Server Crashes with OutOfMemoryError

I upgraded the server from 1.13 to 1.14 and then shortly after to 1.14.1. The server seems to be crashing with an OutOfMemoryError despite being configured with enough memory. It normally runs with 2Gb but I also tried with 4Gb just in case. In jconsole it runs with around 300Mb in heap before it crashes.