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I have a couple of domains running on my VPS with VirtualMin.

I have DKIM enabled, reverse DNS is setup and SPF records are added by Virtualmin.

Now I have a main account (admin) which I can easily use to send emails to gmail accounts with, they don't appear in the spam folder.

When I use an additional user from the same domain they ALWAYS go in to spam folder of Gmail.

I tried a couple of spam checkers and they all come back like this:

Main account:
Summary of Results
SPF check:          pass
DomainKeys check:   neutral
DKIM check:         pass
Sender-ID check:    pass
SpamAssassin check: ham

Another user from the same domain:

SPF check:          pass
DomainKeys check:   neutral
DKIM check:         pass
Sender-ID check:    pass
SpamAssassin check: ham

I cannot check gmails spam score, or why they are marked as spam, but are there things I can do? This happends with every domain on the virtualmin installation.

I also found out that some businesses that I wrote to also didn't get my email, probably filtered, but when I wrote them with the main mail address they received it. Exact same message, same outlook 2013 client.

  • I assume you also checked that your MTA IP isn't blacklisted on some DNSBL, for example with this tool? GMail unfortunately doesn't insert any explanatory headers like SpamAssassin does, so I really don't know what else to check :/ – Martin von Wittich Sep 16 '13 at 23:05
  • Yeah I checked that, not listed... – Roger Far Sep 17 '13 at 1:13
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Spam filters work in a very wide variety of ways and there is no specific standard for how they work or how they take things into account in totality.

If DKIM is enabled, you should investigate why exactly the check is "neutral". It can't help you, and generally indicates there is some kind of error in your _domainkeys record or you are generating syntactically invalid signatures.

Besides this, the spam filter might take into account that previous messages were spam, and the content of the message and any attachments, and even the "look" of the account name sending it, among other things. The reasons are kind of unlimited.

Consider setting up a _dmarc record, giving a return address for a summary report of messages flagged as spam. This will give you a better idea of where to start.

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