There have been several other posts on this issue dating back a few years, such as this one.
On Windows 10, if I am using SEGGER's RTT Viewer and I flash a nRF52832 with SEGGER's J-Flash Lite, I experience no problems. The nRF52832 reboots and I immediately start to see messages in the RTT viewer.
However, if I instead flash the nRF52832 with nrfjprog, the connection to RTT Viewer is broken. If I reset the RTT Viewer connection then the messages restart.
Trying to flash with Zephyr's west tool while RTT Viewer breaks the RTT connection AND gives errors:
-- runners.nrfjprog: Flashing file: C:\Users\Chris\Nordic\v1.6.1\zephyr\samples\net\wifi\build\zephyr\zephyr.hex
Applying system reset.
Verified OK.
ERROR: JLinkARM DLL reported an error. Try again. If error condition
ERROR: persists, run the same command again with argument --log, contact Nordic
ERROR: Semiconductor and provide the generated log.log file to them.
FATAL ERROR: command exited with status 33: nrfjprog --pinresetenable -f NRF52 --snr 8010XXXXX
It should be possible for the RTT Viewer connection to remain connected since SEGGER is able to make this work, even though the RTT connection and the flashing are happening through SWD.