Ask Leo! by Leo A. Notenboom

Why is my mail to HotMail (or AOL, Yahoo, etc.) subscribers not being delivered?

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This is why I refuse to enable my ISP's spam filter option -- I want control of what gets flagged as "possible spam" and what happens to it, and "silently throw it into the bit-bucket" is not what I want. (I use other filtering options, but they're under my control, not my ISP's.)

Unfortunately, I can't choose what method is used by the recipients of any e-mail I send.

Posted by: Ken at August 23, 2006 9:42 AM

Also unfortunately, some ISPs do additional filtering that you can't control. Both HotMail and AOL examples in the article had nothing to do with user preferences - it was ISP systemic.

Posted by: Leo A. Notenboom at August 23, 2006 11:36 AM

This was very helpful. I have a cousin that I have been trying to e-mail but it does come back with a message. I have tried from my aol, msn, and yahoo accounts and it still bounces back. I will try what you have suggested.
Thank-You

Posted by: Albert H Dowler JR at August 26, 2006 1:21 PM

I maintain an email database for the company I work for. Another problem I often see is people using a "challange/response" system to stop spam (especially EarthLink users) but then subscribing to email lists. A challenge/response system sends and email back to the sender saying something like "In order to stop spam, member John Doe has requested we check that you are a real person and not a spam program sending bulk email. Please respond to this message to have your message delivered." People do this without realizing they are also stopping the legitimate emails they signed up for because the mailing list system that sent the original message isn't smart enough to know how to respond so the original legitimate message will be allowed through.

Leo, I agree, it is very frustrating because people get mad at us for emails getting blocked by their ISP. Even some of the ones who have turned on the challenge/response feature provided by their ISP. There is a certain percent of the population who just don't get it - those are the ones who get scammed by spam and illegitimate emails and it is the rest of us who end up putting up with the consequences.

On the issue of users who delete mail by marking it is spam, part of the problem there is the person creating the email message sometimes hasn't made it easy enough to opt out of the mailing list. I can't tell you how many times I have seen the unsubscribe instructions at the bottom of an email in such a tiny font that it is all but unreadable - making it impossible for readers with less than perfect vision to read the unsubscribe instructions. This text should be as easy to read as the rest of the text in the email.

Posted by: Bryan Miller at August 28, 2006 12:58 PM

is there any other way i can check my emails without accessing hotmail.com as my computer will not allow me to access this page?

Posted by: natalie at August 30, 2006 3:32 PM

I'm a secretary for a chapter of the CMA A(Christian Motorcycle Association) and I send many group e mails. All of a sudden, all aol addresses are causing an error, like aol is blocking me from sending to their people. They won't help me and the Earthlink people are suppose to be contacting them on my behalf, but as time goes by, nothing is being done. I've checked the postmasters explanation and it looks like according to them, I've met a quota of too much email being sent. Very frustrating and making me not able to do my job.

Posted by: Hotcakes at October 24, 2006 1:32 PM

If yahoo provides this type of service, you will loose business slowly.

Posted by: sanjaydash at January 11, 2007 5:53 PM

We are still fighting just to hear from Hotmail. They will simply not respond to my emails to request reasoning why theya re blocking my mail server that is not a relay and only has 12 domains on it. I have monitored the mail and it is now way an excessive amount. They simple refuse mail from my sever's ip.

Posted by: Ross Cornette at January 16, 2007 12:20 PM

Just thought I would chime in here. I work for a online social network and we send millions of mail on a daily basis. Both newsletters to legitimate users as well as relay from legit users to other users are processed through the same mail cluster. Hotmail has caused us to re-architect parts of our mail cluster because, like mentioned in a previous post, hotmail has deemed legitimate mail from our host(s) as spam despite all our efforts to reform mail headers, educate users, enroll in hotmails "Junk e-mail" reporting program and "Smart Network Data services". Yet we STILL get blocked on a daily basis. What's missing I ask? Well, simply put, we have not paid the $20k fee to the 3rd party "sender score certification" program http://www.senderscorecertified.com/. So while we wait the 90 days for this to process, I have stumbled across an error we get in the mailer logs that has helped us in curbing the block rate by hotmail and I hope it will help you too. (I am using Port25's PMTA v3.2) The error is related to Hotmail's rate limiting and thus can be curbed by configuring your sending agent to reduce the amount of mail that is being sent once it receives this error:
2007-01-25 11:26:28 SMTP service unavailable: "421 The mail server IP connecting to Windows Live Mail / Hotmail server has exceeded the rate limit allowed. For troubleshooting information, go to http://postmaster.msn.com" received from mx3.hotmail.com (65.54.245.72) while connected from mail.mydomain.com (xxx.xx.xx.xxx) to mx3.hotmail.com (65.54.245.72)

with this error now in my armory, I was able to configure our mail server to detect this error, and once detected, set the application to go into "back-off" mode, and send only +n number of messages per hour. Since there is no way to tell what the rate limit is set to on hotmail's servers, it has been a trial-and-error thing. This has prevented us from being blocked, but of course will increase the amount of time it takes to deliver a message...but it will get there.
Hope this helps some of you out there having the same issue.

Regards,

-Jesse

Posted by: Jesse Alvarez at January 29, 2007 10:26 AM

Hotmail has a horrible system in place. We send millions of e-mails and I can say that AOL is the "benchmark" of postmasters. As a tech guy that used to hate AOL as a service, I LOVE AOL because of how brilliant they handle postmaster requests. AOL even has postmaster phone support with no hold times! Hotmail.. with their dodgy systems and ignored requests.. no phone support... nobody to help... can't make heads or tails of what's going on.

Only Hotmail will delete e-mail at the router... AOL sure doesn't. if you're blocked at AOL you get a nice little 421 error and a link to tell you exactly why you are being blocked for EVERY email. THANK you AOL.

MSN/Hotmail would probably staff a few more people in the postmaster department if the word got out they were censoring email and people started switching to the new FREE AOL... SPREAD THE WORD!

Posted by: Brent at February 22, 2007 7:09 AM
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