Anyone else struggling with with legacy cloud migration dependencies breaking everything?
We are sitting on a mix of old on prem servers and some pretty outdated aws setups. apps are a mix of java monoliths and some .net stuff that barely runs.
every time we try to move even a small piece to something more modern, something breaks. dependencies we didn’t know about, or performance drops hard once it’s in a new environment.
last attempt we lost a prod db connection for hours because some legacy vpc config didn’t play nicely with eks.
now leadership wants a full migration plan, but it’s hard to see how we do this without downtime or blowing the budget fixing things as we go.
How did you approach this.. any gotchas to watch for, or things that helped keep it stable during the move?