Dockerfile

@@ -19,9 +19,11 @@ FROM node:22-slim
 # clarity in case the base ever drops it. socat is the privileged
 # forwarder for the in-container ssh-agent (see claude_bottle/ssh.py): the agent
 # runs as root and rejects non-root connections, so socat sits between
-# node and the agent socket.
+# node and the agent socket. curl is here so any HTTPS_PROXY-aware
+# tool (curl itself, plus anything that shells out to it) works
+# against pipelock's bumped TLS without the agent needing local DNS.
 RUN apt-get update \
-  && apt-get install -y --no-install-recommends git ca-certificates openssh-client socat \
+  && apt-get install -y --no-install-recommends git ca-certificates openssh-client socat curl \
   && rm -rf /var/lib/apt/lists/*
 
 # Install claude-code globally. Pinned to the version verified in the v1

claude_bottle/backend/__init__.py

@@ -204,24 +204,36 @@ class BottleBackend(ABC, Generic[PlanT, CleanupT]):
         """Build/run the bottle and yield a handle; tear down on exit."""
 
     def provision(self, plan: PlanT, target: str) -> str | None:
-        """Copy host-side files (prompt, skills, SSH keys, .git) into
-        the running bottle. Called from `launch` after the container/
-        machine is up. `target` identifies the running instance in
-        backend-specific terms (Docker: resolved container name; fly:
-        machine id). Returns the in-container prompt path if a prompt
-        was provisioned, else None — the Bottle handle uses it to
-        decide whether to add --append-system-prompt-file to claude's
-        argv.
+        """Copy host-side files (CA cert, prompt, skills, SSH keys,
+        .git) into the running bottle. Called from `launch` after the
+        container/machine is up. `target` identifies the running
+        instance in backend-specific terms (Docker: resolved
+        container name; fly: machine id). Returns the in-container
+        prompt path if a prompt was provisioned, else None — the
+        Bottle handle uses it to decide whether to add
+        --append-system-prompt-file to claude's argv.
 
-        Default orchestration: prompt → skills → ssh → git. Subclasses
-        typically don't override this; they implement the four
-        sub-methods below."""
+        Default orchestration: ca → prompt → skills → ssh → git.
+        CA install runs first so the agent's trust store is rebuilt
+        before anything inside the agent makes a TLS call. Subclasses
+        typically don't override this; they implement the sub-methods
+        below."""
+        self.provision_ca(plan, target)
         prompt_path = self.provision_prompt(plan, target)
         self.provision_skills(plan, target)
         self.provision_ssh(plan, target)
         self.provision_git(plan, target)
         return prompt_path
 
+    def provision_ca(self, plan: PlanT, target: str) -> None:
+        """Install pipelock's per-bottle CA into the agent's trust
+        store so the agent trusts the bumped CONNECT cert pipelock
+        presents. Default impl is a no-op so backends that don't
+        yet support TLS interception (every backend except Docker
+        today) aren't forced to implement it. The Docker backend
+        overrides to docker-cp the cert in and run
+        `update-ca-certificates`."""
+
     @abstractmethod
     def provision_prompt(self, plan: PlanT, target: str) -> str | None:
         """Copy the prompt file into the running bottle. Returns the

claude_bottle/backend/docker/backend.py

@@ -24,6 +24,7 @@ from .bottle import DockerBottle
 from .bottle_cleanup_plan import DockerBottleCleanupPlan
 from .bottle_plan import DockerBottlePlan
 from .pipelock import DockerPipelockProxy
+from .provision import ca as _ca
 from .provision import git as _git
 from .provision import prompt as _prompt
 from .provision import skills as _skills
@@ -47,6 +48,9 @@ class DockerBottleBackend(BottleBackend["DockerBottlePlan", "DockerBottleCleanup
         with _launch.launch(plan, proxy=self._proxy, provision=self.provision) as bottle:
             yield bottle
 
+    def provision_ca(self, plan: DockerBottlePlan, target: str) -> None:
+        _ca.provision_ca(plan, target)
+
     def provision_prompt(self, plan: DockerBottlePlan, target: str) -> str | None:
         return _prompt.provision_prompt(plan, target)
 

claude_bottle/backend/docker/launch.py

@@ -23,6 +23,7 @@ from . import util as docker_mod
 from .bottle import DockerBottle
 from .bottle_plan import DockerBottlePlan
 from .pipelock import DockerPipelockProxy, pipelock_proxy_url, pipelock_tls_init
+from .provision.ca import AGENT_CA_BUNDLE, AGENT_CA_PATH
 
 
 # Where the repo root lives, for `docker build` context. Computed once.
@@ -77,7 +78,11 @@ def launch(
             ca_cert_host_path=ca_cert_host,
             ca_key_host_path=ca_key_host,
         )
-        pipelock_name = proxy.start(proxy_plan)
+        # Re-bind the outer plan so provision_ca (which runs later
+        # from `provision(plan, container)`) can read the populated
+        # CA paths off plan.proxy_plan.
+        plan = dataclasses.replace(plan, proxy_plan=proxy_plan)
+        pipelock_name = proxy.start(plan.proxy_plan)
         stack.callback(proxy.stop, pipelock_name)
 
         container = _run_agent_container(plan, internal_network)
@@ -102,6 +107,16 @@ def _run_agent_container(plan: DockerBottlePlan, internal_network: str) -> str:
         "-e", f"HTTPS_PROXY={proxy_url}",
         "-e", f"HTTP_PROXY={proxy_url}",
         "-e", "NO_PROXY=localhost,127.0.0.1",
+        # CA trust trio for the agent process. Docker propagates
+        # run-time env into `docker exec`, so `claude` sees these
+        # without per-exec threading. NODE_EXTRA_CA_CERTS points at
+        # the cert file (Node appends it to its bundled roots);
+        # SSL_CERT_FILE / REQUESTS_CA_BUNDLE point at the system
+        # bundle that `update-ca-certificates` rebuilds in
+        # provision_ca.
+        "-e", f"NODE_EXTRA_CA_CERTS={AGENT_CA_PATH}",
+        "-e", f"SSL_CERT_FILE={AGENT_CA_BUNDLE}",
+        "-e", f"REQUESTS_CA_BUNDLE={AGENT_CA_BUNDLE}",
     ]
     if plan.use_runsc:
         docker_args.extend(["--runtime", "runsc"])

claude_bottle/backend/docker/provision/ca.py

@@ -0,0 +1,79 @@
+"""Install pipelock's per-bottle CA into the agent container's trust
+store (PRD 0006).
+
+By the time this provisioner runs, `pipelock_tls_init` has generated
+a fresh CA into `plan.stage_dir/pipelock-ca/` and the pipelock sidecar
+is up with `tls_interception: { enabled: true }` referencing the
+in-container CA paths. This step makes the agent trust certs signed
+by that CA so the agent's TLS handshake with the bumped CONNECT
+succeeds.
+
+Cert lands on Debian's standard source path
+(`/usr/local/share/ca-certificates/`); `update-ca-certificates`
+rebuilds `/etc/ssl/certs/ca-certificates.crt`, which is what curl,
+Python `ssl`, and OpenSSL-based tools all read by default. The env
+trio set on the agent's `docker run` covers Node
+(`NODE_EXTRA_CA_CERTS`) and Python `requests` /
+`SSL_CERT_FILE`-honoring libraries that don't load the system
+bundle.
+
+The fingerprint is computed via stdlib (`ssl.PEM_cert_to_DER_cert`
++ `hashlib.sha256`) and logged once to stderr. The private key
+stays on the host (under `stage_dir`) until teardown wipes the
+stage dir; nothing in the agent ever sees it."""
+
+from __future__ import annotations
+
+import hashlib
+import ssl
+import subprocess
+
+from ....log import info
+from ..bottle_plan import DockerBottlePlan
+
+
+# Debian-family path for sources that `update-ca-certificates` reads.
+# Bundle path is what the command rebuilds and what every standard
+# TLS consumer in the image reads.
+AGENT_CA_PATH = "/usr/local/share/ca-certificates/claude-bottle-pipelock-ca.crt"
+AGENT_CA_BUNDLE = "/etc/ssl/certs/ca-certificates.crt"
+
+
+def provision_ca(plan: DockerBottlePlan, target: str) -> None:
+    """Copy pipelock's CA cert into the agent, rebuild the trust
+    bundle, emit a one-line fingerprint log. Called from
+    `BottleBackend.provision` after the agent container is up."""
+    container = target
+    cert_host_path = plan.proxy_plan.ca_cert_host_path
+    if not cert_host_path or not cert_host_path.is_file():
+        # Defensive: provision runs after launch wires CA paths
+        # onto the plan via dataclasses.replace; an empty path here
+        # would mean that wiring was skipped.
+        from ....log import die
+        die(
+            f"pipelock CA cert missing at {cert_host_path or '(empty)'}; "
+            f"launch must have called pipelock_tls_init and re-bound "
+            f"the plan before provision"
+        )
+
+    subprocess.run(
+        ["docker", "cp", str(cert_host_path), f"{container}:{AGENT_CA_PATH}"],
+        stdout=subprocess.DEVNULL,
+        check=True,
+    )
+    subprocess.run(
+        ["docker", "exec", "-u", "0", container, "chmod", "644", AGENT_CA_PATH],
+        stdout=subprocess.DEVNULL,
+        check=True,
+    )
+    subprocess.run(
+        ["docker", "exec", "-u", "0", container, "update-ca-certificates"],
+        stdout=subprocess.DEVNULL,
+        check=True,
+    )
+
+    # Stdlib SHA-256 of the cert's DER bytes — the standard
+    # fingerprint form. Never the private key.
+    der = ssl.PEM_cert_to_DER_cert(cert_host_path.read_text())
+    fingerprint = hashlib.sha256(der).hexdigest()
+    info(f"pipelock ca fingerprint: sha256:{fingerprint[:32]}...")