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For a web application I'm working on right now it's very important that automated e-mails arrive at the recipient. I've set up the mail server on the VPS that the application is going to run on. I've taken all the regular precautions to make sure that the e-mails it sends are not going to be filtered out: SPF, DKIM, e-mails have both a plain text and html part, html part is valid html etc. etc.

Still some services - in particular Microsofts outlook.net addresses - either block the message or automatically mark it as junk mail. I've read up a little on how Microsoft determines if a message is junk and in our case it's most likely the reputation of the mail server. Since it's a new server it doesn't have any reputation yet.

How do other developers deal with this type of problem? Do you use external SMTP services like Google Apps to send mail from your application? Any ideas or tips?

closed as off-topic by GlenH7, thorsten müller, Telastyn, user40980, user22815 Aug 27 '14 at 4:13

  • This question does not appear to be about software engineering within the scope defined in the help center.
If this question can be reworded to fit the rules in the help center, please edit the question.

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    This question appears to be off-topic because it is about sending email and is not about a conceptual programming issue. – GlenH7 Aug 26 '14 at 19:26
  • @GlenH7 Okay thanks. Since it's about sending e-mails from a web application I think it is on-topic here, but if not what other Stack Exchange site could I post this? – Ruben Aug 26 '14 at 19:30
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    I'm not entirely sure, but I think Webmasters Stack Exchange may be the more suitable site. However, they seem to already have a very similar question: webmasters.stackexchange.com/questions/19168/…. If that question doesn't answer yours, please do spend some time reading their help center articles to make sure that your question fits their site. – yannis Aug 26 '14 at 20:24
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If mailing is important for your app consider to use mailing service like Sendgrid, Mandrill, Mailgun etc. It will save your time and most likely will work more reliably than self-configured mailing service.

  • This would be my answer as well, and I'd add Mailchimp to the mix. There's extremely little reason to re-invent the wheel here, there are more than a few excellent email delivery services out there. – yannis Aug 26 '14 at 20:25
  • Yeah, i mentioned Mandrill, it is project by Mailchimp. – Boris Chumichev Aug 26 '14 at 20:28
  • Ah, I see. Didn't know Mandrill was a Mailchimp project, thanks. – yannis Aug 26 '14 at 20:38
  • Thanks. I'll read up on it and see if it solves the filtering problems. At first sight Mandrill seems to do what I'm looking for. – Ruben Aug 26 '14 at 21:32

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