When your container runs in bridge mode and needs the host's Tailscale network
Containers in Docker bridge mode have their own network namespace. They can't see Tailscale interfaces on the host.
docker inspect <container> | grep NetworkMode
# If it says "bridge" or "default", that's your issue
Give the container full access to the host's network stack, including Tailscale.
docker run --network host your-image
Run Tailscale in its own container, share the network namespace with your app container.
docker run -d --name ts-sidecar \
--cap-add NET_ADMIN \
tailscale/tailscale
docker run --network container:ts-sidecar \
your-image
Keep bridge mode but add a route so container traffic to Tailscale IPs goes through the host.
# On the host:
iptables -t nat -A POSTROUTING -s 172.17.0.0/16 \
-d 100.64.0.0/10 -j MASQUERADE
sysctl -w net.ipv4.ip_forward=1
ping 100.95.37.98 (or any Tailscale IP). If it times out, the routing isn't working yet.