Postfix sends email to spam (gmail, hotmail)

Did you setup reverse DNS properly? Make sure the forward and reverse records for your mail server match.


So, Gmail tells you:

Why is this message in Spam? It's similar to messages that have been detected by our spam filters.

This is generally a problem with spammy looking content.

And indeed, if I received a message containing "ciao bello ti invio il codice la prossima volta fammi sapere" I'd probably mark it as spam too. It's certainly spammy looking enough.

You can do two things:

  1. Rewrite your content to be more professional in nature.
  2. Click "Not Spam" a lot.