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  Countless searches through help produced lots of interesting, out-of-date help pages, with ages from 2002 to 2007.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.

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

  1. I’ve had a ton of issues with ATT/Yahoo DSL as well. If it’s any consolation, one of my friends is now the GM of that business unit, so I can pass your post along to him!

  2. Thank you for posting that Yahoo help page, it was tough finding the right answer through their multitude of useless help pages. My Mac Mail is up and running smoothly again, just like I expect of any Apple software.

  3. Thanks for the post. This has been extremely frustrating. I was just about to drop ATT completely. Now all is back to normal.

    I agree with you – am email from yahoo or ATT would have been appropriate.

  4. Pingback: Fixing SMTP errors from Yahoo!/AT&T/SBCGlobal DSL | Eric Cheng’s Journal

  5. Thanks for the post. This has helped resolve my issues. But I beg to differ about AT&T DSL being the worst ISP. Charter Communications is by far the worst ISP I have ever had to deal with. We moved to an area that has Charter; I’ve had them for 3 months and have now switched to AT&T DSL. I’ve been completely without cable and internet service for the past week with Charter.

  6. Found this through googling att yahoo smtp after an hour transferring among idiots at ATT. Is there any legitimate reason for this other than providing a barrier to people who use other web hosts?

    I feel downright codependent continuing to use ATT and would like to end this victimization- any other recommended ISPS for SOMA San Francisco? Speakeasy was 3X the cost…anyone else?

  7. Thanks for this post which I found through Eric’s site. It saved me what could have been countless hours troubleshooting this “intermittent” problem,

  8. I continue to have the same problem, even after verifying all my email accounts with Yahoo. The customer service people are not knowledgeable… they just read from a script. I’ve given up, and now just keep clicking send 10-15 times until my email go through.

  9. It was a good thing your blog came up high in google’s search results. I’ve been floundering around aimlessly trying to find that info in ATT’s worthless help section which is not updated.

    The trouble is compounded by ATT buying SBC and so forth. Now who knows which company is what?

    Whatever ATT implemented, it’s been hell for Mac users using Apple Mail. I still can’t access my dotmac account using Apple Mail.

    Any leads is appreciated. I’ve verified all my webmail addresses and I still can’t get Apple Mail with IMAP to work with dotmac.

  10. I just canceled my at&t internet service because of this. I had it up for a total of 3 hours, 2.5 of which were working with technical support to get it working.

    They suggested I upgrade to at&t business, but the hold wait was well over 20 minutes there, and they don’t offer 6mb service for business.

  11. i want to use incredimail to send e-mail but i,m blocked smtp code25 are there a way to get my mail to go if who i,m sending to has att it blockedi love incredimail because of the voice attchmet since i can,t type it takes me forever to hunt and peck thinks irby wright ps- i also use

  12. This doesn’t work now. I went thru the whole deal, and it finished up telling me I could now use my server as ‘From’ in yahoo webmail.

    not what i wanted.

    anyone figger this out?

  13. Thank you so much for this help! I just moved and switched from Earthlink (no problems with SMTP, ever!) to AT&T. I had spent an HOUR on a web-chat with an AT&T CSR to no avail.

    But your help works!


  14. Dude, you’re a friggin’ genius! THANK YOU THANK YOU THANK YOU!
    I was just ranting on the stupid folks at at&t, but even they couldn’t explain how I could go about getting a different address in the from line.

  15. Thanks! Just updated my defunct 2Wire modem/router with one from Actiontec, and Mail was receiving ok but not sending. Had to verify my MobileMe address.

  16. I was on the phone with AT&T last night for an hour. Once I found out the idiot didn’t even know what an iPad was I hung up. Still haven’t fixed the problem.

Comments are closed.