[Okta Webinar] Learn how to a build a cloud-first strategyRegister Now


Email messages get stuck in queue

Posted on 2009-12-16
Medium Priority
Last Modified: 2013-11-30
All our outgoing email messages get stuck in the Queue folder under mailroot, including the auto-generated Delivery Status Notification messages.

The application server (SharePoint) and the SMTP virtual server are running on the same machine, which is a local domain member. OS is Windows 2003 with IIS 6. Generation of email messages are triggered from within SharePoint web applications.
Running the SMTPDIAG , we cannot see anything wrong (please see the results below):

Searching for Exchange external DNS settings.
Computer name is WEB2.

Checking SOA for gmail.com.
Checking external DNS servers.
Checking internal DNS servers.
SOA serial number match: Passed.

Checking local domain records.
Checking MX records using TCP: xxxxx.com.
Checking MX records using UDP: xxxxx.com.
Both TCP and UDP queries succeeded. Local DNS test passed.

Checking remote domain records.
Checking MX records using TCP: gmail.com.
Checking MX records using UDP: gmail.com.
Both TCP and UDP queries succeeded. Remote DNS test passed.

Checking MX servers listed for chuansu@gmail.com.
Connecting to gmail-smtp-in.l.google.com [] on port 25.
Successfully connected to gmail-smtp-in.l.google.com.
Connecting to alt1.gmail-smtp-in.l.google.com [] on port 25.
Successfully connected to alt1.gmail-smtp-in.l.google.com.
Connecting to alt2.gmail-smtp-in.l.google.com [] on port 25.
Successfully connected to alt2.gmail-smtp-in.l.google.com.
Connecting to alt3.gmail-smtp-in.l.google.com [] on port 25.
Successfully connected to alt3.gmail-smtp-in.l.google.com.
Connecting to alt4.gmail-smtp-in.l.google.com [] on port 25.
Successfully connected to alt4.gmail-smtp-in.l.google.com.
Question by:peuser
  • 2

Expert Comment

ID: 26067012
Did this work before and stopped working, or are you trying to get this to work for the first time?

Author Comment

ID: 26067064
for the first time.
LVL 27

Expert Comment

ID: 26067106
Is everything ok with your IP address? Make sure you have a rDNS and that you are not on any blacklists.

What do the NDR's say? What happens if you manually try to complete a telnet test to gmail servers? What error do you get?

Check blacklist here for your external IP address: www.mxtoolbox.com

The reverse DNS (rDNS \ PTR) record is configured by the people who issued your IP address in most instances (so your ISP).
Below are two articles which explain the general requirements for reverse dns (rDNS\PTR) records for your IP address.
I try to adhere to the following when setting up a rDNS (PTR) record:
Be a Fully Qualified Domain Name (FQDN) such as server.domain.com (not just 'domain.com' or 'server').
Should not contain 'in-addr-arpa' and should not include words like pool or dyn etc.
Should match what you use in your SMTP HELO\EHLO hostname if possible.
For neatness and as a good rule of thumb, if your incoming mail is delivered to the same server that you use for Outgoing you should make sure all the following FQDN's match:
MX record
rDNS (PTR) record
SMTP EHLO hostname
http://www.amset.info/exchange/dnsconfig.asp (Courtesy of EE member Mestha)


Accepted Solution

the_b1ackfox earned 2000 total points
ID: 26069587
Since this is being setup for the first time:

based on your information, I can already tell you you have basic connectivity...    So I think this boils down to one of two possible issues...   1) No reverse DNS and gmail is rejecting your emails because of it.  or 2) you mention sharepoint, and that could be misconfigured, but you aren't going to make much headwind until you verify the exchange server is running properly.  So test the basics first by sending an email into the exchange server (from like yahoo or something)...   if that works, half the battle is over... next, get on the exchange server and telnet to one of the ipaddresses from your first message...  if it connects to anything on port 25, you know you don't have anything blocking the communications out, and then you can concentrate on the virtual server and make sure the servers default gateway is pointing out of the network (and DNS is working properly)

Yeah, I tem 2 is bigger than Item 1

Featured Post

What does it mean to be "Always On"?

Is your cloud always on? With an Always On cloud you won't have to worry about downtime for maintenance or software application code updates, ensuring that your bottom line isn't affected.

Question has a verified solution.

If you are experiencing a similar issue, please ask a related question

Have you ever run into that annoying problem where the computer won't boot?  Wouldn't it be great if you had a tool that would make that disk boot again?  I have found one tool that works more often than not ...
Steps to fix error: “Couldn’t mount the database that you specified. Specified database: HU-DB; Error code: An Active Manager operation fail”
With the power of JIRA, there's an unlimited number of ways you can customize it, use it and benefit from it. With that in mind, there's bound to be things that I wasn't able to cover in this course. With this summary we'll look at some places to go…
Whether it be Exchange Server Crash Issues, Dirty Shutdown Errors or Failed to mount error, Stellar Phoenix Mailbox Exchange Recovery has always got your back. With the help of its easy to understand user interface and 3 simple steps recovery proced…
Suggested Courses

834 members asked questions and received personalized solutions in the past 7 days.

Join the community of 500,000 technology professionals and ask your questions.

Join & Ask a Question