Add tooling-tailscale skill: containerized Tailscale SOCKS5 proxy for VPN coexistence #97

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opened 2026-05-29 01:03:53 +00:00 by coilysiren · 0 comments

coilysiren commented

2026-05-29 01:03:53 +00:00

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Context

Tailscale and a WireGuard-based commercial VPN cannot share one macOS host route table: both install a utun interface and a default-route override, last writer wins, the other silently breaks. The stable escape hatch is running Tailscale in userspace mode inside a Docker container, exposing a SOCKS5 proxy, and routing SSH through it. The container's network namespace never touches the host route table, so the host VPN keeps the default route uncontested.

This issue

Add the public tooling-tailscale skill documenting:

the host-route conflict and the workarounds that do not work
the containerized userspace/SOCKS5 escape hatch (compose plus an ssh ProxyCommand)
the sharp edges: tailnet identity shift, skipping MagicDNS, a dedicated tag:proxy, and an IaC-minted reusable+ephemeral key

The second VPN is kept generic so no specific product name lands in the public repo.

## Context Tailscale and a WireGuard-based commercial VPN cannot share one macOS host route table: both install a utun interface and a default-route override, last writer wins, the other silently breaks. The stable escape hatch is running Tailscale in userspace mode inside a Docker container, exposing a SOCKS5 proxy, and routing SSH through it. The container's network namespace never touches the host route table, so the host VPN keeps the default route uncontested. ## This issue Add the public `tooling-tailscale` skill documenting: - the host-route conflict and the workarounds that do not work - the containerized userspace/SOCKS5 escape hatch (compose plus an ssh ProxyCommand) - the sharp edges: tailnet identity shift, skipping MagicDNS, a dedicated `tag:proxy`, and an IaC-minted reusable+ephemeral key The second VPN is kept generic so no specific product name lands in the public repo.

coilysiren referenced this issue from a commit

2026-05-29 18:44:22 +00:00

feat(skills): add tooling-tailscale for containerized VPN coexistence

coilysiren closed this issue

2026-05-29 18:44:22 +00:00

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coilyco-flight-deck/agentic-os#97

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