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Re:Helm: Personal Email Server by specialp on Wednesday October 17, 2018 @11:56AM (#18240288)
It depends on whom you send to. Like ironically I sent an abuse complaint to Verizon for a spammer and got rejected because they blocked all of Digital Ocean's IP space. Yahoo was particularly difficult too sending me a response saying they won't take my mail immediately on a single email to my brother. I had to go through a lot to get that fixed. Again this was due to being on cloud provider IP space.

GMail is more reasonable with perhaps being spam filtered but never blocked outright. I have also been blocked by government labs and academic institutions. I also have complied with RDNS, DKIM, SPF and got a top score on mx toolbox. Now that I have been up for a while I have had less issues besides with the ones that block cloud provider spaces.

Re:Helm: Personal Email Server by jethro_tell on Wednesday October 17, 2018 @12:16PM (#18240530)
Microsoft is the toughest one. Fortunately, I don't have friends that use outlook.com or w/e
Re:Helm: Personal Email Server by jedieaston on Wednesday October 17, 2018 @04:04PM (#18243205)
Does your email get blocked if it is sent to a business on O365?
Re:Helm: Personal Email Server by jethro_tell on Wednesday October 17, 2018 @04:50PM (#18243693)
haven't tried in a while. It can, they dont' follow all the rules and do a little more blocking in the interest of their users or based off a ML spam detection or something.

Some things that should be delivered are not. I'd have to dig back into this to see what the exact issue is.

Re:Helm: Personal Email Server by gsreenivas on Wednesday October 17, 2018 @08:00PM (#18244889)
unfortunately DO does not seem to be as active as Amazon in maintaining the reputation of their IPs.