Servers not updating to new version

I'm not sure what is going on, but the last update(s) are showing my servers in red on the multiplayer. I have done updates via WindowsGSM and steamCMD and can't seem to get them to update. Two out of three show different lines of text in the console like it is "new" but one still will not update in any way. I tried the "app_update 339010 -validate" in steamCMD and it loaded and that doesn't work. I have verified the files in steam, I have "update and validate" in WindowsGSM, I have restarted computer, restarted windowsGSM, restarted Steam, sold my soul to the Devil and nothing seems to work.

Has anyone else have an idea why this is not working properly or know the super secret solution?

two servers give me this:

And the one that refuses to update in any way gives me this:

Quote from SonoBionda

I host my server via GTX. I always have to trigger the updates myself there and use a button to clear the Steam cache beforehand; otherwise, nothing gets updated.

Unfortunately, though, I can't tell you exactly what that button does to make it work.

In the Steam client settings, under "Downloads," there is also an option to clear the download cache—I don't know if the two are related.

I triggered update, update validate, restart everything and I did do that cache clear like you mentioned and still not work. I redid SteamCMD, "app_update 339010 -validate" and still wont get the game update.