Tailscale has raised $160M

I've got conflicted feels about Tailscale. I love their product and a bunch of the people I know use their free tier, including myself.

But their enterprise strategy destroys their good will. I can only assume it's focused on killing old school VPN products. The free tier that we love is a marketing expense. And it’s not even a conversion play.

People are complaining about ~10/user/month -- add basic things that you'd need to manage more than 10 peeps (SAML/SCIM support) and you're talking ~20/user/month. For us, a small sub 200 person company, they immediately lost their chance. We have lots of problems in the security space, some we're willing to spend more than 20/user/month to solve. Legacy network access is not one of them.

If 20$/user/month is too much, maybe you could apin up headscale and plug in your OIDC provider?

Never tried it myself, I only manage small tailnets so the free tier is fine

Assuming they wouldn't want to take on server maintenance workload, wouldn't something like NetBird be a better fit? The free version has ACL already, the $5/user/month has OIDC integration, and the business version (MDM integration and auditing) is $12. Then the server is still open source so if they wanted to transition to doing it themselves they still would have that option down the road.

> I can only assume it's focused on killing old school VPN products.

Given how goddamn terrible Cisco anyconnect is, I hope they succeed.