Here is the section of the advancedconfig that uses worldguard region: http://pastebin.com/36hKgPie
Console says "Autorank: Config files have been correctly setup!"

I made the region quite sizable to hopefully improve chances of it working. The worldguard region matches the case of the region specified in the Autorank config. Using the command "/ar hooks" shows worldguard is an available hook.

What I've done to try to fix it:
Tried different region
Tried /ar check while meeting all requirements
Purged all player data, started fresh
Reinstalled AutoRank - (kept configs)

I'm hoping you see an error in the pastebin, or this is a known issue - it would explain a lot.

Hmm, what version of Autorank and Worldguard are you using?

Autorank 3.7.3
Worldguard 6.1
MC: 1.9.2

It seems like your AdvancedConfig is correct and the server log doesn't show any errors. Could you try making a 'TestRegion' and also set the worldguard region requirement to 'TestRegion'? That should definitely work (as I've tried that myself just now).

For the links, see this updated AdvancedConfig file: https://github.com/Armarr/Autorank-2/blob/master/AdvancedConfig.yml

Hmm, this is odd. I've tested it and it seems to work for me. Did you make sure it is typed correctly? It is case-sensitive.

I was testing last night and I need to isolate this issue. Its not just world guard anymore. I reset all player data again, added myself to the default group and joined the server fresh. After the first rankup requirement of 15 minutes it still didn't promote me. Something else is wrong for my case.

Is there any typical mistake people make that would stop Autorank from promoting? Is it something with the config?

I remember getting errors in my config when I used certain types of fireworks. The 'large' firework triggered an exception so I had to change the large fireworks to 'ball' fireworks and it said it was correct. I will try taking out firework results tonight and see if that, for some reason, effects it.

Could you show me your whole advanced config and server log? Most problems will be shown there :=

Server log: http://pastebin.com/AFp7Wr3C
Adv config: http://pastebin.com/y19mPwh9

Also, pasting that in reminded me, I want to know if there is another source for the reference links at the bottom of the default adv config for effects and firework types. Those jd.bukkit.org links have shown 404 errors since I first tried accessing them (about a week ago).

Tried it with a different region, also cleared all plugin data prior to testing. Also I thought the problem coincided with when I added all the firework results and updated to 3.7.3. So I removed firework results from the config as well with still no luck :(. I found the repository on bukkit, i'll try an old version.

Tried 3.7.2 and it worked!

Now it will promote me once i meet the requirements. But it throws up a lot of console errors.
http://pastebin.com/AXau01pb

Heres what it did when it was just a timed promotion:
http://pastebin.com/dTXgyTQS