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Why you should not use Microsoft live/hotmail/outlook.com

[:de] 2. August 2014[:en]August 2, 2014 - [:de]14:36 Uhr[:en]2:36 pm

Subtitle: The new bussiness model of freemail hosters.
How can you make money from free e-mail?
Easy: Charge Admins for getting their mails delivered.

If you are not interested in my story, just skip to the most important part at the end.

Months ago Microsoft decided to classify mail from my server as spam and did not deliver it to the inbox of their freemail services like live.com, outlook.com, hotmail.com, … This was even before I migrated to my new system with IPv6 (OK Microsoft doesn’t care) and another V4 IP. I even tried with both machines and the same thing happend.

A few weeks ago now – suddenly – Microsofts’ servers started to bounc all my mails with the message: “Please contact your Internet service provider since part of their network is on our block list.” Of course I immediately checked public blacklisting services to see if my IP is listed somewhere – but nothing. All the other big providers also worked fine.

I double-checked their guidelines such as that reverse DNS and SPF must be configured properly, but everything was fine.
So I finally decided to open a ticket to ask to remove me from the blacklist. They in fact did this “for conditional mitigation” as they wrote and now I’m back to normal: Mails are delivered to the spam folder.

But what has happend?

I asked them to tell me why I had been blacklisted to avoid this in the future but only got a standard response not meaning anything.
So I don’t know what actually caused the issue.

After doing some research it turns out that they have some kind of reputation system.
Only mailservers with a good reputation get their mail delivered to the inbox. This means your mailserver has to send a certain amount of non-spam messages to qualify itself as a trustworthy sender. While this is not usually a problem for big providers like Google, Yahoo or GMX, small companies operating their own mailserver have virtually no chance to get on this white-list. I (fortunately) don’t know many people with a Microsoft account, so I reckon about 2 mails per Month from my server so definitely not enough so that they even notice me.

Microsoft also urges Administrators to join a couple of free services to monitor what happens with their mails. Because “these programs help you proactively manage your email eco-system to help better ensure deliverability to Outlook.com users”. In other words – nobody knows what they are for. Oh yes – the internet knows, because some people joined. And in looks like in my case they would have told me that my IP is on an internal blacklist. What a valuable news…

Saying that I’ve found lots of postings from people having similar problems. An still no solutions.

All this is done for the sake of Spam prevention of course. But why do I receive plenty of Junk at my live.com account – which I only use for testing – while there is virtually nothing coming through to my Googlemail address – which is very public at all sorts of places.

Payed whitelisting!

And did I mention that Microsoft offers me to join a third-party certification program to qualify myself as a good guy?
This would put me on some kind of white-list – not for free of course, because certification is hard work….!

This reminds me of some big German providers having started an initiative called “E-Mail made in Germany” (german website).
If you use their web interface to send a mail to an address hosted by any of their members you get a green icon leading you to believe your mail delivery is secure and private. Again, other companies have no chance to get this (virtually useless – german article) indicator shown up for delivery to their mailboxes.
Unless…. – they run through a (not very cheap) certification program (german announcement).

You see Microsoft is not the only one using such – can you call it mafia-style? – methods, even though their implementation is more radical.

What happend to the Internet?
I love to use E-Mail. Even though there are definitely downsides and it is – despite PGP – not a perfectly secure system, it still is one of the last popular but open systems.
Other than Facebook, WhatsApp and the like I’m not tied to be at the mercy of some companies but can freely choose my hoster or – providing enough knowledge – even run my own mailserver.

But what now happens is a rather normal thing in economy: Those with the big maket share try to knock out the small ones.
Laymen users don’t see what’s actually the problem because mostly everything is fine. Or even worse, they switch to one of the big ones, because there they experience less problems with mail delivery there.

So what should we do?

For now I keep my own mailserver and recommend you to do the same.
But how could we carry on with this problem?

Just put up with it and join one of the big providers?
Abandon mail and switch to another means of communication?
Or will this at some point (or is already) be faced with similar issues?

I’d appreciate your point of view and suggestions.

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