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OS X Yosemite brings quite a lot of new features, some of which are better known, some of which are not. One of the lesser known is a feature of the native email client, the application Email. This feature doesn't have a name, but what it does in a nutshell is ask your email provider's server for the optimal Mail settings and readjust the application according to the answer.

The problem occurs when there is no response from the server and the function gets stuck in a loop. The entire client then behaves as if it is not responding to your requests. Worst case scenario, you don't send any mail at all. If you are facing these issues, the following procedure may be the solution.

  1. Open Mail settings (⌘,).
  2. Select a bookmark from the top menu Accounts.
  3. In the sidebar, select the problem account and on its tab Advanced uncheck the option Automatically detect and maintain account settings.
  4. Go to another tab from the top menu (for example In general) and confirm the changes made.
  5. Go back to the bookmark Accounts, select the same account, but this time stay on the first tab Account information.
  6. In the item Outgoing mail server (SMTP) select an option Edit list of SMTP servers…. A new window will open.
  7. Select the SMTP server of the problem account and on the tab Advanced uncheck the option Automatically detect and maintain account settings.
  8. Close everything and confirm the changes.
  9. Quit Mail (⌘Q) and relaunch it.
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