Explanation of Microsoft Hotmail Mailings

After much discussion with Microsoft I am now able to confirm that we will be forever unable to send messages to Hotmail, MSN or live.com users. This is down to the way Microsoft Hotmail determines whether people are spammers.

Microsoft have given me a list of reasons why our server may be blocked by them – and I have given them a response indicating that almost none of them apply to us, however we are still blocked.

The following is their final advice, and I’ll annotate why (if it is) it is irrelevant in our case;

Your IP ( was blocked by MSN Hotmail because the vast majority of all the email that you send to us has been judged to be spam by MSN Hotmail’s internal filtering system.

While I cannot guarantee email deliverability from your IP I can offer you some advice that may help your situation.

Segment your mailing infrastructure by IP. Marketing e-mail, transactional corporate, “forward to a friend” e-mail and signup e-mails should be sent from different IP’s. This will help to identify what types of messages are being flagged by Hotmail customers.

Segmenting the mailing infrastructure would require sending DearDiary.Net e-mails from it’s own server. It would also require running the 100+ other domains that are hosted on the server on their own seperate server and means the notion of providing Web Hosting services for £66/yr is somewhat unfeasible. Given that Microsoft are apparently providing free web hosting services in the near future one would expect them to understand that the costs significantly outweigh the income for this.

Strengthen the sign up process. Confirm that you are using a double-opt-in sign up process. This will not help in removing existing Hotmail customers from your e-mail lists but it will confirm the authenticity of those who sign-up on for your e-mail campaigns and newsletters.

As DD users are well aware, people cannot sign up to be on someone’s notify list unless they are signed in to their own account. It isn’t possible for someone else to sign you up to be on their notify list. Thus, anyone on someone’s notify list is entirely authentic and has requested to be on the list.

If you have any feedback loops setup with other ISPs you should look for trends to try and determine possible causes – a new data source? New advertisement? Maybe folks signing up don’t recognize the mail?

DearDiary.Net notifies have not changed format in 7 years, so they’re hardly a new anything…

Maybe folks don’t recognize the mail, but I don’t see how I could make it any clearer. It has [Username NOTIFY] in the subject, and a large footer explaining they received the mail because they’re on Username’s friend list at DearDiary.Net.

Clearly mark your e-mails so that Hotmail customers are able to quickly and easily identify that they requested e-mails from your service.

As above.

Do some analysis on the data regarding complaints – look at Hotmail customers who have never clicked, opened, responded or bounced in any way. These poor performers could contain many bad addresses.

I don’t have access to any data about who’s clicked, opened or responded to a notify request. To do so would require insertion of some unique code on the URL and then I run into all sorts of privacy concerns because I’d be able to see whom is reading whose diaries! Not to mention most of the Personal Firewall or anti ‘webbug’ software that almost everyone uses would destroy such insertions and render them useless.

Clean up your lists. Remove those who do not want to receive the emails. Make the unsubscribe process more visible.

The unsubscribe process could hardly be clearer. It’s in the footer of each e-mail and clearly says ‘If you no longer wish to receive these notifications, please go to http://www.deardiary.org/secure/manageFriends.pl’.

However since most spam also contains unsubscribe options, and most people have been educated NOT to click on such links because ‘It proves to the spammer that your address is actually valid’ it is little wonder this doesn’t work.

Enroll in the Sender Score program. This is the only Whitelist which Hotmail uses. It is owned and operated by Return Path. You can find information about this program at “www.senderscore.com”.

I investigated the sender score program. It’s minimum fee is $1000 per year, with a $400 signup. DearDiary.Net doesn’t make that much in a year, so I don’t think it’s really an option. I also object to paying for it on principal because we’re not spammers and I don’t see why I should have to pay to send e-mails to Hotmail customers.

Of course if Hotmail customers feel that strongly about getting their notifies they can either give me $1000/yr for Sender Score Certification, and $2500/yr for the server to run it on, or they can move to a provider that isn’t requesting people pay to send e-mails to them.

Please visit http://www.senderbase.org to verify that your IP is not being targeted by any 3rd party block lists.

This was one of the first things I checked and it is not.

Now, since Microsoft won’t tell me which specific thing has caused me to be blocked – ie, I cannot see any of the messages that my server has allegedly sent and had marked as spam – I cannot begin to actually fix it. All I can do is assume that it’s because people have signed up for notifies, and then later are marking them as spam rather than going to their Manage Friends links and removing themselves. Perhaps they forgot their password and can’t get in to Manage Friends. Perhaps they forgot they signed up for DearDiary.Net entirely.

Perhaps, and I suspect this is the crux, it’s just easier to mark the message as spam from the Hotmail control bar and then next time it comes in it’ll just get put into the Junk folder.

But really, without proper feedback from Microsoft on why, who knows?

What I do know is that I have spent hours trying to negotiate with Microsoft to get the block removed AND to tell me specifically what caused it so that I can ensure it doesn’t happen again. They refuse. This was their final word on the matter;


As Bruce stated, the majority of the email that you send to us has been judged to be spam by MSN Hotmail filters. Your best bet for improving the deliverability of messages from your domain, is to follow the suggestions he provided.

Thank you,

HotMail is right, I am wrong. That’s their last word on it.

The only remaining feasible suggestion in Bruce’s list was to therefore not send notifies from DearDiary.Net.

So there you have it. Microsoft does not want you to receive mail that you have specifically asked for at HotMail. What you do with this information is entirely up to you – but you cannot receive any e-mail from the DearDiary.Net system to Hotmail and it seems unlikely you ever will be able to.

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    im guessing most of us by now have shifted over addresses, thanks for all the effort you put in trying to get these guys to see light! hotmail is just obsoletising itself.

  2. Perhaps this is the wave of the future on the internet. More and more entities that ‘do not play well with others’.

    Though, spam IS a horrific plague on the net and customers ARE riled up about it. Seems to me if you identify (and they can certainly come by DD and see what we are doing over here) yourself to them, they should be able to allow us.


  3. I wonder if it would help if all of us wrote microsoft and complained..???
    I know several of my DDland buddies have switched email accounts over this..
    and they are all fine with it, but still..
    I think it was a dirty trick of MS in general
    anything we can do ???? To help you, help us??
    Just holler..

  4. Sounds like they are giving you the long chinese version of an excuse–in other shorter words, they don’t know why DD is being blocked and they either don’t have the time or are too lazy to check into it. At least you did try to resolve it, your conscience should be clean.

  5. Good grief. I continue to be amazed by beauracies and their clueless human robots. What a crock.

    Thanks for letting us know what has been going on.


    PS Let’s all migrate to Yahoo! No, wait! Everybody sign up for a Premium account, and then they can get their notifies at [email protected]!

  6. I’m just so sorry that you’ve had a lot of bother with all this. You always do your best for us here at DD and for that, the majority of us are very grateful to you. You did your best. There are umpteen alternatives and people can use them. Thanks anyway Steve. 🙂

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