There is a DETACH ALL item in Visual Studio DEBUG menu which does a friendly debug end process.  According to AI this option and the direct chip command in a Command Window are similar but with subtle variations:

In the DEBUG menu of Visual Studio their is an item called "Detach all" which seems to stop the debug session and release the target MCU to freely run.  Debug START or RE-ATACH then both seem to work, is this doing the same thing as the command:  Debug.MIDebugExec monitor reset run

Comparing how detach and disconnect differ in mechanism.
Not quite the same thing, but it reaches a similar end state by a different route, and it’s arguably the tidier fix.

Detach is a GDB command that works at the debugger level:

GDB removes all the breakpoints it had set in the target.
It resumes the CPU if it was halted.
It then closes the connection to OpenOCD.
The chip is not reset. Your program carries on running from wherever it was, with its variables and state intact.

monitor reset run works at the chip level:

OpenOCD resets the CPU, so your program restarts from the beginning.
The reset also wipes the breakpoint registers as a side effect, but GDB isn’t told, so it’s a blunt way of cleaning up.
Your original problem was a chip left halted or holding stale breakpoints after the red stop button. Detach fixes that cause directly, because it clears the breakpoints and resumes the target before disconnecting. The reset command fixes it indirectly by wiping everything. So if Detach All followed by Start or Re-attach works reliably for you, it’s a perfectly good replacement for the Command Window step, and it avoids restarting your program.

My guess is that the red stop button does a GDB kill or terminates the debugger more abruptly, without the clean-up, which would explain the stuck state. I can’t confirm that from the outside, though.

Two things to be aware of:

If the CPU is halted at a breakpoint when you detach, it resumes from that point, which is usually what you want.
Choose reset instead if you specifically want the program to start over, for example when testing boot behaviour or a clean power-up state.