Troubleshooting Broken Software Tools Still Sucks

20+ years of professionally building software, and here is how my last hour or so went.

heroku login -> zsh: killed heroku login

hmmm...why did ZSH kill Heroku? It turns out it is just reporting what happened.

Open the crash reports and get a bunch of text I barely understand.

I remember that I have a second brain that knows what this crap means. ChatGPT, can you help me?

It does a decent job of educating me on what the reports (segfault on the main thread implies not even the hand of God can save this process).

When in doubt, just re-install.

No dice.

Google shows me others with similar problems, but none related to Heroku, and nothing that looks promising.

I wonder what the (brew) Doctor thinks about this (Heroku was installed this way).

The doctor takes her good old time getting back to me on this older Mac. But when she does respond, she says, "Dawg, your shit is F'ed Up!"

I am paraphrasing, but there are unlinked things, kegs with no formula,, dry taps, an unbrewed dylibs, and likely most importantly, this:

This is weird because I had previously checked for an update after an OS update, and I had tried to re-install the tools just to be safe.

In both cases, it said, "there are no updates, go away".

Anywho, I run the following:

sudo rm -rf /Library/Developer/CommandLineTools

sudo xcode-select --install

Eventually, notice the popup window (because why install them from the terminal), click OK to continue, and 10 minutes or so later, we are back in business.

The key takeaways:

1. This shit isn't hard, it just takes patience.
2. Even those who have done it for a long time still get stuck.
3. There is nothing wrong with yelling profanities at a computer from the comfort of your basement.