sending Mail through website to gmail account not working

Hello everyone,

I have very strange problem with our mail server......
Situation like this....I have multi domain setup on our email server...

We can send mail through all domains to gmail account when i setup email account on outlook        ( email client).

I have notice that same email account if i use to send mail though our website to gmail account mail is not going to gmail account while if i setup smae email account on outlook mail is forwarded to gmail account..

Here is the log when we send mail through one of website to gmail account which is not going to gmail account........

Here is the SMTP log from server... I have changed all ip and domain info here.....
10.1.1.x   [00000B0C] Thu, 09 Jul 2009 18:42:27 -0700 Connected
10.1.1.x   [00000B0C] Thu, 09 Jul 2009 18:42:27 -0700 >>> 220-mail.cash1loans.com ESMTP Cash 1 Mail Server v2.0; Thu, 09 Jul 2009 18:42:27 -0700
10.1.1.x   [00000B0C] Thu, 09 Jul 2009 18:42:27 -0700 <<< EHLO SQLSERVER
10.1.1.x   [00000B0C] Thu, 09 Jul 2009 18:42:27 -0700 >>> 250-mail.cash1loans.com Hello SQLSERVER2005 [10.1.1.x], pleased to meet you.
10.1.1.x   [00000B0C] Thu, 09 Jul 2009 18:42:27 -0700 <<< AUTH LOGIN
10.1.1.x   [00000B0C] Thu, 09 Jul 2009 18:42:27 -0700 >>> 334 VXNlcm5hbWU6
10.1.1.x   [00000B0C] Thu, 09 Jul 2009 18:42:27 -0700 <<< ****************
10.1.1.x   [00000B0C] Thu, 09 Jul 2009 18:42:27 -0700 >>> 334 UGFzc3dvcmQ6
10.1.1.x   [00000B0C] Thu, 09 Jul 2009 18:42:27 -0700 <<< ********
10.1.1.x   [00000B0C] Thu, 09 Jul 2009 18:42:27 -0700 >>> 235 2.0.0 Authentication successful
10.1.1.x   [00000B0C] Thu, 09 Jul 2009 18:42:27 -0700 <<< MAIL FROM:<xxx@mydomain.com>
10.1.1.x   [00000B0C] Thu, 09 Jul 2009 18:42:27 -0700 >>> 250 2.1.0 <xxx@mydomain.com>... Sender ok
10.1.1.x   [00000B0C] Thu, 09 Jul 2009 18:42:27 -0700 <<< RCPT TO:<yyy@gmail.com>
10.1.1.x   [00000B0C] Thu, 09 Jul 2009 18:42:27 -0700 >>> 250 2.1.5 <yyy@gmail.com>... Recipient ok; will forward
10.1.1.x   [00000B0C] Thu, 09 Jul 2009 18:42:27 -0700 <<< DATA
10.1.1.x   [00000B0C] Thu, 09 Jul 2009 18:42:27 -0700 >>> 354 Enter mail, end with "." on a line by itself
10.1.1.x   [00000B0C] Thu, 09 Jul 2009 18:42:27 -0700 *** <xxx@mydomain.com> <yyy@gmail.com> 1 4861 00:00:00 OK
10.1.1.x   [00000B0C] Thu, 09 Jul 2009 18:42:27 -0700 >>> 250 2.6.0 4861 bytes received in 00:00:00; Message accepted for delivery
SYSTEM          [000009E0] Thu, 09 Jul 2009 18:42:27 -0700 Client session Connecting to "10.1.x.x"
10.1.x.x       [000009E0] Thu, 09 Jul 2009 18:42:31 -0700 Client session Connected
10.1.x.x       [000009E0] Thu, 09 Jul 2009 18:42:31 -0700 Client session <<< 220 mail.cash1loans.com ESMTP
10.1.x.x       [000009E0] Thu, 09 Jul 2009 18:42:31 -0700 Client session >>> EHLO mail.cash1loans.com
10.1.x.x       [000009E0] Thu, 09 Jul 2009 18:42:31 -0700 Client session <<< 250 SIZE 10485760
10.1.x.x       [000009E0] Thu, 09 Jul 2009 18:42:31 -0700 Client session >>> MAIL From:<xxx@mydomain.com> SIZE=5040
10.1.x.x       [000009E0] Thu, 09 Jul 2009 18:42:31 -0700 Client session <<< 250 sender <xxx@mydomain.com> ok
10.1.x.x       [000009E0] Thu, 09 Jul 2009 18:42:31 -0700 Client session >>> RCPT To:<yyy@gmail.com>
10.1.x.x       [000009E0] Thu, 09 Jul 2009 18:42:31 -0700 Client session <<< 250 recipient <yyy@gmail.com> ok
10.1.x.x       [000009E0] Thu, 09 Jul 2009 18:42:31 -0700 Client session >>> DATA
10.1.x.x       [000009E0] Thu, 09 Jul 2009 18:42:31 -0700 Client session <<< 354 go ahead
10.1.x.x       [000009E0] Thu, 09 Jul 2009 18:42:31 -0700 Client session <<< 250 ok:  Message 1143322 accepted
10.1.x.x       [000009E0] Thu, 09 Jul 2009 18:42:31 -0700 Client session *** <xxx@mydomain.com> <yyy@gmail.com> 1 5040 00:00:00 OK
10.1.x.x       [000009E0] Thu, 09 Jul 2009 18:42:31 -0700 Client session >>> QUIT
10.1.x.x       [000009E0] Thu, 09 Jul 2009 18:42:31 -0700 Client session <<< 221 mail.cash1loans.com
SYSTEM          [000009E0] Thu, 09 Jul 2009 18:42:31 -0700 Client session Disconnected

------------------------------------------------------------------------------------------------------------------
Here is the log of same  user setup on outlook and send email to same gmail account which sent successfully.....

10.1.1.x [00000C10] Thu, 09 Jul 2009 20:46:17 -0700 Connected
10.1.1.x [00000C10] Thu, 09 Jul 2009 20:46:17 -0700 >>> 220-mail.cash1loans.com ESMTP Cash 1 Mail Server v2.0; Thu, 09 Jul 2009 20:46:17 -0700
10.1.1.x [00000C10] Thu, 09 Jul 2009 20:46:17 -0700 <<< EHLO WWWWxxxx [10.1.1.x], pleased to meet you.
10.1.1.x [00000C10] Thu, 09 Jul 2009 20:46:17 -0700 <<< AUTH LOGIN
10.1.1.x [00000C10] Thu, 09 Jul 2009 20:46:17 -0700 >>> **********
10.1.1.x [00000C10] Thu, 09 Jul 2009 20:46:17 -0700 <<< YmhhcmF0
10.1.1.x [00000C10] Thu, 09 Jul 2009 20:46:17 -0700 >>> 334 UGFzc3dvcmQ6
10.1.1.x [00000C10] Thu, 09 Jul 2009 20:46:17 -0700 <<< *********
10.1.1.x [00000C10] Thu, 09 Jul 2009 20:46:17 -0700 >>> 235 2.0.0 Authentication successful
10.1.1.x [00000C10] Thu, 09 Jul 2009 20:46:18 -0700 <<< MAIL FROM: <xxx@mydomain.com>
10.1.1.x [00000C10] Thu, 09 Jul 2009 20:46:18 -0700 >>> 250 2.1.0 <xxx@mydomain.com>... Sender ok
10.1.1.x [00000C10] Thu, 09 Jul 2009 20:46:18 -0700 <<< RCPT TO: <yyy@gmail.com>
10.1.1.x [00000C10] Thu, 09 Jul 2009 20:46:18 -0700 >>> 250 2.1.5 <yyy@gmail.com>... Recipient ok; will forward
10.1.1.x [00000C10] Thu, 09 Jul 2009 20:46:18 -0700 <<< DATA
10.1.1.x [00000C10] Thu, 09 Jul 2009 20:46:18 -0700 >>> 354 Enter mail, end with "." on a line by itself
10.1.1.x [00000C10] Thu, 09 Jul 2009 20:46:18 -0700 *** <xxx@mydomain.com> <yyy@gmail.com> 1 1966 00:00:00 OK
10.1.1.x [00000C10] Thu, 09 Jul 2009 20:46:18 -0700 >>> 250 2.6.0 1966 bytes received in 00:00:00; Message accepted for delivery
SYSTEM          [00000510] Thu, 09 Jul 2009 20:46:18 -0700 Client session Connecting to "10.1.x.x"
10.1.1.x [00000C10] Thu, 09 Jul 2009 20:46:20 -0700 <<< QUIT
10.1.1.x [00000C10] Thu, 09 Jul 2009 20:46:20 -0700 >>> 221 2.0.0 mail.cash1loans.com closing connection
SYSTEM          [00000C10] Thu, 09 Jul 2009 20:46:20 -0700 Disconnected
10.1.x.x       [00000510] Thu, 09 Jul 2009 20:46:21 -0700 Client session Connected
10.1.x.x       [00000510] Thu, 09 Jul 2009 20:46:21 -0700 Client session <<< 220 mail.cash1loans.com ESMTP
10.1.x.x       [00000510] Thu, 09 Jul 2009 20:46:21 -0700 Client session >>> EHLO mail.cash1loans.com
10.1.x.x       [00000510] Thu, 09 Jul 2009 20:46:21 -0700 Client session <<< 250 SIZE 10485760
10.1.x.x       [00000510] Thu, 09 Jul 2009 20:46:21 -0700 Client session >>> MAIL From:<xxx@mydomain.com> SIZE=2140
10.1.x.x       [00000510] Thu, 09 Jul 2009 20:46:21 -0700 Client session <<< 250 sender <xxx@mydomain.com> ok
10.1.x.x       [00000510] Thu, 09 Jul 2009 20:46:21 -0700 Client session >>> RCPT To:<yyy@gmail.com>
10.1.x.x       [00000510] Thu, 09 Jul 2009 20:46:21 -0700 Client session <<< 250 recipient <yyy@gmail.com> ok
10.1.x.x       [00000510] Thu, 09 Jul 2009 20:46:21 -0700 Client session >>> DATA
10.1.x.x       [00000510] Thu, 09 Jul 2009 20:46:21 -0700 Client session <<< 354 go ahead
10.1.x.x       [00000510] Thu, 09 Jul 2009 20:46:21 -0700 Client session <<< 250 ok:  Message 1143385 accepted
10.1.x.x       [00000510] Thu, 09 Jul 2009 20:46:21 -0700 Client session *** <xxx@mydomain.com> <yyy@gmail.com> 1 2140 00:00:00 OK
10.1.x.x       [00000510] Thu, 09 Jul 2009 20:46:21 -0700 Client session >>> QUIT
10.1.x.x       [00000510] Thu, 09 Jul 2009 20:46:21 -0700 Client session <<< 221 mail.cash1loans.com
SYSTEM          [00000510] Thu, 09 Jul 2009 20:46:21 -0700 Client session Disconnected

please let me know what should i need to do here to troubleshoot this problem. I desparately need to solve this problem...

please advise..

thanks,
Bharat
bharatp80Asked:
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Rick FeeMessaging Engineer - Disaster Recovery EngineerCommented:
Well you are sending with the same email domain (mydomain.com) from both your mail server and website?

If so your mail server is probably setup correctly with MX records and reverse DNS.     My guess is your webserver is remote (on different ip address) and does not have any reverse DNS records up and GMAIL is dropping the connection.

If your webserver is on the same local network (or even remote) of your mail server I would set your webserver to relay off the mail server.
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bharatp80Author Commented:
Hi Endurekona,

thanks for such a valuable tips.

Yes that web sever is on different domain and i have taked off the server from relaying.

I did not checked about RDNS of that webserver. let me check about this and i will post the resluts. but i think you deserve my points.

Let me check and i will be back with you in just couple of minutes.

Thanks,
Bharat
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bharatp80Author Commented:
Hi Endurekona,

sorry to say but i just checked and that web server has rdns record.

if you look at the both log file when the email is sent through website ....the connection between mailserver/webserver does not closed...
while when mai lsent from outlook the connection is closed between mailserve/outlook once the authentication completed and send receive address verified....

do you think is this the problem?

one more think i would like to add here......

We have multi domain setup on just one mail server.

any idea please let me know.

Thanks,
Bharat
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Rick FeeMessaging Engineer - Disaster Recovery EngineerCommented:
Ok your mail server is mydomain.com and your webserver is sending mydomain.com.  

you indicated that the webserver has RDNS setup but does it have the same name space?   Do you have a SPF record for your domain?  If so does it include the webserver IP?  

Is the webserver IP on any real time black lists?

http://www.mxtoolbox.com/blacklists.aspx
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Rick FeeMessaging Engineer - Disaster Recovery EngineerCommented:
It appears on both that GMAIL "Message accepted for delivery"   Are you able the check the GMAIL account to ensure the email from the webserver is not being placed in the spam folder for the account?
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bharatp80Author Commented:
Thanks once again.

ok i checked and found that i both earlier my mail were under spam folder.

but i am not seeing other three mails that i sent today in afternoon.

Also i have ocnfirmed with our software person that he receives mail most of the times but sometime it misses.what is the reason for sometime miss.

Thanks once again for your valuable time.

thanks,
Bharat
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Rick FeeMessaging Engineer - Disaster Recovery EngineerCommented:
I'm wondering in the misses if it drops the connection.    In GMAIL select the email from the webserver in the spam folder and click the Not Spam button.   It should whitelist the email and resolve the issue.    You will just have to test to ensure you get the email.

Or this might not be real easy get a email account for your software person on a more configurable system.   Gmail is out of your hands for the most part.
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bharatp80Author Commented:
Please explianme this..........

you indicated that the webserver has RDNS setup but does it have the same name space?   Do you have a SPF record for your domain?  If so does it include the webserver IP?  

as i did not understand ...................


let me tell you in detial about how we configured everythin.

(1) webserver is on different subnet , has different ip address and it has different name
(2)  the email address that is used to send email from website is a different domain name which is configured on mail server.

thanks,
Bharat.
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bharatp80Author Commented:
Sorry once again one more last query...

the current is testing setup.once we confirmed this is working fine and when we make this live

at that time if web site is reside at different location with different ip address but still it use the same email account which is on this mail server and sends mail to the gmail client.....

do i need to create rdns record for that new ip address where website is hosted?

becausei am confused here ...even though web site has different ip address but the mails are going through mail server only and mail server has rdns record.still gmail checks that senders ip has no rdns and drop connection or not?

whcih ip address gmail will see in this case ?
my mail server ip or actul ip of mail originated.

Thanks,
Bharat
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Rick FeeMessaging Engineer - Disaster Recovery EngineerCommented:
  • "do i need to create rdns record for that new ip address where website is hosted?"
                > Yes this will help you from not being blocked.

You website is sending directly out I thought?  If you are allowing a mail relay from that website IP this should improve delivery.   But you want to make sure you only open relay for that one specific IP.   If this is not correct you can then be used as a relay for spammers.

Gmail will look at the senders domain and see if they have permissions to send, MX records and reverse DNS.

A improvement would be to setup a SPF record.

Example:
v=spf1 ptr ip4:24.33.94.184 ip4:66.15.12.13 ~all

You can use Sender ID Framework SPF Record Wizard                                                             
http://www.microsoft.com/mscorp/safety/content/technologies/senderid/wizard/   or
http://old.openspf.org/wizard.html

http://en.wikipedia.org/wiki/Sender_Policy_Framework
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