Selfhosted
A place to share alternatives to popular online services that can be self-hosted without giving up privacy or locking you into a service you don't control.
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Unfortunately some apps require the certificate be bound to the internal application, and need to be done so through cli or other methods not easily automated. We could front load over reverse proxy but we would still need to take the proxy cert and bind to the internal service for communication to work properly. Thankfully that's for my other team to figure out as I already have a migration plan for systems I manage.
Why can't you just have a long lived internally signed cert on your archaic apps and LE at the edge on a modern proxy? It's easy enough to have the proxy trust the internal cert and connect to your backend service that shouldn't know the difference if there's a proxy or not.
Or is your problem client side?
That’s actually a really good idea. I’m not the person you replied to, but I’m taking notes.