Email is an open system, right? Anyone can send a message to anyone... unless they are on Gmail! School Interviews uses two email servers t...

Email is an open system, right? Anyone can send a message to anyone… unless they are on Gmail! School Interviews uses two email servers t…

  •  elgordio   ( @elgordio@kbin.social ) 
    23•1 year ago

    In my experience Office 365 is even harder to deliver to. The email envelope can be in perfect shape and sent via sendgrid (their recommended partner) and it will still silently drop mails for no obvious reason and if it does deign to deliver them it will often mark them junk.

    I’m only sending low volume transactional emails. The amount of time I have to spend tweaking the email content just to persuade Microsoft to deliver the mail is absurd.

    •  1993_toyota_camry   ( @1993_toyota_camry@beehaw.org ) 
      8•1 year ago

      In my experience Office 365 is even harder to deliver to.

      Yep, this is my experience as well.

      I’ve had some issues with google, but at least they tend to put them in Junk, or tell me the messages are being rejected.

      Microsoft will give me a 250 message, and then route the message to /dev/null.

      That’s contrary to the RFCs, and really annoying. Since it doesn’t end up in Junk, the receiver can’t say ‘not junk’, and since it doesn’t bounce, the sender thinks it has been sent.

      I’m signed up for Microsofts junk mail reporting, and when this happens the UI shows no issues with my ip, and doesn’t admit to any e-mail filtering. The only way I can detect it is by sending messages to my test accounts, or waiting for users to yell.

      Fwiw, anyone else who runs in to this scenario, expect your first support ticket with microsoft to be rejected. Keep responding to it. On the second or third try they might end up removing the silent ban.

    •  smagjus   ( @smagjus@feddit.de ) 
      2•1 year ago

      Outlook showed really weird behavior on my end. The first email I created was on hotmail and in the last year it exceedingly treated mails as junk. Sometimes even Microsofts own emails would land in the junk folder. Marking them as safe or adding them as contact did not help.

      Then I created a new account and suddenly the same emails would be treated properly. No idea what is wrong with the old account.