diff --git a/claude_bottle/cli/dashboard.py b/claude_bottle/cli/dashboard.py
index 3000f69..04faefd 100644
--- a/claude_bottle/cli/dashboard.py
+++ b/claude_bottle/cli/dashboard.py
@@ -696,10 +696,15 @@ def _attach_to_bottle(
     slug: str,
 ) -> str:
     """Handoff: curses.endwin → attach claude → curses refresh.
-    Returns the post-attach status-line message."""
+    Re-entry into a running bottle from the dashboard always
+    passes `--resume` so claude picks up its prior conversation
+    rather than starting a fresh transcript — the first attach
+    happens via `_new_agent_flow` which sets up the transcript
+    in the first place. Returns the post-attach status-line
+    message."""
     curses.endwin()
     try:
-        exit_code = attach_claude(bottle, remote_control=False)
+        exit_code = attach_claude(bottle, remote_control=False, resume=True)
     except BaseException:
         stdscr.refresh()
         raise
@@ -855,6 +860,30 @@ def _try_init_green() -> int:
         return 0
 
 
+def _quit_without_teardown(bottles: dict) -> None:
+    """Exit the dashboard process WITHOUT triggering Python's normal
+    cleanup of the `bottles` dict's context managers.
+
+    The dict holds `@contextmanager`-decorated objects whose
+    underlying generators have implicit close-on-GC behavior:
+    when Python's interpreter shutdown collects them, each
+    generator's `finally` block runs, which invokes that bottle's
+    teardown (`docker compose down`). PRD 0020 explicitly DOESN'T
+    want that — quitting the dashboard should leave running
+    bottles running. `os._exit` skips all Python-level cleanup
+    (GC, atexit, stdio flush, etc.), so the docker compose
+    projects survive the dashboard exit untouched.
+
+    The `bottles` arg is accepted for the explicit
+    documentation-of-intent — we're choosing not to close
+    these. Curses gets its terminal restored via the explicit
+    `endwin` below since `os._exit` doesn't run
+    curses.wrapper's finally."""
+    del bottles  # nothing to do with it; the os._exit is the point
+    curses.endwin()
+    os._exit(0)
+
+
 # PRD 0019 chunk 3: which pane the j/k/arrow keys move through.
 # Tab toggles. The proposals pane is the default focus — proposal
 # action keys (a/m/r/Enter) require it; agent-scoped keys (e/p,
@@ -935,7 +964,8 @@ def _main_loop(stdscr: "curses._CursesWindow") -> None:
         status_line = ""
 
         if key in (ord("q"), 27):  # q or ESC
-            return
+            _quit_without_teardown(bottles)
+            return  # unreachable; _quit_without_teardown os._exit's
         if key == 9:  # Tab
             focus = PANE_AGENTS if focus == PANE_PROPOSALS else PANE_PROPOSALS
             continue
diff --git a/claude_bottle/cli/start.py b/claude_bottle/cli/start.py
index 1647b18..87c5b31 100644
--- a/claude_bottle/cli/start.py
+++ b/claude_bottle/cli/start.py
@@ -92,15 +92,22 @@ def prepare_with_preflight(
 
 
 def attach_claude(
-    bottle: Bottle, *, remote_control: bool = False,
+    bottle: Bottle, *, remote_control: bool = False, resume: bool = False,
 ) -> int:
     """Run claude inside `bottle` as an interactive session. Blocks
     until the session ends; returns the claude process's exit code.
 
+    `resume=True` adds `--continue` so claude picks up its most
+    recent session non-interactively (no session-picker prompt) —
+    the right shape for the dashboard's Enter re-attach (PRD 0020
+    chunk 3), where a bottle typically has exactly one session.
+    First-attach paths (`./cli.py start`, the dashboard's new-agent
+    flow) leave it False.
+
     Used as the inner step of `./cli.py start` (one-shot) and by the
-    dashboard (PRD 0020), which calls it from inside a `curses.endwin
-    → … → stdscr.refresh()` handoff so the curses surface gets out
-    of the terminal's way while claude has it."""
+    dashboard, which calls it from inside a `curses.endwin → … →
+    stdscr.refresh()` handoff so the curses surface gets out of the
+    terminal's way while claude has it."""
     info(
         "attaching interactive claude session "
         "(Ctrl-D or 'exit' to leave; container will be removed)"
@@ -108,6 +115,10 @@ def attach_claude(
     claude_args = ["--dangerously-skip-permissions"]
     if remote_control:
         claude_args.append("--remote-control")
+    if resume:
+        # `--continue` jumps straight to the most recent session
+        # without showing the picker `--resume` would surface.
+        claude_args.append("--continue")
     return bottle.exec_claude(claude_args, tty=True)