Solved

Operation Failed when sending Email

Posted on 2013-06-20
7
800 Views
Last Modified: 2013-07-15
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.
0
Comment
Question by:snyperj
[X]
Welcome to Experts Exchange

Add your voice to the tech community where 5M+ people just like you are talking about what matters.

  • Help others & share knowledge
  • Earn cash & points
  • Learn & ask questions
  • 5
  • 2
7 Comments
 
LVL 6

Expert Comment

by:arroryn
ID: 39263240
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
0
 

Author Comment

by:snyperj
ID: 39263464
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....
0
 

Author Comment

by:snyperj
ID: 39263616
Disregard last post.  I found it.  See screenshot.  Yes, appears to be fully patched.
Capture.JPG
0
Office 365 Training for IT Pros

Learn how to provision tenants, synchronize on-premise Active Directory, implement Single Sign-On, customize Office deployment, and protect your organization with eDiscovery and DLP policies.  Only from Platform Scholar.

 
LVL 6

Accepted Solution

by:
arroryn earned 500 total points
ID: 39266506
Thanks. Sorry for the delay responding, will give this a look-over tonight if you're still having the issues?
0
 

Author Comment

by:snyperj
ID: 39266568
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!
0
 

Author Comment

by:snyperj
ID: 39310385
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.)
0
 

Author Comment

by:snyperj
ID: 39327059
Determined it to be two HP bundled software items...privacy manager and daystarter causing the problem.
0

Featured Post

Online Training Solution

Drastically shorten your training time with WalkMe's advanced online training solution that Guides your trainees to action. Forget about retraining and skyrocket knowledge retention rates.

Question has a verified solution.

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

Mailbox Overload?
In-place Upgrading Dirsync to Azure AD Connect
This video demonstrates how to sync Microsoft Exchange Public Folders with smartphones using CodeTwo Exchange Sync and Exchange ActiveSync. To learn more about CodeTwo Exchange Sync and download the free trial, go to: http://www.codetwo.com/excha…
There are cases when e.g. an IT administrator wants to have full access and view into selected mailboxes on Exchange server, directly from his own email account in Outlook or Outlook Web Access. This proves useful when for example administrator want…
Suggested Courses

617 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