The Ramblings Of John Campea

Life Beyond The Movies

5 Reasons Not To Use Hotmail

I’ve been telling my friends for YEARS to not use hotmail. I came across this good article on Dedicated Server Doc on this very topic

1. Hotmail spam filtering is too aggressive – ask any ISP and they will tell you that anti-spam filtering of customer emails is a tricky business. The ISP has a responsibility to ensure that their customers receive all legitimate emails. At the same time they need to provide some sort of filtering. Without any filtering at all, the email service would be unusable for some customers – particularly long time customers who have had the same email address for several years or more. So, most ISPs and email services will handle this in a couple of ways. Firstly, their email filtering will generally be non-aggressive by default. That means that it will block the obvious spam, but the occassional spam email may get through. So, they will offer you the option to increase the aggressiveness of the filtering AND provide a folder or login where you can review all filtered emails. This is what the ‘Junk’ folder is also used for.

Hotmail, by default, has very aggressive spam filtering. So aggressive in fact that messages that do not exhibit any spam characteristics whatsoever are filtered.

2. Hotmail Silently Deletes Messages – this is just plain irresponsible. Mind you, it is a FREE service so I guess Hotmail feel that they have no real responsibilities as the customers aren’t paying. Most mail services and ISP mail servers will notify the sending system that they are not delivering an email message and will provide a reason why. This is sometimes in the form of a ‘bounce’ email and it can also appear as a response from the mail server that is logged in your server log.

Not so with Hotmail. I have tried diagnosing Hotmail delivery issues many times and in most cases the Hotmail mail servers will respond with a message indicating that the email was successfully delivered – but it is silently deleted by the Hotmail mail filters. None of the other major mail providers do this. If a message is blocked or filtered by Yahoo Mail then there will be an indication as to why in the server log file. The same applies to GMail.

3. Hotmail’s filtering process is flawed – I had a client who was starting up a site and was finding that his emails weren’t being delivered to Hotmail. The business was new and the domain was new. The messages were simple one line notifications. Hotmail silently deleted these messages. Whitelisting doesn’t help – these messages don’t make it to the junk folder and they don’t even arrive when the sending address is whitelisted. Why have a whitelist and a junk folder if you are going to delete messages before they get to the recipient?

4. Hotmail’s Approval Process Is Flawed – Yes, there is a way that you can request that your domain be allowed to send email to Hotmail accounts – but this process is flawed and it gives a very real example of how broken Microsoft and Hotmail’s email filters are. I sent a message per their instructions. The instructions said to send an email to their address with the domain or list of domains in the blody of the message. I immediately received a bounce message that said:

Diagnostic-Code: smtp; 5.1.0 – Unknown address error 550-‘5.7.1 <Your e-mail was rejected by an

anti-spam content filter on gateway (205.248.106.32). Reasons for rejection may be: obscene

language, graphics, or spam-like characteristics. Removing these may let the e-mail

through the filter.>’ (delivery attempts: 0)

That was a message that had the domain, per their instructions, in the body of the email. I tried sending from three different addresses, none of which have ever been blacklisted. In fact all of the domains had a valid SPF record and reverse MX entry.

5. You Get What You Pay For – If you experience any of these sorts of issues, don’t expect any assistance from Hotmail. You are not paying them for the service and they have no way of handling thousands of complaints each day (which is what they would get if even a small percentage of Hotmail users were aware of how unreliable the Hotmail email service is). Strictly speaking, email is not considered a particularly reliable method of communication. Hotmail takes iot to a whole new level though.

If you absolutely MUST have a free email account then you would be much better off choosing either GMail or Yahoo mail. Both of those services are many times more reliable than Hotmail.

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June 2, 2008 - Posted by | Tech

1 Comment »

  1. Your blog is so informative … ..I just bookmarked you….keep up the good work!!!!

    I’m Out! 🙂

    Comment by online stock trading advice | January 11, 2010 | Reply


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