The numerous experiments I ran about sending mail to Hotmail tend to
prove that it is a reputation system based on the sending email
service, and that SPF is totally ignored by Hotmail (and can be even
harmful in some cases). Mails sent through controlledmail.com,
hotmail.com, aol.com, msn.com and some others get through just fine;
mails sent by other providers like mailsnare.net, tuffmail.com,
yahoo.com end up in Hotmail's junk mail folder.
For the time being I am using controlledmail.com to send my mails to
Hotmail, but I also have a free aol.com and a premium msn.com account
in case my preferred service controlledmail.com falls in Hotmail's
disgrace for some obscure reason.
Another way to make sure that your email will get through to Hotmail
is to attach a jpg or txt of at least 500kb - that will bypass any
filters (even if you put "Viagra" in the subject!).
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