Exchange bouncing internal emails

[HCHTech]

On-premise SBS2011 server. We have germlin somewhere. Last year there was a summer intern. User account & email was created for that period. Summer ends, user account and email account deleted. 8 months go by and that same person was hired as an employee. User account and email address created again - same as before. When someone in the company sends this person an email by typing in their displayname (or choosing their name from the "To" list), the name resolves, but the email bounces. When they type out the full email address, it goes through.

The bounce message is unenlightening. It says:

"The e-mail address you entered couldn't be found. Please check the recipient's e-mail address and try to resend the message. If the problem continues, please contact your helpdesk."

The important lines from the error detail are:

Generating server: XXXXXXX.YYYYYY.local
IMCEAEX-_O=FIRST+20ORGANIZATION_OU=EXCHANGE+20ADMINISTRATIVE+20GROUP+20+28FYDIBOHF23SPDLT+29_CN=RECIPIENTS_CN=FIRSTNAME+20LASTNAMEB5F@YYYYYY.local
#550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found ##

I have combed over her account in active directory and Exchange manager, but don't see where the problem is.

The header looks normal, too:

Received: from XXXXXX.YYYYYY.local ([fe80::2148:8900:66a7:30f0]) by
XXXXXX.YYYYYY.local ([fe80::2148:8900:66a7:30f0%11]) with mapi id
12.34.5678.001; Tue, 19 Jun 2018 14:35:21 -0400
Content-Type: application/ms-tnef; name="winmail.dat"
Content-Transfer-Encoding: binary
From: Firstname Lastname <emailaddress1@domain.com>
To: FIrstname2 Lastname2 <emailaddress2@domain.com>
Subject: Canceled: blah blah blah
Thread-Topic: blah blah blah

Anyone?

 

[Markverhyden]

Was the exact same name used? Exchange can be a really cranky animal sometimes. I'm wondering if there is some undocumented feature where deleting the account, as was done last year, does not really delete the account in Exchange even if it's gone from AD.

 

[fencepost]

As a side note, this is why I always try to disable AD accounts instead of deleting them. Deletion is forever because the internal GUID is gone.

Obviously disabled accounts can be moved into a separate OU.

 

[autumn]

I have had maybe the same error, same situation, deleted user and recreated sometime late and the users couldn't send to the new account.

This was due to the sending users where using the cached address it the to and cc area, I think from memory if they selected the user from the address book it would work. The only solution I found was for the senders to delete the cached address and type the address in full (or select it from the address book) until it is cached again.

 

[TurricanII]

Indeed you need to clear out the autocomplete cache using nk2edit is the easiest option when you have lots of problems like this however as it's only one person you can simply delete their name as it is offered in Outlook is an autocomplete option.

When you send internal emails Outlook remembers the old x400 address to the old mailbox it doesn't use the email address.