[New_California]

On the contrary, it is so much easier to upgrade a small app every week or so because you have little to test and probability of breaking changes affecting you is minimal.

You should be upgrading all the time since day one, adding necessary infrastructure gradually as your app grows.

[ravloony]

Absolutely. I was leading a team a while ago and I instituted this practice to good effect.

Conversely, I was called by a company that I had built an app for previously. They had not upgraded the framework it was built with (Laravel), and ended up offering me consulting days to jump several versions. The irony is that the job ended up being quick and easy to do.

[yurishimo]

Laravel is relatively painless to upgrade as long as you have the autonomy to get the work done in a timely manner. I've seen upgrade projects drag on for weeks causing issues upstream since most of the team was still working on the product or fixing bugs while one developer was tasked with the upgrade.

Did you use a tool like Shift to help with the upgrade? What about frontend dependencies? The recent move from Mix to Vite is great, but if you have a large frontend, it can be a major PITA to update. More so if you have any sort of custom webpack configuration.

[jonwinstanley]

Yes, Laravel does a good job of making upgrades relatively simple

[riffraff]

You need to have the right infrastructure/organizational maturity tho.

For example in many organizations partial deployments don't exist and rollback is not easy, so having a "once a quarter we test everything and bump" is less traumatic and expensive than handling minor breakages every week.

You can invest into that infrastructure/maturity but it may not be the best use of your time and money if you don't even know that your company will exist next year.