Server not 'closing' at restart with players online.

My server has scheduled restarts and as it goes into the restart it 'hangs'.

23:00:08 CONSOLE: [INFO] Saving worlds
23:00:08 CONSOLE: [INFO] Saving chunks for level 'Huggercraft'/Overworld
23:00:08 CONSOLE: [INFO] Saving chunks for level 'Huggercraft'/Nether
23:00:08 CONSOLE: [INFO] Saving chunks for level 'Huggercraft'/The End
23:00:10 CONSOLE: Shutdown Thread/INFO]: Stopping server
23:00:10 CONSOLE: Shutdown Thread/INFO]: Saving players

At this point it's shut-down and has not initiated the restart sequence, I have to manually log in and restart myself.