I'm having a hard time debugging some virtual machine code because GDB won't break where it's supposed to

A quick follow-up. The GDB folks were able to reproduce this in an XUbuntu 20.04 VM. I don't know if they tried straight Ubuntu, but as the main difference between the two is the user interface it seems likely the bug might surface there as well.

The use of a VM thus provides another option as a workaround for me, though my simple-minded label-to-line number script works as well.

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