This issue was caused by the hosts file being reset to defaults on the system.
On all UCLAW laptop systems, the WIndows "hosts" file is modified to include a null pointer to autodiscover.uchicago.edu, otherwise UCLAW email users with a front-facing @uchicago.edu email identity will be asked to enter a password within Outlook for "autodiscover.uchicago.edu". Regardless of credentials entered, the box will keep popping up.
The solution is to make sure the following line is entered in the <systemroot>\system32\drivers\etc\hosts file
127.0.0.1 autodiscover.uchicago.edu #autoRedirect
Between each entry, there is a TAB, not spaces