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I followed the instruction on this page Debian Exim and configured my exim with a single file via the dpkg-reconfigure exim4-config setup.

Now I can send mails between local users (from root to myuser or from webmaster to myuser). Additionally I can receive mails from my googlemail.com account.

But when I'm sending mail to this googlemail account it never gets delivered.

In the /var/log/exim4/mainlog I see the following:

2015-02-26 15:51:25 1YQzmf-0000sP-W3 <= myuser@myserver.domain.com U=myuser P=local S=587
2015-02-26 15:51:27 1YQzmf-0000sP-W3 => account@googlemail.com R=dnslookup T=remote_smtp H=gmail-smtp-in.l.google.com [2a00:1450:4013:c01::1a] X=TLS1.2:RSA_ARCFOUR_SHA1:128 DN="C=US,ST=California,L=Mountain View,O=Google Inc,CN=mx.google.com"
2015-02-26 15:51:27 1YQzmf-0000sP-W3 Completed

I searched for hours on Google, but can't figure out what causes this problem..

Any suggestions or information you may need to give me hints on what I have to do are very welcome!

EDIT #1:

However if I'm mailing from my server to my @icloud.com address, this mail gets delivered!

Content of /etc/exim4/update-exim4.conf.conf

dc_eximconfig_configtype='internet'
dc_other_hostnames='domain.com'
dc_local_interfaces=''
dc_readhost=''
dc_relay_domains=''
dc_minimaldns='false'
dc_relay_nets=''
dc_smarthost=''
CFILEMODE='644'
dc_use_split_config='false'
dc_hide_mailname=''
dc_mailname_in_oh='true'
dc_localdelivery='mail_spool'
  • Paste the output of /etc/exim4/update-exim4.conf.conf into your question, anonymizing as necessary, please. This would normally include what you input into dpkg-reconfigure exim4-config. You write "never says hello to my inbox". Are you saying that mail sent rom your machine is not received by your Gmail account? – Faheem Mitha Feb 26 '15 at 22:23
  • Hi @FaheemMitha - I added the content to my question. Additionally I updated the confusing sentence about my Google inbox. Yes the server mail never gets delivered to my Google account. – rogaa Feb 27 '15 at 8:14
  • It's weird that the result would depend on the destination. That suggests the problem is not with your local server. You can run exim in debug mode - that is how I managed to debug a really annoying and obscure problem with exim a couple of years ago. – Faheem Mitha Feb 27 '15 at 8:16
  • Your mail was probably marked as spam by gmail, so you will find it in your spam folder. This is because gmail apply filters even based on the originating IP address and mark spam mails from dialup lines. Try to add your From addree in google contact, this could lower the probability of marking spam your message. Or add SPF and/or DKIM in order to make stronger trust on your email server. – eppesuig Feb 27 '15 at 8:22
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Okay, finally I resolved my issue...

I have (obviously I've forgotten this...) an active forwarding @googlemail.com address to my current active @gmail.com address.

Google is blocking those E-Mails from my server (which are sent to the @googlemail.com account) and marks them as spam.

Therefore I don't see any incoming E-Mails in my active inbox @gmail address.

Nevertheless I still have to sign my outgoing mails with DKIM / SPF - thanks to @eppesuig.

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