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.
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.
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.
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.
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.