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snyperjFlag for United States of America

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Outlook - Operation Failed message when sending mail

We have some users that use Outlook 2010 and have recently changed from online mode (Exchange 2010) to cache mode.

For the most part. things are working well, however some users occasionally get an error dialog when trying to send an email message.  The error message simply says 'Operation Failed' and the message will not send.   Typically if they save it as a 'draft' and then open and close Outlook and then resend it from the drafts folder it will send ok.  

It is becoming a nuisance and not sure why it is only happening to 2-3 users out of the 15-20 we recently converted to cache mode....
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AllTrip
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Dhanukadam - this only happened after these clients switched to  cache exchange mode. Not sure how your provided info applies?

AllTrip: I hate to do that, the user is remote, but if that is the only fix then I will need to try it.
Hey Snyperj,

If my first suggestion doesn't work, check this setting:

Go to the location of the Outlook.exe file and right click Properties.  This brings up a Outlook Properties dialogue box.  Click the Compatibility tab and uncheck the Compatibility mode box that says "Run this program in Compatibility Mode for".  Not sure what causes it to become checked, but I've seen that in the past as well.
Deleteing the .ost file while not affect anything on their machine.  I don't think you should have to recreate their Outlook profile all together, just the .ost file.  It's bascially a local file that caches their exchange profile on their machine in the event that they are offline and want to view their mail.
First ensure that you are running the latest Outlook 2010 hotfixes. What is the exact version of outlook.exe you are running? It should something like 14.0.6123.5000 or greater.
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Exact version is 14.0.6129.5000

How does one know if they are running the lastest hotfixes?

Thanks for all this info- I have not been able to connect to this remote user yet, but I am making a list.
Here is the KB I check whenever I want to see what the latest Outlook update is:
http://support.microsoft.com/kb/2625547

14.0.6131.5000 (http://support.microsoft.com/kb/2553391) appears to be the latest Outlook build.
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It seems as though we tracked it down to corrupted entries in users auto-complete list.  Deleting those email addresses and then re-keying them manually solved the Operation Failed message the user was getting.
This issue is most likely to be caused because of Images present in the email
(most common being Signatures containing Hyperlink Images )

This issue is less seen when Outlook is in Cached Exchange mode,
you may check following KB on same, https://support.microsoft.com/en-us/kb/2763886
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you realize, of course, that this topic is 3 years old?
found a query without a right answer, answered!!!