I will check your debug logs, thanks for sending them.
Unfortunately, this is a forever-catching-up sort of issue. The GDB/Python pretty printing integration is a poorly designed mechanism with respect to the GDB/MI (machine interface). No attempt is made for the output of pretty printers to conform to the MI protocol, or to honor simple settings such as limits on how many elements of an array to print before stopping. Try to print an oversized or uninitialized array, and GDB will hang and eventually run out of memory. So, every release, they change something and create something new for debugger implementors to chase down and work around. It's not going to change, but I felt like I should explain why we can not always keep up with this particular ever-changing target.