Migrate from Twingate to Tailscale with self-hosted Headscale

[bancey]

Plan and execute the migration from Twingate to Tailscale using a self-hosted Headscale instance.

Child Issues:

• Deploy and configure Headscale server for lab VPN
• Rollout Tailscale clients to lab devices

Steps:

• Inventory current Twingate resources and access policies
• Define user requirements and network segmentation
• Deploy and configure Headscale server (including authentication and DERP setup)
• Set up ACLs matching current access rules
• Pilot the Tailscale rollout for non-critical users/services
• Gradually migrate all users and services
• Monitor and document the process
• Decommission Twingate after successful migration

Acceptance Criteria:

• All users able to access required resources via Tailscale/Headscale
• Documentation updated
• Twingate access removed
• Rollback procedure documented