Server Connection Issues, Worked For 1 Whole Day

I’m new to Plex, but so far I am having quite a time trying to get Plex up and running. It was running the first day, but now everything is dead. I’ve installed the server on my primary MacBook, with no external drives, nothing fancy in the network, all very basic, so I don’t get why none of it’s working.
Just trying to load it locally on my server (MacBook) results in errors. From app.plex.tv it says “There was an unexpected error”, from 127.0.0.1:32400/web/index.html it says the server cannot connect securely. I don’t get how the server cannot connect securely when it’s physically the same machine. Other computer with a managed user cannot connect as well, but I’ve had a Fire TV connected and working fine just yesterday.
While just writing this I decided to refresh the pages, and what do you know, it’s suddenly working again. Is there something I’m completely missing? I don’t get why there is no actual application interface and I find that quite annoying. What is the difference between app.plex.tv and the localhost? This whole system design is strange and ambiguous. Is there a place I can get some status information about the server? Is it running? Connected? Logs?

Side note, I just checked the devices list and the safari web accessed an hour ago that didn’t work lists 3.20.7 and now there’s a new one listed as 3.23.1.

Any help would be greatly appreciated.

To Plex staff,
These are some really big errors that a new comer (experienced in networking and tech) should not have to deal with. There is no readily available information in any of the errors messages that help at all. On one page it just says “There was an unexpected error, please visit our forums if you continue to experience problems” and to top that off the link that says “Go to forums” doesn’t even work.
Also, for all of the forum sections that are available in the category drop down, there is not a single support category listed. Not one for connection issues.

If I can’t get this figured out quickly I will be asking for a full pass refund and I will be looking for an alternative solution.

Edit: My first post had my email address showing for me, but after going to https://forums.plex.tv/sso it started showing username.
https://forums.plex.tv/discussion/241696/hide-email-address

You didn’t need to post this three times.
Post 1: Here…
Post 2: https://forums.plex.tv/discussion/293012/server-connection-issues-worked-for-1-whole-day#latest
Post 3: https://forums.plex.tv/discussion/293011/server-ran-for-1-whole-day#latest

I didn’t mean to. The forum site seems to be glitchy as well. I hit post once and the page wouldn’t redirect or update.

A proper catergory/subforum would have been this: https://forums.plex.tv/categories/mac Since you are running PMS on mac. But please don’t post another three times :wink:
Can’t help, not a mac guy. But since you are a tech guy, maybe the server logs help:
https://support.plex.tv/hc/en-us/articles/200250417-Plex-Media-Server-Log-Files

The support pages have a lot of information and maybe this is also a good read for you, apart from that log-file article.