[zepearl]

My IP reputation is absolutely >>pure<< and my domain name is ok.

Still, usually when sending emails to Gmail & Hotmail my emails are "lost" (they don't even appear in the spam-inbox of the receivers).

My usual workaround used to be to 1) login into my throwaway-account on their Gmail/Hotmail systems 2) send an email to my domain 3) reply to that email. After that usually my emails got accepted by those service providers, at least for a while.

I admit that nowadays I don't even do that anymore - when I see a Gmail/Hotmail recipient I just ask for another email address at a different provider or I send the email using my provider's system.

[shiftpgdn]

Is your domain name a .com? I've found that domains that are not .com domain names generally get flagged by the evil algorithim even if everything else is perfect.

[zepearl]

Come on - nowadays most domains are non-".com"... .

[shiftpgdn]

That's not even remotely true. I've worked in cloud/web hosting for years and 99% of users are using .com domains. Yes more new users may be registering ccTLDs or gTLDs but that's generally because they're cheap. And because they're so cheap it creates a nuisance as spammers use them. Look a the .xyz tld. It gives you a hugely negative score on any sort of mailbox spam scoring algorithm.

[jlgaddis]

I used to keep statistics on this, although I don't anymore. I remember seeing one day that not a single e-mail I received was a .info domain was legit -- that is, 100% of e-mails received from any .info domain was spam.

No idea if that's still the case, though.