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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DhanukadamConnect With a Mentor Commented:
An Outlook client may receive an “Operation failed” error message in Outlook when the following conditions are true:
- The client is Outlook 2007 or 2010 in online mode. (This does not reproduce in cached mode)
- The client is connected to an Exchange 2010 SP1 server. Confirmed on RU3 and higher.
- The client composes an HTML message with inline JPG images.
- The client saves the message in progress to the drafts folder
- The client opens the message from the drafts folder and attempts to send or edit/change the message.
Current FAQs:
Q:  Will upgrading to Exchange 2010 SP2 or SP2 RU1 make a difference?
A:  No.  This issue still occurs in Exchange 2010 SP2 RU1.
Q:  Is there an ETA on a fix?
A:  At this point it is not possible to provide a timeline.  This is a highly complex issue and our team is fully engaged on the issue.
Q:  Where is the problem?
A:  Based on EE review, it appears the issue resides in the store process on the mailbox server.
Q:  What are the next steps?
A:  The store process includes your database engine.  This is a complex part of Exchange and while we have identified the failure point, we have not identified the best way to resolve the issue.  Changes in store cannot be taken lightly as your data is at stake, and any changes must be carefully reviewed and tested.  If you are uncertain if the problem you are encountering matches the scenario we are currently investigating, please contact Microsoft Support to open a service request.
- Copy the body of the saved message into a new message and send it
- Switch to Cached Exchange Mode
- Switch the message from HTML => RTF => HTML and then send it
- An alternate workaround is to log into the mailbox from OWA and send the message.
AllTripConnect With a Mentor Commented:
You issue is with a bad .ost file.  My guess is that their .ost file did not build properly when you made the change over to cached exchange mode.  Occasionally when an .ost file is building something happens during the process and the .ost file becomes corrupt.   If you disable cached exchange mode, close Outlook, delete .ost, launch Outloook, close Outlook, re-enable cached exchange mode and let the .ost file rebuild.  That should resolve the issue.
snyperjAuthor Commented:
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.
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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.
snyperjAuthor Commented:
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:

14.0.6131.5000 (http://support.microsoft.com/kb/2553391) appears to be the latest Outlook build.
snyperjAuthor Commented:
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.
Akhilesh KatkarExchange Support EngineerCommented:
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
snyperjAuthor Commented:
you realize, of course, that this topic is 3 years old?
Akhilesh KatkarExchange Support EngineerCommented:
found a query without a right answer, answered!!!
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