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Simon Willison
@simonwillison.net

I gave a talk last night about "Living dangerously with Claude", on the joys and perils of --dangerously-skip-permissions and how critical it is that we run coding agents in a sandbox so that we can unlock their full potential simonwillison.net/2025/Oct/22/...

simonwillison.netLiving dangerously with ClaudeI gave a talk last night at Claude Code Anonymous in San Francisco, the unofficial meetup for coding agent enthusiasts. I decided to talk about a dichotomy I’ve been struggling …

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Jason Roy
@jasonroy.com

But none of this works if you need to access things over a VPN or through tunnels… I can’t get web versions to make the requests to internal dev URLs secured through short lived VPN connections. I never fully yolo anyways but get close, letting it modify vault secrets even. Too cumbersome!

Simon Willison
@simonwillison.net

Have you tried Tailscale? I wonder if it's possible to get Claude Code for web to download a Tailscale Go binary and proxy traffic to a Tailnet somehow... might even be the kind of thing you can solve with a skill

Jason Roy
@jasonroy.com

Hmm, I haven’t…. That’s a good idea though. I’ll see what I can setup. We use cloudflare zerotrust so I’ll see what is possible. I imagine this is an issue for lots of people behind private network APIs not connected to the internet (sometimes behind AWS SSO sessions too)

jake
@yetanotheruseless.com

But you can unlock their full potential even *easier* if you —dangerously-skip-permissions *without* a sandbox! YOLO-mode no parachute bay-bee! :|