How to Fix SMTP Errors from Yahoo/AT&T DSL on Mac OS X Mail

I probably shouldn’t blog about this while I’m fuming, but right now it feels like AT&T Yahoo DSL is literally the worst ISP in the history of the Internet.  Give me a few moments to calm down.


About 3-4 weeks ago, I started getting a lot of spurious SMTP errors in Mac OS X from different accounts.  This surprised me, because I’ve been careful to set up my various mail accounts with the correct SSL port settings

The symptoms were strange because outgoing mail would go through usually on the 2nd or 3rd try.  Annoying, but I assumed it was some sort of spurious error on the AT&T side.

Fine, Pick on Me, But Not My Family

Then things got worse.  My mother & father started complaining to me that they were getting errors trying to send mail.  My wife started complaining.  My grandmother.  All the same symptoms.  Countless searches through help produced lots of interesting, out-of-date help pages, with ages from 2002 to 2007.  Nothing fixed the problem.

Gmail to the rescue… not quite

Last week I found a workaround. offers an SMTP server for anyone with a Google account.  GREAT!  Only problem is, it converts the “From:” and “Reply-To:” addresses to your Gmail account.  Drat.  No good.

Finally, the answer.

Today, I finally found the answer.  Yahoo even has a help page for it.  Too bad it never showed up for any onsite searches.  I found it by searching the Apple Insider forums.

Here is the deal: in order to send mail from any account, you now have to go online to Yahoo Mail and register every single account, verifying some of them (not all), and linking them to you Yahoo account.

Now, given the spam issues, I’m sure Yahoo needs to implement protection to prevent abuse of its servers.  Fine.  And I’m sure I am atypical because I actually have 12 different email accounts configured on one client.  Fine.  But seriously, let’s count the mistakes in handling this problem:

  1. AT&T/Yahoo could have sent mail to every user that had used SMTP on it’s services for another account ahead of time.  They didn’t.
  2. AT&T/Yahoo could have allowed connections through a certain number of times, and emailed a warning message giving users instructions on how to register.
  3. AT&T/Yahoo could have given accounts with over 12 months good standing a free pass (grandfathering)
  4. AT&T/Yahoo could have given everyone a free pass to use a small number of accounts in any 24 hour period – not a spam pattern.  Or a small number of messages (under 100).
  5. AT&T/Yahoo could have made the errors absolute – very strange to get the error/bounce sporadically.  Made it seem like a “bug” not a “Feature”
  6. AT&T/Yahoo could have trained their support staff on this issue.  They didn’t.
  7. AT&T/Yahoo could have implemented a help search on their site that actually returned the right answer.
  8. AT&T/Yahoo could have updated their existing help content with a pointer to this new issue.
  9. AT&T/Yahoo could have found a different solution to this security issue.

Instead, AT&T/Yahoo basically just created a huge amount of churn in its user base around it’s most important function – email.  Great.

You can bet that when I upgrade to HD through Comcast, I’ll be taking a close look at their ISP package.  Sometimes I miss the 1990s when there was hope for independent ISPs… I guess we can all hope that someday, some new technology (WiMax?) will eviscerate the cable & phone companies.  They just shouldn’t be in the customer service business at all.