Basically;
1. Don't use Nemesis if you can help it (AFAIK it is used and developed by 
Schlund & Partner - 1&1). I have had issues with 1&1's Nemesis server before as 
Nemesis doesn't support Linux style linebreaks (LF). So if the sent email 
message body contains them it ignores the linebreaks and throws a "500 line 
limit exceeded" error as the message body can then contain too many characters 
per line (if it's a long email). Your issue may be related to this or you might 
have hit another bug (or feature) with "Nemesis".

2. Yes, use the Postfix smarthost if you can. You can use any domain you like 
as your sending address when sending through a smarthost - it all depends on 
the smarthost provider's policy. Here in UK for instance BT won't let you email 
through their smtp servers with a domain not approved by them. So you need to 
call them & provide proof of ID & that you own the domain in question & then 
they will let you relay. It may be the same with smtp.free.fr - the only way to 
find out is to contact them & ask. Most providers allow you to relay with any 
email address as long as you are trusted in some way - i.e. you authenticate 
first or you are on one of their trusted networks.

Hope that helps.

Mike. 

-----Original Message-----
From: [email protected] 
[mailto:[email protected]] On Behalf Of Andreas 
Reuleaux
Sent: 14 January 2013 05:04
To: [email protected]
Subject: [exim] Could it be that my mail was filtered as spam? - seeking some 
advice

I am on debian wheezy using exim in a smarthost configuration.

For years my smart host was smpt.web.de and everything worked smoothly. 
Choosing smtp.web.de as my smart host seemed only natural given my web.de email 
address.

I have moved to France meanwhile, but kept my German web.de email address and I 
really want to stick with it, after all that's the address by which everyone 
knows me. No problem so far: I can reach my smtp.web.de smart host from France 
as well.

Then I discovered about a year ago, that some important emails of mine were 
silently discarded, i. e. smpt.web.de accepted them just fine, but somehow on 
their way to their destination they where lost without giving me any "delivery 
failed" message.

Telnetting smtp.web.de revealed that it's running a "Nemesis ESMTP"
server

  $ telnet smtp.web.de 587
  Trying 213.165.67.108...
  Connected to smtp.web.de.
  Escape character is '^]'.
  220 web.de (mrweb002) Nemesis ESMTP Service ready

I don't really know much about this Nemesis server, and maybe I am not giving 
it the justice it deserves, but I had the idea of trying out my French 
telephone operator Free's smtp server smtp.free.fr instead, as it is running 
Postfix, a well know open source server, and I generally have more confidence 
in open source systems. Also I heard that the guys at free.fr are smart, and I 
figured they would make an effort to keep their system up to date, perhaps more 
so than the web.de guys.

  $ telnet smtp.free.fr 587
  Trying 212.27.48.4...
  Connected to smtp.free.fr.
  Escape character is '^]'.
  220 smtp1-g21.free.fr ESMTP Postfix

I could/can use this smtp.free.fr server, as I a got with my free.fr 
subscription also a free.fr email account, which I don't use however, as I 
prefer to continue using my web.de address (as explained above).

So what I am currently doing, is sending emails with my @web.de sender address 
through my smtp.free.fr smart host.

This seems to work - not always, though.

I experienced not to long ago the same issues as with my web.de smart
host: some emails of mine were silently discarded. Another problem was that 
some emails took ages to arrive, but they finally arrived at least.

I am not 100% sure at this point, if this was a temporary problem of free.fr 
which is fixed by now. - Of course I can just continue using smtp.free.fr and 
see if it works.

My other suspicion - and my real question - is this: maybe some email servers 
on the Internet inspect my emails and sort them out as spam as my sender 
address doesn't match my smarthost.

To be clear: smtp.free.fr *does* accept my @web.de emails, this sorting out / 
discarding must happen somewhere later, either within free.fr without telling 
me, or later on the way to their destination.

Should I expected my emails to arrive at its final destination once 
smtp.free.fr has accepted them (and it's free.fr's responsibility to convince 
other servers that it's not spam), or is my configuration just so obviously 
lousy, that other smtp servers will consider my mail as spam.

Can I configure my exim maybe to demand some additional status information, say 
some notification from every hop my email takes?

Any advice is welcome.

-Andreas

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