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> Most large places have legacy tech you’ll work on, but an “ain’t broke don’t fix” approach to technical debt is a red flag. A push to web apps is a green flag.

Very happy to see this up near the top so I know I can disregard the rest of the article. That's the attitude that helps drive enshittification of everything.

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> A push to web apps is a green flag.

This is the part that had me going 'WTF?!'.

I get that there is some signal there, but calling out 'web apps' as green flag pointing toward a better culture against technical debt had me confused.

Yeah, I almost feel like a better way to find red flags is to ask if I have to use web apps to manage systems or if there’s a nice suite of command line tools to use for day to day tasks.

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