Office 2010 "The operation failed. The messaging interfaces have returned an unknown error. If the p

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Hi All,

I see others are having this problem too, I have Office 2010 and when I try to send an email to a group I get the following message

" The operation failed. The messaging interfaces have returned an unknown error. If the problem persists, restart Outlook. Cannot resolve recipient."

I have set up the group again from scratch, and run scanpst, I also changed the SMTP encryption settings from none to auto as was suggested by someone else which made no difference. I am reluctant to set up another profile as I do not know if that will cure it plus I will have to enter the details of my 9 email addresses all over again which would be time consuming!

Any Ideas, please help,

thanks in advance

Despite your reluctance, it would be worth trying a new mail profile. Add the account you're trying to use to send the message. That, at least, may tell you whether or not the old profile has a problem.



Hi Brian,

thanks for your reply, I have set up another profile which has led to another problem. When I try to send an email to test it none of my contacts are there! I have even imported all my PST files (outlook,archive and archive1) but the contacts do not appear.

When you go to the contacts button on the software near the calendar button they are there, but you cannot use them when you want to send an email to a group because it is not showing.

thanks in advance for any answers,


Roady [MVP]

Verify that your Contacts folder has been marked as an Outlook Address List.

See Contacts are not available in the Address Book

Also note that importing is not the way to restore your Outlook data. You can connect to exisitng pst-files via File-> Open-> Open-> Outlook Data File. You can set it as the delivery location via your account settings.

Robert Sparnaaij



Hi Roady,

I actually tried both ways, I used the " open" method as you say, when I realised the contacts were not being used as an address book I then took the decisaion to import them all.

I followed your link but unfortunately that does not seem to work with Office 2010,

thanks in advance for any other help,




I have tried a new profile, got the address book to work that has not solved the original problem, so I am still at square 1, I cannot send to a group via outlook 2010.

I have deleted the additional profile as it is no longer needed,



Hi folks,

Likewise I have recently installed Office 2010 (including Outlook) and I have had the same problem (within Vista) BUT I think I have found a work-around. Bear with me as it's a bit long-winded to describe . . .

I noticed that most of my destination email addresses were displayed in the " To" field as: SURNAME, Forename <name@server.extension> . . any email with addresses in this format failed with the error message that has been noted in most of these posts, however I also noticed that emails I sent to a destination ONLY showing SURNAME, Forename (which is my preferred method offiling contacts) were despatched with no problem whatsoever.

I have just spent most of the evening editing my contacts to display only as SURNAME, Forename - once completed I have 'refreshed' all of my contact groups and I can now send emails to group addresses.

There is possibly a much quicker way to work around it, but this is how I have done it . . .

In the Contact list, double-click a contact to open .... highlight the " File as" entry, right click and copy it. Now " Save & Close" . Re-open the contact, highlight the " Display as" field, then right-click and paste. Click " Save & Close" once again.

Repeat for each contact (some may already be in the SURNAME, Forename only format - in which case you can bypass those)

I tried to open the contact and do everything without the " Save & Close" step in between but found that I was having to go through it twice before it would save. With over 500 email addresses you can possibly see why it has taken most of the evening! (And my 'mouse' fingers are killing me too!)

Once you have edited all of your individual contacts, open your contact groups and click on " Update now" . You will see all the <name@server.extension> removed from the list(s). " Save & Close" and you SHOULD be 'good to go'

Russ Valentine

Off the mark. What the Email Display As field showed was irrelevant. What you did was reset autoresolution for each of your Contacts. How and why your Outlook address book service became corrupt in the first place is anyone's guess.Russ Valentine



I have the same exact problem and my issue is that every single time I reply to a message from somebody who has its label as " Name Surname <email address>" Outlook shows the same error message. From that point on I cannot even create a new contact, no matter what I input in the File As field. The only solution is to restart Outlook, create the contact without the <email address> in the File As field, go back to the original message, choose reply, delete the To: field and select the contact I know have in my Contact List.

As you can imagine the process is quite cumbersome and in particular when I have many contacts to reply to in the original email and the contacts are not in my contact list.

I hope I have not been too confusing in the above description and I sincerely hope that you could drive me through a process to attempt to find a solution.

For the record I use:

Outlook 2010 (upgraded to 2010 because I had the issue also with 2007 and I was hoping for a solution with the new version)

Win 7

1 x Exchange email account

1 x Google Apps Premiere account

Various IMAP accounts

I have already created new profiles from scratch without success

I have already scanned the PST/OST files for errors and all looks fine

Thanks in advance for your help.


Russ Valentine

Sorry, you have only posted a series of random observations and assumptions, but no clear description of your problem and nothing we could use to troubleshoot. The fact that you are having problems with replies actually takes your Contacts, Outlook Address Book service and the File As... fields out of the equation, so this is not the " exact same problem."

The fact that you have so many disparate mail account types in a single profile is a red flag. Odds are you aren't even aware of which account is being used to send a reply and that you haven't configured Outlook correctly to authenticate to the server in question. I make it a habit not to include an Exchange account with Internet mail accounts to avoid conflicts and confusion over what the default sending account will be.

For future reference, updating an Outlook version in hopes of fixing an existing problem is a distinctly bad idea. You will be far more likely to make the problem worse, which you may have now done.

If you need help, you would need to provide a complete and accurate description of how you are sending messages including precisely how recipients are selected, what mail account is used, what happens and the exact error message(s) you receive.

Russ Valentine
Russ - I'm having the same basic problem. I went from Office 2007 to office 2010 (and we won't even discuss the 5 days it took me to completely strip each and every vestige of 2007 items before 2010 would actually configure for authentication.) Once I got it installed on three of our workstations, we discovered that none of the people could reply to an e-mail they received, nor could they use their contact folders to send to anyone. Nor could they even generate a new e-mail, type the address from memory and send.

At first the messages were that the addresses could not be resolved. So I spent last evening repairing their office 2010 installations. Wow is that slow on older machines. (This is a non profit foundation so no sight of new workstations soon.) Now we are getting " The operation failed. The messaging interfaces have returned an unknown error. If the problem persists, restart Outlook. Cannot resolve recipient."

This is on three separate machines, all different profiles, but all sending from POP3.

Russ Valentine

To restore the Outlook Address Book Service in Outlook 2010 requires a completely new profile (from scratch: copy nothing), then correct migration of the data file you wish to use. Use manual configuration for your new profile's mail accounts in Outlook 2010 (always preferable). It has a nice new option that lets you connect to a pre-existing data file when creating a new profile instead of having to jump through all the hoops of creating a new file, connecting to the pre-existing file, then disconnecting the new file.

Russ Valentine


Hi Russ,

Thank you for your reply. Let me clarify few points so that it maybe could simplify the troubleshoot of the issue. I understand that the long description of the problem could have confused the analysis. However let me simplify all I said:

- Every time I answer to a message where the email address is in the format " Name <Email Address>" I get the error

- To fix it I just have to replace the address with the version without the <Email Address> and must be taken from my contact list. No needs to change account, no needs reset the application. Therefore it's clear that the message is sent from the proper email account and all PST/OST files are not corrupted. The real issue is that if I don't have such contact in my address book I need to create it first (that's where the Save As comes into the picture).

Oulook is configured properly for all Exchange, IMAP and POP accounts. Otherwise the simple change of the address wouldn't fix the delivering of the message. I don't want to sound arrogant, but I prefer to specify that I am not a novice. I already recreated profiles from scratch and I always used multiple emails accounts in the past.

My impression is that the send command triggers some sort of verification of the consistency of the email format (such as calling a form or a VB process). However there are no forms created for as much as I can tell. One more information is that I previously installed Comodo to certify the email. Then I decided to remove it and all looks clean. Question is if Comodo left some hidden processes installed. I cannot confirm that the issue started just after that, but it could be an added info in case other users experiencing the same problem went through the same path.

Kind Regards,


Russ Valentine

Just to clarify: every message you send goes successfully unless it is a reply. Is that correct?Russ Valentine


That is correct.

Since never the addresses in my contact list are pulled in the format " Name <Mail Address>" I don't have a problem when I create a new message.

To be more specific, in case the sender appears not to have the format " Name <Mail Address>" I can also reply without problems.



Russ Valentine

Very strange. I still don't believe this is a problem of a corrupt Outlook Address Book service which was what this thread was about. The format " Name <Mail Address>" is not likely the problem. Look at the Internet Header of the messages to which you can't reply and examine the format of the Return Path statement. See how it differs from addresses to which you can send. Also, since replies will use the transport of the sender, not your default transport, make sure the replies are using an account with a valid configuration in your profile.Russ Valentine



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 include multiple Exchange/IMAP accounts in the same profile. 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.




I too have Win7 x64, Office 2010 x64, and the same problem described in this thread. I also have Exchange, Google Apps, and Gmail IMAP configured.

Replacing the email address with the same email address does the trick (removing the address from the File As field).