It seems Email Battles can’t do an article about any web-based mail system without somebody complaining about Hotmail.

Since it was founded in 1996, Hotmail has drawn fire as a:

  • major source of spam;
  • magnet for spam, and;
  • blackhole for message delivery.

Senders regularly claim messages go in, but they never get delivered. How bad is it? In February, Miles Costello wrote in Times Online UK:

Businesses which range from consultancies to online retailers, say Microsoft is unfairly blocking them from sending e-mails to customers with Hotmail addresses as part of a flawed attempt to filter out unwanted spam messages. They say this is happening even when a customer has specifically agreed to receive mails.

Hotmail Hosts: Stable Over 15 Tests[Hotmail Mail Server Profile]

Businesses accuse Microsoft of refusing to explain its criteria for the Hotmail blacklisting, which prevents them from sending out operational as well as marketing e-mails to individual customers or business subscribers.

And they complain that, as well as the possible loss of trade and trust with their customers, blacklisted businesses have to pay a fee running into thousands to then gain a so-called “whitelisting”.

Suggestions for timely Hotmail message delivery abound. Microsoft says you should deploy its lightly used Sender-ID email authentication (which requires alterations to DNS) and/or pay for SenderScoreCertified (previously known as “bondedsender”).

Will the Sender-ID + SenderScoreCertified combination help messages through the gauntlet of overlapping filtration provided by SmartScreen heuristics and Brightmail sweeps? While we haven’t found any comments from those who have so complied, our guess is a powerfully lukewarm “Maybe.”

Why? Because, in our tests, Hotmail servers predictably “answered the phone.”

After querying hotmail.com with our on-line Mail Server Profiler, we found four mail server MX records pointing to 16 IP addresses. The first IP address listed for each MX list was always closed to incoming traffic. But the rest of the IP addresses were always open and responsive, in each of 15 queries over a 30 minute period.

This is in stark contrast to our test of Yahoo! Mail’s servers, which seemingly engage in a rolling blackout, making it entirely conceivable that a sender would give up before ever actually connecting with a Yahoo! Mail server.

Why is that important? If you never pick up the phone when it rings, a caller has no way to tell you anything, whether it’s your mother telling you Dad’s fallen ill, or the T!#-Gr33n Lawn Care salesman annoying you at dinner.

By answering, Hotmail servers can “listen” to what you say, before hanging up… Which also opens the opportunity to somehow decide to let your message pass.

Theoretically, theoretically.

On the client side, travel site Busabout Europe advises that Hotmail users follow these instructions to ensure delivery:

  • If the filter is set to “Enhanced” you should ensure that “Deliver to junk mail folder and delete later” is selected so you can check in the junk mail for replies from Busabout, if it is set to “Delete junk mail immediately” you cannot recover the mail. Alternatively add info@busabout.com to your “contacts” or “safe list”
  • If the filter is set to “Exclusive” you MUST ensure that the addresses info@busabout.com is in either your “contacts” or “safe list”.
  • Set up another email account with a provider such as Yahoo! We do not have any delivery problems with other providers.

Last but not least, Wikipedia reports that some browsers don’t seem to have much luck implementing all of Hotmail’s Internet Explorer-centric features. So finicky Hotmail users may require IE.

Go figure.

Email Battles Backgrounder: