Operation Failed when sending Email

Recently we converted a group of our users to offline cache mode in Outlook.  We are using Outlook 2010 on laptops with Exchange.

We have been plagued with 'Operation Failed' messages when trying to send mail.  No pattern. Only happens sometimes, and it does not matter if it is an internal or external email address.  The users are frustrated.

What we have tried:
1.) Deleting the address(es) from the users AutoComplete list and then manually re-typing the address in the "to" field.  That always solves the immediate need... but days or weeks later that same address may again kick up the 'Operation Failed' message suddenly.
2.) Clearing the entrire AutoComplete list from Outlook options.  Again, works short term, but the Operation Failed message eventually returns without warning.  Some users have dumped this list multiple times.
3.) Extending the setting for 'automatically save items that have not been sent after this many minutes:' from a default of 3 minutes to 20 minutes.
4.) deleting and recreating the users mailbox from the local computer and rbuilding the .ost file.

In all cases, the 'Operation Failed' message eventually returns...

What else can we try?  We have very frustrated users.  Most frustrating to them is when the Operation Failed messages occurs on a mail message with multiple recipients (sometimes 10-20 recipients.) because it cannot be easily determined which address in the auto-complete list is causing the failure.
snyperjAsked:
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arrorynConnect With a Mentor Commented:
Thanks. Sorry for the delay responding, will give this a look-over tonight if you're still having the issues?
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arrorynCommented:
What version is your Exchange server, and is this fully patched?

Reference:

http://support.microsoft.com/kb/2763886 and http://support.microsoft.com/kb/2785908
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snyperjAuthor Commented:
Interesting.  Yes- we have Exchange 2010...  I am kind of on my own researching this.. how can I tell if it is fully patched?  I do have the ability to login to the exchange server but I am not sure where to check to see how up to date the patches are....
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snyperjAuthor Commented:
Disregard last post.  I found it.  See screenshot.  Yes, appears to be fully patched.
Capture.JPG
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snyperjAuthor Commented:
Yes.  Brutal.  No pattern.  Thanks for anything you can offer.

I just recently rebulit a users .ost and cleared the autocomplete list (just to be sure thety were starting with a fresh everything.)

Two days later they received the 'operation failed' error  on two emails he was trying to send.  

Each email had only 1 recipient and that recipient was an internal address off of the Global Address list that he had already successfully sent and email to since the new .ost file was created (thus it was back in the autocomplete list.)  Arrgghh!
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snyperjAuthor Commented:
Any further thoughts on this?  I just received this from a user this morning:

"It’s happening over and over and over again.  Email “operation failed”  gets worse day by day.  Whatever is causing this needs to be fixed.  I can’t keep finding ways to type in names different ways just to send an email.  PLEASE!"

This is a user who has already cleared the autocomplete list entirely several times.
Thanks for any ideas (they are lining up with pitchforks.)
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snyperjAuthor Commented:
Determined it to be two HP bundled software items...privacy manager and daystarter causing the problem.
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