5 ms·
Yeah, gmail is really not great. I host my own email but use gmail for work. I hate everything in gmail, from the UI to the lack of really simple way to filter
by boudin 7y ago
Yeah, gmail is really not great. I host my own email but use gmail for work. I hate everything in gmail, from the UI to the lack of really simple way to filter thing (like sieve) and to the totally random behaviour like you described.
In the end, I don't really read emails on gmail anymore because it's just a huge pain.
My own server has a good reputation, but it meant setting up SPF, DKIM, DMARC etc.... Where it was the most painful was with microsoft email (I don't know the name of their service now, still live maybe). By default mails goes to spam, but really quickly they goes in limbo if people don't respond (on the smtp side the email is accepted but the recipient never see it, not even in spam). On new microsoft accounts I was always able to send a few emails in spam before it went into limbo.
I ended up creating ~20 different accounts on their system (it was before they enforced giving a phone number) and had random discussions with myself for a while which was enough to build a reputation and not being put in spam anymore.
I don't know if this behaviour was intended or not, I try to get in touch with someone from microsoft but couldn't find a way. Since then I do strongly advise not to use their system because that makes it really unreliable.
- roblabla 7y agoI have exactly the same problem on my personal email server, ms silently drops my email! Their server replies with OK, but the email is nowhere to be found in the recipient’s inbox. Even if the conversation was initiated by the microsoft account and I merely reply to it, the email still disappears. I’ve got everything setup properly, all test websites come up green, and google receives my email just fine. SPF, DMARK, DKIM, PTR, HELO are all setup correctly. This isn’t an isolated problem either, the ms forums are filled with people reporting similar problems.
- stiray 7y agoSame expirience here, but I must say it is becoming better since I have reverse resolve. Previously every mail went into spam. Regardless of SPF and DKIM.
- rsync 7y ago"I have exactly the same problem on my personal email server, ms silently drops my email! Their server replies with OK, but the email is nowhere to be found in the recipient’s inbox." Slightly tangential ... I heard recently that "proper" in-line responses (ie, not top-posting) is somehow penalized by Microsoft (or Exchange online or Outlook online or ... ?) and was advised to stop my very proper 1990s style in-line email quoting/responding and just top-post to avoid either non-delivery or something like the body of the email not being shown ... Or something ? Does anyone know what I am referring to and can shed some light here ?
- yellowapple 7y agoYeah, I only bottom-reply when I know (or can reasonably expect, e.g. on a mailing list) that the recipient is using a mail client that's not entirely brain damaged. Otherwise, I'll either top-reply or (if I really do want to respond to things in-line) actually say "See below for responses in-line" to clue in the recipient that yes, there's actually content in this email. But yeah, that's usually more an issue with the mail client (or perhaps the mail server if it's being exceptionally stupid and modifying emails before final delivery). Top-replies became the norm for some god-forsaken reason, and now clients treat the quote and everything below it as entirely optional to display.
- boudin 7y agoOne thing I've noticed too, make sure that your time is synchronized with an NTP server. Even with a good reputation , MS drops emails with no error if you're a bit off.
- snagglegaggle 7y agoMS is really bad at this, a few web forums I am involved with are unable to sign people up at all.
- gothroach 7y agoI've run my own personal email for around 20 years at this point using the same IP address, and have set up all the bells and whistles (SPF, DKIM) over the years as they became in vogue. To my knowledge, I haven't had any issues with getting caught up in Google's or MS's spam filters, but I have to wonder if that's simply because I don't send a lot of messages and for the most part reply to emails rather than being the initiator of a conversation.