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So have I, and I have experienced mounting difficulties over the last couple of years, despite decent efforts to keep up with protocol and defense mechanisms. D

So have I, and I have experienced mounting difficulties over the last couple of years, despite decent efforts to keep up with protocol and defense mechanisms. Delivery to gmail and hotmail/outlook accounts is becoming a game of chance. I shall probably, with huge regret, hand over the delivery process to an external operator in the near future.

drdaeman 10y ago
> Delivery to gmail and hotmail/outlook accounts is becoming a game of chance. I haven't had any issues recently, but wonder... Are the failures still well-noticeable? I mean, when Gmail/Hotmail reject the letter - do they do it properly (SMTP 4xx/5xx rejection) or maybe they're now silently discarding it? When I had the issues (even with large mail providers), my MTA had always generated me a bounce, and it had always contained something sensible and immediately useful - like a message that my DNS records got messed up or IP got in a blacklist. Every error message I saw contained links or clues to how the delivery problem could be resolved. Had this changed?
- NathanOsullivan 10y ago
  Yes, hotmail will in some instances accept mail at SMTP level and then silently discard it. You cannot even request de-listing.
  - xyzzy123 10y ago
    I had to deal with delivery issues to hotmail (few years ago though) and despite a few hoops, found them pretty reasonable to deal with. Some tools here: https://mail.live.com/mail/services.aspx https://mail.live.com/mail/services.aspx and https://mail.live.com/mail/troubleshooting.aspx https://mail.live.com/mail/troubleshooting.aspx
- interfixus 10y ago
  No, that's the horror. Often they just drop the thing without as much an error code.
  - drdaeman 10y ago
    Dropping the connection with mere TCP RST (or whatever it is) is fine by me. Accepting the message, saying 200 and then not delivering it (not even to the "spam" folder) — that's what I feared.
    - jamiepenney 10y ago
      We used to have issues sending password reset emails to users with Outlook hosted email - Outlook would return a 250 status code, then silently discard the email. It never turned up, not even in the spam filter.

drdaeman 10y ago

> Delivery to gmail and hotmail/outlook accounts is becoming a game of chance. I haven't had any issues recently, but wonder... Are the failures still well-noticeable? I mean, when Gmail/Hotmail reject the letter - do they do it properly (SMTP 4xx/5xx rejection) or maybe they're now silently discarding it? When I had the issues (even with large mail providers), my MTA had always generated me a bounce, and it had always contained something sensible and immediately useful - like a message that my DNS records got messed up or IP got in a blacklist. Every error message I saw contained links or clues to how the delivery problem could be resolved. Had this changed?

NathanOsullivan 10y ago
Yes, hotmail will in some instances accept mail at SMTP level and then silently discard it. You cannot even request de-listing.
- xyzzy123 10y ago
  I had to deal with delivery issues to hotmail (few years ago though) and despite a few hoops, found them pretty reasonable to deal with. Some tools here: https://mail.live.com/mail/services.aspx https://mail.live.com/mail/services.aspx and https://mail.live.com/mail/troubleshooting.aspx https://mail.live.com/mail/troubleshooting.aspx
interfixus 10y ago
No, that's the horror. Often they just drop the thing without as much an error code.
- drdaeman 10y ago
  Dropping the connection with mere TCP RST (or whatever it is) is fine by me. Accepting the message, saying 200 and then not delivering it (not even to the "spam" folder) — that's what I feared.
  - jamiepenney 10y ago
    We used to have issues sending password reset emails to users with Outlook hosted email - Outlook would return a 250 status code, then silently discard the email. It never turned up, not even in the spam filter.