Cannot reply to email sent from internal users on exchange 2013

Hi, when we receive internal mails via our exchange server from other active directory domain users (but in different exchange address lists), there appears a question mark in front of their name. Also when I reply to that email, outlook for mac tells me that the address is invalid. So I have to change the recipients address manually and send the e-mail.
The same behavior happens in Apple Mail (yosemite). The strange thing is that it does not happen in other versions of OSX and also not in outlook for Windows.

Anybody has an idea?

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Jason CrawfordTransport NinjaCommented:
This sounds like a content conversion issue to me based on the question mark in front of the email address.  Mac clients are notorious for this due to the Rich Text Format of Outlook email not being recognized.  Conversion options are set in three places:

1. Remote Domain settings
2. Contacts and Mail Users
3. Outlook settings

The affected email is being sent to a mailbox and not a contact or a mail user, correct?  Definitely worth following up with if you're unsure since our options are different if the email isn't being sent to a mailbox.

Try manually setting the format of the email to HTML before sending as a test and see if the rogue question marks remain.
AAuthor Commented:
Hi, thanks for your comment.

Yes I'm talking about real mailboxes, not groups or contacts.
I did ome testing from other mail clients and found some things:

The problem only occurs when the mailbox I try to reply resides in an other Exchange addresslist policy. As long as I am in the same addresslist, there is no problem when replying at all.

FYI, when I reply from Apple Mail I get the following in the address field instead of the email address:

This problem also happens with the same user when accepting a calendar invitiation from my iphone. It cannot send the confirmation to the 'address' John Doe </O=CONTOSO/OU=EXCHANGE ADMINISTRATIVE GROUP /CN=RECIPIENTS/CN=174DFAD4C7B22B5F16963F1EDC8AF0D8-JOHN DOE>
Jason CrawfordTransport NinjaCommented:
Check the AD user in ADUC and verify there are no special characters anywhere, ie Display Name, Alias, etc.  Apple doesn't handle special characters well when performing an LDAP query.

Also, the address you listed has the legacyExchangeDn in between the brackets.  This is most often seen when an Autocomplete entry for a contact is saved in Outlook.  When you send an email to an internal address (ie from to, it's not actually sent to the email address, it's sent to the legacyExchangeDn assigned to the mailbox.  You can verify this by exporting your contact list to a .csv file.  In it you'll notice all internal contacts include the legDN where an email address should be.  The fix is to either delete the Autocomplete entry or save the legacyExchangeDn as an x500 alias in the proxyAddresses field.  Here is the command to do so:


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