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The main thing a big company IT admin wants is control over the users. At a previous company, they would ship really crappy software, by our own admission, to "enterprise" customers and all we had to do to keep them happy was to give a fancy control-panel that make then feel like king.

Yes, flattery works, pandering-to-ego works. Too bad, you can only push it so far...at some point, CTO/CEO notices.



Agreed. In this company the IT team was being spread thin without their budget being increased so Tailscale was the obvious solution here, but a non-starter for them. "We already pay for a VPN. Let's just use that."

We managed to survive with our solution for a while thanks to it being super simple and "free" besides the instance running wireguard. Last I heard (I left), they shut that all down a few years ago.




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