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Exchange 2003 Case Sensitve?

Posted on 2008-10-14
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Last Modified: 2013-11-30
We have an AD environment running Exchange 2003. Sometime in the past few months, when a new user is created and we setup their Outlook 2003 client their email address becomes case sensitive. So if we set them up in the AD as "JSmith@web.com, then "jsmith@web.com" will not work.  Now I can go back into the AD and change just the email back to lowercase, but I'd rather not have to do that for all of my users.  Is there a way to turn off case-sensitivity in Exchange?

Thanks
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Question by:blinkme323
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Expert Comment

by:flyingsky
ID: 22711713
Never heard exchange is case sensitive. Got to be something else
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by:LeeDerbyshire
ID: 22711726
No email system treats email addresses as case-sensitive.  There must be another reason for the non-delivery.  Do you have an example of an NDR generated when you try to send to one of the affected email addresses.
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Author Comment

by:blinkme323
ID: 22711847
Here is the NDR:

The original message was received at Tue, 14 Oct 2008 10:12:59 -0400
from localhost [127.0.0.1]

   ----- The following addresses had permanent fatal errors -----
<xxxxx@xxxxxxx.com>
    (reason: 550 5.1.1 User unknown)

   ----- Transcript of session follows -----
... while talking to xxxxxl.xxxxxxx.com.:
>>> DATA
<<< 550 5.1.1 User unknown
550 5.1.1 <xxxxxxxxx@xxxxxxxxx.com>... User unknown
<<< 503 5.5.2 Need Rcpt command.


Now if I go into the AD and change the email address to all lowercase, it goes through fine....
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by:devlex
ID: 22711944
To clarify, using your example of JSmith@web.com

If you send 2 emails, 1 to JSmith@web.com and 1 to jsmith@web.com they both come back undeliverable or just one? You may want to test this. Instead of being an issue of case, it could be that the account is not connecting to the mailbox, so when you go into AD and update it to lowercase it's updating.

Also, after you change it to lowercase in AD does the original JSmith@web.com work or only jsmith@web.com?
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Author Comment

by:blinkme323
ID: 22712087
When sending to both JSmith and jsmith, I only receive one email, which is to JSmith.  The alias of the AD account is setup as just "JSmith"

However, now I am not receiving an NDR, I'm just not getting the second email at all.
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by:blinkme323
ID: 22712167
Interesting -- after reseting the password for one of the accounts in question, I am now getting both emails.  However, the one for JSmith is coming through to my inbox, while the one for jsmith is getting routed to my junk mail folder.
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by:flyingsky
ID: 22712238
check your anti-spam settings.
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devlex earned 500 total points
ID: 22712305
Are both e-mails coming from the same sender? Outlook is probably just picking it up as spam.

Resetting the password definitely points to a synchronization issue. Do you have a password age policy? For example, if a user was forced to change their password after 30 days and you're noticing that they're not receiving their email after this period.
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by:blinkme323
ID: 22713019
I think it was the age policy that was throwing a wrench into things.  I've set it to never expires.  Thanks for all of the help.
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