fix(install): honor HEADROOM_PORT in install apply and deploy (#3085)

## Description

`headroom install apply --preset persistent-service` and `headroom
deploy` ignored an explicit `HEADROOM_PORT` and always configured port
8787, even though `headroom proxy --port` honors `HEADROOM_PORT`. Anyone
running a second instance, or avoiding a port conflict, got a silently
wrong configuration, and the failure is especially confusing because the
override *appears* supported on the direct proxy path.

Root cause: the `--port` options on the `install apply` and `deploy`
commands were declared with a hardcoded `default=8787` and **no**
`envvar` binding:

```python
@click.option("--port", "-p", default=8787, type=int, show_default=True, help="Persistent proxy port.")
```

The proxy command's `--port` already carries `envvar="HEADROOM_PORT"`,
so the two paths disagreed. `build_manifest` /
`_build_deployment_manifest` already thread the `port` argument all the
way through to the generated `HEADROOM_PORT` base-env and the health
URL, so the value was simply never resolved from the environment at the
CLI boundary.

## Fix

Bind both `--port` options to `envvar="HEADROOM_PORT"`, matching the
proxy command. Click resolves the value from the environment when
`--port` is not passed, and an explicit `--port` still wins over the env
var (standard Click precedence: explicit CLI argument over `envvar` over
`default`).

## Scope

This addresses **bug 1** of #3072. Bug 2 (`install status` reporting
`Status: stopped` alongside `Healthy: yes`, disagreeing with `doctor`)
is an unrelated status-reporting concern that the reporter offered a
live repro for; it is left for a separate follow-up rather than bundled
here.

## Type of Change

- [x] Bug fix (non-breaking change that fixes an issue)
- [ ] New feature
- [ ] Breaking change
- [ ] Documentation update
- [ ] Performance improvement
- [ ] Code refactoring (no functional changes)

## Changes Made

- `headroom/cli/install.py`: add `envvar="HEADROOM_PORT"` to the
`--port` option on both `install apply` and `deploy` (and note the env
var in each help string), matching `headroom proxy --port`.
- `tests/test_cli/test_install_cli.py`: added
`test_install_apply_honors_headroom_port_env`,
`test_install_apply_explicit_port_overrides_env`, and
`test_deploy_honors_headroom_port_env`, capturing the `port` that
reaches the manifest builder.

## Testing

- [x] Unit tests pass (`pytest`)
- [x] Linting passes (`ruff check`)
- [x] Type checking passes (`mypy`)
- [x] New tests added

### Test Output

```text
tests/test_cli/test_install_cli.py  40 passed
# uvx ruff@0.15.22 check  -> All checks passed!
# uvx mypy@1.20.2 headroom/cli/install.py -> Success: no issues found in 1 source file
```

## Real Behavior Proof

- Environment: Windows 11, Python 3.12.11, project venv, pytest 9.1.1,
ruff 0.15.22 and mypy 1.20.2 via uvx.
- Exact command / steps: reverted the source fix and ran the two new
env-var tests to capture the bug (`python -m pytest
tests/test_cli/test_install_cli.py::test_install_apply_honors_headroom_port_env
tests/test_cli/test_install_cli.py::test_deploy_honors_headroom_port_env`
-> both failed with `assert 8787 == 8788`, proving `HEADROOM_PORT=8788`
was dropped); restored the fix; re-ran the full file (`python -m pytest
tests/test_cli/test_install_cli.py` -> 40 passed); then `uvx
ruff@0.15.22 format`, `uvx ruff@0.15.22 check`, and `uvx mypy@1.20.2
headroom/cli/install.py`.
- Observed result: with the fix, `HEADROOM_PORT=8788 headroom install
apply` (and `deploy`) resolves `port=8788` into `build_manifest`, so the
generated service config and `HEADROOM_PORT` base-env use 8788; passing
`--port 9999` alongside the env var still yields 9999.
- Not tested: an end-to-end persistent-service install on a machine with
a running supervisor (the CLI-to-manifest port resolution is verified
through the manifest builder, which already owns the downstream wiring
covered by the existing planner tests).

## Runtime Rollout Safety

- Rollout-managed feature(s): none. This is a CLI option-binding fix on
the install/deploy commands, not a rollout-channel-gated runtime
feature.
- Minimum rollout channel: N/A (no rollout-managed behavior).
- Stable/default behavior changed: only when `HEADROOM_PORT` is set in
the environment. Previously it was ignored (config wired to 8787); now
the install/deploy path honors it, matching `headroom proxy`. With no
`HEADROOM_PORT` set and no `--port`, the default is still 8787, so
existing installs are unaffected.
- Kill switch / disable path: unset `HEADROOM_PORT` (or pass `--port
8787`) to keep the prior port.
- Unsafe override required: no.
- Qualification impact: `install apply` / `deploy` now provision the
proxy on the operator's requested port instead of always 8787, so a
second instance or a port-conflict workaround configures correctly.
- Rollback path: revert this PR; the `--port` options return to ignoring
`HEADROOM_PORT`.

## Review Readiness

- [x] I have performed a self-review
- [x] This PR is ready for human review

## Checklist

- [x] My code follows the project's style guidelines
- [x] I have performed a self-review of my code
- [x] I have commented my code, particularly in hard-to-understand areas
- [x] My changes generate no new warnings
- [x] I have added tests that prove my fix is effective
- [x] New and existing unit tests pass locally with my changes
- [x] I did **not** edit `CHANGELOG.md`: it is generated by
release-please from my Conventional Commit PR title

## Additional Notes

Reported by @vsg-prog (split out of #3040 into #3072). The `--port`
option already carried the correct `type`/range validation and threaded
through the manifest builder; the only gap was the missing `envvar`
binding at the CLI boundary.

Author: abhay-codes07

headroom/cli/install.py

@@ -505,9 +505,10 @@ def _echo_installed(manifest: DeploymentManifest, *, prefix: str = "Installed pe
     "--port",
     "-p",
     default=8787,
+    envvar="HEADROOM_PORT",
     type=click.IntRange(1, 65535),
     show_default=True,
-    help="Persistent proxy port.",
+    help="Persistent proxy port (env: HEADROOM_PORT).",
 )
 @click.option(
     "--backend",
@@ -682,7 +683,13 @@ def install_apply(
 @main.command("deploy")
 @click.option("--profile", default="default", show_default=True, help="Deployment profile name.")
 @click.option(
-    "--port", "-p", default=8787, type=int, show_default=True, help="Persistent proxy port."
+    "--port",
+    "-p",
+    default=8787,
+    envvar="HEADROOM_PORT",
+    type=int,
+    show_default=True,
+    help="Persistent proxy port (env: HEADROOM_PORT).",
 )
 @click.option(
     "--backend",

tests/test_cli/test_install_cli.py

@@ -250,6 +250,104 @@ def fake_build_manifest(**kwargs):
     assert captured["no_http2"] is True
 
 
+def _patch_apply_pipeline(monkeypatch, captured: dict[str, object]):
+    """Stub out the apply side effects and capture ``build_manifest`` kwargs."""
+
+    class Manifest:
+        profile = "default"
+        preset = "persistent-service"
+        runtime_kind = "python"
+        supervisor_kind = "service"
+        scope = "user"
+        health_url = "http://127.0.0.1:8787/readyz"
+        targets = ["claude"]
+        mutations: list = []
+        artifacts: list = []
+
+    def fake_build_manifest(**kwargs):
+        captured.update(kwargs)
+        return Manifest()
+
+    monkeypatch.setattr("headroom.cli.install.build_manifest", fake_build_manifest)
+    monkeypatch.setattr("headroom.cli.install.load_manifest", lambda profile: None)
+    monkeypatch.setattr("headroom.cli.install.apply_mutations", lambda deployment: [])
+    monkeypatch.setattr("headroom.cli.install.install_supervisor", lambda deployment: [])
+    monkeypatch.setattr("headroom.cli.install.save_manifest", lambda deployment: None)
+    monkeypatch.setattr("headroom.cli.install.start_supervisor", lambda deployment: None)
+    monkeypatch.setattr("headroom.cli.install.start_detached_agent", lambda profile: None)
+    monkeypatch.setattr(
+        "headroom.cli.install.wait_ready", lambda deployment, timeout_seconds=45: True
+    )
+
+
+def test_install_apply_honors_headroom_port_env(monkeypatch) -> None:
+    """An explicit HEADROOM_PORT must reach build_manifest, like `proxy --port` honors it.
+
+    Regression for #3072 bug 1: `install apply` ignored HEADROOM_PORT and always
+    configured 8787 because the --port option had no envvar binding.
+    """
+    captured: dict[str, object] = {}
+    _patch_apply_pipeline(monkeypatch, captured)
+    monkeypatch.setenv("HEADROOM_PORT", "8788")
+
+    result = CliRunner().invoke(main, ["install", "apply"])
+
+    assert result.exit_code == 0, result.output
+    assert captured["port"] == 8788
+
+
+def test_install_apply_explicit_port_overrides_env(monkeypatch) -> None:
+    """An explicit --port still wins over HEADROOM_PORT (Click precedence)."""
+    captured: dict[str, object] = {}
+    _patch_apply_pipeline(monkeypatch, captured)
+    monkeypatch.setenv("HEADROOM_PORT", "8788")
+
+    result = CliRunner().invoke(main, ["install", "apply", "--port", "9999"])
+
+    assert result.exit_code == 0, result.output
+    assert captured["port"] == 9999
+
+
+def test_deploy_honors_headroom_port_env(monkeypatch) -> None:
+    """`headroom deploy` must honor HEADROOM_PORT the same way (#3072 bug 1)."""
+    captured: dict[str, object] = {}
+
+    plan = SimpleNamespace(
+        preset="persistent-service",
+        runtime="python",
+        reason="test",
+        supervisor_kind="service",
+        base_env={},
+    )
+    manifest = SimpleNamespace(
+        profile="default",
+        preset="persistent-service",
+        runtime_kind="python",
+        supervisor_kind="service",
+        scope="user",
+        port=0,
+        health_url="http://127.0.0.1:8788/readyz",
+        targets=["claude"],
+    )
+
+    def fake_build(**kwargs):
+        captured.update(kwargs)
+        return manifest
+
+    monkeypatch.setattr(
+        "headroom.cli.install._select_turnkey_plan", lambda prefer_docker=True: plan
+    )
+    monkeypatch.setattr("headroom.cli.install._build_deployment_manifest", fake_build)
+    monkeypatch.setattr("headroom.cli.install._apply_manifest", lambda m: None)
+    monkeypatch.setattr("headroom.cli.install._echo_installed", lambda m, prefix="": None)
+    monkeypatch.setenv("HEADROOM_PORT", "8788")
+
+    result = CliRunner().invoke(main, ["deploy"])
+
+    assert result.exit_code == 0, result.output
+    assert captured["port"] == 8788
+
+
 def test_install_apply_help_lists_no_http2() -> None:
     runner = CliRunner()