My guess is that this is a consistency issue caused by the async task that updates the service status either not running, or being executed with a significant delay. If you click the refresh button on the service page (the one in your first screenshot), does the status update correctly?

You might want to look at task logs to see if there are things stuck in the queue

It doesn't update. I'm just running everything from docker. Is there a troubleshooting guide? I'm not sure if by task log you just mean the logs of the containers.

HTTP checks work / send e-mail when failing but not jenkins

Can you allocate more resources? This sounds like a docker config error to me.

Yes, by task logs I mean logs of the worker processes. You might want to try playing with machine resources - it sounds like you might be overloading your containers?

Cool. I'll look into that. Something to note is I've been trying to run this on Windows, but I'm switching to trying to run it on Ubuntu next just because docker is way easier on linux. If I have the same issue, I'm going to try to run all of the containers except for the worker and then debug the worker in pycharm and see if I find any errors.