Epicor Emails Work From Live - Not From Pilot

I have the same settings in both live and pilot. Live sends the email without issue. Pilot consistently refuses with this error:

The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 Client not authenticated to send mail. Error: 535 5.7.139 Authentication unsuccessful, the user credentials were incorrect. SANITIZED

Live works using both the legacy, and modern SMTP libraries. Pilot won’t work for either. I have obviously verified my user is correct, and the password has been updated. I verified this by changing the PW, then updating live. When emails worked in Live, I updated the password in Pilot, but still get the error above.
I cannot figure out why one works and the other doesn’t. Wait a sec.. cache?? F12+Long click refresh Empty Cache and Hard Refresh… Nope that didn’t help…

Here is a clip of what Epicor sends in the live test email:

Current Settings:

SMTP Server : smtp.office365.com, SMTP Port: SANITIZED, User: SANITIZED, SSL Enabled True, Mailer type: Modern SMTP sender.

Application Server: SANITIZED, Current Company: VTAERO, Current User NATHAN.

Gah! Well a good old log out and back in helped! I was able to properly reset the password in the pilot account, and now it seems to be sending fine!