The following info is from a Rackspace doc:
Update the Password Authentication Method for Apple Mail
For this error:
Connections to host secure.emailsrvr.com on the default ports failed.
proceed as follows:
To configure the settings for Apple Mail correctly, perform the following steps:
- In Apple Mail, go to Mail->Preferences.
- Click Accounts, then click the Server Settings tab.
- Click Outgoing Mail Server and select Edit SMTP Server List.
- Click the Server Settings tab.
- For Authentication, select Password rather than MD5 Challenge-Response.
- Click OK to close the SMTP window and click OK again to close Preferences.
For this error:
Connections to host secure.emailsrvr.com on the default ports failed.
proceed as follows.
- To configure the settings for Apple Mail correctly, perform the following steps:
- In Apple Mail, go to Mail->Preferences.
- Click Accounts, then click the Server Settings tab.
- Click Outgoing Mail Server and select Edit SMTP Server List (may need to scroll down to bottom on drop-down menu)
- Click the Server Settings tab.
- For Authentication, select Password rather than MD5 Challenge-Response. (if you do not see Authentication, uncheck Automatically manage connection settings)
- Click OK to close the SMTP window and click OK again to close Preferences (or red dot on top left corner of window).
Additional Resources
When You Can’t Send Mail: Fixing SMTP Problems
Use Connection Doctor in Mail on Mac
- In the Mail app on your Mac, choose Window > Connection Doctor.
- Review the status information. …
- When you're done, click Check Again to verify if your actions resolved the problem.
02052025