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Apple Mail – Friend or Foe?

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Just when everything seems to be working well, you get the dreaded SMTP error and your outgoing email remains stuck in the Outbox. Yet you’re able to seamlessly receive email messages. So what’s the deal with that?

That’s because, for some reason (and Apple will never admit there is a problem with its software), its Mail program has trouble with outgoing mail. Yes, even though it worked fine an hour ago and you haven’t tinkered with the settings, you’ll still get an error message when attempting to send email. The message usually reads “Cannot send message using the service mail.optonline.net” or something similar.

Does this happen to you? And do you know what to do when you get this message? It seems it’s a flaw in Apple’s Mail program. Users with Optimum as their ISP (Internet Service Provider) tend to have this issue, but it’s not limited to Cablevision users; other email providers fall prey to this glitch.

I’ve found that the best way to quickly fix this issue is to delete the outgoing mail server and then reinstate it. This is accomplished by performing the following:

  • Launch Mail
  • Select PREFERENCES from under the MAIL menu in the upper left corner of the screen
  • Click ACCOUNTS icon on the top of the Preferences window
  • Highlight your mail account in the left-hand column
  • Pull down on the OUTGOING MAIL SERVER (SMTP) dropdown menu and select EDIT SMTP SERVER LIST…
  • Select the mail.optonline.net server (or whatever outgoing mail server is causing you grief) and click the MINUS (-) button in the lower left corner of the server window
  • Once the server has been expunged, click on the PLUS (+) button, located to the right of the MINUS (-) button
  • Click on the ACCOUNT INFORMATION tab, and in both the DESCRIPTION and SERVER NAME fields, enter the following: mail.optonline.net
  • Click on the ADVANCED tab and select USE DEFAULT PORTS (25, 465, 587)
  • In the AUTHENTICATION dropdown menu, select PASSWORD and enter your user name (your Optimum email address WITHOUT the @optonline.net suffix) in the USER NAME field and your Optimum email password in the PASSWORD field

If you’re using an outgoing (SMTP) server that isn’t Optonline, then you should consider making print screen of the information (Command-Shift-4) for your records. And please record your password! If you need help with your passwords, I suggest an extremely helpful e-book, 12 Quick Tips for Creating, Recording & Remembering Your Computer Names & Passwords, available at Amazon as well as Apple’s iBooks Store.

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