outlook 2010 operation failed when sending message using autocomplete

outlook 2010 operation failed when sending message using autocomplete, I have to delete the contact from suggested and then it will send but the problem recurrs
joerotondoPresidentAsked:
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Lee IngallsDirector of IT/TS, Quality and FinanceCommented:
I use NK2Edit to edit/repair autocomplete file. Use it to correct the email address.
http://www.nirsoft.net/utils/outlook_nk2_edit.html
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joerotondoPresidentAuthor Commented:
This is for Outlook 2010 there is no NK2 file
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Neil RussellTechnical Development LeadCommented:
Correct there is NO NK2 file, its all stored at the exchange level now.
When you say it recurrs, instantly? Only if you Reply to an old email? If you send one having deleted the autocomplete, try and send another straight away, does that one go?
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GlingoSystem AdministratorCommented:
Hi Joe,

Looks like the autocomplete file is the problem. If you are ok with losing the autocomplete entries that are not in your contacts you could do the following:

Rename your autocomplete file in %appdata%\Local\Microsoft\Outlook\RoamCache (you can just add OLD at the end of the file's name).
Open Outlook.
Create a new email.
Select all your contacts (from TO
-- the trick: Disconnect your Internet connection..
Send the email
(because you don't have internet access, the email is going to sit on the Outgoing folder)
Close Outlook
Open Outlook
delete the email that was sitting on the Outgoing folder
Close outlook
Get the internet connection active again
Back to Outlook and you're good to go :)
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Neil RussellTechnical Development LeadCommented:
Why do people not read a thread before posting! This is for OUTLOOK 2010. There is NO separate autocomplete file.
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GlingoSystem AdministratorCommented:
Well I read your thread and yes there is an autocomplete file for 2010/2013, it's not a .NK2 but a .DAT file, it looks like this:

Stream_Autocomplete_0_{a long string of numbers/letters}.dat

And it's located at the path I provided on my previous answer...
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jgerbasiCommented:
Glingo is correct in that the autocomplete is the .dat file. However the fastest way to complete this is to go to the users computer and start typing the email address of the "bad" record, when the autocomplete comes up for completeion click on the 'x' next to the entry and manually enter the email address you wish to send to.

The autocomplete will add the new address for future emails.

Remember most of the time the email address will be correct in the autocomplete but the UID associated with that entry is no longer correct. So simply editing the entry will not always work as it often needs to be removed and re added.
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GlingoSystem AdministratorCommented:
Looks like joerotondo already tried that (he said he can send the mail if he deletes the address from the autocomplete but the problem comes back afterward) :)
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VB ITSSpecialist ConsultantCommented:
Neilsr: the NK2Edit tool which Lee Ingalls linked has the ability to modify the AutoComplete cache for Outlook 2010 and 2013. Don't get confused by the name of the tool itself. I used this tool just today to modify some AutoComplete entries in Outlook 2013 so I can confirm it works.

@joerotondo have a look at the NK2Edit tool in Lee's reply as it has the ability to back up the contents of your existing AutoComplete cache and import it into a new one.
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GlingoSystem AdministratorCommented:
Nice one VB, good to know we can use nk2edit tools on the autocomplete cache files, thx :)
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