It turned out that my ISP was filtering port 25. Too bad I realized it this 
late.

Anyway, big thank you to everynoe who tried to help me with this!

On Wednesday 30 June 2010 06:01:43 Dave Lowe wrote:
> You will be glad to know I have the same problem here.
> I can't even telnet to smtp.gmail.com on tcp port 25.
> I can do this to other MTA's, just not gmails. No 3 way handshake (Not
> responding to my syns')
> 
> Looks as though perhaps SMTPS is now required for gmail as I used to have
> this working. (Although not on this workstation). I can telnet to tcp port
> 465 successfully.
> 
> You will also notice that nmap shows the port as filtered:
> # nmap -sT -p 25 smtp.gmail.com
> 
> Starting Nmap 5.00 ( http://nmap.org ) at 2010-06-30 12:55 EST
> Interesting ports on px-in-f109.1e100.net (74.125.155.109):
> PORT   STATE    SERVICE
> 25/tcp filtered smtp
> 
> I don't think your issue is site specific....
> 
> 
> Dave
> 
> 
> On Wed, Jun 30, 2010 at 1:38 AM, Ivan Lezhnjov Jr. <
> 
> [email protected]> wrote:
> > I tried tcpdump, as you suggested, and what it reported was that
> > apparently communication was being established at port 25 but for
> > whatever reason GMail
> > wouldn't respond:
> > 
> > GMail
> > r...@roosevelt:/home/ilj % tcpdump -ni eth0 host 74.125.43.27
> > tcpdump: verbose output suppressed, use -v or -vv for full protocol
> > decode listening on eth0, link-type EN10MB (Ethernet), capture size
> > 65535 bytes 12:19:08.251414 IP 91.194.239.113.41831 > 74.125.43.27.25:
> > Flags [S], seq 53304775, win 5840, options [mss 1460,sackOK,TS val
> > 120648163 ecr 0,nop,wscale
> > 6], length 0
> > 12:19:11.251229 IP 91.194.239.113.41831 > 74.125.43.27.25: Flags [S], seq
> > 53304775, win 5840, options [mss 1460,sackOK,TS val 120649063 ecr
> > 0,nop,wscale
> > 6], length 0
> > 12:19:17.251213 IP 91.194.239.113.41831 > 74.125.43.27.25: Flags [S], seq
> > 53304775, win 5840, options [mss 1460,sackOK,TS val 120650863 ecr
> > 0,nop,wscale
> > 6], length 0
> > ^C
> > 3 packets captured
> > 6 packets received by filter
> > 0 packets dropped by kernel
> > 
> > I tried another e-mail service which is very popular and pretty decent in
> > the
> > RuNet, the Yandex.Mail. All in all, the result was exactly the same:
> > 
> > Yandex
> > r...@roosevelt:/home/ilj % tcpdump -ni eth0 host 77.88.21.38
> > tcpdump: verbose output suppressed, use -v or -vv for full protocol
> > decode listening on eth0, link-type EN10MB (Ethernet), capture size
> > 65535 bytes 18:07:17.642244 IP 91.194.239.113.50441 > 77.88.21.38.25:
> > Flags [S], seq 1208570375, win 5840, options [mss 1460,sackOK,TS val
> > 126914980 ecr 0,nop,wscale 6], length 0
> > 18:07:20.639119 IP 91.194.239.113.50441 > 77.88.21.38.25: Flags [S], seq
> > 1208570375, win 5840, options [mss 1460,sackOK,TS val 126915880 ecr
> > 0,nop,wscale 6], length 0
> > 18:07:26.639116 IP 91.194.239.113.50441 > 77.88.21.38.25: Flags [S], seq
> > 1208570375, win 5840, options [mss 1460,sackOK,TS val 126917680 ecr
> > 0,nop,wscale 6], length 0
> > ^C
> > 3 packets captured
> > 3 packets received by filter
> > 0 packets dropped by kernel
> > 
> > For whatever reason the SMTP servers' replies wouldn't come in to my
> > router.
> > The firewall is out of question so it's something else.
> > 
> > On Monday 28 June 2010 16:13:23 dan (ddp) wrote:
> > > You could try using tcpdump to see if there is an error returned from
> > > the remote smtp server.
> > > 
> > > On Fri, Jun 25, 2010 at 5:24 AM, Ivan Lezhnjov Jr.
> > > 
> > > <[email protected]> wrote:
> > > > Yes, there are plenty but all the same. It's a message that states
> > > > "ERROR: Error Sending email to 74.125.43.27 (smtp server)" nothing
> > 
> > else,
> > 
> > > > even with debug mode turned on.
> > > > 
> > > > 2010/06/25 06:18:21 ossec-maild: DEBUG: Starting ...
> > 
> > > > 2010/06/25 06:18:21 ossec-maild: INFO: Chrooted to directory:
> > /var/ossec,
> > 
> > > > using user: ossecm
> > > > 2010/06/25 06:18:21 ossec-maild: INFO: Started (pid: 3266).
> > > > 2010/06/25 06:18:40 ossec-syscheckd: INFO: Starting syscheck database
> > > > (pre- scan).
> > > > 2010/06/25 06:19:46 ossec-syscheckd: INFO: Finished creating syscheck
> > > > database (pre-scan completed).
> > > > 2010/06/25 06:21:46 ossec-syscheckd: INFO: Starting syscheck scan
> > > > (forwarding database).
> > > > 2010/06/25 06:22:17 ossec-maild(1223): ERROR: Error Sending email to
> > > > 74.125.43.27 (smtp server)
> > > > 2010/06/25 06:22:27 ossec-maild(1223): ERROR: Error Sending email to
> > > > 74.125.43.27 (smtp server)
> > > > 2010/06/25 06:25:10 ossec-syscheckd: INFO: Ending syscheck scan
> > > > (forwarding database).
> > > > 2010/06/25 06:25:30 ossec-rootcheck: INFO: Starting rootcheck scan.
> > > > 2010/06/25 06:28:58 ossec-rootcheck: INFO: Ending rootcheck scan.
> > > > 
> > > > I'm wondering what causes the error. The error message itself isn't
> > > > really helpful.
> > > > 
> > > > On Thursday 24 June 2010 16:52:00 dan (ddp) wrote:
> > > >> Are there any errors in ossec.log regarding email? Have you tried
> > > >> running the daemon in debug mode?
> > > >> 
> > > >> OSSEC's email daemon is pretty bare bones, so it might be worth
> > > >> while to route it through the system's smtpd.
> > > >> 
> > > >> On Tue, Jun 22, 2010 at 3:19 AM, Ivan Lezhnjov Jr.
> > > >> 
> > > >> <[email protected]> wrote:
> > > >> > Hey guys!
> > > >> > 
> > > >> > I've been using OSSEC for a while on two Linux based routers and I
> > > >> > noticed that e-mail notifications on one of them is working almost
> > > >> > perfectly, meaning that e-mail notifications are sent out and
> > > >> > OSSEC can connect to the GMail's SMTP server but there's a
> > > >> > problem. At irregular intervals OSSEC fails to connect to GMail's
> > > >> > SMTP.
> > > >> > 
> > > >> > The second machine wasn't able to send out even a single e-mail
> > > >> > notification.
> > > >> > 
> > > >> > Both machines use identical configuration (my e-mail address was
> > > >> > 
> > > >> > mangled to spam-protect myself):
> > > >> >  <global>
> > > >> >  
> > > >> >    <email_notification>yes</email_notification>
> > > >> >    <email_to>[email protected]</email_to>
> > > >> >    <smtp_server>gmail-smtp-in.l.google.com</smtp_server>
> > > >> >    <email_from>[email protected]</email_from>
> > > >> >  
> > > >> >  </global>
> > > >> > 
> > > >> > Each machine is located in a different network (autonomous
> > > >> > systems/ISPs).
> > > >> > 
> > > >> > I have trouble seeing why one machine would send out e-mail
> > > >> > notifications successfully, albeit sometimes it fails to, due to
> > > >> > its inability to connect to the specified SMTP server, so I
> > > >> > thought I'd ask this here.
> > > >> > 
> > > >> > Also, why another machine never succeeded at sending at least a
> > 
> > single
> > 
> > > >> > e-mail notification remains a complete mystery to me. It simply
> > > >> > doesn't make sense when I try to approach and understand this
> > > >> > issue with the "traditional" knowledge of e-mail infrastructure
> > > >> > workflow. Identical configurations
> > > >> > 
> > > >> > My goal is to have robust e-mail notifications and working. So,
> > > >> > I've been wondering for a while why OSSEC works so unreliably
> > > >> > with
> > 
> > GMail's
> > 
> > > >> > SMTP and if it's the same story with any other SMTP (I never tried
> > > >> > any other).
> > > >> > 
> > > >> > Also, I've been thinking about setting up my own SMTP server on
> > 
> > these
> > 
> > > >> > two routers but I'm not really sure what kind of setup I should
> > > >> > aim for and/or if this will help at all. I'd appreciate it if
> > > >> > someone gave a hint on this.
> > > >> > 
> > > >> > --
> > > >> > 
> > > >> >  Ivan Lezhnjov Jr.
> > > >> >  
> > > >> >  Europe, Ukraine, Simferopol
> > 
> > +---------------------------------------------------------------------
> > 
> > > >> > -+
> > > >> > 
> > > >> >           Key ID 0x5811D90C
> > > >> >  
> > > >> >  Key Fingerprint 2A52 5C8C 38BE C04F D8DE  A169 19E2 E49A 5811
> > > >> >  D90C
> > > >> >  
> > > >> >          Use GPG Exercise Your Right To Privacy
> > > > 
> > > > --
> > > > 
> > > >  Ivan Lezhnjov Jr.
> > > >  
> > > >  Europe, Ukraine, Simferopol
> > 
> > +----------------------------------------------------------------------+
> > 
> > > >           Key ID 0x5811D90C
> > > >  
> > > >  Key Fingerprint 2A52 5C8C 38BE C04F D8DE  A169 19E2 E49A 5811 D90C
> > > >  
> > > >          Use GPG Exercise Your Right To Privacy
> > 
> > --
> > 
> >  Ivan Lezhnjov Jr.
> >  
> >  Europe, Ukraine, Simferopol
> > 
> > +----------------------------------------------------------------------+
> > 
> >           Key ID 0x5811D90C
> >  
> >  Key Fingerprint 2A52 5C8C 38BE C04F D8DE  A169 19E2 E49A 5811 D90C
> >  
> >          Use GPG Exercise Your Right To Privacy
-- 

  Ivan Lezhnjov Jr.

  Europe, Ukraine, Simferopol

+----------------------------------------------------------------------+

           Key ID 0x5811D90C
  Key Fingerprint 2A52 5C8C 38BE C04F D8DE  A169 19E2 E49A 5811 D90C
          Use GPG Exercise Your Right To Privacy 

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