Using classic Outlook for Windows in business environments
Your observation is very consistent with mine. It seems in the last couple of days, the prompt happens when I switching from mobile to non-mobile data network, and between one network and another (happened when I enabled VPN and again when I disabled VPN). It seems like MS systems authenticates and grants permission weighing heavily on IP address, so if the device suddenly changes IP address/network, it would fail the new attempts, even if it was previously authorized on those networks. Given competing platform/email system handle the same situation gracefully, it suggest these are MS issues or possibly design flaws with their security protocols.