state/<identity>/
behind forever — metadata.json on every run, plus per-bottle
Dockerfile + transcript snapshot on capability-block rebuilds. The
metadata accumulated debris across launches; the only state worth
keeping was the capability-block rebuild bundle.

Make cleanup the default; preserve only on capability-block.

- bottle_state.py: .preserve marker helpers (mark_preserved,
  is_preserved, clear_preserve_marker, preserve_marker_path) +
  cleanup_state(identity) that rm -rf's the per-bottle dir.
- capability_apply.apply_capability_change writes mark_preserved
  before teardown so cli.py's session-end cleanup keeps the dir.
- prepare.py clears any leftover marker at launch (start or resume),
  so a marker from a prior capability-block doesn't keep state
  alive past a subsequent normal session-end.
- cli/start.py runs the cleanup decision AFTER the launch context
  closes: if is_preserved → print resume hint; else cleanup_state.
  The resume hint moves out of the launch with-block (was previously
  printed unconditionally — would have misled the operator about
  whether state was actually kept).

Future-proof: cli.py never persists state speculatively. If the
agent wants to be resumable, it has to go through capability-block.

Co-Authored-By: Claude Opus 4.7 <noreply@anthropic.com>

claude_bottle/backend/docker/bottle_state.py

@@ -45,6 +45,10 @@ _STATE_SUBDIR = "state"
 _PER_BOTTLE_DOCKERFILE_NAME = "Dockerfile"
 _TRANSCRIPT_SUBDIR = "transcript"
 _METADATA_NAME = "metadata.json"
+# Empty marker file. capability_apply writes it before teardown so
+# cli.py's session-end cleanup knows to preserve the state dir for
+# `cli.py resume <identity>`. Absent = clean up.
+_PRESERVE_MARKER = ".preserve"
 
 # 5 chars of base36 alphabet ≈ 60M combinations. Plenty for human
 # operators starting bottles by hand; collision-free in practice.
@@ -155,14 +159,61 @@ def transcript_snapshot_dir(identity: str) -> Path:
     return bottle_state_dir(identity) / _TRANSCRIPT_SUBDIR
 
 
+# --- Preserve-on-close marker ----------------------------------------------
+
+
+def preserve_marker_path(identity: str) -> Path:
+    return bottle_state_dir(identity) / _PRESERVE_MARKER
+
+
+def mark_preserved(identity: str) -> Path:
+    """Mark this bottle's state for preservation across session
+    teardown. Written by capability_apply.apply_capability_change so
+    cli.py's session-end cleanup leaves the state dir intact for a
+    subsequent `cli.py resume`."""
+    path = preserve_marker_path(identity)
+    path.parent.mkdir(parents=True, exist_ok=True)
+    path.touch()
+    return path
+
+
+def is_preserved(identity: str) -> bool:
+    return preserve_marker_path(identity).exists()
+
+
+def clear_preserve_marker(identity: str) -> None:
+    """Idempotent removal. Called at fresh launch (start or resume)
+    so a marker left from a prior capability-block doesn't keep
+    state alive past the next normal session-end."""
+    try:
+        preserve_marker_path(identity).unlink()
+    except FileNotFoundError:
+        pass
+
+
+def cleanup_state(identity: str) -> None:
+    """Remove the per-bottle state dir entirely. Called by cli.py
+    when a bottle session ends and is_preserved(identity) is False.
+    Idempotent — missing dir is success."""
+    import shutil
+    state_dir = bottle_state_dir(identity)
+    if state_dir.is_dir():
+        shutil.rmtree(state_dir, ignore_errors=True)
+
+
 __all__ = [
     "BottleMetadata",
     "bottle_identity",
     "bottle_state_dir",
+    "cleanup_state",
+    "clear_preserve_marker",
+    "is_preserved",
+    "mark_preserved",
     "metadata_path",
     "per_bottle_dockerfile",
     "per_bottle_dockerfile_path",
     "per_bottle_image_tag",
+    "preserve_marker_path",
     "read_metadata",
     "transcript_snapshot_dir",
     "write_metadata",

claude_bottle/backend/docker/capability_apply.py

@@ -37,6 +37,7 @@ from pathlib import Path
 
 from ...log import info, warn
 from .bottle_state import (
+    mark_preserved,
     per_bottle_dockerfile,
     per_bottle_dockerfile_path,
     transcript_snapshot_dir,
@@ -117,6 +118,11 @@ def apply_capability_change(slug: str, new_dockerfile: str) -> tuple[str, str]:
     _snapshot_transcript(slug)
     _push_working_tree(slug)
     write_per_bottle_dockerfile(slug, new_dockerfile)
+    # Set the preserve marker BEFORE teardown so cli.py's session-end
+    # cleanup sees it and keeps the state dir intact for the
+    # operator's `cli.py resume <identity>`. Without the marker the
+    # state dir would be deleted as part of normal session end.
+    mark_preserved(slug)
     _teardown_bottle(slug)
 
     return before, new_dockerfile

claude_bottle/backend/docker/prepare.py

@@ -30,6 +30,7 @@ from .git_gate import DockerGitGate, git_gate_container_name
 from .bottle_state import (
     BottleMetadata,
     bottle_identity,
+    clear_preserve_marker,
     per_bottle_dockerfile,
     per_bottle_dockerfile_path,
     per_bottle_image_tag,
@@ -73,6 +74,10 @@ def resolve_plan(
         copy_cwd=spec.copy_cwd,
         started_at=datetime.now(timezone.utc).isoformat(),
     ))
+    # Clear any leftover preserve marker from a prior capability-block
+    # so this fresh launch can be cleaned up at session-end unless
+    # the agent triggers another capability-block.
+    clear_preserve_marker(slug)
 
     # PRD 0016 capability-block: if a per-bottle Dockerfile has been
     # written (via apply_capability_change), the base image becomes

claude_bottle/cli/start.py

@@ -17,6 +17,7 @@ import tempfile
 from pathlib import Path
 
 from ..backend import BottleSpec, get_bottle_backend
+from ..backend.docker.bottle_state import cleanup_state, is_preserved
 from ..log import die, info
 from ..manifest import Manifest
 from ._common import PROG, USER_CWD, read_tty_line
@@ -99,13 +100,29 @@ def _launch_bottle(
                 claude_args.append("--remote-control")
             bottle.exec_claude(claude_args, tty=True)
             info(f"session ended; container {bottle.name} will be removed")
-            if identity:
-                info(f"to resume this bottle: ./cli.py resume {identity}")
-            return 0
+        # Context exited → containers + networks gone. Now decide
+        # what to do with the per-bottle state dir on the host:
+        # capability-block apply sets the preserve marker before it
+        # tears the bottle down, so the operator can resume from the
+        # new Dockerfile + transcript snapshot. Any other session
+        # end (normal exit, agent crash, Ctrl-C) leaves no marker,
+        # and the state dir gets cleaned up so ~/.claude-bottle/state/
+        # doesn't accumulate per-launch debris.
+        _settle_state(identity)
+        return 0
     finally:
         shutil.rmtree(stage_dir, ignore_errors=True)
 
 
+def _settle_state(identity: str) -> None:
+    if not identity:
+        return
+    if is_preserved(identity):
+        info(f"to resume this bottle: ./cli.py resume {identity}")
+        return
+    cleanup_state(identity)
+
+
 def _identity_from_plan(plan: object) -> str:
     """Backend-specific: the docker plan exposes the identity as
     `.slug`. Other backends in the future would expose their own

tests/unit/test_bottle_state.py

@@ -114,6 +114,60 @@ class TestBottleIdentity(unittest.TestCase):
         self.assertTrue(identity.startswith("my-agent-"))
 
 
+class TestPreserveMarker(_FakeHomeMixin, unittest.TestCase):
+    """The .preserve marker is how capability_apply tells cli.py's
+    session-end cleanup to keep the state dir instead of removing it."""
+
+    def setUp(self):
+        self._setup_fake_home()
+
+    def tearDown(self):
+        self._teardown_fake_home()
+
+    def test_default_is_unpreserved(self):
+        self.assertFalse(bottle_state.is_preserved("dev-x"))
+
+    def test_mark_then_is_preserved(self):
+        bottle_state.mark_preserved("dev-x")
+        self.assertTrue(bottle_state.is_preserved("dev-x"))
+
+    def test_clear_removes_marker(self):
+        bottle_state.mark_preserved("dev-x")
+        bottle_state.clear_preserve_marker("dev-x")
+        self.assertFalse(bottle_state.is_preserved("dev-x"))
+
+    def test_clear_is_idempotent(self):
+        # No marker present — should not raise.
+        bottle_state.clear_preserve_marker("never-existed")
+        self.assertFalse(bottle_state.is_preserved("never-existed"))
+
+    def test_marker_path_under_state_dir(self):
+        path = bottle_state.preserve_marker_path("dev-x")
+        self.assertTrue(str(path).endswith("/.claude-bottle/state/dev-x/.preserve"))
+
+
+class TestCleanupState(_FakeHomeMixin, unittest.TestCase):
+    """cleanup_state removes the entire per-bottle state dir.
+    Called by cli.py when a session ends without the preserve marker."""
+
+    def setUp(self):
+        self._setup_fake_home()
+
+    def tearDown(self):
+        self._teardown_fake_home()
+
+    def test_removes_state_dir_and_contents(self):
+        bottle_state.write_per_bottle_dockerfile("dev-x", "FROM x\n")
+        d = bottle_state.bottle_state_dir("dev-x")
+        self.assertTrue(d.is_dir())
+        bottle_state.cleanup_state("dev-x")
+        self.assertFalse(d.exists())
+
+    def test_idempotent_when_dir_missing(self):
+        # Never created — should not raise.
+        bottle_state.cleanup_state("never-existed")
+
+
 class TestBottleMetadata(_FakeHomeMixin, unittest.TestCase):
     def setUp(self):
         self._setup_fake_home()

tests/unit/test_capability_apply.py

@@ -107,6 +107,14 @@ class TestApplyCapabilityChange(_FakeHomeMixin, unittest.TestCase):
             self._calls,
         )
 
+    def test_marks_preserved_before_teardown(self):
+        # cli.py's session-end cleanup reads the marker after the
+        # bottle is torn down. The marker must therefore be written
+        # before teardown — otherwise the cleanup would see no
+        # marker and rm the state dir we just populated.
+        apply_capability_change("dev", "FROM new\n")
+        self.assertTrue(bottle_state.is_preserved("dev"))
+
     def test_first_change_falls_back_to_repo_dockerfile_for_before(self):
         # No per-bottle override yet — before-diff comes from the
         # repo's Dockerfile.