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Calypso

Calypso is a platform-abstracted deployment gatekeeper for a single repository workflow. It currently runs with Slack + GitHub + DigitalOcean by default, while exposing provider abstractions for communication, code-host, deploy, email, AI, and error-tracking integrations. It tracks merged pull requests in Postgres, requires explicit testing confirmation, blocks production deploys when untested changes exist, posts scheduled review recap messages, can poll one environment health endpoint for outage alerts, and can track customer support emails from Gmail or Outlook as an actionable queue, can draft support-email replies through OpenAI or Anthropic, and can poll Sentry or Rollbar for newly tracked unresolved error groups.

What It Does

  • Ingests merged code-host pull requests into pull_requests as untested.
  • Tracks open PR review lifecycle in open_pr_review_state.
  • Reconciles open PR review state from code host once per day (when code-host API token is configured).
  • Exposes a communication-platform command surface (/calypso for Slack).
  • Supports status and release workflow commands:
    • /calypso help
    • /calypso config time-format:human|long
    • /calypso config timezone:America/New_York
    • /calypso config communication-provider:slack|microsoft_teams
    • /calypso config code-host-provider:github|bitbucket
    • /calypso config deploy-provider:digitalocean|aws
    • /calypso config email-provider:gmail|outlook
    • /calypso config ai-provider:openai|anthropic
    • /calypso config error-tracking-provider:sentry|rollbar
    • /calypso config review-recap-channel:<#CHANNEL|CHANNEL_ID>
    • /calypso config review-recap-window:<all|last-day|last-week|last-month>
    • /calypso config review-recap-recency:<Nd|Nw> (legacy)
    • /calypso config review-recap-schedule:<daily|weekday>@HH:MM[,HH:MM...]
    • /calypso config review-recap-send-weekends:<on|off>
    • /calypso config review-recap-send-holidays:<on|off>
    • /calypso config environment-status:on|off
    • /calypso config environment-status-url:https://example.com/healthz
    • /calypso config environment-status-channel:<#CHANNEL|CHANNEL_ID|channel-name>
    • /calypso config error-tracking:on|off
    • /calypso config error-tracking-channel:<#CHANNEL|CHANNEL_ID|channel-name>
    • /calypso config error-tracking-project:<PROJECT_SLUG>
    • /calypso config error-tracking-environment:<ENVIRONMENT|any>
    • /calypso config email-monitor:on|off
    • /calypso config email-channel:<#CHANNEL|CHANNEL_ID|channel-name>
    • /calypso config email-on-call <@USER|USER_ID> <Nh|Nd|Nw>
    • /calypso config email-on-call off
    • /calypso config github-slack-user-map:<GITHUB_USER>=<@USER|USER_ID|@HANDLE>
    • /calypso sync
    • /calypso status
    • /calypso errors
    • /calypso reviews [<GITHUB_USER>] [<day|week|month>]
    • /calypso emails
    • /calypso emails draft <EMAIL_ID> [ADDITIONAL_INSTRUCTIONS...]
    • /calypso emails responded <EMAIL_ID>
    • /calypso tested <PR_NUMBER>
    • /calypso must-test <PR_NUMBER>
    • /calypso must-test off <PR_NUMBER>
    • /calypso deploy staging
    • /calypso deploy prod
  • Enforces deploy blocking rules:
    • A blocker is any PR with merged_at > last_prod_deploy_at and status not in tested, deployed.
  • Optionally triggers deploy-platform production deploy when gate is clear.
  • Optionally triggers staging deploy directly when staging app/pipeline is configured.
  • Optionally polls one configured environment URL and posts transition-based outage/recovery alerts.
  • Optionally polls one configured Sentry or Rollbar project/environment scope and posts one alert per new or regressed unresolved issue group.
  • Optionally ingests Gmail or Outlook support mailbox activity into support_email_threads, posts new-email notifications, and lets responders mark queued items handled.
  • Optionally drafts support-email replies for queued items through the active AI provider.
  • Runtime display config is per communication user (defaults: time format human, timezone America/New_York).
  • Review recap schedule config is workspace-wide (defaults: Monday 9:00 AM America/New_York, recap window all).

Architecture

Calypso is a single Node.js service composed of:

  • Communication platform provider (Slack implemented; Microsoft Teams implemented).
  • Code-host platform provider (GitHub implemented; Bitbucket implemented).
  • Deploy platform provider (DigitalOcean implemented; AWS CodePipeline implemented).
  • Email platform provider (Gmail implemented; Outlook implemented).
  • AI platform provider (OpenAI implemented; Anthropic implemented).
  • Error-tracking platform provider (Sentry implemented; Rollbar implemented).
  • Express HTTP server for webhooks.
  • Postgres persistence through pg.

Unknown providers fail fast at startup.

Command System Design

Commands are structured for extensibility:

  • registry:
    • Command lookup and dispatch by command name.
  • types:
    • One file per command type (help, config, status, tested, must-test, deploy, unknown).
    • Each command encapsulates its own parse + execute behavior.
  • base class:
    • Shared command contract and helpers.

To add a new command:

  1. Create a new command class in src/commands/types/.
  2. Register it in src/commands/registry/command_registry.js.

Project Layout

src/
  app.js
  config.js
  commands/
    command_router.js
    parsing/
      command_parser.js
    registry/
      command_registry.js
    services/
      command_service.js
    types/
      base_command.js
      emails_command.js
      errors_command.js
      help_command.js
      config_command.js
      status_command.js
      tested_command.js
      deploy_command.js
      unknown_command.js
  db/
    index.js
    migrations/001_init.sql
  background_jobs/
    error_tracking_scheduler.js
    environment_status_scheduler.js
    scheduler.js
    review_recap_scheduler.js
    support_email_scheduler.js
    syncer.js
    tasks/
      review_sync_task.js
      untested_merged_sync_task.js
  platform/
    shared/
      errors.js
    communication/
      base_communication_platform.js
      factory.js
      resolution.js
      providers/
        slack_communication_platform.js
        microsoft_teams_communication_platform.js
    code_host/
      base_code_host_platform.js
      factory.js
      providers/
        github/
          code_host_platform.js
          client.js
          webhook.js
          verify_signature.js
        bitbucket/
          code_host_platform.js
          client.js
          webhook.js
          verify_signature.js
    deploy/
      base_deploy_platform.js
      factory.js
      providers/
        digitalocean_deploy_platform.js
        aws_deploy_platform.js
        aws/
          client.js
        digitalocean/
          client.js
    ai/
      base_ai_platform.js
      factory.js
      providers/
        anthropic/
          ai_platform.js
          client.js
        openai/
          ai_platform.js
          client.js
    error_tracking/
      base_error_tracking_platform.js
      factory.js
      providers/
        rollbar/
          client.js
          error_tracking_platform.js
        sentry/
          client.js
          error_tracking_platform.js
    email/
      base_email_platform.js
      factory.js
      providers/
        gmail/
          client.js
          email_platform.js
          webhook.js
        outlook/
          client.js
          email_platform.js
  shared/
    durations.js
  util/
    format.js
test/
  *.test.js

Prerequisites

  • Node.js 18+ (Node 20 recommended).
  • For local hosting only:
    • ngrok installed and authenticated.
    • PostgreSQL CLI tools installed (initdb, pg_ctl, psql) for automated local stack start.
  • A Slack app with:
    • Socket Mode enabled.
    • Slash command /calypso.
    • Relevant Slack message event subscriptions/history scopes if you want Calypso to nudge users who type deploying prod.
  • Optional support-email setup:
    • A Gmail or Outlook mailbox for customer support.
    • For Gmail: Google Cloud Pub/Sub topic + authenticated push subscription pointing at POST /email/webhook.
    • For Gmail: Google OAuth client credentials + refresh token with Gmail API access.
    • For Outlook: Azure/Microsoft Entra app credentials with Microsoft Graph mail read access for the support mailbox.
  • Optional:
    • DigitalOcean App Platform app and token for live deploy trigger.

Environment Variables

Always required:

  • DATABASE_URL
  • BOT_NAME (default: Calypso)
  • COMMUNICATION_PROVIDER (default: slack)
  • CODE_HOST_PROVIDER (default: github)
  • DEPLOY_PROVIDER (default: digitalocean)
  • EMAIL_PROVIDER (default: gmail)
  • AI_PROVIDER (default: openai)
  • ERROR_TRACKING_PROVIDER (default: sentry)

Required when COMMUNICATION_PROVIDER=slack:

  • COMMUNICATION_BOT_TOKEN
  • COMMUNICATION_APP_TOKEN

Required when CODE_HOST_PROVIDER=github or CODE_HOST_PROVIDER=bitbucket:

  • CODE_HOST_WEBHOOK_SECRET
  • CODE_HOST_REPOSITORY (example: croft-eng/croft)
  • CODE_HOST_MAIN_BRANCH (example: main)

Optional:

  • PORT (default 3001)
  • POSTGRES_PASSWORD (required when using docker-compose.droplet.yml)
  • CADDY_EMAIL (used by Caddyfile.droplet for TLS contact email)
  • DEPLOY_TOKEN
  • DEPLOY_PROD_APP_ID
  • DEPLOY_STAGING_APP_ID
  • DEPLOY_POLL_INTERVAL_SECONDS (default 10)
  • DEPLOY_TIMEOUT_SECONDS (default 1200)
  • CODE_HOST_TOKEN (recommended for daily open-PR reconciliation)
  • CODE_HOST_CODEX_USER_LOGINS (default: codex,codex[bot])
  • CODE_HOST_OPEN_PR_SYNC_INTERVAL_HOURS (default 24)
  • CODEX_APPROVAL_POLL_INTERVAL_MINUTES (default 5)
  • ENVIRONMENT_STATUS_POLL_INTERVAL_SECONDS (default 60)
  • ENVIRONMENT_STATUS_TIMEOUT_SECONDS (default 60)
  • ENVIRONMENT_STATUS_FAILURE_THRESHOLD (default 3)
  • ENVIRONMENT_STATUS_RETRY_INITIAL_DELAY_SECONDS (default 5)
  • ENVIRONMENT_STATUS_RETRY_BACKOFF_MULTIPLIER (default 3)
  • ENVIRONMENT_STATUS_RETRY_MAX_DELAY_SECONDS (default 45)
  • ENVIRONMENT_STATUS_CONNECTIVITY_PROBE_URL (recommended)
  • ERROR_TRACKING_POLL_INTERVAL_SECONDS (default 300)
  • ERROR_TRACKING_TIMEOUT_SECONDS (default 15)
  • ERROR_TRACKING_SENTRY_BASE_URL (default https://sentry.io)
  • ERROR_TRACKING_SENTRY_AUTH_TOKEN
  • ERROR_TRACKING_SENTRY_ORGANIZATION_SLUG
  • ERROR_TRACKING_ROLLBAR_BASE_URL (default https://api.rollbar.com)
  • ERROR_TRACKING_ROLLBAR_ACCESS_TOKEN
  • EMAIL_PROVIDER (default gmail)
  • AI_PROVIDER (default openai)
  • AI_TIMEOUT_SECONDS (default 30)
  • AI_OPENAI_API_KEY
  • AI_OPENAI_MODEL
  • AI_OPENAI_BASE_URL (default https://api.openai.com/v1)
  • AI_ANTHROPIC_API_KEY
  • AI_ANTHROPIC_MODEL
  • AI_ANTHROPIC_BASE_URL (default https://api.anthropic.com)
  • AI_SUPPORT_EMAIL_SYSTEM_PROMPT
  • EMAIL_GMAIL_ADDRESS
  • EMAIL_GMAIL_CLIENT_ID
  • EMAIL_GMAIL_CLIENT_SECRET
  • EMAIL_GMAIL_REFRESH_TOKEN
  • EMAIL_GMAIL_PUBSUB_TOPIC
  • EMAIL_WEBHOOK_AUDIENCE
  • EMAIL_PUSH_SERVICE_ACCOUNT_EMAIL
  • EMAIL_OUTLOOK_ADDRESS
  • EMAIL_OUTLOOK_TENANT_ID
  • EMAIL_OUTLOOK_CLIENT_ID
  • EMAIL_OUTLOOK_CLIENT_SECRET
  • EMAIL_WATCH_RENEW_INTERVAL_HOURS (default 24)
  • EMAIL_SYNC_FALLBACK_INTERVAL_MINUTES (default 5)

Provider support matrix:

  • Communication:
    • slack: implemented
    • microsoft_teams: implemented
  • Code host:
    • github: implemented
    • bitbucket: implemented
  • Deploy:
    • digitalocean: implemented
    • aws: implemented (CodePipeline)
  • Email:
    • gmail: implemented
    • outlook: implemented
  • AI:
    • openai: implemented
    • anthropic: implemented
  • Error tracking:
    • sentry: implemented
    • rollbar: implemented

How To Get Each Value

COMMUNICATION_PROVIDER

  • Provider selector for communication integration.
  • Supported values: slack (implemented), microsoft_teams (implemented).
  • Default: slack.

CODE_HOST_PROVIDER

  • Provider selector for code-host integration.
  • Supported values: github (implemented), bitbucket (implemented).
  • Default: github.

DEPLOY_PROVIDER

  • Provider selector for deploy integration.
  • Supported values: digitalocean (implemented), aws (implemented via CodePipeline).
  • Default: digitalocean.

EMAIL_PROVIDER

  • Provider selector for support-email integration.
  • Supported values: gmail (implemented), outlook (implemented).
  • Default: gmail.

AI_PROVIDER

  • Provider selector for AI-assisted drafting.
  • Supported values: openai (implemented), anthropic (implemented).
  • Default: openai.

ERROR_TRACKING_PROVIDER

  • Provider selector for error-tracking integration.
  • Supported values: sentry (implemented), rollbar (implemented).
  • Default: sentry.

DEPLOY_REGION

  • Deploy provider region.
  • Used by AWS CodePipeline deploy provider.
  • Default: us-east-1.

DEPLOY_ACCESS_KEY_ID

  • Access key id used by AWS deploy provider request signing.

DEPLOY_SECRET_ACCESS_KEY

  • Secret access key used by AWS deploy provider request signing.

DEPLOY_SESSION_TOKEN

  • Optional session token for temporary AWS credentials.

BOT_NAME

  • Display name used in bot-generated help and error messages.
  • Default: Calypso.

COMMUNICATION_BOT_TOKEN

  • Slack App -> OAuth & Permissions -> install/reinstall app -> copy Bot User OAuth Token (xoxb-...).
  • Add bot scope users:read so Calypso can detect workspace admins for deploy authorization.
  • Add the matching Slack history scopes for any surfaces where Calypso should detect deploying prod messages.
  • If you want /calypso config email-on-call @handle ..., keep users:read enabled so Calypso can resolve Slack handles to user IDs.

COMMUNICATION_APP_TOKEN

  • Slack App -> Socket Mode -> enable -> generate app-level token with connections:write scope -> copy token (xapp-...).

COMMUNICATION_COMMAND_PATH

  • Provider-agnostic HTTP path for incoming communication command requests.
  • Used by microsoft_teams provider for Calypso command ingestion.
  • Default: /communication/commands.

COMMUNICATION_WEBHOOK_URL

  • Provider-agnostic outbound webhook URL for communication platforms that support webhook posting.
  • Used by microsoft_teams for in-channel recap posts and follow-up channel messages.

COMMUNICATION_ADMIN_USER_IDS

  • Optional comma-separated user IDs treated as workspace admins when COMMUNICATION_PROVIDER=microsoft_teams.

DATABASE_URL

  • If using npm run start managed local runtime, use:
  • If using your own Postgres, set your own host/port/user/db:
    • postgresql://<user>:<password>@<host>:<port>/<database>
  • If using DigitalOcean Managed PostgreSQL, use the connection string from DO with:
    • ?sslmode=require (Calypso enables TLS automatically when this is present)

CODE_HOST_WEBHOOK_SECRET

  • Generate a random secret, for example:
    • openssl rand -hex 32
  • Use the same value in .env and in GitHub repo webhook settings.

CODE_HOST_REPOSITORY

  • Set to the exact full repo name:
    • <owner>/<repo> (example: willakins/Test-repo)
  • Must exactly match payload.repository.full_name from GitHub webhook events.

CODE_HOST_MAIN_BRANCH

  • Usually main (or your default protected branch, like master).
  • Must match the base branch of merged PRs you want Calypso to track.

CODE_HOST_TOKEN (optional, enables daily PR reconciliation)

  • GitHub -> Settings -> Developer settings -> Personal access tokens (fine-grained or classic).
  • Minimum needed access for this repo: read pull requests.
  • Used only for scheduled read-only sync of open PR and review state.

CODE_HOST_CODEX_USER_LOGINS (optional)

  • Comma-separated GitHub logins that count as "Codex approved" when they react 👍 to the PR description.
  • Default: codex,codex[bot].
  • Example: CODE_HOST_CODEX_USER_LOGINS=codex,openai-codex[bot]

CODE_HOST_OPEN_PR_SYNC_INTERVAL_HOURS (optional)

  • How often Calypso reconciles open PR review state from GitHub API.
  • Default: 24.

CODEX_APPROVAL_POLL_INTERVAL_MINUTES (optional)

  • How often Calypso refreshes Codex 👍 approval from PR-description reactions.
  • Default: 5.

PORT (optional)

  • HTTP port Calypso binds to (used by local runtime, ngrok tunnel, and Droplet Docker/Caddy stack).
  • Default is 3001; only set this if you need a different port.

DEPLOY_TOKEN (optional unless using /calypso deploy prod or /calypso deploy staging)

  • DigitalOcean -> API -> Tokens/Keys -> generate personal access token.
  • Recommended custom scopes for this app-deploy flow:
    • app:update (plus required read dependencies auto-added by DO).

DEPLOY_PROD_APP_ID (optional unless using /calypso deploy prod)

  • DigitalOcean App Platform app UUID.
  • Find it with:
    • doctl apps list --format ID,Spec.Name

DEPLOY_STAGING_APP_ID (optional unless using /calypso deploy staging)

  • DigitalOcean App Platform staging app UUID (or AWS staging pipeline name).
  • Find it with:
    • doctl apps list --format ID,Spec.Name

DEPLOY_POLL_INTERVAL_SECONDS (optional)

  • Poll interval for checking deployment completion status after deploy trigger.
  • Default: 10 seconds.

DEPLOY_TIMEOUT_SECONDS (optional)

  • Max time Calypso waits for deployment completion follow-up message.
  • Default: 1200 seconds (20 minutes).

ENVIRONMENT_STATUS_POLL_INTERVAL_SECONDS (optional)

  • How often the environment monitor polls the configured URL.
  • Default: 60 seconds.

ENVIRONMENT_STATUS_TIMEOUT_SECONDS (optional)

  • Request timeout for each environment poll.
  • Default: 60 seconds.

ENVIRONMENT_STATUS_FAILURE_THRESHOLD (optional)

  • Number of consecutive failed app probes required in one monitoring cycle before Calypso marks the app unhealthy.
  • Default: 3.

ENVIRONMENT_STATUS_RETRY_INITIAL_DELAY_SECONDS (optional)

  • Delay before the first retry after a failed app probe.
  • Default: 5 seconds.

ENVIRONMENT_STATUS_RETRY_BACKOFF_MULTIPLIER (optional)

  • Exponential multiplier applied between failed app-probe retries.
  • Default: 3.

ENVIRONMENT_STATUS_RETRY_MAX_DELAY_SECONDS (optional)

  • Maximum delay between failed app-probe retries.
  • Default: 45 seconds.

ENVIRONMENT_STATUS_CONNECTIVITY_PROBE_URL (optional but recommended)

  • HTTPS endpoint Calypso uses to verify its own outbound connectivity before probing the app URL.
  • Should be lightweight, operator-controlled, and independent from the monitored app origin.
  • If unset, environment monitoring stays skipped even when /calypso config environment-status:on is enabled.

ERROR_TRACKING_POLL_INTERVAL_SECONDS (optional)

  • How often Calypso polls the configured error-tracking project scope.
  • Default: 300 seconds.

ERROR_TRACKING_TIMEOUT_SECONDS (optional)

  • Request timeout for each Sentry API poll.
  • Default: 15 seconds.

ERROR_TRACKING_SENTRY_BASE_URL (optional)

  • Base URL for Sentry API requests.
  • Defaults to https://sentry.io.
  • Override this for self-hosted Sentry-compatible installs.

ERROR_TRACKING_SENTRY_AUTH_TOKEN (optional, required to enable Sentry polling)

  • Sentry auth token used for organization project lookup and unresolved issue polling.
  • Minimum recommended scopes: event:read and org:read.

ERROR_TRACKING_SENTRY_ORGANIZATION_SLUG (optional, required to enable Sentry polling)

  • Organization slug used in Sentry API paths, for example acme.

ERROR_TRACKING_ROLLBAR_BASE_URL (optional)

  • Base URL for Rollbar API requests.
  • Defaults to https://api.rollbar.com.

ERROR_TRACKING_ROLLBAR_ACCESS_TOKEN (optional, required to enable Rollbar polling)

  • Rollbar project or account access token used to list active items.

EMAIL_GMAIL_ADDRESS (optional, enables support-email integration when paired with the Gmail credentials below)

  • Support mailbox address Calypso should monitor, for example [email protected].
  • Also used to ignore messages sent from the support mailbox itself.

EMAIL_GMAIL_CLIENT_ID and EMAIL_GMAIL_CLIENT_SECRET (optional)

  • Google Cloud OAuth client credentials for the Gmail API.
  • Create an OAuth client in Google Cloud Console and enable the Gmail API for the project.

EMAIL_GMAIL_REFRESH_TOKEN (optional)

  • Long-lived refresh token for the support mailbox OAuth grant.
  • Calypso exchanges this for short-lived Gmail access tokens at runtime.

EMAIL_GMAIL_PUBSUB_TOPIC (optional)

  • Full Pub/Sub topic name used by Gmail users.watch.
  • Example: projects/<gcp-project>/topics/calypso-support-email.

EMAIL_WEBHOOK_AUDIENCE (optional, recommended when using the Gmail webhook)

  • Expected audience claim for the authenticated Pub/Sub push JWT.
  • Set this to the exact public webhook URL, for example https://calypso.example.com/email/webhook.

EMAIL_PUSH_SERVICE_ACCOUNT_EMAIL (optional)

  • Extra verification for the Pub/Sub authenticated push token.
  • Set this to the service account email used by the push subscription if you want Calypso to reject tokens from other service accounts.

EMAIL_OUTLOOK_ADDRESS (optional, enables Outlook support-email integration when paired with the Outlook credentials below)

  • Support mailbox address Calypso should monitor with Microsoft Graph, for example [email protected].
  • Also used to ignore messages sent from the support mailbox itself.

EMAIL_OUTLOOK_TENANT_ID, EMAIL_OUTLOOK_CLIENT_ID, and EMAIL_OUTLOOK_CLIENT_SECRET (optional)

  • Microsoft Entra application credentials used to fetch Microsoft Graph access tokens.
  • The app needs application permission to read mail for the configured mailbox.

EMAIL_WATCH_RENEW_INTERVAL_HOURS (optional)

  • How often Calypso attempts to renew the Gmail watch before expiration.
  • Used only by the Gmail provider.
  • Default: 24 hours.

EMAIL_SYNC_FALLBACK_INTERVAL_MINUTES (optional)

  • Fallback support-email sync cadence.
  • For Gmail, this is the fallback history-sync interval when no push notification arrives.
  • For Outlook, this is the main polling interval.
  • Default: 5 minutes.

Hosting

Pricing Snapshot (DigitalOcean)

Estimated monthly costs as of 2026-02-16:

  • App Platform web service (apps-s-1vcpu-0.5gb) starts at $5/mo.
  • Managed PostgreSQL single node (1 GiB) starts at $15/mo.
  • Basic Droplets currently show $4/mo (512 MiB) and $6/mo (1 GiB).

Practical options:

  • App Platform + Managed PostgreSQL: about $20/mo minimum.
  • Single Droplet hosting app + Postgres yourself: about $4-$6/mo minimum.
  • Droplet + Managed PostgreSQL: about $19-$21/mo minimum.

Notes:

  • App Platform static sites have a free tier, but Calypso needs a running web service.
  • App Platform additional outbound transfer is billed at $0.02/GiB.

Host Locally (Fastest Development Setup)

  1. Install dependencies:
npm install
  1. Create .env with required values.
  2. Start the managed local stack:
npm run start

This local command starts:

  • Temporary Postgres at .tmp/calypso-pg (first run initializes it).
  • ngrok tunnel on PORT (default 3001) with --pooling-enabled by default.
  • Calypso app process.

If your ngrok config points multiple local apps at the same public URL, ngrok will load-balance requests across them when pooling is enabled. Set a different ngrok URL for each repo if you need isolated traffic, or set NGROK_POOLING_ENABLED=false before npm run start to disable pooling for Calypso.

  1. Configure your code-host webhook to the printed ngrok URL:
  • https://<ngrok-domain>/codehost/webhook

If you enable Gmail support-email monitoring locally, also configure your Pub/Sub push subscription to:

  • https://<ngrok-domain>/email/webhook
  1. Stop local runtime:
npm run stop

Optional local mode (you run your own Postgres + tunnel):

npm run dev

Host on DigitalOcean App Platform (Managed PaaS)

Calypso is already set up for this:

  • Dockerized runtime (Dockerfile).
  • HTTP health endpoint (GET /healthz).
  • Public webhook route (/codehost/webhook).
  • Public Gmail push route (/email/webhook).
  • Startup migrations run automatically.

Steps:

  1. Create a DigitalOcean Managed PostgreSQL cluster.
  2. Copy DB URL and keep sslmode=require in DATABASE_URL.
  3. Create App Platform app from this repo using the root Dockerfile.
  4. Configure as a Web Service, one instance.
  5. Set environment variables in App Platform:
    • Required:
      • DATABASE_URL
      • COMMUNICATION_PROVIDER=slack
      • COMMUNICATION_BOT_TOKEN
      • COMMUNICATION_APP_TOKEN
      • CODE_HOST_PROVIDER=github
      • CODE_HOST_WEBHOOK_SECRET
      • CODE_HOST_REPOSITORY
      • CODE_HOST_MAIN_BRANCH
    • Optional:
      • BOT_NAME
      • PORT (defaults to 3001)
      • CODE_HOST_TOKEN (enables /calypso sync and scheduled backfill)
      • DEPLOY_PROVIDER=digitalocean
      • DEPLOY_TOKEN
      • DEPLOY_PROD_APP_ID
      • DEPLOY_STAGING_APP_ID
  6. Configure App health check path to /healthz.
  7. Deploy the app.
  8. Set webhook URL to https://<your-app-domain>/codehost/webhook.
  9. If using Gmail support email monitoring, set Pub/Sub push endpoint to https://<your-app-domain>/email/webhook.
  10. Smoke test:
  • /calypso help
  • /calypso status
  • merge a PR and confirm webhook delivery 200.

Host on a DigitalOcean Droplet (Cheapest Always-On)

This repo includes docker-compose.droplet.yml and Caddyfile.droplet for this flow.

  1. Create an Ubuntu Droplet (1 GiB recommended).
  2. Point a domain A record to the Droplet IP (example: calypso.example.com).
  3. Open inbound ports 22, 80, 443 in DO firewall.
  4. SSH in and install Docker:
sudo apt update
sudo apt install -y docker.io docker-compose-plugin git
sudo systemctl enable --now docker
  1. Clone this repo and create .env in repo root.
  2. In .env, use a local Compose DB URL:
    • POSTGRES_PASSWORD=<strong-password>
    • [email protected]
    • PORT=3001 (optional; change only if you want a different app/proxy port)
    • DATABASE_URL=postgresql://calypso_user:<POSTGRES_PASSWORD>@db:5432/calypso
  3. Update Caddyfile.droplet:
    • replace calypso.example.com with your domain
  4. Start the stack:
docker compose -f docker-compose.droplet.yml up -d --build
  1. Verify health:
curl https://<your-domain>/healthz
  1. Configure webhook:
  • https://<your-domain>/codehost/webhook
  1. If using Gmail support email monitoring, configure Pub/Sub push endpoint:
  • https://<your-domain>/email/webhook

Operational notes:

  • Slack Socket Mode means slash commands do not require a public Slack request URL.
  • Slack deploying prod tips require the app to receive the relevant Slack message events for the channels or conversations you want monitored.
  • Gmail support-email monitoring requires a public POST /email/webhook endpoint plus a valid Gmail watch configuration.
  • Outlook support-email monitoring is polling-only and does not require a public email webhook.
  • Keep one primary Calypso runtime for stable webhook ingestion and schedulers.
  • If you use the Droplet Compose DB service, do not expose 5432 publicly.

Pricing references:

Code-Host Webhook

Endpoint:

  • POST /codehost/webhook

Rules:

  • Requires valid X-Hub-Signature-256 HMAC signature.
  • Processes pull_request and pull_request_review events.
  • Only processes events for configured CODE_HOST_MAIN_BRANCH and configured CODE_HOST_REPOSITORY.
  • Merged PR close events upsert to deploy-gating table as untested.
  • Open PR lifecycle and review submissions update open_pr_review_state.

Gmail Email Webhook

Endpoint:

  • POST /email/webhook

Rules:

  • Expects Google Pub/Sub authenticated push with a bearer JWT.
  • Verifies issuer, signature, token expiry, and optional audience/service-account constraints.
  • Ignores Gmail notifications for mailboxes other than configured EMAIL_GMAIL_ADDRESS.
  • Stores the greatest pending Gmail history id so the background scheduler can sync mailbox changes.

Daily Open PR Sync

  • Runs as a background scheduler in the app runtime.
  • Performs a full open-PR reconciliation for CODE_HOST_REPOSITORY + CODE_HOST_MAIN_BRANCH.
  • Frequency is controlled by CODE_HOST_OPEN_PR_SYNC_INTERVAL_HOURS (default every 24 hours).
  • Requires CODE_HOST_TOKEN; without it, webhook-based tracking still works but no periodic backfill runs.
  • Reconciles Codex approval by checking current 👍 reactions on PR descriptions from configured CODE_HOST_CODEX_USER_LOGINS.
  • Upserts all currently open PR review-state rows and marks stale local open rows as closed.
  • Backfills merged PRs newer than last prod deploy into deploy-gating state as untested (without downgrading already tested/deployed rows).

Codex Approval Sync

  • Runs as a separate background scheduler in the app runtime.
  • Refreshes codex_approved using PR-description 👍 reactions from configured CODE_HOST_CODEX_USER_LOGINS.
  • Frequency is controlled by CODEX_APPROVAL_POLL_INTERVAL_MINUTES (default every 5 minutes).
  • Requires CODE_HOST_TOKEN.

Slash Command Behavior

/calypso help

  • Returns usage.

/calypso config review-recap-channel:<#CHANNEL|CHANNEL_ID>

  • Sets workspace recap target channel for scheduled in-channel posts.

/calypso config review-recap-recency:<Nd|Nw>

  • Sets recap lookback window in legacy mode (for example 1w, 2w, 2d).

/calypso config review-recap-window:<all|last-day|last-week|last-month>

  • Sets recap PR selection scope.
  • all includes every open, non-draft PR.
  • last-day, last-week, and last-month apply rolling lookback windows.

/calypso config review-recap-schedule:<daily|weekday>@HH:MM[,HH:MM...]

  • Sets one or more recap send slots using daily or weekday + 24h clock.
  • Examples: daily@09:00, daily@09:00,17:00, mon@09:00,17:30, tue@10:15.

/calypso config review-recap-send-weekends:<on|off>

  • Controls whether recap posts are sent on Saturday/Sunday.
  • Default is off.

/calypso config review-recap-send-holidays:<on|off>

  • Controls whether recap posts are sent on observed US federal holidays.
  • Default is off.

/calypso config environment-status:on|off

  • Enables or disables environment polling.

/calypso config environment-status-url:https://example.com/healthz

  • Sets the single environment endpoint Calypso should poll.
  • Health is exact HTTP 200; all other responses, timeouts, and network errors are unhealthy.
  • Observer-side network loss does not mark the app down; Calypso first verifies outbound DNS + HTTPS reachability through ENVIRONMENT_STATUS_CONNECTIVITY_PROBE_URL.

/calypso config environment-status-channel:<#CHANNEL|CHANNEL_ID|channel-name>

  • Sets the channel that receives environment down and recovery alerts.

/calypso config error-tracking:on|off

  • Enables or disables error-tracking polling.

/calypso config error-tracking-channel:<#CHANNEL|CHANNEL_ID|channel-name>

  • Sets the channel that receives new-issue and regression alerts.

/calypso config error-tracking-project:<PROJECT_SLUG>

  • Sets the active error-tracking project scope.
  • For Sentry, use the project slug.
  • For Rollbar, use the numeric project id if you want Calypso to filter the items API to one project.

/calypso config error-tracking-environment:<ENVIRONMENT|any>

  • Sets the active error-tracking environment filter.
  • Use any to clear the environment filter.

/calypso config email-monitor:on|off

  • Enables or disables support-email ingestion for the active email provider.

/calypso config email-channel:<#CHANNEL|CHANNEL_ID|channel-name>

  • Sets the channel for automatic support-email notifications.

/calypso config email-on-call <@USER|USER_ID> <Nh|Nd|Nw>

  • Sets the support-email on-call recipient until the provided duration expires.
  • Slack mention form is used automatically in notifications when Calypso is running on Slack.

/calypso config email-on-call off

  • Clears the configured support-email on-call user and expiration.

/calypso config github-slack-user-map:<GITHUB_USER>=<@USER|USER_ID|@HANDLE>

  • Maps a GitHub username to a Slack identity used in production deploy summaries.
  • Prefer Slack mention or user ID for reliable tagging: <@U123ABC> or U123ABC.
  • Example: /calypso config github-slack-user-map:octocat=<@U123ABC>

/calypso config timezone:America/New_York

  • Sets timezone (IANA), used by human timestamps and recap schedule rendering.

/calypso config communication-provider:slack|microsoft_teams

  • Sets communication platform provider in runtime config.
  • Takes effect immediately for /calypso command handling.

/calypso config code-host-provider:github|bitbucket

  • Sets code-host platform provider in runtime config.
  • Takes effect immediately for /calypso command handling.

/calypso config deploy-provider:digitalocean|aws

  • Sets deploy platform provider in runtime config.
  • Takes effect immediately for /calypso command handling.

/calypso config email-provider:gmail|outlook

  • Sets the support-email provider in runtime config.
  • Resets provider-specific email sync state so the new provider can establish a fresh baseline.

/calypso config ai-provider:openai|anthropic

  • Sets the AI provider in runtime config.
  • Takes effect immediately for /calypso command handling.

/calypso config error-tracking-provider:sentry|rollbar

  • Sets the error-tracking provider in runtime config.
  • Resets provider-specific error-tracking sync state so the new provider can establish a fresh baseline.

/calypso sync

  • Triggers open PR reconciliation immediately using GitHub API.
  • Requires workspace admin or Calypso deploy-whitelist access.
  • Returns counts for both sync paths:
    • review-state sync (open PRs upserted + stale open rows closed)
    • merged-untested sync (merged PRs backfilled as untested)

/calypso status

  • Shows blockers since last production deployment.
  • If no deployments exist, baseline is epoch (1970-01-01T00:00:00.000Z).

/calypso reviews [<GITHUB_USER>] [<day|week|month>]

  • Lists open PRs waiting on review from review-tracking state.
  • Optional GitHub user filter (author login).
  • Optional recency filter (day, week, month).
  • Supports recent keyword variant: /calypso reviews recent <day|week|month>.
  • Uses the same PR row format as review recap, including Last modified date (M/D/YYYY).
  • Groups rows by Last modified age with subheaders: last month, last 3 months, and 3+ months.

/calypso emails

  • Lists pending customer support email items oldest-first.
  • Each line includes Calypso's email queue id, first sender, and subject.

/calypso emails draft <EMAIL_ID> [ADDITIONAL_INSTRUCTIONS...]

  • Drafts a support-email reply for one queued item using the active AI provider.
  • Returns the draft ephemerally and does not send or persist the generated reply.
  • Restricted to workspace admins or the current support-email on-call user.
  • Uses the first tracked inbound customer message for context.

/calypso emails responded <EMAIL_ID>

  • Marks one pending support-email item as responded.
  • Does not talk back to Gmail in v1; this is a manual queue-management action.

/calypso tested <PR_NUMBER>

  • Marks the PR as tested.
  • Idempotent when already tested.
  • Returns clear message if PR not found.

/calypso tested all

  • Marks all currently untested PRs as tested.

/calypso tested recent <day|week|month>

  • Lists PRs tested in the selected recent timeframe.
  • Includes PR number, repo, status, tester, and tested timestamp.

/calypso must-test <PR_NUMBER>

  • Marks a PR as requiring testing before deploy prod force can bypass blockers.
  • Restricted to workspace admins or already-whitelisted users.

/calypso must-test off <PR_NUMBER>

  • Removes the force-deploy test requirement for that PR.
  • Restricted to workspace admins or already-whitelisted users.

/calypso whitelist <@USER>

  • Restricted command for workspace admins or already-whitelisted users.
  • Adds a user to Calypso deploy whitelist.
  • Whitelisted users can run deploy commands even if they are not workspace admins.

/calypso deploy prod

  • Blocks when untested blockers exist.
  • Access restricted to workspace admins and whitelisted users.
  • Blocks when channel topic marks production as red.
  • If no blockers and DigitalOcean env vars missing, returns "deploy not configured".
  • If configured and deploy succeeds:
    • inserts a deployments row
    • marks tested PRs since last deploy as deployed
    • includes a Deployed PRs list in the response with PR title links and mapped author handles
  • If deploy fails:
    • does not write deployment row
    • does not mark PRs deployed
  • After trigger, Calypso sends a follow-up message when DigitalOcean finishes the deployment.

/calypso deploy staging

  • Access restricted to workspace admins and whitelisted users.
  • Triggers deployment using DEPLOY_STAGING_APP_ID.
  • Blocks when channel topic marks staging as red.
  • Does not run prod blocker checks.
  • Does not mark PRs as deployed.
  • Sends a deployment-completion follow-up when provider returns an external deployment id.

/calypso deploy prod force (or /calypso deploy prod forced)

  • Bypasses blocker checks and triggers deploy anyway.
  • Cannot bypass blockers that are explicitly marked as must-test.
  • Still requires deploy configuration (DEPLOY_TOKEN, DEPLOY_PROD_APP_ID).
  • Marks merged PRs since last prod deploy as deployed, even if they were untested.
  • Includes those PRs in the Deployed PRs response list.

Review Recap

  • Runs as a background scheduler in the app runtime.
  • Checks once per minute for configured recap slot (daily@HH:MM or <weekday>@HH:MM).
  • Optionally skips scheduled recap posts on weekends and/or observed US federal holidays.
  • Posts in-channel message in configured review-recap-channel containing:
    • Header: PR Review Recap — {scope}
    • Bold sections in priority order:
      • Approved By Reviewers (Unmerged)
      • Codex Approved, Waiting On Human Approval
      • Other Open Pull Requests
    • Multi-line PR rows with PR reference, title, author, review state, Codex state, and Last modified date (M/D/YYYY).
  • Includes empty state (• No open non-draft pull requests in scope.) when no PRs match.
  • PR matching rule:
    • lifecycle_state = open
    • is_draft = false
    • opened_for_review_at (or fallback opened_at) within configured scope window.

Environment Status Monitoring

  • Runs as a background scheduler in the app runtime.
  • Polls one configured URL every ENVIRONMENT_STATUS_POLL_INTERVAL_SECONDS (default 60).
  • Before each app probe, Calypso verifies observer connectivity by resolving the probe host with DNS and fetching ENVIRONMENT_STATUS_CONNECTIVITY_PROBE_URL over HTTPS.
  • If the observer connectivity preflight fails, Calypso skips the app probe, preserves the last known app state, and records the observer-side failure without posting a down alert.
  • Uses GET with timeout ENVIRONMENT_STATUS_TIMEOUT_SECONDS (default 60) for the app endpoint.
  • App health is still strict: only HTTP 200 is healthy.
  • Failed app probes use exponential backoff with:
    • ENVIRONMENT_STATUS_FAILURE_THRESHOLD consecutive failures required to confirm an outage
    • ENVIRONMENT_STATUS_RETRY_INITIAL_DELAY_SECONDS for the first retry delay
    • ENVIRONMENT_STATUS_RETRY_BACKOFF_MULTIPLIER for the backoff curve
    • ENVIRONMENT_STATUS_RETRY_MAX_DELAY_SECONDS as the delay cap
  • Posts only on confirmed state transitions:
    • a down alert posts only after the configured failure threshold is reached in one cycle
    • repeated unhealthy checks stay quiet
    • recovery posts once when the endpoint returns HTTP 200 again
  • First healthy observation only establishes baseline state; it does not post a recovery message.
  • Rollout guidance:
    • Set ENVIRONMENT_STATUS_CONNECTIVITY_PROBE_URL before enabling environment monitoring.
    • Verify the probe URL is reachable from the Calypso runtime, for example with curl https://<probe-host>/healthz.
    • Re-enable environment monitoring after changing the target URL or probe configuration so the monitor starts from a clean baseline.

Error Tracking Monitoring

  • Runs as a background scheduler in the app runtime.
  • Polls one configured Sentry or Rollbar project scope every ERROR_TRACKING_POLL_INTERVAL_SECONDS (default 300).
  • Provider is selected at runtime with /calypso config error-tracking-provider:sentry|rollbar.
  • Sentry uses ERROR_TRACKING_SENTRY_AUTH_TOKEN and ERROR_TRACKING_SENTRY_ORGANIZATION_SLUG.
  • Rollbar uses ERROR_TRACKING_ROLLBAR_ACCESS_TOKEN.
  • First successful sync after enablement or project/environment scope change establishes baseline state and does not back-alert existing unresolved issues.
  • Posts only on transitions:
    • first observation of a newly tracked unresolved issue posts one alert
    • repeated unresolved observations stay quiet
    • a resolved issue that reappears posts one regression alert
  • /calypso errors lists unresolved tracked issues from Postgres for the active project/environment scope.

Support Email Monitoring

  • Runs as a background scheduler in the app runtime.
  • Provider is selected at runtime with /calypso config email-provider:gmail|outlook.
  • First enablement performs a one-time 7-day inbox backfill.
  • Gmail mode requires OAuth refresh-token credentials plus a Pub/Sub topic for users.watch.
  • Gmail push notifications update pending history, and Calypso also runs fallback history sync every EMAIL_SYNC_FALLBACK_INTERVAL_MINUTES (default 5).
  • Outlook mode uses Microsoft Graph with app credentials and polls the mailbox every EMAIL_SYNC_FALLBACK_INTERVAL_MINUTES (default 5).
  • New inbox threads create rows in support_email_threads with:
    • subject
    • first sender
    • first inbound message text
    • source provider
    • received timestamp
    • manual response state
  • New queue items trigger an automatic notification in the configured email channel.
  • If an unexpired on-call user is configured, Calypso appends On call: <@USER> on Slack notifications.
  • Notification delivery is separate from ingestion, so a temporary post failure is retried without losing the email record.

AI Drafting

  • AI provider is selected at runtime with /calypso config ai-provider:openai|anthropic.
  • OpenAI uses AI_OPENAI_API_KEY and AI_OPENAI_MODEL.
  • Anthropic uses AI_ANTHROPIC_API_KEY and AI_ANTHROPIC_MODEL.
  • AI_SUPPORT_EMAIL_SYSTEM_PROMPT can append organization-specific drafting guidance on top of Calypso's default support-email guardrails.
  • Draft generation uses the first tracked inbound customer email plus optional operator instructions from /calypso emails draft ....

Testing

Run full test suite:

npm test

Current tests cover:

  • Command parsing and routing.
  • High-level command lifecycle flow.
  • Config validation behavior.
  • GitHub signature verification and webhook decision gates.
  • DigitalOcean client request/response handling.
  • Formatting behavior.

Enforce PR Test Passes Before Merge

This repo includes GitHub Actions workflow CI (.github/workflows/ci.yml) that runs npm test on every PR to main.

To block merges when tests fail, enable branch protection on main:

  1. GitHub repo -> Settings -> Branches -> add/edit protection rule for main.
  2. Enable Require status checks to pass before merging.
  3. Select required check: CI / test.
  4. Save the rule.

Local Validation Tips

  • Offline-first validation is supported.
  • Live smoke tests are optional and useful for final confidence:
    • Slack /calypso ... command flow in a real workspace.
    • GitHub webhook through ngrok/cloudflared.
    • Real DigitalOcean deploy trigger with test-safe app config.

Security Notes

  • Never commit .env or secrets.
  • If secrets are exposed, rotate immediately.
  • Keep CODE_HOST_WEBHOOK_SECRET and API tokens scoped and rotated periodically.