when i  remove all the settings i have a set it up according to this
   [1]http://elliotli.blogspot.com/2007/03/use-exim-with-gmail-smtp-on-fe
   dora.html
   with 1 router, 1 transport and 1 authenticator i can send through
   gmail
   I know 0 about network sniffing
   anyone able to help me with the config I need for tcpdump ( its a
   headless server ) ?
   Ive tried it with SSH ing to the server and then starting on the
   server
   tcpdump  -vv host smtp.gmail.com
   ping from the server  to smtp.gmail.com is captured
   but capture nothing when i send from my LAN email client -> exim on
   the server ->  smarthost
   On 14/12/11 21:23, Heiko Schlittermann wrote:

paul cooper [2]<[email protected]> (Di 13 Dez 2011 22:59:59 CET):

im trying to go through this and sort out which bit of it is failing

my smtp_user file is this
root@server2:~# cat /etc/exim4/smtp_users
*@isp.org smarthost="localhost::26" auth_name=[3]"[email protected]"
auth_pass="password"
*@gmail.com: smarthost="smtp.gmail.com::587"
auth_name=[4]"[email protected]" auth_pass="password"

router

the authenticator
login:
driver = plaintext
public_name = LOGIN
client_send = ": ${extract{auth_name}{${lookup{$sender_address}wildlsearch{/etc
/exim/smtp_users}{$value}fail}}}\
: ${extract{auth_pass}{${lookup{$sender_address}wildlsearch{/etc/exim/smtp_user
s}{$value}fail}}}"

I start thinking that your Exim does not even starts an attempt to
authenticate.

SIZE=1646: host smtp.gmail.com [209.85.229.108]: 530-5.5.1
Authentication Required. Learn more at\n530 5.5.1
[5]http://mail.google.com/support/bin/answer.py?answer=14257
dj9sm185520wib.6

I did some tests:

- using no authentication at all:
<~* 530-5.5.1 Authentication Required. Learn more at

<~* 530 5.5.1 [6]http://mail.google.com/support/bin/answer.py?answer=14257 j20s
m14974667eej.8

- using corrent auth data (but no application specific password)
<~* 535-5.7.1 Application-specific password required. Learn more at

<~* 535 5.7.1 [7]http://www.google.com/support/accounts/bin/answer.py?answer=18
5833 j20sm14978410eej.8

- using wrong password
<~* 535-5.7.1 Username and Password not accepted. Learn more at

<~* 535 5.7.1 [8]http://mail.google.com/support/bin/answer.py?answer=14257 j20s
m14986449eej.8

References

   1. 
http://elliotli.blogspot.com/2007/03/use-exim-with-gmail-smtp-on-fedora.html
   2. mailto:[email protected]
   3. mailto:[email protected]
   4. mailto:[email protected]
   5. http://mail.google.com/support/bin/answer.py?answer=14257
   6. http://mail.google.com/support/bin/answer.py?answer=14257
   7. http://www.google.com/support/accounts/bin/answer.py?answer=185833
   8. http://mail.google.com/support/bin/answer.py?answer=14257
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