Two separate issues here:
**1. Shell syntax** — `export VAR=value command` doesn't work like that. Run them on separate lines:
```bash
export OLLAMA_TAILSCALE_IP=100.112.152.5
python3 cowork/scripts/ollama-healthcheck.py --verbose
2. Ollama not running on WSL — the Tailscale IP is reachable (machine is online, last seen 10:12 AM) but port 11434 is refusing connections. Ollama isn't installed or isn't running yet. On WSL:
# Install Ollama (if not done)
curl -fsSL https://ollama.com/install.sh | sh
# Start it (binds to localhost by default — need 0.0.0.0 for Tailscale)
OLLAMA_HOST=0.0.0.0 ollama serve &
# Pull the model
ollama pull qwen2.5-coder:7b
# Verify it's listening
curl http://localhost:11434
Then re-run the healthcheck from macOS. The Tailscale tunnel itself is fine — wsl-ubuntu2604-jadecli (100.112.152.5) is on your tailnet and your MacBook can reach it. The missing piece is just Ollama binding to 0.0.0.0 instead of 127.0.0.1.
Also want me to dispatch draft-tos-now to the legal queue now?
Ollama isn't running on WSL yet. Switch to your Windows machine and run these in WSL:
# Install Ollama
curl -fsSL https://ollama.com/install.sh | sh
# Start with 0.0.0.0 binding (required for Tailscale access)
OLLAMA_HOST=0.0.0.0 ollama serve
Leave that terminal open, open a second WSL terminal:
# Pull the model
ollama pull qwen2.5-coder:7b
# Confirm it's listening on all interfaces
curl http://localhost:11434
# → "Ollama is running"
# Confirm Tailscale can reach it from WSL itself
curl http://100.112.152.5:11434
# → "Ollama is running"
Once that last curl returns "Ollama is running", go back to macOS and re-run the healthcheck — it'll pass.
Yes, dispatching draft-tos-now to legal now:Dispatched and committed (f1978705). Legal-coworker has a priority-5 task in its queue — next /legal-coworker session will claim it and produce cowork/apps/legal/tos-draft.md.
Once Ollama is running on WSL (OLLAMA_HOST=0.0.0.0 ollama serve), the healthcheck will pass immediately — no other changes needed.
2. Ollama not running on WSL — the Tailscale IP is reachable (machine is online, last seen 10:12 AM) but port 11434 is refusing connections. Ollama isn't installed or isn't running yet. On WSL:
Then re-run the healthcheck from macOS. The Tailscale tunnel itself is fine —
wsl-ubuntu2604-jadecli(100.112.152.5) is on your tailnet and your MacBook can reach it. The missing piece is just Ollama binding to0.0.0.0instead of127.0.0.1.Also want me to dispatch
draft-tos-nowto the legal queue now?Ollama isn't running on WSL yet. Switch to your Windows machine and run these in WSL:
Leave that terminal open, open a second WSL terminal:
Once that last curl returns "Ollama is running", go back to macOS and re-run the healthcheck — it'll pass.
Yes, dispatching
draft-tos-nowto legal now:Dispatched and committed (f1978705). Legal-coworker has a priority-5 task in its queue — next/legal-coworkersession will claim it and producecowork/apps/legal/tos-draft.md.Once Ollama is running on WSL (
OLLAMA_HOST=0.0.0.0 ollama serve), the healthcheck will pass immediately — no other changes needed.