Thursday, August 11, 2011

SMTP server connection problems (Exchange to Google)

  • Can you connect to the SMTP server?

    To better diagnose the problem, you'll need to run a telnet test, which will check that your computer can contact our SMTP servers.

    If you're running Windows Vista, you'll first need to enable the Telnet feature:

    1. Click the Start button, then Control Panel, andPrograms.
    2. Click Turn Windows Features On or Off.
    3. If you are prompted for an administrator password or confirmation, type the password or provide confirmation.
    4. In the Windows Features box, check the box labeledTelnet Client, and click OK. (It may take a few minutes for the installation to complete.)

    To run the telnet test on a Windows computer:

    1. Open the Start menu, and select Run.
    2. Enter command in the Open: field, and click OK.
    3. Enter 'telnet smtp.gmail.com 465,' and hit Enter, or if you're using Outlook 2007, enter 'telnet smtp.gmail.com 587' instead. (Does the information in the prompt window clear? If not, please note the message that appears.)
    4. Close the prompt window.

    To run the Telnet test on a Mac:

    1. Click the Macintosh Hard Drive icon, and open theApplications folder.
    2. Open Utilities, and select Terminal.
    3. Depending on what port you're using to send, type 'telnet smtp.gmail.com 25' or 'telnet smtp.gmail.com 587' in the prompt window and press Enter.

    If you receive an error message after performing step 3, your network administrator or security software has blocked access to our servers. We recommend contacting your local network administrator or Internet Service Provider (ISP) for more information.


    First, check to make sure your resolver is properly configured. You can't send mailif you can't find the recipient's servers. Go to a shell prompt on your server and try a command like this:

    $ nslookup > set q=mx > gmail.com Server:         10.0.0.1 Address:        10.0.0.1#53      Non-authoritative answer: gmail.com       mail exchanger = 50 gsmtp147.google.com. gmail.com       mail exchanger = 50 gsmtp183.google.com. gmail.com       mail exchanger = 5 gmail-smtp-in.l.google.com. gmail.com       mail exchanger = 10 alt1.gmail-smtp-in.l.google.com. gmail.com       mail exchanger = 10 alt2.gmail-smtp-in.l.google.com.

    In the above example we are looking for the MX (Mail Exchanger) servers forgmail.com (Google Mail). The above results are correct – we were told the addresses of five servers that receive mail for that domain. If you do not get these results, your resolver (DNS) is broken and you must fix its configuration before Citadel can send mail.

    Assuming that your resolver is good, now you can test to see whether you actually have the ability to reach external mail servers. Try to telnet to one of the servers you just learned about, on port 25. For example:

    $ telnet gmail-smtp-in.l.google.com 25 Trying 209.85.133.114... Connected to gmail-smtp-in.l.google.com. Escape character is '^]'. 220 mx.google.com ESMTP b12si3344116ana.1

    If you get this far you can type 'QUIT' to end the connection. You are looking for the remote server to answer immediately and display a protocol prompt that begins with a three-digit number starting with the numeral 2.

    If you get any other result, you have a problem. For example, you might get a "Connection refused" error, or perhaps the session will simply hang while waiting for a connection. Either your server does not have a proper connection to the Internet, or more likely your ISP is blocking outbound connections on port 25.

    Port 25 blocking allows ISP's to block spam sent out through their networks, but it tends to punish the innocent that have a need to send through e-mail servers other than those belonging to their ISP. The ISP's that block port 25 require theirSMTP server to be used instead of the remote SMTP server or a SMTP server running on your computer. If this is the case, you have several options:

    * Ask your ISP if they will unblock port 25 for you

    * Switch to a more server-friendly ISP

    * Configure Citadel to send all email through your ISP's own SMTP server (which will probably not be blocked). You will need to use Citadel's "smart host" option in order to do this.

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Question: I have an issue with my exchange. I am not able to send emails to only gmail

from my exchange server. It gets stacked in the gmail smtp connector queue. I
am able to recive emils from gmail through our exchange server. When i
checked in the queue the gmail smtp connector does not have tick mark with
grean circle around it. Apart from this every thing is working fine. I am
able to send and recieve emails from every other email address. 

We have an issue with our gamil smtp connector in exchange. We are not able to send emails to only gmail addresses. We are able to send and recieve emails from all the external email addresses. We are able to recieve emails from gmail. when we try to send email through our exchange it get scacked up in gmail smtp connector queue. In exchange system manager--> Queue the status for gmail smpt connector is showing as Active but not Ready.It does not have a tick mark with green circle around it. If i restart smtp service it will send the emails that are stacked in the queue but it is not solving the problem because again when some one tries to send email it is getting stacked up in the queue. I am not able to find any errors in the log in regards to this. The Address space is set to use '*'. 

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Answer: Please check the SMTP queue again and make sure it is a "SMTP connector" of
gmail. If so, please go to Exchange Server Management and double check that
Gmail connector configurations.

Meanwhile, could you please let us know "why you'd need a special
connector only for Gmail."? If you can send to other domains correctly and
you don't set any filtering for Gmail, this issue should not occur. If
possible, please temporarily delete(or reinstall) the Gmail SMTP connector
to have a try.

How to use Queue Viewer to troubleshoot mail flow issues in Exchange Server
2003
http://support.microsoft.com/kb/823489/en-us


How to troubleshoot for Exchange Server 2003 transport issues
<http://support.microsoft.com/kb/821910/en-us>

Also, I recommend you run the Exchange Best Practices Analyzer v2.8 to
detect and analyze you Exchange organization. Access the functionality for
Exchange Performance Troubleshooting, Database Recovery Management, and
Mail Flow Troubleshooter through single tools.

Microsoft Exchange Analyzers
<http://technet.microsoft.com/en-us/exchange/bb288481.aspx>


In some cases email will simply not go. Setup an SMTP connector to send email via a smart host - your ISPs SMTP Server.http://www.amset.info/exchange/smtp-connector.asp

Put your domain in to one of the online testing tools like dnsreport.com and see if it flags anything. If your DNS is not configured correctly and that includes reverse DNS records then you will have problems delivering email to the major ISPs and email services. 


Sent from my iPad

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