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I created an exchange mailbox early 2019 and deleted it in december 2019 I think. Then I re-created AD and exchange account with same name and same email address in september 2020. Since, we have difficulties to send email to this person because it seems that sometimes outlook use the old UID instead of the new.

I tried to use contact in "All address list" instead of "Global address list" and I think it is better but, I always have this problem again after few weeks/months.

So I looked for an old UID in all exchange address lists with :

$AL = Get-AddressList -Identity "EACH_ADDRESS_LIST"; Get-Recipient -ResultSize unlimited -RecipientPreviewFilter $AL.RecipientFilter | select * | Export-Csv -Path "C:\temp\export.csv"

Every ID seems ok, there is no differences.

Does someone already had this issue ? Or have an idea ?

Also, we moved from exchange 2010 to exchange 2016 in 2020 and to exchange 2019 in 2021.

Thank you

yeedooz
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  • Hi, any update here? Have you tried adding the x500 address then verify the result again? – joyceshen May 09 '22 at 06:55
  • Hi thank you both for your answers. I don't have the old AD because it was 2 years ago. Or maybe I didn't understand well where to find the address – yeedooz May 13 '22 at 07:46

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The problem is the LegacyExchangeDN. You need to export the original LegacyExchangeDN for each user from the old AD and add it as an x500 address to all mailboxes in the new AD. The link below will help.

https://blog.valeconsulting.co.uk/2014/10/07/powershell-scripts-to-export-and-import-legacy-exchange-x500-addresses/

joeqwerty
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I agree with the suggestion above, because Exchange auto-complete cache uses X.500 addresses for e-mail sent to addresses within the Exchange organization, it will bounce back messages from a re-created mailbox even after you give the user account all the old SMTP addresses. This is because the old X.500 address in the auto-complete cache is missing, and this causes Exchange to reject the messages.

The solution to the problem is actually quite simple – add the old legacyExchangeDN X.500 address to the new mailbox as a proxy address. You can add an X.500 proxy address through the Exchange Management Console, or the Exchange Management Shell.

Refer to the links below to get more information:

Exchange E-mail Addresses and the Outlook Address Cache

Rename an existing shared mailbox and re-use the same primary smtp address and display name

joyceshen
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  • You can add the old value which looks like this: /o=Organisation/ou=Administrative Group/cn= Recipients/cn=Username ; You'll have to get the old legacyExchangeDN (x500) address, which I think comes back to you in the bounceback you get when someone replies to the old account. It should say something like "couldn't find "/o=Organisation/ou=Administrative Group/cn= Recipients/cn=Username" ... Just add that to their account. – joyceshen May 16 '22 at 07:43