So I may be the only person in the entire interwebs having this issue but this plugin is not triggering a restart when tf2 receives an update anymore.
I'm running Debian 6 (I know its old this may be an issue)
I'm running SM version 1.8.0.6041
I'm running MM version 1.10.6
Steamtools is version 0.10.0+54fdc51 (it's not throwing errors)
Today I tried to join my server and my client through the "Server is running older version of.........." error
I checked and auto_steam_update was running (v1.9.1A)
I connected via ssh to my console and ran the "quit" command forcing the server to restart when I did it saw there was an update and downloaded it.
Back on my client I retried connecting and was successful this time.
I am unsure why this plugin has failed on my server. I am trying the version of this plugin that relies on SteamWorks. Here ->
https://forums.alliedmods.net/showthread.php?p=2238058
Update: It seems the one relying on Steamworks is working fine... Not sure what went wrong... ¯\_(ツ)_/¯