I've been able to reproduce the problem on 32-bit Ubuntu 20.04 for RPi4.
The problem reproduces when the following is linked:

ld-linux-armhf.so.3 -> ld-2.31.so*

fostja@cptr280-arm:~/code/asm$ gdb -q hello
GEF for linux ready, type `gef' to start, `gef config' to configure
75 commands loaded for GDB 9.2 using Python engine 3.8
[*] 5 commands could not be loaded, run `gef missing` to know why.
Reading symbols from hello...
gef➤  set debug infrun 1
gef➤  b _start
Breakpoint 1 at 0x1016c: file hello.s, line 5.
gef➤  start
infrun: infrun_async(1)
infrun: proceed (addr=0xb6fd5a80, signal=GDB_SIGNAL_0)
infrun: proceed: resuming process 10100
infrun: resume (step=0, signal=GDB_SIGNAL_0), trap_expected=0, current thread 
[process 10100] at 0xb6fd5a80
infrun: prepare_to_wait
infrun: target_wait (-1.0.0, status) =
infrun:   -1.0.0 [process -1],
infrun:   status->kind = ignore
infrun: handle_inferior_event status->kind = ignore
infrun: prepare_to_wait
infrun: target_wait (-1.0.0, status) =
infrun:   -1.0.0 [process -1],
infrun:   status->kind = ignore
infrun: handle_inferior_event status->kind = ignore
infrun: prepare_to_wait


When I revert to the following then things work properly:

ld-linux-armhf.so.3 -> ld-2.28.so*

So I have a work-around. It appears that the problem was introduced
between 2.28 and 2.31.

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https://bugs.launchpad.net/bugs/1901966

Title:
  Unable to stop at breakpoint in 32-bit executable

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