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Unable to send outbound smpt email from Sharepoint 2010

Posted on 2013-01-04
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Last Modified: 2013-01-26
I'm not sure if this falls under a Sharepoint or Exchange issue but our environment is Sharepoint 2010 and Exchange 2003 SP2.  We would like to send email directly from our Sharepoint portal but it currently cannot make it past the outbound smtp queue in Exchange.

In sharepoint Central Administration  Outgoing E-Mail Settings  we have the following configured.

Outbound SMTP Server - Using IP or DNS name for the Exchange server produces the same unsuccessful result.

From address - the smtp email address we are using.
Reply-to-address - the smtp address we are using.
Character Set - 65001 (Unicode UTF-8)

When an email from sharepoing is initiated it is received into our exchange smtp queue but it puts a very odd string on the email before the actual adress.  If I right click on the email in the queue on the message properties this is what it lists as the sender.
 "=?utf-8?B?Sm9sZWVuJ3MgVGVzdGluZyBTaXRl?=" <InSite@domain.com>  

It only stays in the queue for a couple minutes before it disappears but then comes back on a retry status and repeats that process over and over until I do a delete no ndr on it.

The acutal email address if insite@domain.com does not exist in our AD as according to sharepoint administraion documentation it does not need to but is set to forward to an external email adress outside our domain.  We have no issues emailing to that address directly from inside our organization and even if we setup an address that does actually exist in AD to email from within sharepoint it produces the same result.

Any ideas?
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Question by:TSG-IDS
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Assisted Solution

by:Justin Smith
Justin Smith earned 350 total points
ID: 38745058
If it's getting out of SharePoint, it's not a SharePoint issue.  Must be a policy or permission thing on Exchange.
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Author Comment

by:TSG-IDS
ID: 38745296
Could be but it seems to be more of an issue about the email coming directly from sharepoint.

As I mentioned the smtp address we have setup in the sharepoint portal is not actually within our AD.  When I add it to our AD and send an email from an outlook client to it, it correctly forwards off to the external address outside our domain we want it to go to.

There's something about initiating the email from within the Sharepoint portal itself that Exchange does not like and adds the odd string each time.   The string is always the same as posted above.
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Expert Comment

by:Rainer Jeschor
ID: 38745345
Hi,
the most common issue with outgoing emails is that Exchange server has to be configured to allow relaying the emails from the SharePoint server.

SharePoint sends outgoing email as anonymous SMTP.   All you have to do is to allow the SharePoint server IP as an allowed relay under the SMTP virtual server.

HTH
Rainer
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Author Comment

by:TSG-IDS
ID: 38745371
I forgot to mention but I have done that.  In ESM on the virutal server I right click > Properties> and under the Access Tab and then relay I have the IP of the sharepoint server in there.
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Expert Comment

by:Inderjeetjaggi
ID: 38745575
Check if outgoing e-mail is set properly:
Launch Central Administration / Application Management / Manage Web Applications.
Select one of your Web Applications and then select “General Settings” from the Ribbon.
Select “Outgoing E-Mail” from the drop down.


Check if SMTP is insatlled properly
Configure incoming e-mail (SharePoint Foundation 2010):
http://technet.microsoft.com/en-us/library/cc287879.aspx

Log checking:
Enable verbose mode of logging and let me know if you see any thing related to SMTP or outgoing e-mail in ULS log file at C:\Program Files\Common Files\Microsoft Shared\Web Server Extensions\14\LOGS
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Expert Comment

by:KoenVosters
ID: 38750181
Make sure that if you have multiple web frontends that all the ip's of the webfrontends are configured.

You can easily check if it is SharePoint that is messing things up if you install smtp4dev on the frontends. This will capture the smtp message directly on the server when it is being sent out.
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Author Comment

by:TSG-IDS
ID: 38751577
Outgoing email is setup properly.

Why do I need to configure incoming email on the sharepoint server?  This is an outbound issue where mail sent directly from Sharepoint cannot get out of the smtp queue on Exchange.  Outgoing email setttings is setup properly.

We enabled verbose mode of logging and kicked off an email from sharepoint but I don't see anything specifically related to email in the logs.  Anything I can search on specifically?

I tried to install smtp4dev on the frontend mail server but get an error that it can't update or find a specified path.  When the gui comes up it says "server failed: only one usage of each socket address is normally permitted."
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Expert Comment

by:Justin Smith
ID: 38751853
You don't have to mess with inbound, disregard that user's comment.

You will get that error in SMTP4DEV when the SMTP service is running on your server (in services.msc), since it binds itself to port 25.
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Author Comment

by:TSG-IDS
ID: 38752000
I stopped the smtp service on our front end OWA server and now the tool installs and when I open, it says it is listening on port 25 but no mail is seen.  When I click options I get an error message saying " unhandled exception has occured in your application. could not load file or assembly system core, version 3.5.0.0 the system could not find the file specified.

After a while the program just closes and when I try to reopen I get the socket error again and it's no longer listening on port 25 even though the smtp service is still stopped.
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Expert Comment

by:Justin Smith
ID: 38752008
Are you the exchange admin?  Or do you have one?  Are you absolutely certain you granted access on the correct send connector?

I'm going back to my original comment, if it's getting out of SharePoint, the problem isn't in SharePoint.  That's been my experience in 99% of the cases with outbound email.
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Author Comment

by:TSG-IDS
ID: 38752090
I am close as there is to an exchange admin here.  I'm 100% that I allowed the sharepoint server to relay through the exchange server.  In ESM on the default smtp virtual server if you right click, choose properties, go to access and then relay the IP of the SP server is granted in there.

As far as System Policies in ESM the only ones we have setup in Exchange are mailbox size limits for executives and staff on certain mailbox stores.
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Author Comment

by:TSG-IDS
ID: 38752785
I should also add that we are able to email users within the domain from the sharepoint portal and this is only affecting our ability to send email to external users from sharepoint.
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Expert Comment

by:Justin Smith
ID: 38752799
What version of Exchange?
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Author Comment

by:TSG-IDS
ID: 38752811
2003 SP2
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Expert Comment

by:Justin Smith
ID: 38753102
I'm no Exchange guru, but the fact that internal people get messages and external do not, should clue an Exchange person into the issue, in my opinion.  SharePoint doesn't format the messages any different.
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Expert Comment

by:KoenVosters
ID: 38753821
With Achilles on this one. If the external emails get messed up, then it is not a SP problem.
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Author Comment

by:TSG-IDS
ID: 38755108
It probably is an exchange issue but there is some tie in with sharepoint also.  We have no issues sending external mail but when one is initiated from sharepoint it puts the same "=?utf-8?B?Sm9sZWVuJ3MgVGVzdGluZyBTaXRl?="  at the beginning of the email?  Is there a different character set we should choose in the outbound email settings from sharepoint central administration??
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Expert Comment

by:Justin Smith
ID: 38755161
I've never used anything but the default, which is what you are using.
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Author Comment

by:TSG-IDS
ID: 38760984
To the person who asked me to enable verbose logging on the sharepoint server.  There appears to be a log that is created each time I send an email from the sharepoint server.

01/09/2013 15:21:02.75 w3wp.exe (0x05A4)                       0x1DC8 SharePoint Foundation                 Service Connections                           ev2x      Verbose               <TraceRecord xmlns="http://schemas.microsoft.com/2004/10/E2ETraceEvent/TraceRecord" Severity="Information"><TraceIdentifier>http://msdn.microsoft.com/en-US/library/System.ServiceModel.Security.SecurityBindingOutgoingMessageSecured.aspx</TraceIdentifier><Description>The security protocol secured the outgoing message.</Description><AppDomain>/LM/W3SVC/2/ROOT/17292dbae0b347a49581016f35da63e0-1-130021481606088033</AppDomain><ExtendedData xmlns="http://schemas.microsoft.com/2006/08/ServiceModel/SecurityProtocolTraceRecord"><SecurityProtocol>System.ServiceModel.Security.TransportSecurityProtocol</SecurityProtocol><Action>http://tempuri.org/ISearchSiteAdministrationServiceApplication/GetChangedConsumersResponse</Action></ExtendedData></TraceRecord>


Notice the part where it says "the security protocol secured the outgoing message?"

Could that be why it is placing that weird string on the email before the actual address of  "=?utf-8?B?Sm9sZWVuJ3MgVGVzdGluZyBTaXRl?="  

That string is the same each time an email from sharepoint comes into the smtp que with an external address on the email.  Exchange clearly does not like it and why it fails to send, drops from the queue and then keeps looping back into a retry status to send but never does.

Is there any place to adjust or set security parameters in sharepoint to change or lower them?
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Accepted Solution

by:
TSG-IDS earned 0 total points
ID: 38776259
I was able to resolve this.  It was an issue with Antigen for Microsoft Exchange that was installed on the server.
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Author Comment

by:TSG-IDS
ID: 38776459
I've requested that this question be closed as follows:

Accepted answer: 0 points for TSG-IDS's comment #a38776259

for the following reason:

No previous answers pointed me to this resolution.
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Expert Comment

by:Justin Smith
ID: 38776298
Don't just delete this question.  We helped verify that the issue was not inside of SharePoint, but was on your mail server.  At a minimum, accept your answer and comment 38745058 as the answers.  

Again, if the message is getting out of SharePoint, the problem isn't with SharePoint.
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Author Comment

by:TSG-IDS
ID: 38776319
My solution and comment http:#a38745058 provided the answer for this.
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LVL 38

Expert Comment

by:Justin Smith
ID: 38776460
See the author's decision.
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Expert Comment

by:KoenVosters
ID: 38777225
Supporting Achilles. You clearly stated this question as being a SharePoint problem (therefor also posted in the SharePoint area). Clearly indicated and troubleshooted with you to provide you a clear understanding on where the problem is surfacing and ruling out SharePoint as the source of the problem.

That you solved it by finding it in Antigen, nice job. But if it weren't for this topic, you would still be blaming SharePoint.
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Expert Comment

by:Justin Smith
ID: 38790433
The author already made his recomendation.
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