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.
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