Bug in the Server

I opened up my server for my friend to play, but he kept telling me after a few minutes the server kept crashing, but when I went back each time, the server said offline, not crashed. The log didn't say much, but I tried turning the server on one more time, and kept watching the site to see if anything was off. The server started and the timer that starts before someone logs into the server was going, but it kept going even after he logged in. The website even recognized it because it said "1/10 players", but the timer still kept counting down. I've refreshed, restarted, and researched, but I can't find any solution to this bug.