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I've searched serverfault and found this question pop-up quite a bit. Unfortunately others problems aren't exactly like mine, and because I'm a true beginner I wanted some more "specific to me" help. If you don't mind.

I just set-up a new computer for a user. Copied over her auto-populate and archive emails. Her email, for the most part, works fine. But when she tries to send anything to BSMITH@mydomain.com she gets the #550 5.1.1 error. If she uses the exchange webapp she does not have the issue. I can send email to BSMITH, and so can everyone else. The user, as far as I can tell from the EMC reports, is the only person having emails sent back to them and only from BSMITH.

I have googled the crap out of this, and attempted some of the solutions to no avail. I've looked for the bmith account in the disabled accounts and copied and attempted to add "IMCEAEX-_O=CHILD+20STUDY+20CENTER_OU=FIRST+20ADMINISTRATIVE+20GROUP_CN=RECIPIENTS_CN=BSMITH@mydomain.com" as an X500 email.

I honestly am just following instructions though and I don't really understand what it is I'm doing.

Diagnostic information for administrators:

Generating server: FS2.FS1D.local

IMCEAEX-_O=CHILD+20STUDY+20CENTER_OU=FIRST+20ADMINISTRATIVE+20GROUP_CN=RECIPIENTS_CN=BSMITH@mydomain.com
#550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found ##

BTW I love this site and only found out about it a few weeks ago. My girlfriend now loves the photo.stackexchange. So thanks for such a helpful community.

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Maybe even if someone could tell me if the problem seems to be with bsmith or the user that is sending the email tmabery? If it's tmabery I might just make her a new email account. –  gtaylor85 Feb 8 '11 at 18:14

2 Answers 2

up vote 1 down vote accepted

You're correct this is an X500 address. It needs to either map to a legacyExchangeDN on an object in AD, or an X500 proxy in an object's proxyAddresses attribute. This is how Outlook caches things in the auto-complete cache. I would simply delete the entry on the user's machine and let it be regenerated. You can simply press delete to remove it when it's displayed in Outlook.

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I ran into similar issues to this when switching a company over to hosted exchange. Their old auto-complete were not working when trying to use them for sending email. They got the same type of bounce-backs as mentioned here.

I know the best solution likely is to just tell them they need to re-generate the auto-complete, and hope they don't use it as their "address book". Unfortunately we don't live in a world where our clients are going to be fine with this answer. Most of my clients would likely flip to hear this as the resolution to the issue.

That being said, the auto-complete can be re-created. Here's how.

Go over to nirsoft and get NK2View. Run it and you'll see the current auto-complete entries from the current NK2 file. You can select the file you would like as well if you want to get the entries from a different file.

Select all entries and then right click and "Save Selected Items". Save them as "Comma delimited text file (*.csv)

Open Outlook (if it wasn't already) and run an import to the Contacts using this file. Be sure to map the correct values to the correct attributes.

Close Outlook and change the name of the currently used NK2 file. I usually just add an _old to the filename.

Open Outlook and send a test message to someone by manually typing in the email address. This will recreate a brand new NK2 file.

Close Outlook and open NK2View again. Select File and then "Add Items From Address Book". Find the Contacts within the Address book. Select all of the contacts you want to add and then click the "To >>" button, then click OK.

You should now have a full auto-complete file that works fine again.

I did run into an issue on one computer where the "Add Items From Address Book" option did nothing. I ended up having to create a new NK2 file outside of the Outlook directory, renaming it to the same name as the current NK2 file, then copying and replacing the currently used one with the new one - after doing the "Add Items From Address Book" option on the new file first, of course.

I hope that helps someone. I will come back and update what I did for the Outlook 2010 clients once I have figured those ones out.

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