Send & Receive issues are the most complex to troubleshoot. There are many variables that need to be checked. Usually when messages are not sending or receiving, it’s a result of Mail not remembering your password. You can check in Connection Doctor. Under Window in the Menu bar, select Connection Doctor.
You will see green to indicate a connection and red to show there is a problem. You want to see all green symbols.
Verify that you have the correct password. You can test the password by logging into your email account in your browser via webmail.
1. If you can receive but not send then you have a bad SMTP configuration (Incoming)
2. If you can send but not receive you have a bad POP or IMAP configuration (Outgoing)
3. Usually it’s a missing password that is causing the connection issue.
Settings like SSL, ports and authentication vary with email providers. Apple provides this link to help with your settings, but you might need to search your host for the correct info. https://www.apple.com/support/mail-settings-lookup/
EDIT SMTP SETTINGS (Outgoing)
In Accounts window under Account Information tab, you’ll find Outgoing Mail Server SMTP: Select to Edit SMTP Server list… from popup.
Select account in the list. (It’s not uncommon to find extra SMTP servers listed. When you remove account, Mail does not delete the smtp info. You might need to do some clean up in the list to remove the extras.)
Note: there is no save when you make changes to SMTP settings like changes to Incoming settings.
Under Advanced Tab:
Apple previously defaulted to the ports (25,465, 587), but in El Capitan it will default to port 587 for most email providers. Some servers prefer a custom port. Check to see what port your email provider recommends. Gmail for example, likes 465, Outlook.com 587. Some providers use ports: 80, 2525, 3535 or other ports. There is no way to guess. You need to check with your provider for email setup instructions.
Note: if your provider still uses port 25, see this article on why Comcast no longer supports port 25. It’s highly advised that you use secure settings whenever possible.
Verify if your server require SSL.
User Name: Enter full email address eg. UserName@gmail.com (most providers require the full email address not just your user name before the @ sign)
Add password if it is blank.(If you have two step authentication setup, you’ll need to get an app specific password more info for Gmail two-step
After entering the password, check again in Connection Doctor to see if you are seeing green for the account.
EDIT INCOMING SETTINGS (receive)
There are three tabs in the Account window:
Account Information, Mailbox Behaviors, Advanced
Under Account Information, be sure your password is entered. If it’s blank, add your password. After adding you need to click out to save.
Under Advanced, you might need to tweak your settings. This is where the incoming server port is set. Only your provider can give you the correct port to enter.
Port 110 – non-encrypted port
Port 995 – POP secure connection. Users SSL
Port 143 – IMAP non-encrypted port
Port 993 – IMAP secure connection. Uses SSL
You will need to check with your provider to see if SSL is required. Occasionally, you need to check ‘Allow insecure authentication’.
Back to the Connection Doctor to see if your account is now showing green for connection.
It’s not uncommon to have to enter the password several times before it sticks. However, some users have to delete the account then add it back in order to save a password. Other users have issues with the Keychain that stores the password. This is a bit more complicated to fix.
KEYCHAIN ACCESS TROUBLESHOOTING
Apple stores your passwords in Keychain Access. You’ll find this app in Applications/Utilities.
- Open Keychain Access
- In the top search box, enter the email account that is not saving the password.
- Under Category, select Passwords. Your email account will have the blue @ symbol.
You should see an entry for incoming and outgoing for each account. It’s not uncommon to find many old entries for the account. Keychain doesn’t delete old or duplicate entries. Often you need to delete all then let Mail add the password back to Keychain Access.
- Double click to open the entry. Check the box to “Show Password”. This requires your login password to view.
- Is the password entered correctly? You can edit to save correctly or if it’s blank you can add the correct password then Save Changes.
- Go back to Mail > Connection Doctor and see if your account is connecting now.
Option 1)tSome users have to create a new keychain in order to fix password issues.
Create a new keychain by going to the “File” menu, then “New” and selecting “New Keychain”.
You can now make this keychain your default if you desire by selecting it, then going to the “File” menu and selecting “Make ‘(name of keychain)’ Default”
If Keychain First Aid finds an issue that it can’t repair, or if you don’t know your keychain password, you might need to reset your keychain.
Resetting a keychain sets aside the original default keychain file and creates a new one.
To reset your keychain in Mac OS X 10.4, Mac OS X 10.5, and Mac OS X 10.6 Snow Leopard or later:
Open Keychain Access, which is in the Utilities folder within the Applications folder.
From the Keychain Access menu, choose Preferences.
Click General, then click Reset My Default Keychain.
Authenticate with your account login password.
Quit Keychain Access.
Restart your computer.
If your connection problems are an on/off issue, the problem is most likely with your provider and not with your Mail settings.