fix(gateway): persist mitmproxy CA on the host, not a named volume (#450)

The shared gateway self-generates a mitmproxy CA that every bottle installs
to trust its TLS interception. It was persisted on a Docker named volume,
which survives `docker rm` but is silently wiped by `docker volume prune` /
`docker system prune --volumes` during routine host maintenance. When that
happens the gateway mints a fresh CA on restart, and every already-running
bottle fails the TLS handshake even after it re-resolves and reconnects to
the moved gateway — a re-attachment blocker distinct from #443/#445.

Move CA persistence to a host bind-mount under the app-data root
(`bot_bottle_root()/gateway-ca`, via `host_gateway_ca_dir()`), mirroring how
the shared DB and control-plane token already live on the host. Docker never
prunes a path under the root, and it stays inspectable + rotatable from the
host. mitmproxy already adopts an existing CA and generates one only on first
run, so the bind-mount gives adopt-existing/generate-on-first-run for free.

Add an explicit rollover path: `rotate_gateway_ca()` clears the persisted CA
so the next start remints it, and `python -m bot_bottle.orchestrator.rotate_ca`
wires that together with dropping the running gateway container (whose
mitmproxy still holds the old CA in memory). Rotation stays an operator action
— it doesn't auto-re-provision running bottles, which re-attach to pick up the
new anchor.

Scope: the Docker infra/gateway path (the "infra container" in the report).
The macOS (`container`-only volume) and Firecracker (VM-attached ext4) backends
persist the CA differently and are unaffected.

Co-Authored-By: Claude Opus 4.8 <noreply@anthropic.com>

bot_bottle/orchestrator/gateway.py

@@ -27,6 +27,7 @@ from ..paths import (
     CONTROL_PLANE_TOKEN_ENV,
     host_control_plane_token,
     host_db_path,
+    host_gateway_ca_dir,
 )
 from ..supervise import DB_PATH_IN_CONTAINER
 
@@ -48,14 +49,23 @@ GATEWAY_LABEL = "bot-bottle-orch-gateway=1"
 # the source IP the gateway attributes by is the address on this network.
 GATEWAY_NETWORK = "bot-bottle-gateway"
 
-# mitmproxy's CA dir in the bundle. A persistent named volume here keeps the
-# gateway's self-generated CA STABLE across container recreation — every agent
-# installs this one CA to trust the shared gateway's TLS interception, so it
-# must not rotate when the gateway restarts.
+# mitmproxy's CA dir in the bundle. The host's gateway-CA dir (see
+# `host_gateway_ca_dir`) is bind-mounted here so the gateway's self-generated
+# CA stays STABLE across container recreation — every agent installs this one
+# CA to trust the shared gateway's TLS interception, so it must not rotate when
+# the gateway restarts. A host bind-mount rather than a named volume: a named
+# volume is silently wiped by `docker volume prune`, minting a fresh CA that
+# breaks every running bottle (issue #450).
 MITMPROXY_HOME = "/home/mitmproxy/.mitmproxy"
-GATEWAY_CA_VOLUME = "bot-bottle-gateway-mitmproxy"
 GATEWAY_CA_CERT = f"{MITMPROXY_HOME}/mitmproxy-ca-cert.pem"
 
+# The CA material mitmproxy writes into its confdir. mitmproxy reuses these on
+# startup when present and generates them only on first run, so persisting them
+# is what makes the CA stable; deleting them (see `rotate_gateway_ca`) forces a
+# fresh CA on the next start. `mitmproxy-ca.pem` (cert + private key) is the
+# signing identity; the rest are derived encodings agents/clients consume.
+GATEWAY_CA_GLOB = "mitmproxy-ca*"
+
 # The gateway data-plane image + its Dockerfile. Kept as a local constant
 # rather than imported from the backend layer, which would drag
 # the whole backend layer into the lean orchestrator (see #359); unify when
@@ -73,6 +83,26 @@ def _host_db_dir() -> str:
     return str(db_dir)
 
 
+def rotate_gateway_ca(ca_dir: Path | None = None) -> list[Path]:
+    """Delete the persisted mitmproxy CA so the next gateway start mints a
+    fresh one — the explicit, deliberate CA-rollover path (issue #450).
+
+    Persistence keeps the CA stable across restarts precisely because mitmproxy
+    reuses the on-disk CA; rotation is therefore just removing that material.
+    Returns the files removed (empty when there was no CA yet); idempotent.
+
+    This only clears the on-disk CA. It does NOT stop the running gateway (whose
+    mitmproxy still holds the old CA in memory) or re-provision agents — the
+    caller recreates the gateway to mint the new CA and re-attaches bottles.
+    `rotate-ca` on the orchestrator CLI wires those steps together."""
+    ca_dir = ca_dir if ca_dir is not None else host_gateway_ca_dir()
+    removed: list[Path] = []
+    for path in sorted(ca_dir.glob(GATEWAY_CA_GLOB)):
+        path.unlink()
+        removed.append(path)
+    return removed
+
+
 class GatewayError(Exception):
     """The shared gateway failed to build/start/stop (non-zero `docker` exit)."""
 
@@ -221,9 +251,10 @@ class DockerGateway(Gateway):
             "--name", self.name,
             "--label", GATEWAY_LABEL,
             "--network", self.network,
-            # Persist the self-generated CA so it survives restarts (agents
-            # trust it) — see GATEWAY_CA_VOLUME.
-            "--volume", f"{GATEWAY_CA_VOLUME}:{MITMPROXY_HOME}",
+            # Persist the self-generated CA on the host so it survives both
+            # container recreation AND docker volume pruning (agents trust it)
+            # — see host_gateway_ca_dir / issue #450.
+            "--volume", f"{host_gateway_ca_dir()}:{MITMPROXY_HOME}",
             # Share the one host DB: the supervise daemon queues proposals
             # into the same file the orchestrator (and the operator, over
             # HTTP) reads — no second, disconnected DB in the container.
@@ -272,7 +303,7 @@ class DockerGateway(Gateway):
 
 
 __all__ = [
-    "Gateway", "DockerGateway", "GatewayError",
+    "Gateway", "DockerGateway", "GatewayError", "rotate_gateway_ca",
     "GATEWAY_NAME", "GATEWAY_LABEL", "GATEWAY_IMAGE", "GATEWAY_NETWORK",
-    "GATEWAY_CA_VOLUME", "GATEWAY_CA_CERT",
+    "GATEWAY_CA_CERT", "GATEWAY_CA_GLOB",
 ]

bot_bottle/orchestrator/lifecycle.py

@@ -23,10 +23,14 @@ from pathlib import Path
 
 from .. import log
 from ..docker_cmd import run_docker
-from ..paths import CONTROL_PLANE_TOKEN_ENV, bot_bottle_root, host_control_plane_token
+from ..paths import (
+    CONTROL_PLANE_TOKEN_ENV,
+    bot_bottle_root,
+    host_control_plane_token,
+    host_gateway_ca_dir,
+)
 from ..supervise import DB_PATH_IN_CONTAINER
 from .gateway import (
-    GATEWAY_CA_VOLUME,
     GATEWAY_DOCKERFILE,
     GATEWAY_IMAGE,
     GATEWAY_NETWORK,
@@ -194,8 +198,10 @@ class OrchestratorService:
             # gateway_init always starts the orchestrator on DEFAULT_PORT (8099)
             # inside the container; self.port is the host-side published port.
             "--publish", f"127.0.0.1:{self.port}:{DEFAULT_PORT}",
-            # Persist the mitmproxy CA so it survives container recreation.
-            "--volume", f"{GATEWAY_CA_VOLUME}:{MITMPROXY_HOME}",
+            # Persist the mitmproxy CA on the host so it survives container
+            # recreation AND docker volume pruning (issue #450): every agent
+            # trusts this one CA, so a fresh one would break all running bottles.
+            "--volume", f"{host_gateway_ca_dir()}:{MITMPROXY_HOME}",
             # Shared supervise DB (same file the operator reads over HTTP).
             "--volume", f"{_host_db_dir()}:{_SUPERVISE_DB_DIR_IN_CONTAINER}",
             "--env", f"SUPERVISE_DB_PATH={DB_PATH_IN_CONTAINER}",

bot_bottle/orchestrator/rotate_ca.py

@@ -0,0 +1,62 @@
+"""Rotate the shared gateway's mitmproxy CA (issue #450).
+
+    python -m bot_bottle.orchestrator.rotate_ca
+
+A deliberate CA rollover has two halves: drop the *persisted* CA so a fresh one
+is minted, and drop the *running* gateway so its mitmproxy (which holds the old
+CA in memory) is replaced. This one-shot command does both:
+
+  1. Delete the persisted CA under the host gateway-CA dir — the next gateway
+     start generates a new one (mitmproxy reuses an existing CA, generates only
+     when absent).
+  2. Force-remove the infra / standalone-gateway containers so the stale
+     in-memory CA is gone; the next bottle launch's idempotent `ensure_running`
+     brings the gateway back up and mints the fresh CA.
+
+It does NOT re-provision the new CA into already-running bottles — those must be
+re-attached so they install the new trust anchor. Rotation is thus an explicit,
+operator-driven action with a brief egress interruption, not an automatic one.
+"""
+
+from __future__ import annotations
+
+import sys
+from pathlib import Path
+
+from ..docker_cmd import run_docker
+from ..paths import host_gateway_ca_dir
+from .gateway import GATEWAY_NAME, rotate_gateway_ca
+from .lifecycle import INFRA_NAME
+
+# The containers whose mitmproxy would still be serving the old CA from memory:
+# the consolidated infra container and the standalone per-host gateway.
+_GATEWAY_CONTAINERS = (INFRA_NAME, GATEWAY_NAME)
+
+
+def _out(msg: str) -> None:
+    sys.stdout.write(f"rotate-ca: {msg}\n")
+
+
+def main(argv: list[str] | None = None) -> int:
+    del argv  # no flags — a single deliberate action
+    ca_dir: Path = host_gateway_ca_dir()
+    removed = rotate_gateway_ca(ca_dir)
+    if removed:
+        _out(f"removed {len(removed)} CA file(s) from {ca_dir}")
+    else:
+        _out(f"no persisted CA under {ca_dir}; a fresh one is minted on next start")
+
+    # Drop any running gateway so its in-memory (now-stale) CA is replaced on
+    # the next launch. `rm --force` on an absent name is a tolerated no-op.
+    for name in _GATEWAY_CONTAINERS:
+        proc = run_docker(["docker", "rm", "--force", name])
+        if proc.returncode == 0 and proc.stdout.strip():
+            _out(f"removed running container {name}")
+
+    _out("done — the next bottle launch remints the CA; re-attach bottles to "
+         "install the new trust anchor")
+    return 0
+
+
+if __name__ == "__main__":
+    raise SystemExit(main())