That "update everything immediately" advice nearly cost me a client in Austin last week

Everybody online screams that you should patch and update all your software the second it drops. I used to follow that like gospel, you know? Well last week I was doing some remote work for a small law firm in Austin and pushed a Windows update right when it came out. Turns out that update broke their VPN connection and their entire document system was locked down for 6 hours. The partner was furious and I almost lost the contract. Now I wait at least 3 days before touching any updates on a client's system unless it's a critical security flaw. Makes me wonder how many people have gotten burned by this same rush to update thing. Has anyone else had a forced update wreck their workflow?

3 comments

3 Comments

jake_owens24d ago

Is it really that deep though? Like yeah it sucks when an update breaks stuff but that's what backups are for. Seems like you dodged a bullet learning that lesson early.

wyatt5224d ago

I read somewhere that something like 70% of people don't have any kind of backup system, which is kind of wild. My buddy runs IT for a small law firm and he said the first thing they teach new hires is to never trust a major update the day it drops. Wait three days, let the early adopters be the crash test dummies. Backups are great in theory but most people find out theirs are either incomplete or they never actually tested restoring from them. You're right though, learning that lesson with one bad update is a lot cheaper than finding out when your whole drive dies.

terry_lewis2124d agoMost Upvoted

Jake Owens is way off here. Backups aren't some magical fix for every update problem. A backup only helps if you can actually restore the system in a reasonable time frame. In a small law firm that means lawyers can't bill for 6 hours while you're trying to roll back a broken VPN and document system. That's real money lost, not just a minor inconvenience. Most small firms don't have IT staff on site to handle that kind of emergency either. Waiting three days lets the big companies find the bugs first so you don't have to be the guinea pig. It's about protecting your reputation and your client's business, not just having a backup file sitting on a drive somewhere.