Unstable software - constantly breaking update processes

Every few months, I run into random issues like this:

Not always the same. This past month it was this issue. 2-3 months ago, it was some other issue caused by untested changes being merged that broke the web-based update process.

I don’t need help right now, but I do think that Discourse team would serve the community well by avoiding creating these issues in the first place. The software development process being employed now seems optimized at creating brittle, unreliable software.

Is there an effort to ensure these types of regressions and web-based-update-killers are caught before they reach user installations?

The latest branch will have continued updates, where some might receive bugs. If you want a more stable version, you can switch to esr.