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Outlook 2010-Operation Failed on Send

    Question

  • Hello, I just installed Oulook 2010 on a PC running Win 7 Ultimate. The upgrade to Outlook 2010 was prompted by the need of solving the same problem I am going to describe hereafter and that I was experiencing also with Outlook 2007.

    Every time I reply to a message where the email address is in the format "Name <email@domain>" (without the quote but with < and >) I get the error "The operation failed. The messaging interface have returned an unknown error. If the problem persists, restart Outlook. Cannot resolve recipient". Please notice that the problem appears exclusively when I reply to an incoming message.

    As soon as I replace the email address using the one in my contacts or re-typing the email in a plane format I can send the message normally.

    To be considered that:

    - I use Exchange, therefore Scanpst should not help. Moreover the PST/OST shouldn't be corrupted since I can send the email just replacing the email address

    - I already attemped to recreate profiles multiple times

    Any help is very much appreciated.

    Thanks,
    Paolo

     

    Saturday, October 16, 2010 3:32 PM

All replies

  • Hi,

     

     

    This issue may occur as the email profile is corrupted. Try to create a new Outlook profile for the users.

    For detailed steps on how to create a new Outlook profile, you can refer to this article:

    How to Create a new Outlook Profile

    http://www.outlook-tips.net/beginner/2007_profile.htm     

    Also, there is a KB article about the similar issue:

    Error message when you try to use the Tools menu in Outlook: "The operation failed due to a registry or installation problem"

    http://support.microsoft.com/kb/315048  

     

    Regards,

     

    Harry

    • Proposed as answer by Harry Yuan Tuesday, October 19, 2010 2:21 AM
    • Unproposed as answer by Jennifer Zhan Monday, November 01, 2010 2:28 AM
    Tuesday, October 19, 2010 2:20 AM
  • Hi Harry, Thank you for taking the time to help but, as I said in my message, I did already recreate the profile multiple times without success. Regards, Paolo
    Tuesday, October 19, 2010 2:33 AM
  • PMO, I am having a similar problem  I am getting the error "Operation Failed" only when sending to several emails withing my company.  The strange thing is I can reply to them, but no send a new email.  I am running Outlook 2010 under Windows 7.  I have tried everything including uninstalling and reinstalling Outlook, creating new profiles, and nothing.  This is becoming a serious problem  Does anyone have an answer to this problem?
    Saturday, November 20, 2010 1:54 AM
  • Hi Raytony,

    unfortunately I have not been able to solve my issue. In fact I have added my request for help into another thread (http://social.answers.microsoft.com/Forums/en-US/outlookacct/thread/bdd2d604-e652-4fe5-96a3-038191f55d3c) where you can maybe  find other suggestions that could help with your case. I have narrowed down my problem and now is clear that I can never deliver a message to somebody I don't have in my contact list already. The address in the "<>" makes the name not retrievable and therefore it gives me the error.

    Regards

     

     

    Saturday, November 20, 2010 1:11 PM
  • Hi,

    For everybody information I have bypassed the issue changing the setup of my accounts.

    Digging and trying with different options I have found out that my configuration which includes an Exchange account and an IMAP account with Google Apps Premiere was the cause of the issue. I have to say that the reason for upgrading to Outlook 2010 was actually the possibility to manage multiple Exchange/IMAP accounts. However it looks like something is not managed properly in such case.

    Now that I have two profiles one with the Exhange account and the other with the IMAP (vs. Google Apps) + Various POP3 accounts the problem disappeared.

    I hope that this can help for your troubleshooting.

    Regards,
    Paolo

    Thursday, November 25, 2010 6:57 PM
  • I'm having the same problem under the same secific information as PMO-Milan:  I have an Outlook file with an Exchange account, a Google Apps Premier account, and a POP3 account.  When I type an email address on the To line (even without special characters like < or >) and lick Send, I get a popup saying "The operation failed."

     

    Thursday, January 06, 2011 2:40 PM
  • Here is the situation I am experiencing....

    I have Office 2010 Professional running on Win7 Enterprise. In Outlook when I attempt to send an email with an image embedded in the body of the email I get the "Operation Failed" error. I get the same when I attempt to attach any type of document. This holds true even when the only image in the body is the background image from a theme.

    I have the email format set to HTML but have tried Richtext and plain text.

    When I attempt to reply to an email with an embedded I get "Cannot send this item." I can however forward an email with images but I still cannot attach docs.

    I have deleted the profile many times. I have checked all the options that I can think of but can not find anything. I eventually deleted my profile from the Users folder and the registry. This worked for one day and now the problem has returned.

    Any ideas?

     

    Tuesday, March 15, 2011 5:34 PM
  • Hi PMO-Milan,

    I had the same problem on my HP workstations. They seem to install a Security software plugin to encrypt your email. If you create a certificate or uninstall the software it works. Hope this helps you out.

    • Proposed as answer by Nikkirby Tuesday, July 17, 2012 3:42 PM
    Tuesday, April 12, 2011 9:54 AM
  • Hi PMO-Milan,

    I had the same problem on my HP workstations. They seem to install a Security software plugin to encrypt your email. If you create a certificate or uninstall the software it works. Hope this helps you out.


    it's working in my case. thanks.
    Tuesday, April 26, 2011 7:13 AM
  • Hello Richard,

    What Security software are you talking about? I'm having the same exact problem with my HP Probook. Initially I thought it has something to do with the way I added my contacts. I have two accounts on my Outlook 2010 Exchange + Pop3 in which Pop3 is set to default.

     

    Please help!

    Saturday, August 13, 2011 9:54 AM
  • So you're saying you separated the two accounts into two profiles?

    Saturday, August 13, 2011 9:55 AM
  • Hi all guys..

    i face a problem in outlook2010, my Boss using Exchange account in outlook2010. sometime he get error"Operation Failed Error" on sending mail.But sometime mail send smoothly.i recreate his profile but issue cannot resolve.plz if anyone knw about this issue help me.m wait your nice response.

     

     


    Irshad Ahmed MCS-MCSE-MCITP-MCTS-MCP-CCNA
    Thursday, October 13, 2011 5:13 AM
  • What Security softwate that you are talking? I am having same problem.
    Friday, November 11, 2011 6:41 AM
  • HI Irshad,

    i am having same issue with one of my client. did u find any solutions about this? any work around will be appreciated..

    thank you in advance

    Sunday, January 29, 2012 10:21 AM
  • Hello Richard,

    What Security software are you talking about? I'm having the same exact problem with my HP Probook. Initially I thought it has something to do with the way I added my contacts. I have two accounts on my Outlook 2010 Exchange + Pop3 in which Pop3 is set to default.

     

    Please help!

    I had a user with this problem using an HP elitebook as well. Disabled all of the HP addins (HP insant PIM addin, Privacy Manager Add-in, and the Privacy Manager Form Region Addin) and it works fine now.
    • Proposed as answer by SSprinterSS Wednesday, December 05, 2012 3:53 PM
    Thursday, February 09, 2012 5:17 PM
  • HI:

    This is could be happen when the cache email address is wrong. Type the email address and check.

    Dayan Kannangara.

    Tuesday, February 28, 2012 3:59 AM
  • Hello Richard,

    What Security software are you talking about? I'm having the same exact problem with my HP Probook. Initially I thought it has something to do with the way I added my contacts. I have two accounts on my Outlook 2010 Exchange + Pop3 in which Pop3 is set to default.

     

    Please help!

    I had a user with this problem using an HP elitebook as well. Disabled all of the HP addins (HP insant PIM addin, Privacy Manager Add-in, and the Privacy Manager Form Region Addin) and it works fine now.
    thx i got this issue too and your solution works perfectly :)
    Thursday, March 01, 2012 10:37 AM
  • After months of looking for a solution, I've finally found the problem...this has finally closed the case for me and I'm hopeful this will help others. I specifically had an HP ProBook running Windows7 and Office 2010. 

    The key to getting rid of the dreaded 'Operation Failed' message is to first remove the add-ins that are lurking within Outlook installed by 3rd party vendors. You'll need to do this as the admin. 

    Full details can be obtained here:

    http://www.howtogeek.com/howto/microsoft-office/make-outlook-faster-by-disabling-unnecessary-add-ins/

    Enjoy!

    Thursday, April 05, 2012 2:14 AM
  • Hi-PMO-Milan - Uninstalling HP Security Sofware fixed my issue. Thanks!
    Tuesday, July 17, 2012 3:43 PM
  • Had the same problem.  Turns out it was with email addresses that were auto-completed.  The solution was to empty the auto complete list (under options/mail/send messages).  Once done, haven't had the problem and slowly am rebuilding my auto complete list.
    Thursday, August 16, 2012 8:26 PM
  • Hello Richard,

    What Security software are you talking about? I'm having the same exact problem with my HP Probook. Initially I thought it has something to do with the way I added my contacts. I have two accounts on my Outlook 2010 Exchange + Pop3 in which Pop3 is set to default.

     

    Please help!

    I had a user with this problem using an HP elitebook as well. Disabled all of the HP addins (HP insant PIM addin, Privacy Manager Add-in, and the Privacy Manager Form Region Addin) and it works fine now.
    Uninstalled all HP addins and works fine now. Thx a lot!!!
    Wednesday, December 05, 2012 3:55 PM
  • I had the same issue and I was able to get around by changing my format to plain text (select Format Text ribbon --> select on Format section Aa Plain Text).
    Thursday, July 11, 2013 7:46 PM
  • Have a similar problem with both Outlook 2007 and Outlook 2010 when reply to external address.

    In the RPC Log on Exchange 2010 SP3 can see:

    2013-11-13T08:18:49.718Z,213,460,/o=*******/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipients/cn=*******,,OUTLOOK.EXE,14.0.7104.5000,Classic,,,ncacn_ip_tcp,,,1127 (rop::InvalidRecipients),00:00:00,,"RopHandler: SubmitMessage: [InvalidRecipientsException] Recipient ""'user@domain.com'"" isn't resolved. All recipients must be resolved before a message can be submitted."

    Wednesday, November 13, 2013 8:58 AM
  • In my case it was Kaspersky Outlook Anti-Virus Add-In (part of Kaspersky Endpoint Security 8.1.0.1042) to cause recipient resolve porblem

    Friday, November 15, 2013 9:27 AM