Hello w_holdman,
Let's start off by checking the helpful steps in this article which can help with this issue: If Mail on your Mac keeps asking for your password - Apple Support. Follow this guidance:
"Check your password in Internet Accounts preferences
Depending on the type of email account you're using, you might be able to correct the password as follows:
- Quit Mail. If it doesn't quit, you can force it to quit.
- Choose Apple menu > System Settings (or System Preferences), then click Internet Accounts.
- Click your mail account.
- Click the Details button, if present.
- If you see a password field for your account, delete the password and type the correct password.
- Close the settings window, then open Mail and try using your account again.
If Mail still asks for your password, the password is probably incorrect. Your email provider can help you verify your email settings and make sure that you're using the correct password.
Test using webmail
- Many email providers offer webmail, which is a way to use email with a web browser such as Safari, instead of with an email app such as Mail. For example, if you're using an iCloud Mail account, you can use iCloud.com to send and receive email.
- Because the password that you use with Mail is usually the same password that you use with webmail, try signing in to webmail with that password. If it doesn't work there either, your password is probably incorrect. Your email provider can help you verify your email settings and make sure that you're using the correct password for the Mail app.
Remove your account, then add it back
If no other solutions work, try setting up your email account again. To do that, follow these steps:
- Remove your email account in Mail.
- Add your email account in Mail again."
Let us know if we can help with anything else at all or if this doesn't settle your issue so we can look into this further with you. Thanks and have a fabulous day!