Octo needs restart via Putty

Hi everyone. I´m running 1.4.0 on a Pi3+. More often than not I must restart Octoprint via Putty when I issue a new print job.
Lets say a print I send from Cura finished and I want to send another one then Octo just sits there, receiving the gcode, but does not bother to start printing. it wont even load it for printing.
When I try to reload Octoprint or restart the whole Pi from the menu button it won´t do nothing. All I can do is Putty into it and reboot. But then again this does not work all the time. Just now I had to restart the Pi two times to get it printing again.
What could be the issue here?

I would suggest that you enable serial logging, reboot your RPi, send a print job, send another print job and then provide the logs (use the link) generated by this process. Additional details like the client system OS, browser used, step-by-step and names of "buttons".

The more you give us, the more help we can give you.

Logs logs logs.