It’s ME vs. MICROSOFT – Who Will Win ?

About every 90 days or so, Microsoft decides that is a spammer, and totally blacklists our IP. I don’t mean they send our mail into the Hotmail “bulk” folders, I mean they totally “blackHole” all of our email – it just goes nowhere.. This time around they are further insulting me by returning all my mail with the following lovenote: “550 Your e-mail was rejected for policy reasons on this gateway” – and I can’t even send email FROM hotmail TO my domain!Each time this happens I go to the Report Hotmail Email Problem page at Microsoft and file a report, they send me an email to do a bunch of tests, then after two or three days they fix their screwup and email starts being delivered again. Never once have they said they’re seeing spam coming from my server, never have they said there is a problem with my SPF or my SenderID file, they just say “sorry for the inconvenience”.

After this happened the second time I replied and complained a bit, and asked why they continued to blacklist my IP. After going back and forth a few times with a very helpful technician, he sent me an email from his HOME email address and indicated that my IP was blacklisted due to other spammers in the neighborhood. That’s right – other servers in my IP-block were sending out floods of spam, so Microsoft decides to blacklist the entire IP range. This is a bit like arresting everybody in an entire apartment complex because the guy down in apt. 3C is selling crack! So Microsoft’s super-sophisticated anti-spam techniques that they boast so much about boils down to finding a spammer then blocking all IP’s anywhere near it. And, if they find they accidentally blocked an innocent webmaster, they are totally clueless on what to do or how to fix it… I hardly think this is what Bill Gates had in mind, and I’m sure he knows nothing of how stupid his little MSN/Hotmail network appears to be..This time around I again asked whatΒ I can do so that they don’t make the same mistake again, and they replied to me with two options:

  1. Ask all my website members & newsletter subscribers to add to their safe-list
  2. Subscribe to at the low-low price of only $400 to start and $1000/year.

Now, the only problem with #1 is that IT DOES NOT WORK. When Microsoft blackholes your email, or bounces it with “550 Your e-mail was rejected for policy reasons on this gateway.“, no amount of client whitelisting is going to help (I tried it). This leaves me with option #2 – well I say “F-You Microsoft, I’m not paying for YOUR STUPID MISTAKES!”

So I guess now I’m taking off the gloves and playing dirty.

Earlier today I sent the following email to the rocket-scientists over at MSN/Hotmail:

So if i understand this correctly, i must now pay to use because Microsoft’s multi-million dollar anti-spam system is unable to figure out that NOT ONE PIECE OF SPAM HAS EVER BEEN EMITTED FROM MY MAIL SERVER? Am i missing something? Also, I cannot ensure that my customers will receive my email by adding my domain to their whitelist as described by you (below) when all my mail is rejected due to “550 Your e-mail was rejected for policy reasons on this gateway” – Adding my domain to their whitelist also does not do any good when MSN/Live ‘blackholes” my email as has happened several other times this year.

I am not asking for any special treatment, and I am not asking for you to disclose any proprietary information about how your spam filtering system works. I am simply asking that you not block email from my server OR show me evidence that MY server or MY IP has been used for spamming so that I can fix it – i think that if you review the history of my IP/server since I took ownership of it approx one year ago, you will find nothing even remotely spam-related has ever been sent from it. I also am not concerned about other servers or other IP’s in my address-block that may or may not be spam-farms.. They are not of my concern, and surely a company as sophisticated as Microsoft is able to tell the difference between a server at IP address “X” and a server at IP address “Y” – even if X and Y are very close to each other.

At this point I respectfully request that you escalate this issue to whoever it is that would review this type of problem and resolve it permanently. If you have any questions, need any further information, or wish to contact me for any other reason I can be contacted at (xxx) xxx-xxxx virtually any time between 8am and 11pm Pacific Time, 7-Days a week.

Please also note that the promised mitigation has not taken place, and mail is STILL BEING rejected by Microsoft.

Thank you –

After sending this email I made a post at asking all of our members that use MSN/Hotmail to go to the Hotmail support page and open a ticket complaining that they are not getting email from us.

During my research looking for ways to get this problem fixed I’ve run across several posts in forums from other webmasters with the same problem. After going through all the hoops like I have (SPF, SenderID, MS Smart Network Data Services, etc) the final answer usually ends up being either pay-up or give-up .. Well, I’m not going to pay, and I’m too pissed off now to give up – so it’s me VS. Microsoft.


*EDIT October 1, 2007:

After two promises from Microsoft to temporarily correct THEIR problem, they are STILL rejecting all of our email. It is clear that Microsoft/Hotmail is asleep at the wheel. They also have not responded to my request to have this problem escalated to someone capable of doing something about it.

*EDIT October 2, 2007:

Last night I received this in response to my email pointing out that after two promises of unblocking our IP they still had done nothing:

Hello Rand,

I do see that you did have a rescue signature in place. These are only temporary and yours may have expired. I will send this to our filtering team to find out. We will contact you as soon as we hear from them


Windows Live Hotmail Domain Support

Does anyone know WTF a “rescue signature” is?

I have posted an update to this post HERE.Β 

28 thoughts on “It’s ME vs. MICROSOFT – Who Will Win ?

  1. I suggest we all stop using Microsoft products. Open-source alternatives exist. Even non-open-source alternatives are preferable. I use for mail. I switched away from Microsoft’s hotmail right around the time when I learned that hotmail ran on unix servers. Hahaha. Ubuntu is my operating system. It’s easy to install, and works really well for anything I want to use a computer for. There are hundreds of people at who are willing to help you set up your Linux box. I heartily suggest we all go for broke and just plain quit using Bill Gates’s products. We don’t need to take this crap..

  2. I can see that you’re in a very annoying situation right now… I hope that you’ll be able to get your site out of Hotmail’s blacklist.

    Anyway, Microsoft’s Hotmail sucks! I’m not going to use it~

  3. I hope your letter will change the situation! Also because changing e-mail address can be very annoying with people being unable to reach you… your current situation….
    What a mess! Maybe I have to review my positive comments about hotmail I posted in my blog recently…

  4. It’s not microsoft’s fault, I can’t stand em as much as the next guy personally. But the way they block spam via IP they have to block an entire geographical area. You see the way DHCP works is that there is a pool of IP addresses that can be used by a group of people… say a zip code. Now every time you connect to the internet you get a new IP address. So because of this the only way to block the spammers is to block the entire IP range, otherwise the spammers would just release/renew their own IP address to get a different one that isn’t blocked.

    So yes I’m afraid the best way to go about this would be to pay πŸ™ I’m not sure if this would work but you might want to look into routing everything through a proxy server. It’s not very secure but it might fix the problem of getting blacklisted based on IP alone.

    Good luck, and I hope you don’t have to pay up, that would suck


  5. @Eric;
    The only flaw in that theory is that my IP as well as all the others in my block are static IP’s that all belong to dedicated servers.

    also, even on my dynamic IP at home which does use DHCP, a new address is not given out each time I connect.. a new IP is only given if my DHCP “lease” expires – which means i’d have to leave my computer off for over 14 days.

  6. I just got another email from Hotmail support indicating that they are putting a “temporary mitigation” on my IP to allow mail to be delivered. This is basically a carbon-copy of the email they sent me 5 days ago saying the exact same thing. The email states it will take 24-48 hours to take effect so i guess i’ll just have to keep waiting.

    I’ve still gotten no response from my request to escalate this problem.

  7. [quote comment=”202″]Dugg the story but I really don’t think it would help. Hope it goes all the well for you though :)[/quote]

    My hope is that if we can get it to the front page of Digg it might embarrass Microsoft.. Still a few more Diggs to go though.. πŸ™

  8. Microsoft was a company with great and brilliant ideas.

    Those ideas were made by Bill Gates and now are being taken over.

    Honestly, Microsoft now has become farrr more ridiculous than I ever imagined and Bill Gates himself could not be proud of it.

    We need to follow in the footsteps of all the countries and areas who have banned it.

    for example, Amsterdam has now set in motion that all businesses MUST use opensource related software and OS’s. Microsoft is being abolished there and I think they have the right idea. Every country needs to follow this example and we need to stop Microsoft from its gripping power abilities. It’s becoming insane, they run and control too much, whether it be directly or indirectly. The company is consuming everyone. PErsonally I don’t use ANYTHING microsoft related, and I guarantee I’ve saved myself thousands and thousands of dollars just by doing so.

  9. You have a third option, which I believe you should do, should MS blacklist you again: SUE! Your civil rights are being violated and need to be protected. Yes, it takes some money, but you ask for every bit of lawsuit expenses to be included in your prayer amount. Yes, it will take some time on your part, which again, you ask for every bit of your time be compensated in your prayer amount. You have a valid case of breach of contract.

  10. [quote comment=”196″]I suggest we all stop using Microsoft products. Open-source alternatives exist. Even non-open-source alternatives are preferable. I use for mail. I switched away from Microsoft’s hotmail right around the time when I learned that hotmail ran on unix servers. Hahaha. Ubuntu is my operating system. It’s easy to install, and works really well for anything I want to use a computer for. There are hundreds of people at who are willing to help you set up your Linux box. I heartily suggest we all go for broke and just plain quit using Bill Gates’s products. We don’t need to take this crap..[/quote]

    How absolutely ridiculous can you be? I know you nerds hate bill gates, for whatever reason, but for christ sake act like you have more than noodles for brains. You think that if the 100 people that read this stop using microsoft products, there will be some sort of revolution, some sort of better way? I find people like you, and the absolutely moronic ideas you spew, to be absolutely hilarious, and far from real solutions….

    Oh, oh, and this last guy, gregg, he wants you to sue. For using a free webmail that doesn’t do what you want. Is this lame brain serious? I mean really, I stumbleupon to this site, and I read the comments, and I thank the almighty spaghetti monster that I have never ran into people as stupid as you, and your legion of grown up geeks. Amazing you guys have even made it past the warning labels on electric razors.

  11. Again, if you want total access to anything, you need to pay. That is how it works, and to sue someone because they wronged you on something that is free? Oh my goodness, I WISH you would waste your money on legal bills. I would laugh so hard at how moronic you were, the same way I am laughing hard at how moronic your audience is.

  12. Why use it if it is giving you so much hassle. Just change your ISP/mail provider or whatever for f**ks sake!!

    Oh yeah, static IP sux get yourself onto a dynamic IP asap.

  13. [quote comment=”220″]
    Oh yeah, static IP sux get yourself onto a dynamic IP asap.[/quote]

    Go and read up about hosting a service and the differences between dynamic and static addressing A.S.A.P. Perhaps then you’d be able to comment on the topic without saying something which isn’t complete nonsense.

    I could give you a hundred reasons why you’re wrong, but they would be totally lost on you…

  14. Had to dig this. . .
    πŸ™‚ David and Goliath reference was great. . .

    But ugh. . . I’m very glad I’m not having your problem. . . I would be one tired and mad part time webmaster.

  15. The “David and Goliath” references here are amazing. I cannot believe that you morons can equate this with that story. FYI, in that story, David had something to stand for. You guys, on the other hand, have absolutely nothing, and I love it. Fight all you want, and let us all watch you crumble under the system. Hands down, microsoft can do whatever they want. It is even in their TOS. I would suggest reading it sometime, and then pay for your own mail service. You don’t have to go through microsoft at all! You can even get free mail through other services, but you idiots are too caught up in trying to pin microsoft as something they are not. I guarantee they will not pander to your lack of reading abilities. Read the TOS before you sign up next time, you half wits.

  16. If you google this right, “550 hotmail email” – you get plenty of hits. Microsoft just earned a permanent place in my forum’s hall of shame. This is an absolute failure to webmasters everywhere, and to anyone that wants to use their MSN nor hotmail account with a website. Just forget about it. I placed an announcement on my front page that pretty much says, “Guess what, bad news, if you use hotmail or MSN, you are NOT supported because Microsoft has it’s head up it’s @$$!”

    This hurts my bottom line. I’m sure it hurts a lot of bottom lines. I want to kick Microsoft in the bottom line! Cumulatively, a failure of this magnitude has to be responsible for tens of millions in lost profits.

  17. The exact same thing has happened at the company I work for. But, forget fighting Microsoft. They’re not the problem, so they’re not motivated to fix it. It’s the people who think that it’s a good idea to use a Hotmail e-mail account that are the problem. If you want to do something useful, educate people in how to go about selecting information services that meet their needs. If Hotmail meets their needs, i.e. some e-mail reaches them, some doesn’t, then forget them.

  18. Good luck… I used work for a company that sent out a legitimate mailing to 600,000 people every week. These days it’s grown to about 1,200,000.

    Of the 600,000 back when I was working there, about 80,000 were sent to Hotmail. Hotmail always caused problems. We actually separated the Hotmail addresses out before sending so they wouldn’t mess with everybody else’s emails.

    Mostly, the worst that happened was that we could only send about 1 email per second but sometimes we would find that one of Hotmail’s 4 MX servers would just reject all connections from us. Just one. The other three were fine.

    Once Yahoo bought BT, they gained a total of about 60,000 email addresses on our list and we never had any troubles at all with them. In fact, no other email provider ever caused any troubles at all… not even AOL !

  19. Hi Randy,

    Oh my god!! when I came across your site and read your fight with Microsoft Hotmail…

    Well guess what…

    I have a company offering Internet services to several SMEs and associations in the South of France.

    With networking, linux, unix, oscommerce, drupal, open source expertise…

    I have also been going through this hell situation with MS and Hotmail in particular for months. Despite several emails to MS I have not yet received a “single answer” from them.

    Imagine, I have a small company… compared to MS
    and not ready yet to pay for those very expensive services that some offer for email “whatever” programs.

    Despite correcting a few months ago my SPF records in all of my DNS servers, and despite recording my servers in the SenderID program from MS, none of my customers are able to send emails to their hotmail users…

    It is very unfortunate that Microsoft does not act upon our emails and attempts for correcting the situation.

    I have been on the net and offering full Internet services since 1987… This situation is now becoming a big big problem for us.

    I don’t know what to do anymore.
    And how to convince my customers to convince their own customers “not to use” Hotmail anymore.
    Since it seems to be the only direction to go…

    Come on Microsoft, please do something and improve your Technical Support contacts!!! And provide us with valid answers as to why so many legitimate emails are blocked !

    Randy, I hope you will leave those posts up as long as possible.

    If you have any ideas on the best course of action, I am most probably willing to participate and invest some time in order that the smaller ones have their VOICES heard by MS.

    Many thanks for your very good documentation of the problems. We are most likely thousands out there being left over by MS… What a shame!

    No wonder I am using OPEN SOURCE even more every day since 1993. I will continue…

    I actually have no choice!

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