Mail won't connect in certain cases

Hey there Streeme,

It sounds like Mail is not connecting to any of your Mail servers at all. Thanks to the screenshot you posted of the Connection Doctor, I recommend this info from the following article, named:

OS X Mail: Troubleshooting sending and receiving email messages

Click here if a "Could not connect to this (server type) server…" message appears

Check for third-party firewall software

Third-party firewall software, such as Little Snitch or Symantec Norton Personal Firewall, could be blocking the necessary ports. If such software is installed, make sure the firewall is not blocking these ports:

• ports 25, 465, and 587 (for sending email via SMTP)
• ports 143 and 993 (if you use IMAP email)
• ports 110 and 995 (if you use POP email)

If you're not sure how to enable the correct ports, try disabling the third-party firewall completely, then test for the Mail issue. Note: The Mac OS X v10.6 firewall does not interfere with ports needed to send email.

Check for Internet Service Provider port blocking

Your Internet Service Provider may be blocking the SMTP ports needed to send email.

You can use Apple's MobileMe service to find out if your Internet Service Provider is blocking the sending email protocol SMTP:

1. Open Network Utility.
2. Click the "Port Scan" tab.
3. Enter "smtp.me.com" in the "Enter an Internet or IP address to scan for open ports" field.
4. Enable "Only test ports between _ and _", and enter 25 for both port fields.
5. Click "Scan" to test.

If you do not see "Open TCP Port: 25 smtp", contact your Internet Service Provider or visit their support website for further assistance. If you do see "Open TCP Port: 25 smtp", your Internet Service Provider is not blocking the SMTP ports needed to send email. Go to the "'Trying to log in to this (email server provider name) account failed…' message or any other error message appears" section below if the email issue persists.

Thank you for using Apple Support Communities.

Regards,

Sterling

Thank you for using the Apple Support Community. Due to the nature of your issue you may find more information by using another one of Apple's support resources - https://getsupport.apple.com/GetproductgroupList.action.