Hi @jharrity
Tried to replicate the error and noticed that "From contains" works fine when it's a 'common' email, but it fails when it's an exchange account. Don't know if that's your case.
To find out the email address PAD is considering, populate only 'Subject contains' to retrieve the specific message you're targeting, then check the 'RetrievedEmails' variable in the flow variables panel (double-click on it). By clicking 'More' in the target mail, you'll be able to see details of the retrieved messages, Check what's in the '.From' field:

When I do the same with a message sent from an exchange account, '.From' looks like this:
