Hi Alex,
Here is my debug configuration.
I think I set it the same as yours, but I still get two reboots before the debugger halts.
My Flash driver reset handling was set to SOFT instead of Default, but changing it made no difference, neither did specifying a Reset handling option or setting disconnect behavior to No Change
I also tested with the freertos_hello demo and get the same response.
I also tested with the hello_world demo that does not use FreeRTOS. Same result.
Glenn