Should I self-host Zendesk?

# Chatwoot — support inbox; rails web + sidekiq + postgres(pgvector) + redis
x-cw-env: &cw-env
  SECRET_KEY_BASE: 0123456789abcdef0123456789abcdef0123456789abcdef
  FRONTEND_URL: http://localhost:3006
  POSTGRES_HOST: cw-db
  POSTGRES_USERNAME: chatwoot
  POSTGRES_PASSWORD: chatwoot
  POSTGRES_DATABASE: chatwoot
  REDIS_URL: redis://cw-cache:6379
  RAILS_ENV: production
  NODE_ENV: production
  INSTALLATION_ENV: docker
services:
  chatwoot-web:
    image: chatwoot/chatwoot:latest
    container_name: chatwoot-web
    restart: unless-stopped
    depends_on:
      cw-db:
        condition: service_healthy
      cw-cache:
        condition: service_healthy
    environment: *cw-env
    entrypoint: docker/entrypoints/rails.sh
    command: sh -c 'bundle exec rails db:chatwoot_prepare && bundle exec rails s -p 3000 -b 0.0.0.0'
    ports:
      - "3006:3000"
    healthcheck:
      test: ["CMD-SHELL", "wget -qO- http://localhost:3000/api >/dev/null || exit 1"]
      interval: 10s
      timeout: 10s
      retries: 60
      start_period: 120s
  chatwoot-worker:
    image: chatwoot/chatwoot:latest
    container_name: chatwoot-worker
    restart: unless-stopped
    depends_on:
      cw-db:
        condition: service_healthy
      cw-cache:
        condition: service_healthy
    environment: *cw-env
    entrypoint: docker/entrypoints/rails.sh
    command: sh -c 'bundle exec sidekiq -C config/sidekiq.yml'
    healthcheck:
      test: ["CMD-SHELL", "ps aux | grep -q '[s]idekiq' || exit 1"]
      interval: 10s
      timeout: 5s
      retries: 30
      start_period: 60s
  cw-db:
    image: pgvector/pgvector:pg16
    restart: unless-stopped
    environment:
      POSTGRES_USER: chatwoot
      POSTGRES_PASSWORD: chatwoot
      POSTGRES_DB: chatwoot
    volumes:
      - cw-db:/var/lib/postgresql/data
    healthcheck:
      test: ["CMD-SHELL", "pg_isready -U chatwoot"]
      interval: 5s
      timeout: 5s
      retries: 12
  cw-cache:
    image: redis:7-alpine
    restart: unless-stopped
    healthcheck:
      test: ["CMD", "redis-cli", "ping"]
      interval: 5s
      timeout: 5s
      retries: 12
volumes:
  cw-db:

Want a guided install instead? caniselfhostit.com/zendesk has AI-agent prompts that assume a bare machine — that's their half of the stool, and it's good.

# Zendesk — verdict log

- **Date:** 2026-08-10
- **Verdict:** YES — worth it
- **Protocol:** v1 (2GB reference env, Docker preinstalled, AI assistant: claude-code)

## Setup evidence

- Compose: `compose/zendesk-chatwoot.yml`
- Boot to healthy: **91s** measured this session
- Setup time recorded: 42 min (boot + configuration to first working workflow)

## What broke / notes

- Boot to healthy measured at 91s on the 2GB reference env

## The call

Chatwoot gives you shared inboxes, live chat widgets, canned responses and automations — the Zendesk core — per agent forever, for the price of a mid VPS. The rails stack is heavier than most on this list; it's still a weekend, not a career.