When using Mail for accessing your e-mail, you might run into a problem where Mail repeatedly asks for your password, either when you are checking for new messages (such as when opening Mail for the first time), or when attempting to send messages.
This can be frustrating to deal with if it happens, but if it does there are several things you can do to fix the situation.
Toggle your internet off and on
Often Mail prompting for a password is from its inability to properly connect to your service provider. This can happen if you have lost your connection in the midst of communicating, so try toggling your Wi-Fi or other network connections off and then back on, to see if this helps the situation.
Wait a short while
It may be instinctive to try entering your password repeatedly in the authentication window that pops up, followed by clicking the “Get Mail” button to ensure it takes; however, while worth one try, if the password box pops up again, then this approach is likely a waste of time. Sometimes odd problems with mail account servers can prevent authentication for a short while, so if this happens, consider waiting about 10-15 minutes before trying again.
Quit and relaunch Mail
In addition to waiting, quit and relaunch Mail to see if the problem is simply a temporary fault with how Mail’s configuration has loaded.
Ensure the password is correct
While passwords should be stored in your Mac’s keychain, if you have entered the password again and then re-saved it in your keychain, then you might have simply entered it incorrectly. Therefore, try again and ensure you have put in the right password.
Open the Keychain Access utility, and search for the affected e-mail account (username and domain) to locate any keychain entries used for accessing this service. Select any relevant ones (especially if there are duplicates), and delete them from your keychain. Following this, go back to Mail and supply your password when prompted, and choose the option to save the password.
In addition to using the Mail password prompts, you can manually enter passwords in Mail’s settings. This may be especially pertinent if the password prompt is only happening when you try to send mail, or when you try to receive mail:
Go to Mail’s preferences and click “Accounts” (not the Accounts option in the Mail menu)
- Select the affected account in the list to the left
- In the Account Information tab, update your password in the “Password” field
- In the Outgoing Mail Server (SMTL) menu, choose “Edit SMTP Server List…”
- Select the SMTP server you use with this account
- Click the Advanced tab
- Again re-type your password, followed by clicking OK to save
In addition to updating your password, ensure your outgoing server’s port number and SSL options are set appropriately, according to the configuration requirements for your mail service. You might need to search on the Web or otherwise with your service provider to see what these settings are. Lastly, try toggling the box to automatically detect and maintain account settings, to see if this setting may be causing the problem.
If re-entering passwords does not seem to fix the issue, then try repairing your login keychain. To do this, open Keychain Access and select your keychain, followed by choosing Keychain First Aid in the Keychain Access menu (or press Option-Command-A). In the window that pops up, click Start to verify, and if you see any problems pop up (especially if they are related to your mail account passwords), then click the Repair radio button and again click Start. Following this, you might need to re-supply your password again to save it.
I find that the removing all entries in the Keychain related to the email account(s) in question is frequently the resolution to this issue. Note that you should quit the Mail app before you do this. And you should log out or restart once you remove the passwords from the keychain. (Technically, this shouldn’t be necessary…. but on many occasions I have observed that troubleshooting Mail requires a log out or restart in order to be successful.)
You suggest” Lastly, try toggling the box to automatically detect and maintain account settings”. I can’t find that option in mail. Where is it?
Funny, that Outlook has a similar issue. Losing the password irregularly, prompting PW entry again and again. . .
There’s a page addressing this problem for Outlook….
FIXED: outlook.live.com hotmail.com etc. The biggest thing was Mac Mail Yosemite would not go “online” with hotmail imap. Account sets up ok but then get error message repeatedly asking me to enter password …but it won’t accept it.
THE FIX: think of Mac Mail as an app for a phone & set up two step authentication ….let windows/outlook.live generate a password for you “app” (Mac Mail)
Copy THAT password and use it for hotmail in Mac Mail …NOT the one you use when you sign into windows.live or outlook or hotmail.
**be sure to also copy it into an email that you will send yourself (or wherever you store you passwords)
Mac Mail then sets EVERYTHING UP AUTOMATICALLY …synchronizes ….it’s only taken me 5 years to find this out ….please share. xoxo 🙂
Thank you so much, this fixed my problem.