Claude Code transcript - page 1/2

Please take a look at issue #35..

$ Bash
View GitHub issue #35
gh issue view 35
title:	Add end to end tests
state:	OPEN
author:	dboreham
labels:	
comments:	0
assignees:	
projects:	
milestone:	
number:	35
--
Currently we don't have any tests that verify that the tool can actually create VMs at Digitalocean with associated DNS.
It should be reasonably straightforward to add such tests, provided there is a test digitalocean environment made available, test DNS zone and so on.
These tests would need to be runnable separately from the existing tests because for cost and run time reasons it wouldn't be reasonable to run them on every commit.
Thinking

Issue #35 requests end-to-end tests that verify the tool can actually create VMs on DigitalOcean with associated DNS. Key requirements:

  1. Tests should actually create/destroy VMs against a real DigitalOcean environment
  2. Need a test DO environment, test DNS zone, etc.
  3. Must be runnable separately from existing unit/integration tests (cost and runtime reasons)

Let me explore the existing test setup and codebase to understand what we're working with.

Agent
Explore codebase for e2e tests
{
  "subagent_type": "Explore",
  "prompt": "Explore this codebase thoroughly to understand:\n1. The existing test setup (find all test files, pytest config, test infrastructure)\n2. How the CLI creates VMs (the create subcommand flow, factory.py, cloud_config.py)\n3. How DNS is set up during VM creation\n4. The config file format (config.py, what keys are expected)\n5. How destroy works\n6. How list/status commands work\n7. Any existing fixtures or test helpers\n\nI need to understand enough to plan end-to-end tests that create real VMs on DigitalOcean.\n\nBe very thorough - read the key files in full."
}
Excellent! Now I have all the information I need. Let me create a comprehensive summary report of my findings.

---

## CODEBASE EXPLORATION SUMMARY

I've thoroughly explored the machine CLI codebase. Here's my comprehensive analysis:

### 1. EXISTING TEST SETUP

**Test Files:**
- `/home/david/projects/stirlingbridge/machine/tests/test_cli_integration.py` - Integration tests running CLI as subprocess
- `/home/david/projects/stirlingbridge/machine/tests/test_input_validation.py` - Input validation tests
- `/home/david/projects/stirlingbridge/machine/tests/test_config.py` - Config expansion tests
- `/home/david/projects/stirlingbridge/machine/tests/__init__.py` - Empty init file

**Test Infrastructure:**
- **Framework:** pytest (in dev dependencies)
- **Test command:** `uv run pytest tests/ -v` (also in Makefile as `make test`)
- **CI/CD:** GitHub Actions workflow `.github/workflows/test.yml` runs tests on push and PR to main
- **No pytest.ini:** Uses default pytest discovery (tests/ directory)
- **Test patterns:**
  - `run_machine(*args, env_override=None)` - Helper that runs CLI as subprocess via `uv run machine`
  - `write_config(path, content)` - Helper that writes YAML config to files
  - Tests use `tmp_path` pytest fixture for temporary config files
  - Tests check stdout/stderr and return codes

**Existing Test Coverage:**
- Version command smoke tests
- Environment variable expansion in config (${VAR} syntax)
- Invalid machine type error handling
- Missing config section validation
- Missing required config keys validation
- --no-initialize flag edge cases (no traceback on missing user_data)

### 2. VM CREATION FLOW (CREATE SUBCOMMAND)

**File:** `/home/david/projects/stirlingbridge/machine/machine/subcommands/create.py`

**Complete Flow:**
1. **Load context & config** from CLI options
2. **Validate inputs:**
   - Region validation against hardcoded list: `NYC1`, `NYC3`, `AMS3`, `SFO2`, `SFO3`, `SGP1`, `LON1`, `FRA1`, `TOR1`, `BLR1`, `SYD1`
   - Image validation (warning only for unknown images)
   - DNS zone check if `--update-dns` requested
3. **Get SSH key** from DigitalOcean (by name) - required for droplet creation
4. **Generate cloud-init user-data** (if `--initialize` flag set):
   - Calls `get_user_data()` from cloud_config.py
   - Creates non-root user with sudo access
   - Installs SSH public key
   - Optionally downloads and runs initialization script
5. **Create droplet** via python-digitalocean API:
   - Name, region, image, size_slug from config or CLI overrides
   - SSH key and user-data
   - Tags: session ID, machine:created, machine:type:*, custom tags
   - `backups=False`
6. **Assign to project** (if configured):
   - Looks up project by name
   - Assigns droplet resource to project
7. **Wait for IP address** (if `--wait-for-ip` or `--update-dns`):
   - Polls droplet.load() every 1 second until ip_address assigned
8. **Create DNS record** (if `--update-dns` and ip_address obtained):
   - Creates A record in dns_zone: `name.<zone>`
   - TTL: 5 minutes (300 seconds)
   - Record tag: `machine:created`

**CLI Options:**
- `--name` (required): Droplet name
- `--type` (required if `--initialize`): Machine type from config
- `--tag`: Custom tag to add
- `--region`: Override config default
- `--machine-size` / `--image`: Override config defaults
- `--wait-for-ip`: Wait for IP assignment
- `--update-dns` (default=True): Create DNS record
- `--initialize` (default=True): Use cloud-init user-data

### 3. CLOUD CONFIG GENERATION

**File:** `/home/david/projects/stirlingbridge/machine/machine/cloud_config.py`

**Function:** `get_user_data(manager, ssh_key_name, fqdn, machine_config) -> str`

**Output:** cloud-config YAML user-data for cloud-init

**Structure:**
```
users:
  - name: <new_user_name>
    groups: sudo
    shell: /bin/bash
    sudo: ['ALL=(ALL) NOPASSWD:ALL']
    ssh-authorized-keys:
      - <ssh_public_key>

runcmd: (optional, if script_url && script_dir && script_path)
  - mkdir -p <script_dir>
  - curl -L <script_url> -o <script_path>
  - chmod +x <script_path>
  - [su, -c, "env MACHINE_SCRIPT_URL=... MACHINE_SCRIPT_DIR=... MACHINE_FQDN=... <script_path> <script_args>", -, <new_user_name>]
```

**Available Variables (in script-args):**
- `$MACHINE_SCRIPT_URL` - Script URL
- `$MACHINE_SCRIPT_DIR` - Script directory
- `$MACHINE_FQDN` - FQDN (e.g., myvm.example.com)

**Notes:**
- Script runs as the new user (via `su`)
- Arguments expanded with environment variables before escaping
- Quotes in script-args escaped properly

### 4. CONFIG FILE FORMAT

**Path:** `~/.machine/config.yml` (or override with `--config-file`)

**File:** `/home/david/projects/stirlingbridge/machine/machine/config.py`

**Structure:**
```yaml
digital-ocean:
  access-token: <string>          # Required
  ssh-key: <string>               # Required - SSH key name
  dns-zone: <string>              # Optional - for DNS operations
  machine-size: <string>          # Required - e.g., s-1vcpu-1gb
  image: <string>                 # Required - e.g., ubuntu-22-04-x64
  region: <string>                # Required - e.g., nyc1
  project: <string>               # Optional - DO project name

machines:
  <type-name>:                     # Any custom name
    new-user-name: <string>        # Required
    script-url: <string>           # Optional
    script-dir: <string>           # Optional
    script-path: <string>          # Optional
    script-args: <string>          # Optional
```

**Config Data Classes:**
- `Config` (dataclass): `access_token`, `ssh_key`, `dns_zone`, `machine_size`, `image`, `region`, `project`
- `MachineConfig` (dataclass): `new_user_name`, `script_url`, `script_dir`, `script_path`, `script_args`

**Environment Variable Expansion:**
- Syntax: `${VAR}` or `${VAR:-default}`
- Applied recursively to all config values (strings, dicts, lists)
- Works in both digital-ocean and machines sections
- Missing var without default = fatal error
- Uses regex pattern: `\$\{([^}]+)\}`
- Handles `:-` syntax for defaults

**Validation:**
- `digital-ocean` section required
- `access-token`, `ssh-key`, `machine-size`, `image`, `region` required in digital-ocean
- `machines` section required for create command
- Each machine must have `new-user-name`
- All script-related fields optional but must all be present or all absent for cloud-init script

### 5. DESTROY FLOW

**File:** `/home/david/projects/stirlingbridge/machine/machine/subcommands/destroy.py`

**For Each Droplet:**
1. **Get droplet** by ID from DigitalOcean
2. **Safety checks** (unless `--all`):
   - Must have `machine:created` tag
   - Must have session ID tag matching current session
3. **Confirmation** (default=True):
   - Requires exact typing of "YES" (not "y" or "yes")
   - Skip with `--no-confirm`
4. **Destroy droplet** via python-digitalocean API
5. **Delete DNS record** (if `--delete-dns` and dns_zone configured):
   - Looks up record by name
   - Deletes by record ID

**CLI Options:**
- `--confirm` (default=True): Require user confirmation
- `--delete-dns` (default=True): Remove associated DNS records
- `--all`: Skip safety checks (destroy even non-machine-created droplets)
- Positional: One or more droplet IDs

### 6. LIST & STATUS COMMANDS

**List Command** (`/home/david/projects/stirlingbridge/machine/machine/subcommands/list.py`):
- **Filter options:** `--id`, `--name`, `--tag`, `--type`, `--region`, `--all`
- **Output formats:** default, `--quiet`, `--output json`
- **Default filtering:** Current session only (unless `--all`)
- **Filtering logic:** API call with session tag, then client-side filtering for other fields
- **Output:** `name (id, region, type): ip_address` or JSON with id, name, tags, region, ip, type
- **Unique check:** `--unique` flag errors if >1 match

**Status Command** (`/home/david/projects/stirlingbridge/machine/machine/subcommands/status.py`):
- **Same filtering** as list command
- **Additional query:** HTTP GET to `http://<ip>:4242/cgi-bin/<status-check>` (default: cloud-init-status)
- **Expected response:** JSON with `{"status": "..."}`
- **Status output:** droplet-status + custom status-check result or "UNKNOWN"
- **Output formats:** default table or JSON

**List Domain** (`/home/david/projects/stirlingbridge/machine/machine/subcommands/list_domain.py`):
- **Zone argument:** Required or from config
- **Filter options:** `--name`, `--type` (default A and AAAA), `--all`
- **Output formats:** default, `--quiet`, `--output json`
- **Default filtering:** Session-based (only records matching session's droplet IPs)
- **Output:** `name\ttype\tdata` or JSON

**Other List Commands:**
- `domains.py` - List all DNS zones
- `ssh_keys.py` - List SSH keys: `id: name (fingerprint)`
- `projects.py` - List DigitalOcean projects
- `types.py` - List configured machine types from config file

### 7. TAGGING & SESSION MANAGEMENT

**Tags applied to droplets:**
- `machine:created` - Identifies machine created by this tool
- `machine:session:<session-id>` - 8-char UUID hex session ID
- `machine:type:<machine-type>` - Lower-cased machine type name
- Custom tags from `--tag` flag

**Session ID:**
- Auto-generated: 8-char random UUID (hex only)
- Stored in: `~/.machine/session-id.yml`
- File format: `id: <session-id>`
- Can be overridden with global `--session-id` option
- Persists across invocations

**Filtering by Session:**
- Most commands default to current session only
- `--all` flag includes machines from all sessions or not created by tool

### 8. UTILITY FUNCTIONS

**File:** `/home/david/projects/stirlingbridge/machine/machine/util.py`

**Key Functions:**
- `projectFromName(manager, name) -> Project` - Find project by name
- `sshKeyFromName(manager, name) -> SSHKey` - Find SSH key by name
- `dnsRecordIdFromName(domain, name) -> str` - Find DNS record ID by name
- `get_machine_type(droplet) -> str` - Extract machine type from tags
- `is_machine_created(droplet) -> bool` - Check for machine:created tag
- `is_same_session(command_context, droplet) -> bool` - Check session ID tag match
- `load_session_id() -> str` - Load or generate session ID
- `droplet_to_json_obj(droplet) -> dict` - Convert droplet to JSON-serializable dict
- `dns_record_to_json_obj(dns_record, zone, droplet) -> dict` - Convert DNS record to JSON

### 9. DEPENDENCY INJECTION & GLOBALS

**File:** `/home/david/projects/stirlingbridge/machine/machine/di.py`

**Simple pattern:** Class `d` with class variable `opt: CliOptions`
- Set in main.py once at startup
- Used throughout for debug/quiet/verbose/dry-run flags
- Note: `--dry-run` flag set but never used in actual implementation

### 10. ARCHITECTURE & KEY INSIGHTS

**CLI Framework:** Click 8.1.7
- Context object carries `MainCmdCtx` with config and session_id
- Global `d.opt` for CLI options
- Commands organized in subcommands/ directory

**Config Loading:**
- Lazy loaded first time needed
- Cached in `_loaded_config.c` class variable
- Environment variable expansion applied on load

**Error Handling:**
- `fatal_error()` prints to stderr and exits(1)
- Input validation prevents tracebacks (graceful error messages)
- Missing config sections caught early

**Cloud Provider Integration:**
- python-digitalocean 1.17.0 library
- Direct API calls, no abstraction layer
- Polling for IP address (1-second intervals)
- Exceptions caught for DNS operations (NotFoundError)

**DNS Integration:**
- Optional feature (controlled by `dns_zone` config + `--update-dns` flag)
- Uses DigitalOcean Domain API
- A records with 5-minute TTL
- Records tagged with `machine:created` for tracking
- Deletion on droplet destroy

### 11. END-TO-END TEST PLANNING CONSIDERATIONS

For real DigitalOcean integration tests:

1. **Test Fixtures Needed:**
   - Real DO API token (env var)
   - Real SSH key name in DO account
   - Real DNS zone (optional)
   - Real DO project (optional)

2. **Droplet Lifecycle:**
   - Create waits for IP (1-second polls)
   - DNS record takes time to propagate
   - Droplet teardown is instant (no waiting)

3. **Idempotency Challenges:**
   - Droplet names must be unique
   - DNS records must be cleaned up
   - Use session IDs or timestamps to avoid conflicts

4. **Test Isolation:**
   - Each test should use unique droplet/DNS names
   - Use session override to group test droplets
   - Ensure cleanup (even on test failure)

5. **Async Considerations:**
   - IP assignment can take 5-10 seconds
   - DNS propagation variable
   - Cloud-init script execution time variable

6. **Safety:**
   - Confirm destroy requires "YES" (not automatable)
   - Can use `--no-confirm` in tests
   - Session-based filtering provides safety isolation

7. **Validation Points:**
   - Droplet exists with correct name/tags
   - IP address assigned
   - DNS record created with correct values
   - Cloud-init executed (script output, user created)
   - Droplet destroyed
   - DNS record deleted

---

**Key File Locations:**
- Entry point: `/home/david/projects/stirlingbridge/machine/machine/main.py`
- Create command: `/home/david/projects/stirlingbridge/machine/machine/subcommands/create.py`
- Destroy command: `/home/david/projects/stirlingbridge/machine/machine/subcommands/destroy.py`
- Config parsing: `/home/david/projects/stirlingbridge/machine/machine/config.py`
- Cloud-init generation: `/home/david/projects/stirlingbridge/machine/machine/cloud_config.py`
- Utilities: `/home/david/projects/stirlingbridge/machine/machine/util.py`
- Test directory: `/home/david/projects/stirlingbridge/machine/tests/`
- Type definitions: `/home/david/projects/stirlingbridge/machine/machine/types.py`
agentId: a42a54498e70cd939 (for resuming to continue this agent's work if needed)
<usage>total_tokens: 47674
tool_uses: 38
duration_ms: 70899</usage>
Thinking

Let me check the existing test infrastructure and Makefile for integration points.

Read
{
  "file_path": "/home/david/projects/stirlingbridge/machine/tests/test_cli_integration.py"
}
     1→"""Integration tests that run the machine CLI as a subprocess, the same way a user would."""
     2→
     3→import os
     4→import subprocess
     5→import textwrap
     6→import pytest
     7→
     8→
     9→def run_machine(*args, env_override=None):
    10→    """Run the machine CLI as a subprocess and return the result."""
    11→    env = os.environ.copy()
    12→    if env_override:
    13→        env.update(env_override)
    14→    result = subprocess.run(
    15→        ["uv", "run", "machine"] + list(args),
    16→        capture_output=True,
    17→        text=True,
    18→        env=env,
    19→    )
    20→    return result
    21→
    22→
    23→def write_config(path, content):
    24→    with open(path, "w") as f:
    25→        f.write(textwrap.dedent(content))
    26→
    27→
    28→class TestVersionCommand:
    29→    """Smoke test: the CLI runs and the version command works without any config."""
    30→
    31→    def test_version_runs(self):
    32→        result = run_machine("version")
    33→        assert result.returncode == 0
    34→        assert result.stdout.strip()  # prints something
    35→
    36→    def test_help_runs(self):
    37→        result = run_machine("--help")
    38→        assert result.returncode == 0
    39→        assert "Usage" in result.stdout
    40→
    41→
    42→class TestEnvVarExpansionIntegration:
    43→    """End-to-end tests that verify environment variable expansion works
    44→    when the actual machine tool is invoked with a config file."""
    45→
    46→    @pytest.fixture()
    47→    def config_dir(self, tmp_path):
    48→        return tmp_path
    49→
    50→    def test_env_var_expanded_in_config(self, config_dir):
    51→        config_file = config_dir / "config.yml"
    52→        write_config(
    53→            config_file,
    54→            """\
    55→            digital-ocean:
    56→              access-token: "${TEST_DO_TOKEN}"
    57→              ssh-key: test-key
    58→              machine-size: s-1vcpu-1gb
    59→              image: ubuntu-22-04-x64
    60→              region: nyc1
    61→              project: test-project
    62→            machines:
    63→              test-machine:
    64→                new-user-name: testuser
    65→            """,
    66→        )
    67→        result = run_machine(
    68→            "--debug",
    69→            "--config-file",
    70→            str(config_file),
    71→            "types",
    72→            env_override={"TEST_DO_TOKEN": "tok_secret_12345"},
    73→        )
    74→        assert result.returncode == 0
    75→        # The debug output on stderr should contain the expanded token value
    76→        assert "tok_secret_12345" in result.stderr
    77→        # And should NOT contain the unexpanded variable reference
    78→        assert "${TEST_DO_TOKEN}" not in result.stderr
    79→        # The types command should list the machine name on stdout
    80→        assert "test-machine" in result.stdout
    81→
    82→    def test_multiple_env_vars_expanded(self, config_dir):
    83→        config_file = config_dir / "config.yml"
    84→        write_config(
    85→            config_file,
    86→            """\
    87→            digital-ocean:
    88→              access-token: "${TEST_TOKEN}"
    89→              ssh-key: "${TEST_SSH_KEY}"
    90→              machine-size: s-1vcpu-1gb
    91→              image: ubuntu-22-04-x64
    92→              region: nyc1
    93→              project: test-project
    94→            machines:
    95→              dev:
    96→                new-user-name: devuser
    97→            """,
    98→        )
    99→        result = run_machine(
   100→            "--debug",
   101→            "--config-file",
   102→            str(config_file),
   103→            "types",
   104→            env_override={"TEST_TOKEN": "expanded_token", "TEST_SSH_KEY": "expanded_key"},
   105→        )
   106→        assert result.returncode == 0
   107→        assert "expanded_token" in result.stderr
   108→        assert "expanded_key" in result.stderr
   109→
   110→    def test_env_var_with_default_uses_default_when_unset(self, config_dir):
   111→        config_file = config_dir / "config.yml"
   112→        write_config(
   113→            config_file,
   114→            """\
   115→            digital-ocean:
   116→              access-token: fake-token
   117→              ssh-key: test-key
   118→              machine-size: "${TEST_SIZE:-s-2vcpu-4gb}"
   119→              image: ubuntu-22-04-x64
   120→              region: nyc1
   121→              project: test-project
   122→            machines:
   123→              myvm:
   124→                new-user-name: admin
   125→            """,
   126→        )
   127→        # Make sure TEST_SIZE is not in the environment
   128→        clean_env = os.environ.copy()
   129→        clean_env.pop("TEST_SIZE", None)
   130→        result = run_machine(
   131→            "--debug",
   132→            "--config-file",
   133→            str(config_file),
   134→            "types",
   135→            env_override={},
   136→        )
   137→        # Run with TEST_SIZE explicitly removed
   138→        result = subprocess.run(
   139→            ["uv", "run", "machine", "--debug", "--config-file", str(config_file), "types"],
   140→            capture_output=True,
   141→            text=True,
   142→            env=clean_env,
   143→        )
   144→        assert result.returncode == 0
   145→        assert "s-2vcpu-4gb" in result.stderr
   146→
   147→    def test_env_var_with_default_uses_value_when_set(self, config_dir):
   148→        config_file = config_dir / "config.yml"
   149→        write_config(
   150→            config_file,
   151→            """\
   152→            digital-ocean:
   153→              access-token: fake-token
   154→              ssh-key: test-key
   155→              machine-size: "${TEST_SIZE:-s-2vcpu-4gb}"
   156→              image: ubuntu-22-04-x64
   157→              region: nyc1
   158→              project: test-project
   159→            machines:
   160→              myvm:
   161→                new-user-name: admin
   162→            """,
   163→        )
   164→        result = run_machine(
   165→            "--debug",
   166→            "--config-file",
   167→            str(config_file),
   168→            "types",
   169→            env_override={"TEST_SIZE": "s-4vcpu-8gb"},
   170→        )
   171→        assert result.returncode == 0
   172→        assert "s-4vcpu-8gb" in result.stderr
   173→        assert "s-2vcpu-4gb" not in result.stderr
   174→
   175→    def test_missing_env_var_without_default_exits_with_error(self, config_dir):
   176→        config_file = config_dir / "config.yml"
   177→        write_config(
   178→            config_file,
   179→            """\
   180→            digital-ocean:
   181→              access-token: "${DEFINITELY_NOT_SET_VAR}"
   182→              ssh-key: test-key
   183→              machine-size: s-1vcpu-1gb
   184→              image: ubuntu-22-04-x64
   185→              region: nyc1
   186→              project: test-project
   187→            machines:
   188→              myvm:
   189→                new-user-name: admin
   190→            """,
   191→        )
   192→        clean_env = os.environ.copy()
   193→        clean_env.pop("DEFINITELY_NOT_SET_VAR", None)
   194→        result = subprocess.run(
   195→            ["uv", "run", "machine", "--config-file", str(config_file), "types"],
   196→            capture_output=True,
   197→            text=True,
   198→            env=clean_env,
   199→        )
   200→        assert result.returncode != 0
   201→        assert "DEFINITELY_NOT_SET_VAR" in result.stderr
   202→
   203→    def test_env_var_in_machine_config_section(self, config_dir):
   204→        config_file = config_dir / "config.yml"
   205→        write_config(
   206→            config_file,
   207→            """\
   208→            digital-ocean:
   209→              access-token: fake-token
   210→              ssh-key: test-key
   211→              machine-size: s-1vcpu-1gb
   212→              image: ubuntu-22-04-x64
   213→              region: nyc1
   214→              project: test-project
   215→            machines:
   216→              web-server:
   217→                new-user-name: "${TEST_USERNAME}"
   218→              db-server:
   219→                new-user-name: admin
   220→            """,
   221→        )
   222→        result = run_machine(
   223→            "--debug",
   224→            "--config-file",
   225→            str(config_file),
   226→            "types",
   227→            env_override={"TEST_USERNAME": "deploy_user"},
   228→        )
   229→        assert result.returncode == 0
   230→        assert "deploy_user" in result.stderr
   231→        # Both machine types should be listed
   232→        assert "db-server" in result.stdout
   233→        assert "web-server" in result.stdout
   234→
Read
{
  "file_path": "/home/david/projects/stirlingbridge/machine/Makefile"
}
     1→# Setup dev environment
     2→dev:
     3→	uv sync
     4→
     5→build:
     6→	./sh/build-package.sh
     7→
     8→test:
     9→	uv run pytest tests/ -v
    10→
    11→lint:
    12→	uv run flake8
    13→
Read
{
  "file_path": "/home/david/projects/stirlingbridge/machine/pyproject.toml"
}
     1→[project]
     2→name = "machine"
     3→version = "1.0.0"
     4→description = "Utility for creating and managing VMs"
     5→readme = "README.md"
     6→license = "AGPL-3.0-only"
     7→requires-python = ">=3.8"
     8→authors = [
     9→    { name = "Stirlingbridge", email = "info@stirlingbridge.website" },
    10→]
    11→classifiers = [
    12→    "Programming Language :: Python :: 3.8",
    13→    "Operating System :: OS Independent",
    14→]
    15→dependencies = [
    16→    "click==8.1.7",
    17→    "python-digitalocean==1.17.0",
    18→    "ruamel.yaml>=0.17.32",
    19→    "requests==2.32.3",
    20→    "expandvars==1.0.0",
    21→]
    22→
    23→[project.scripts]
    24→machine = "machine.main:main"
    25→
    26→[project.urls]
    27→Homepage = "https://github.com/stirlingbridge/machine"
    28→
    29→[build-system]
    30→requires = ["hatchling"]
    31→build-backend = "hatchling.build"
    32→
    33→[dependency-groups]
    34→dev = [
    35→    "flake8",
    36→    "black",
    37→    "pytest",
    38→]
    39→

Now let me look at the create and destroy commands to understand exact CLI args and output.

Read
{
  "file_path": "/home/david/projects/stirlingbridge/machine/machine/subcommands/create.py"
}
     1→import click
     2→import digitalocean
     3→import time
     4→from machine.config import get_machine
     5→from machine.di import d
     6→from machine.log import fatal_error, info, debug, output
     7→from machine.types import MainCmdCtx, TAG_MACHINE_CREATED, TAG_MACHINE_TYPE_PREFIX
     8→from machine.util import projectFromName, sshKeyFromName
     9→from machine.cloud_config import get_user_data
    10→
    11→from machine.types import TAG_MACHINE_SESSION_PREFIX
    12→
    13→
    14→def _validate_region(region: str):
    15→    valid_regions = ["NYC1", "NYC3", "AMS3", "SFO2", "SFO3", "SGP1", "LON1", "FRA1", "TOR1", "BLR1", "SYD1"]
    16→    if region is not None and region.upper() not in valid_regions:
    17→        fatal_error(f"Error: region {region} is not one of {valid_regions}")
    18→
    19→
    20→def _validate_image(image: str):
    21→    valid_images = [
    22→        "almalinux-8-x64",
    23→        "almalinux-9-x64",
    24→        "centos-stream-9-x64",
    25→        "debian-11-x64",
    26→        "debian-12-x64",
    27→        "fedora-39-x64",
    28→        "fedora-40-x64",
    29→        "rockylinux-9-x64",
    30→        "rockylinux-8-x64",
    31→        "ubuntu-20-04-x64",
    32→        "ubuntu-22-04-x64",
    33→        "ubuntu-24-04-x64",
    34→    ]
    35→    if image is not None and image not in valid_images:
    36→        info(f"Warning: image {image} is not one of these known valid images: {valid_images}")
    37→
    38→
    39→@click.command(help="Create a machine")
    40→@click.option("--name", "-n", required=True, metavar="<MACHINE-NAME>", help="Name for new machine")
    41→@click.option("--tag", "-t", metavar="<TAG-TEXT>", help="tag to be applied to new machine")
    42→@click.option("--type", "-m", metavar="<MACHINE-TYPE>", help="create a machine of this type")
    43→@click.option("--region", "-r", metavar="<REGION-CODE>", help="create a machine in this region (overrides default from config)")
    44→@click.option(
    45→    "--machine-size", "-s", metavar="<MACHINE-SLUG>", help="create a machine of this size (overrides default from config)"
    46→)
    47→@click.option("--image", "-s", metavar="<IMAGE-NAME>", help="create a machine from this image (overrides default from config)")
    48→@click.option("--wait-for-ip/--no-wait-for-up", default=False)
    49→@click.option("--update-dns/--no-update-dns", default=True)
    50→@click.option("--initialize/--no-initialize", default=True)
    51→@click.pass_context
    52→def command(context, name, tag, type, region, machine_size, image, wait_for_ip, update_dns, initialize):
    53→    command_context: MainCmdCtx = context.obj
    54→    config = command_context.config
    55→
    56→    if update_dns and not config.dns_zone:
    57→        fatal_error("Error: DNS update requested but no zone configured")
    58→
    59→    manager = digitalocean.Manager(token=command_context.config.access_token)
    60→
    61→    user_data = None
    62→    if initialize:
    63→        if not type:
    64→            fatal_error("Error: a machine type must be supplied")
    65→        machine_config = get_machine(type)
    66→        if not machine_config:
    67→            fatal_error(f"Error: machine type {type} is not defined")
    68→        fqdn = f"{name}.{config.dns_zone}" if config.dns_zone else None
    69→        user_data = get_user_data(manager, config.ssh_key, fqdn, machine_config)
    70→        if d.opt.debug:
    71→            info("user-data is:")
    72→            info(user_data)
    73→
    74→    ssh_key = sshKeyFromName(manager, config.ssh_key)
    75→    if not ssh_key:
    76→        fatal_error(f"Error: SSH key '{config.ssh_key}' not found in DigitalOcean")
    77→
    78→    _validate_region(region)
    79→    _validate_image(image)
    80→
    81→    tags = [
    82→        TAG_MACHINE_SESSION_PREFIX + command_context.session_id,
    83→        TAG_MACHINE_CREATED,
    84→    ]
    85→    if type:
    86→        tags.append(TAG_MACHINE_TYPE_PREFIX + type.lower())
    87→    if tag:
    88→        tags.append(tag)
    89→
    90→    droplet = digitalocean.Droplet(
    91→        token=config.access_token,
    92→        name=name,
    93→        region=region if region is not None else config.region,
    94→        image=image if image is not None else config.image,
    95→        size_slug=machine_size if machine_size is not None else config.machine_size,
    96→        ssh_keys=[ssh_key],
    97→        tags=tags,
    98→        user_data=user_data,
    99→        backups=False,
   100→    )
   101→    # Create the droplet
   102→    # This call returns nothing, it modifies the droplet object
   103→    droplet.create()
   104→    if droplet.id:
   105→        if d.opt.quiet:
   106→            output(f"{droplet.id}")
   107→        else:
   108→            output(f"New droplet created with id: {droplet.id}")
   109→    # If requested, assign to a specified project
   110→    if config.project:
   111→        project_name = config.project
   112→        project = projectFromName(manager, project_name)
   113→        if not project:
   114→            fatal_error(f"Error: Project {project_name} does not exist, machine created but not assigned to project")
   115→        project.assign_resource([f"do:droplet:{droplet.id}"])
   116→        if d.opt.verbose:
   117→            info(f"Assigned droplet to project: {project}")
   118→    # If requested, or if we are going to set a DNS record get the droplet's IPv4 address
   119→    if wait_for_ip or update_dns:
   120→        ip_address = None
   121→        while not ip_address:
   122→            time.sleep(1)
   123→            droplet.load()
   124→            ip_address = droplet.ip_address
   125→            if d.opt.verbose:
   126→                output("Waiting for droplet IP address")
   127→        if d.opt.quiet:
   128→            info(f"{ip_address}")
   129→        else:
   130→            info(f"IP Address: {ip_address}")
   131→    # If requested, and we have the IP address, create a DNS host record for the droplet
   132→    if update_dns and ip_address and config.dns_zone:
   133→        zone = config.dns_zone
   134→        host = name
   135→        if d.opt.debug:
   136→            debug(f"Setting host record {host}.{zone} to {ip_address}")
   137→        domain = digitalocean.Domain(token=config.access_token, name=zone)
   138→        try:
   139→            record = domain.create_new_domain_record(type="A", ttl=60 * 5, name=host, data=ip_address, tag=TAG_MACHINE_CREATED)
   140→        except digitalocean.NotFoundError:
   141→            info(f"Warning: DNS zone '{zone}' not found in DigitalOcean, DNS record not set")
   142→            record = None
   143→        if record:
   144→            if d.opt.verbose:
   145→                info(f"Created DNS record:{record}")
   146→            if not d.opt.quiet:
   147→                info(f"DNS: {host}.{zone}")
   148→
Read
{
  "file_path": "/home/david/projects/stirlingbridge/machine/machine/subcommands/destroy.py"
}
Read
{
  "file_path": "/home/david/projects/stirlingbridge/machine/machine/subcommands/list.py"
}
     1→import click
     2→import digitalocean
     3→
     4→from machine.di import d
     5→from machine.log import debug, fatal_error, output
     6→from machine.util import dnsRecordIdFromName, is_machine_created
     7→from machine.types import MainCmdCtx
     8→
     9→from machine.util import is_same_session
    10→
    11→
    12→@click.command(help="Destroy one or more machines")
    13→@click.option("--confirm/--no-confirm", default=True)
    14→@click.option("--delete-dns/--no-delete-dns", default=True)
    15→@click.option(
    16→    "--all",
    17→    is_flag=True,
    18→    default=False,
    19→    help="Include machines not created by this tool",
    20→)
    21→@click.argument("droplet-ids", nargs=-1)
    22→@click.pass_context
    23→def command(context, confirm, delete_dns, all, droplet_ids):
    24→    command_context: MainCmdCtx = context.obj
    25→    config = command_context.config
    26→    manager = digitalocean.Manager(token=config.access_token)
    27→    for droplet_id in droplet_ids:
    28→        try:
    29→            droplet = manager.get_droplet(droplet_id)
    30→        except digitalocean.NotFoundError:
    31→            fatal_error(f"Error: machine with id {droplet_id} not found")
    32→        name = droplet.name
    33→
    34→        if not is_machine_created(droplet) and not all:
    35→            fatal_error(f'ERROR: Cannot destroy droplet "{name}" (id: {droplet.id}), it was not created by machine.')
    36→
    37→        if not is_same_session(command_context, droplet) and not all:
    38→            fatal_error(
    39→                f'ERROR: Cannot destroy droplet "{name}" (id: {droplet.id}), it was created by a different session of machine.'
    40→            )
    41→
    42→        if confirm:
    43→            output(
    44→                "Type YES (not y or yes or Yes) to confirm that you want to permanently"
    45→                f' DELETE/DESTROY droplet "{name}" (id: {droplet.id})'
    46→            )
    47→            confirmation = input()
    48→            if confirmation != "YES":
    49→                fatal_error("Destroy operation aborted, not confirmed by user")
    50→        result = droplet.destroy()
    51→
    52→        if result and delete_dns and config.dns_zone:
    53→            zone = config.dns_zone
    54→            if d.opt.debug:
    55→                debug(f"Deleting host record {name}.{zone}")
    56→            domain = digitalocean.Domain(token=config.access_token, name=zone)
    57→            if not domain:
    58→                fatal_error(f"Error: Domain {domain} does not exist, machine destroyed but DNS record not removed")
    59→            record_id = dnsRecordIdFromName(domain, name)
    60→            if record_id:
    61→                if d.opt.debug:
    62→                    debug(f"Deleting dns record id={record_id}")
    63→                domain.delete_domain_record(id=record_id)
    64→            else:
    65→                if d.opt.debug:
    66→                    debug(f"No dns record found for {name}.{zone}")
    67→
    68→        if not result:
    69→            fatal_error("Error destroying machine")
    70→
     1→import click
     2→import json
     3→import digitalocean
     4→
     5→from machine.log import fatal_error, output
     6→from machine.types import MainCmdCtx, TAG_MACHINE_TYPE_PREFIX, TAG_MACHINE_SESSION_PREFIX
     7→from machine.util import get_machine_type, is_machine_created, is_same_session, droplet_to_json_obj
     8→
     9→
    10→def print_normal(droplets):
    11→    for droplet in droplets:
    12→        region = droplet.region["slug"] if droplet.region else "unknown"
    13→        output(f"{droplet.name} ({droplet.id}, {region}, {get_machine_type(droplet)}): {droplet.ip_address}")
    14→
    15→
    16→def print_quiet(droplets):
    17→    for droplet in droplets:
    18→        output(droplet.id)
    19→
    20→
    21→def print_json(droplets):
    22→    output(json.dumps([droplet_to_json_obj(d) for d in droplets]))
    23→
    24→
    25→def get_droplets(command_context, id=None, name=None, tag=None, type=None, region=None, all=False):
    26→    manager = digitalocean.Manager(token=command_context.config.access_token)
    27→    droplets = []
    28→    if id:
    29→        droplet = manager.get_droplet(id)
    30→        if droplet:
    31→            droplets.append(droplet)
    32→
    33→    if all:
    34→        droplets = manager.get_all_droplets()
    35→    else:
    36→        droplets = manager.get_all_droplets(tag_name=TAG_MACHINE_SESSION_PREFIX + command_context.session_id)
    37→
    38→    # we can't combine most filters over the API, so we also filter ourselves
    39→    if name:
    40→        droplets = filter(lambda d: d.name == name, droplets)
    41→
    42→    if tag:
    43→        droplets = filter(lambda d: tag in d.tags, droplets)
    44→
    45→    if type:
    46→        droplets = filter(lambda d: TAG_MACHINE_TYPE_PREFIX + type.lower() in d.tags, droplets)
    47→
    48→    if region:
    49→        droplets = filter(lambda d: d.region and region == d.region["slug"], droplets)
    50→
    51→    if not all:
    52→        droplets = filter(lambda d: is_machine_created(d) and is_same_session(command_context, d), droplets)
    53→
    54→    return list(droplets)
    55→
    56→
    57→@click.command(help="List machines")
    58→@click.option("--id", metavar="<MACHINE-ID>", help="Filter by id")
    59→@click.option("--name", "-n", metavar="<MACHINE-NAME>", help="Filter by name")
    60→@click.option("--tag", "-t", metavar="<TAG-TEXT>", help="Filter by tag")
    61→@click.option("--type", "-m", metavar="<MACHINE-TYPE>", help="Filter by type")
    62→@click.option("--region", "-r", metavar="<REGION>", help="Filter by region")
    63→@click.option("--output", "-o", metavar="<FORMAT>", help="Output format")
    64→@click.option(
    65→    "--all",
    66→    is_flag=True,
    67→    default=False,
    68→    help="All machines, including those not created by this tool or by other sessions",
    69→)
    70→@click.option("--quiet", "-q", is_flag=True, default=False, help="Only display machine IDs")
    71→@click.option(
    72→    "--unique",
    73→    is_flag=True,
    74→    default=False,
    75→    help="Return an error if there is more than one match",
    76→)
    77→@click.pass_context
    78→def command(context, id, name, tag, type, region, all, output, quiet, unique):
    79→    command_context: MainCmdCtx = context.obj
    80→
    81→    droplets = get_droplets(command_context, id, name, tag, type, region, all)
    82→    if unique and len(droplets) > 1:
    83→        fatal_error(f"ERROR: --unique match required but {len(droplets)} matches found.")
    84→
    85→    if output == "json":
    86→        print_json(droplets)
    87→    elif quiet:
    88→        print_quiet(droplets)
    89→    else:
    90→        print_normal(droplets)
    91→
Thinking

Now I have a solid understanding. Let me implement the e2e tests.

Read
{
  "file_path": "/home/david/projects/stirlingbridge/machine/machine/types.py"
}
     1→from dataclasses import dataclass
     2→
     3→TAG_MACHINE_CREATED = "machine:created"
     4→TAG_MACHINE_TYPE_PREFIX = "machine:type:"
     5→TAG_MACHINE_SESSION_PREFIX = "machine:session:"
     6→
     7→
     8→@dataclass
     9→class CliOptions:
    10→    debug: bool
    11→    quiet: bool
    12→    verbose: bool
    13→    dry_run: bool
    14→
    15→
    16→@dataclass
    17→class Config:
    18→    access_token: str
    19→    ssh_key: str
    20→    dns_zone: str
    21→    machine_size: str
    22→    image: str
    23→    region: str
    24→    project: str
    25→
    26→
    27→@dataclass
    28→class MainCmdCtx:
    29→    config: Config
    30→    session_id: str
    31→
    32→
    33→@dataclass
    34→class MachineConfig:
    35→    new_user_name: str
    36→    script_url: str
    37→    script_dir: str
    38→    script_path: str
    39→    script_args: str
    40→

Now I'll create the e2e test file, update pyproject.toml with marker config, and add a Makefile target.

📝 Write test_e2e.py
/home/david/projects/stirlingbridge/machine/tests/test_e2e.py
"""End-to-end tests that create real VMs on DigitalOcean.

These tests require a real DigitalOcean environment and are NOT run as part of
the normal test suite. They must be invoked explicitly:

    uv run pytest tests/test_e2e.py -v

Required environment variables:
    E2E_DO_TOKEN    - DigitalOcean API token
    E2E_SSH_KEY     - Name of an SSH key already registered in DO
    E2E_DNS_ZONE    - DNS zone managed by DO (e.g. "test.example.com")

Optional environment variables:
    E2E_REGION      - Region slug (default: nyc1)
    E2E_IMAGE       - Image slug (default: ubuntu-24-04-x64)
    E2E_SIZE        - Machine size slug (default: s-1vcpu-512mb-10gb)
    E2E_PROJECT     - DO project name to assign droplets to
"""

import json
import os
import subprocess
import textwrap
import uuid

import pytest


# ---------------------------------------------------------------------------
# Skip the entire module if credentials are not provided
# ---------------------------------------------------------------------------

E2E_DO_TOKEN = os.environ.get("E2E_DO_TOKEN")
E2E_SSH_KEY = os.environ.get("E2E_SSH_KEY")
E2E_DNS_ZONE = os.environ.get("E2E_DNS_ZONE")
E2E_REGION = os.environ.get("E2E_REGION", "nyc1")
E2E_IMAGE = os.environ.get("E2E_IMAGE", "ubuntu-24-04-x64")
E2E_SIZE = os.environ.get("E2E_SIZE", "s-1vcpu-512mb-10gb")
E2E_PROJECT = os.environ.get("E2E_PROJECT", "")

pytestmark = pytest.mark.e2e

_MISSING = []
if not E2E_DO_TOKEN:
    _MISSING.append("E2E_DO_TOKEN")
if not E2E_SSH_KEY:
    _MISSING.append("E2E_SSH_KEY")
if not E2E_DNS_ZONE:
    _MISSING.append("E2E_DNS_ZONE")

if _MISSING:
    pytestmark = [
        pytest.mark.e2e,
        pytest.mark.skip(reason=f"E2E env vars not set: {', '.join(_MISSING)}"),
    ]


# ---------------------------------------------------------------------------
# Helpers
# ---------------------------------------------------------------------------


def _unique_name(prefix="e2etest"):
    """Generate a short unique droplet name safe for DNS."""
    return f"{prefix}-{uuid.uuid4().hex[:8]}"


def _write_config(path, **overrides):
    """Write a minimal config file for the e2e test run."""
    cfg = {
        "access-token": E2E_DO_TOKEN,
        "ssh-key": E2E_SSH_KEY,
        "dns-zone": E2E_DNS_ZONE,
        "machine-size": E2E_SIZE,
        "image": E2E_IMAGE,
        "region": E2E_REGION,
    }
    if E2E_PROJECT:
        cfg["project"] = E2E_PROJECT
    cfg.update(overrides)

    do_lines = "\n".join(f"  {k}: {v}" for k, v in cfg.items())
    content = textwrap.dedent(
        f"""\
        digital-ocean:
        {do_lines}
        machines:
          e2e-basic:
            new-user-name: e2euser
        """
    )
    with open(path, "w") as f:
        f.write(content)


def run_machine(*args, config_file=None, session_id=None):
    """Run the machine CLI as a subprocess with the given arguments."""
    cmd = ["uv", "run", "machine"]
    if config_file:
        cmd += ["--config-file", str(config_file)]
    if session_id:
        cmd += ["--session-id", session_id]
    cmd += list(args)
    result = subprocess.run(cmd, capture_output=True, text=True, timeout=300)
    return result


# ---------------------------------------------------------------------------
# Fixtures
# ---------------------------------------------------------------------------


@pytest.fixture(scope="module")
def config_file(tmp_path_factory):
    """Write a config file that lives for the whole test module."""
    path = tmp_path_factory.mktemp("e2e") / "config.yml"
    _write_config(path)
    return path


@pytest.fixture(scope="module")
def session_id():
    """A unique session id shared across all tests in this module."""
    return uuid.uuid4().hex[:8]


@pytest.fixture()
def droplet_cleanup(config_file, session_id):
    """Fixture that tracks created droplet IDs and destroys them after the test."""
    created_ids = []
    yield created_ids
    for did in created_ids:
        run_machine(
            "--verbose",
            "destroy",
            "--no-confirm",
            str(did),
            config_file=config_file,
            session_id=session_id,
        )


# ---------------------------------------------------------------------------
# Tests
# ---------------------------------------------------------------------------


class TestDropletLifecycle:
    """Create a droplet, verify it, then destroy it."""

    def test_create_and_list_and_destroy(self, config_file, session_id, droplet_cleanup):
        name = _unique_name()

        # ---- CREATE --------------------------------------------------------
        result = run_machine(
            "create",
            "--name",
            name,
            "--no-initialize",
            "--wait-for-ip",
            config_file=config_file,
            session_id=session_id,
        )
        assert result.returncode == 0, f"create failed: {result.stderr}"
        # Extract the droplet id from output like "New droplet created with id: 12345"
        create_out = result.stdout + result.stderr
        droplet_id = None
        for line in create_out.splitlines():
            if "id:" in line.lower():
                # grab the number after "id:"
                parts = line.split("id:")
                if len(parts) >= 2:
                    candidate = parts[-1].strip()
                    if candidate.isdigit():
                        droplet_id = candidate
                        break
        assert droplet_id, f"Could not find droplet id in output:\n{create_out}"
        droplet_cleanup.append(droplet_id)

        # ---- LIST ----------------------------------------------------------
        result = run_machine(
            "list",
            "--output",
            "json",
            config_file=config_file,
            session_id=session_id,
        )
        assert result.returncode == 0, f"list failed: {result.stderr}"
        droplets = json.loads(result.stdout)
        matched = [d for d in droplets if str(d["id"]) == droplet_id]
        assert len(matched) == 1, f"Expected 1 droplet with id {droplet_id}, got {len(matched)}"
        assert matched[0]["name"] == name
        assert matched[0]["ip"] is not None

        # ---- DESTROY -------------------------------------------------------
        result = run_machine(
            "destroy",
            "--no-confirm",
            droplet_id,
            config_file=config_file,
            session_id=session_id,
        )
        assert result.returncode == 0, f"destroy failed: {result.stderr}"
        # Remove from cleanup list since we already destroyed it
        droplet_cleanup.remove(droplet_id)

        # ---- VERIFY GONE ---------------------------------------------------
        result = run_machine(
            "list",
            "--output",
            "json",
            config_file=config_file,
            session_id=session_id,
        )
        assert result.returncode == 0
        droplets = json.loads(result.stdout)
        matched = [d for d in droplets if str(d["id"]) == droplet_id]
        assert len(matched) == 0, "Droplet still exists after destroy"


class TestDNSLifecycle:
    """Create a droplet with DNS, verify the record, then destroy and verify cleanup."""

    def test_create_with_dns_and_destroy(self, config_file, session_id, droplet_cleanup):
        name = _unique_name()

        # ---- CREATE with DNS -----------------------------------------------
        result = run_machine(
            "create",
            "--name",
            name,
            "--no-initialize",
            "--update-dns",
            config_file=config_file,
            session_id=session_id,
        )
        assert result.returncode == 0, f"create failed: {result.stderr}"
        create_out = result.stdout + result.stderr
        droplet_id = None
        for line in create_out.splitlines():
            if "id:" in line.lower():
                parts = line.split("id:")
                if len(parts) >= 2:
                    candidate = parts[-1].strip()
                    if candidate.isdigit():
                        droplet_id = candidate
                        break
        assert droplet_id, f"Could not find droplet id in output:\n{create_out}"
        droplet_cleanup.append(droplet_id)

        # Verify DNS was mentioned in output
        assert E2E_DNS_ZONE in create_out, f"DNS zone not mentioned in output:\n{create_out}"

        # ---- LIST DOMAIN ---------------------------------------------------
        result = run_machine(
            "list-domain",
            "--name",
            name,
            "--output",
            "json",
            E2E_DNS_ZONE,
            config_file=config_file,
            session_id=session_id,
        )
        assert result.returncode == 0, f"list-domain failed: {result.stderr}"
        records = json.loads(result.stdout)
        a_records = [r for r in records if r.get("name") == name and r.get("type") == "A"]
        assert len(a_records) >= 1, f"No A record found for {name}.{E2E_DNS_ZONE}"

        # ---- DESTROY with DNS cleanup --------------------------------------
        result = run_machine(
            "destroy",
            "--no-confirm",
            "--delete-dns",
            droplet_id,
            config_file=config_file,
            session_id=session_id,
        )
        assert result.returncode == 0, f"destroy failed: {result.stderr}"
        droplet_cleanup.remove(droplet_id)

        # ---- VERIFY DNS RECORD REMOVED -------------------------------------
        result = run_machine(
            "list-domain",
            "--name",
            name,
            "--all",
            "--output",
            "json",
            E2E_DNS_ZONE,
            config_file=config_file,
            session_id=session_id,
        )
        assert result.returncode == 0
        records = json.loads(result.stdout)
        a_records = [r for r in records if r.get("name") == name and r.get("type") == "A"]
        assert len(a_records) == 0, f"DNS A record still exists for {name}.{E2E_DNS_ZONE}"


class TestCreateWithInitialize:
    """Create a droplet with cloud-init and verify it was initialized."""

    def test_create_with_type(self, config_file, session_id, droplet_cleanup):
        name = _unique_name()

        # ---- CREATE with initialization ------------------------------------
        result = run_machine(
            "create",
            "--name",
            name,
            "--type",
            "e2e-basic",
            "--wait-for-ip",
            config_file=config_file,
            session_id=session_id,
        )
        assert result.returncode == 0, f"create failed: {result.stderr}"
        create_out = result.stdout + result.stderr
        droplet_id = None
        for line in create_out.splitlines():
            if "id:" in line.lower():
                parts = line.split("id:")
                if len(parts) >= 2:
                    candidate = parts[-1].strip()
                    if candidate.isdigit():
                        droplet_id = candidate
                        break
        assert droplet_id, f"Could not find droplet id in output:\n{create_out}"
        droplet_cleanup.append(droplet_id)

        # ---- VERIFY TYPE TAG -----------------------------------------------
        result = run_machine(
            "list",
            "--type",
            "e2e-basic",
            "--output",
            "json",
            config_file=config_file,
            session_id=session_id,
        )
        assert result.returncode == 0
        droplets = json.loads(result.stdout)
        matched = [d for d in droplets if str(d["id"]) == droplet_id]
        assert len(matched) == 1
        assert matched[0]["type"] == "e2e-basic"

        # ---- CLEANUP -------------------------------------------------------
        result = run_machine(
            "destroy",
            "--no-confirm",
            droplet_id,
            config_file=config_file,
            session_id=session_id,
        )
        assert result.returncode == 0, f"destroy failed: {result.stderr}"
        droplet_cleanup.remove(droplet_id)


class TestCustomTag:
    """Verify that custom tags are applied to created droplets."""

    def test_custom_tag(self, config_file, session_id, droplet_cleanup):
        name = _unique_name()
        custom_tag = f"e2e-tag-{uuid.uuid4().hex[:6]}"

        result = run_machine(
            "create",
            "--name",
            name,
            "--no-initialize",
            "--tag",
            custom_tag,
            "--wait-for-ip",
            config_file=config_file,
            session_id=session_id,
        )
        assert result.returncode == 0, f"create failed: {result.stderr}"
        create_out = result.stdout + result.stderr
        droplet_id = None
        for line in create_out.splitlines():
            if "id:" in line.lower():
                parts = line.split("id:")
                if len(parts) >= 2:
                    candidate = parts[-1].strip()
                    if candidate.isdigit():
                        droplet_id = candidate
                        break
        assert droplet_id
        droplet_cleanup.append(droplet_id)

        # Verify tag via list --tag filter
        result = run_machine(
            "list",
            "--tag",
            custom_tag,
            "--output",
            "json",
            config_file=config_file,
            session_id=session_id,
        )
        assert result.returncode == 0
        droplets = json.loads(result.stdout)
        matched = [d for d in droplets if str(d["id"]) == droplet_id]
        assert len(matched) == 1, f"Droplet not found with tag {custom_tag}"

        # Cleanup
        result = run_machine(
            "destroy",
            "--no-confirm",
            droplet_id,
            config_file=config_file,
            session_id=session_id,
        )
        assert result.returncode == 0
        droplet_cleanup.remove(droplet_id)
File created successfully at: /home/david/projects/stirlingbridge/machine/tests/test_e2e.py

Now update pyproject.toml to add pytest marker config so e2e doesn't produce warnings, and exclude e2e from default test runs.

✏️ Edit pyproject.toml
/home/david/projects/stirlingbridge/machine/pyproject.toml
[dependency-groups]
+
[tool.pytest.ini_options]
markers = [
    "e2e: end-to-end tests that create real resources on DigitalOcean (require E2E_* env vars)",
]
addopts = "-m 'not e2e'"

[dependency-groups]
The file /home/david/projects/stirlingbridge/machine/pyproject.toml has been updated successfully.

Add Makefile targets for e2e tests.

✏️ Edit Makefile
/home/david/projects/stirlingbridge/machine/Makefile
test:
	uv run pytest tests/ -v

lint:
+
test:
	uv run pytest tests/ -v

test-e2e:
	uv run pytest tests/test_e2e.py -v -m e2e

lint:
The file /home/david/projects/stirlingbridge/machine/Makefile has been updated successfully.

Let me verify the tests pass the linter and that existing tests still work with the e2e exclusion.

$ Bash
Lint the new e2e test file
uv run flake8 tests/test_e2e.py
$ Bash
Collect tests to verify e2e are excluded by default
uv run pytest tests/ -v --co 2>&1 | head -40
Using CPython 3.12.3 interpreter at: /usr/bin/python3
Creating virtual environment at: .venv
   Building machine @ file:///home/david/projects/stirlingbridge/machine
Downloading pygments (1.2MiB)
Downloading black (1.7MiB)
 Downloaded pygments
 Downloaded black
      Built machine @ file:///home/david/projects/stirlingbridge/machine
Installed 25 packages in 17ms
============================= test session starts ==============================
platform linux -- Python 3.12.3, pytest-9.0.2, pluggy-1.6.0 -- /home/david/projects/stirlingbridge/machine/.venv/bin/python
cachedir: .pytest_cache
rootdir: /home/david/projects/stirlingbridge/machine
configfile: pyproject.toml
collecting ... collected 33 items / 4 deselected / 29 selected

<Dir machine>
  <Package tests>
    <Module test_cli_integration.py>
      Integration tests that run the machine CLI as a subprocess, the same way a user would.
      <Class TestVersionCommand>
        Smoke test: the CLI runs and the version command works without any config.
        <Function test_version_runs>
        <Function test_help_runs>
      <Class TestEnvVarExpansionIntegration>
        End-to-end tests that verify environment variable expansion works
        when the actual machine tool is invoked with a config file.
        <Function test_env_var_expanded_in_config>
        <Function test_multiple_env_vars_expanded>
        <Function test_env_var_with_default_uses_default_when_unset>
        <Function test_env_var_with_default_uses_value_when_set>
        <Function test_missing_env_var_without_default_exits_with_error>
        <Function test_env_var_in_machine_config_section>
    <Module test_config.py>
      <Class TestExpandEnvVars>
        <Function test_plain_string_unchanged>
        <Function test_non_string_types_unchanged>
        <Function test_simple_variable_substitution>
        <Function test_variable_embedded_in_string>
        <Function test_multiple_variables_in_string>
        <Function test_default_value_when_var_unset>
        <Function test_default_value_ignored_when_var_set>
        <Function test_default_value_empty_string>
        <Function test_unset_variable_without_default_exits>
        <Function test_dict_values_expanded>
        <Function test_nested_dict_expanded>
        <Function test_list_values_expanded>
        <Function test_mixed_nested_structure>
    <Module test_input_validation.py>

Linting passes and the 4 e2e tests are correctly deselected from the default test run. Let me also verify the existing tests still pass.

$ Bash
Run existing tests to verify nothing broke
uv run pytest tests/ -v 2>&1 | tail -20
tests/test_config.py::TestExpandEnvVars::test_variable_embedded_in_string PASSED [ 41%]
tests/test_config.py::TestExpandEnvVars::test_multiple_variables_in_string PASSED [ 44%]
tests/test_config.py::TestExpandEnvVars::test_default_value_when_var_unset PASSED [ 48%]
tests/test_config.py::TestExpandEnvVars::test_default_value_ignored_when_var_set PASSED [ 51%]
tests/test_config.py::TestExpandEnvVars::test_default_value_empty_string PASSED [ 55%]
tests/test_config.py::TestExpandEnvVars::test_unset_variable_without_default_exits PASSED [ 58%]
tests/test_config.py::TestExpandEnvVars::test_dict_values_expanded PASSED [ 62%]
tests/test_config.py::TestExpandEnvVars::test_nested_dict_expanded PASSED [ 65%]
tests/test_config.py::TestExpandEnvVars::test_list_values_expanded PASSED [ 68%]
tests/test_config.py::TestExpandEnvVars::test_mixed_nested_structure PASSED [ 72%]
tests/test_input_validation.py::TestInvalidMachineType::test_invalid_machine_type_error_message PASSED [ 75%]
tests/test_input_validation.py::TestInvalidMachineType::test_valid_machine_type_accepted PASSED [ 79%]
tests/test_input_validation.py::TestMissingConfigSections::test_missing_digital_ocean_section PASSED [ 82%]
tests/test_input_validation.py::TestMissingConfigSections::test_missing_access_token PASSED [ 86%]
tests/test_input_validation.py::TestMissingConfigSections::test_missing_ssh_key PASSED [ 89%]
tests/test_input_validation.py::TestMissingConfigSections::test_missing_machines_section PASSED [ 93%]
tests/test_input_validation.py::TestMissingConfigSections::test_missing_new_user_name_in_machine PASSED [ 96%]
tests/test_input_validation.py::TestCreateNoInitialize::test_no_initialize_without_type_no_crash PASSED [100%]

======================= 29 passed, 4 deselected in 3.86s =======================

All 29 existing tests pass, 4 e2e tests correctly deselected.

Here's what I've created:

tests/test_e2e.py — End-to-end tests that exercise the full VM lifecycle against real DigitalOcean infrastructure:

  • TestDropletLifecycle — Create a droplet (no cloud-init), verify it appears in list --output json, destroy it, verify it's gone
  • TestDNSLifecycle — Create a droplet with --update-dns, verify the A record via list-domain, destroy with --delete-dns, verify DNS record is removed
  • TestCreateWithInitialize — Create a droplet with --type e2e-basic (cloud-init user-data), verify the type tag is applied
  • TestCustomTag — Create a droplet with --tag, verify filtering by tag works

Design decisions: - Automatically skipped when E2E_DO_TOKEN, E2E_SSH_KEY, or E2E_DNS_ZONE env vars are missing - Excluded from default make test via addopts = "-m 'not e2e'" in pyproject.toml - Run explicitly with make test-e2e or uv run pytest tests/test_e2e.py -v -m e2e - Cleanup fixture ensures droplets are destroyed even if a test fails - Unique names per test run via UUID to avoid collisions - Uses the smallest droplet size (s-1vcpu-512mb-10gb) by default to minimize cost

Amazing! Thank you. Can you write a short markdown document that explains these tests and how to run them?

📝 Write E2E.md
/home/david/projects/stirlingbridge/machine/tests/E2E.md
# End-to-End Tests

These tests verify that `machine` can create and manage real VMs on DigitalOcean, including DNS record lifecycle. They are **not** run as part of the normal test suite due to cost and runtime.

## Prerequisites

You need a DigitalOcean account with:

- An API token
- An SSH key registered in the account
- A DNS zone managed by DigitalOcean (e.g. `test.example.com`)

## Environment Variables

| Variable | Required | Description |
|---|---|---|
| `E2E_DO_TOKEN` | Yes | DigitalOcean API token |
| `E2E_SSH_KEY` | Yes | Name of an SSH key in your DO account |
| `E2E_DNS_ZONE` | Yes | DO-managed DNS zone for test records |
| `E2E_REGION` | No | Region slug (default: `nyc1`) |
| `E2E_IMAGE` | No | Image slug (default: `ubuntu-24-04-x64`) |
| `E2E_SIZE` | No | Droplet size (default: `s-1vcpu-512mb-10gb`) |
| `E2E_PROJECT` | No | DO project to assign droplets to |

## Running

```bash
# Set credentials
export E2E_DO_TOKEN="dop_v1_..."
export E2E_SSH_KEY="my-ssh-key"
export E2E_DNS_ZONE="test.example.com"

# Run e2e tests
make test-e2e

# Or directly
uv run pytest tests/test_e2e.py -v -m e2e
```

The normal `make test` (and CI) will **skip** these tests automatically.

## What's Tested

- **Droplet lifecycle** — create, list, destroy, verify removal
- **DNS lifecycle** — create with `--update-dns`, verify A record, destroy with `--delete-dns`, verify record removal
- **Cloud-init initialization** — create with `--type`, verify type tag
- **Custom tags** — create with `--tag`, verify tag filtering

## Cleanup

Each test cleans up after itself. A safety fixture also destroys any leftover droplets if a test fails mid-run. All test droplets use unique names prefixed with `e2etest-` so they are easy to identify.

## Cost

Tests use the smallest available droplet size (`s-1vcpu-512mb-10gb`) and destroy VMs immediately after verification, so cost is minimal.
File created successfully at: /home/david/projects/stirlingbridge/machine/tests/E2E.md

Done — the doc is at tests/E2E.md.

Thanks. Can you also add a new GitHub actions job for these tests?

Thinking
Read
{
  "file_path": "/home/david/projects/stirlingbridge/machine/.github/workflows/test.yml"
}
     1→name: Test
     2→
     3→on:
     4→  push:
     5→    branches:
     6→      - main
     7→  pull_request:
     8→    branches:
     9→      - main
    10→
    11→jobs:
    12→  test:
    13→    name: "Run Tests"
    14→    runs-on: ubuntu-latest
    15→    steps:
    16→      - name: "Clone project repository"
    17→        uses: actions/checkout@v4
    18→      - name: "Install uv"
    19→        uses: astral-sh/setup-uv@v4
    20→      - name: "Install Python"
    21→        run: uv python install 3.13
    22→      - name: "Install dependencies"
    23→        run: uv sync
    24→      - name: "Run tests"
    25→        run: uv run pytest tests/ -v
    26→
Read
{
  "file_path": "/home/david/projects/stirlingbridge/machine/.github/workflows/build-release.yml"
}
     1→name: Build and Release
     2→
     3→on:
     4→  push:
     5→    branches:
     6→      - main
     7→      - build-test
     8→
     9→jobs:
    10→  publish:
    11→    name: "Build and Release"
    12→    runs-on: ubuntu-latest
    13→    steps:
    14→      - name: "Clone project repository"
    15→        uses: actions/checkout@v4
    16→      - name: "Install uv"
    17→        uses: astral-sh/setup-uv@v4
    18→      - name: "Install Python"
    19→        run: uv python install 3.13
    20→      - name: "Get release tag"
    21→        id: release-tag
    22→        run: |
    23→          release_tag=$(./sh/make-release-tag.sh)
    24→          echo "release-tag=v${release_tag}" >> $GITHUB_OUTPUT
    25→      - name: "Build shiv package"
    26→        run: |
    27→          ./sh/build-package.sh
    28→      - name: "Upload package as a github release"
    29→        uses: softprops/action-gh-release@v2
    30→        with:
    31→          tag_name: ${{ steps.release-tag.outputs.release-tag }}
    32→          draft: ${{ endsWith('build-test', github.ref ) }}
    33→          files: ./build/machine
    34→
📝 Write e2e-test.yml
/home/david/projects/stirlingbridge/machine/.github/workflows/e2e-test.yml
name: E2E Test

on:
  workflow_dispatch:
  schedule:
    # Run nightly at 06:00 UTC
    - cron: "0 6 * * *"

jobs:
  e2e:
    name: "End-to-End Tests"
    runs-on: ubuntu-latest
    environment: e2e
    steps:
      - name: "Clone project repository"
        uses: actions/checkout@v4
      - name: "Install uv"
        uses: astral-sh/setup-uv@v4
      - name: "Install Python"
        run: uv python install 3.13
      - name: "Install dependencies"
        run: uv sync
      - name: "Run E2E tests"
        env:
          E2E_DO_TOKEN: ${{ secrets.E2E_DO_TOKEN }}
          E2E_SSH_KEY: ${{ secrets.E2E_SSH_KEY }}
          E2E_DNS_ZONE: ${{ secrets.E2E_DNS_ZONE }}
        run: uv run pytest tests/test_e2e.py -v -m e2e
File created successfully at: /home/david/projects/stirlingbridge/machine/.github/workflows/e2e-test.yml

Done — .github/workflows/e2e-test.yml is set up with:

  • workflow_dispatch — run manually from the Actions tab anytime
  • schedule — runs nightly at 06:00 UTC
  • environment: e2e — uses a GitHub environment named e2e, which is where you'll configure the secrets

You'll need to create the e2e environment in your repo settings (Settings > Environments) and add three secrets: E2E_DO_TOKEN, E2E_SSH_KEY, and E2E_DNS_ZONE.

Thanks, I like the scheduled execution. We can re-visit later whether to run it on PR creation and merge to main once we understand the runtime and cost implications.

📝 Write project_e2e_tests.md
/home/david/projects/stirlingbridge/machine/.claude/projects/-home-david-projects-stirlingbridge-machine/memory/project_e2e_tests.md
---
name: E2E test CI trigger decision
description: E2E tests currently run nightly + manual only; revisiting PR/merge triggers later based on cost/runtime
type: project
---

E2E tests (`.github/workflows/e2e-test.yml`) are deliberately limited to nightly schedule and manual `workflow_dispatch` triggers.

**Why:** Runtime and cost of creating real DigitalOcean droplets is not yet understood. Running on every PR/merge could be expensive.

**How to apply:** If the user asks about adding PR or push triggers to the e2e workflow, remind them of this decision and check whether they've gathered enough data to revisit.
File created successfully at: /home/david/projects/stirlingbridge/machine/.claude/projects/-home-david-projects-stirlingbridge-machine/memory/project_e2e_tests.md
Glob
{
  "pattern": "/home/david/projects/stirlingbridge/machine/.claude/projects/-home-david-projects-stirlingbridge-machine/memory/MEMORY.md"
}
No files found
📝 Write MEMORY.md
/home/david/projects/stirlingbridge/machine/.claude/projects/-home-david-projects-stirlingbridge-machine/memory/MEMORY.md
# Memory Index

- [project_e2e_tests.md](project_e2e_tests.md) — E2E tests run nightly+manual only; PR/merge triggers deferred pending cost/runtime data
File created successfully at: /home/david/projects/stirlingbridge/machine/.claude/projects/-home-david-projects-stirlingbridge-machine/memory/MEMORY.md

Sounds like a good plan. I've noted that decision so we can revisit it once you have a sense of how long the tests take and what they cost per run.

Caveat: The messages below were generated by the user while running local commands. DO NOT respond to these messages or otherwise consider them in your response unless the user explicitly asks you to.