PGP Encryption (ASCII RADIX-64) Munging by Microsoft Exchange.

From: Jay D. Dyson (jdysonat_private)
Date: Tue Jun 22 1999 - 13:17:50 PDT

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    Hi folks,
    
    	I've searched high and low for other reports regarding this and
    have found none.  Thus, I'm filing this risk report.
    
    	HISTORY: I've been using PGP v2.x for years in conjunction with
    many a mail program: Pine, Eudora, Netscape (v3.x Navigator, not v4.x
    Communicator), and Elm.  In all that time, I never encountered a problem
    with sending or receiving encrypted mail regardless of the Mail Transport
    Agent (MTA) to which I've sent or received mail.
    
    	Until now.
    
    	PROBLEM: After initiating encrypted correspondence, my contact at
    Honeywell and I have come to the distinct conclusion that Microsoft
    Exchange has a "feature" (*gag*choke*retch*) that tries to interpret PGP
    encrypted messages sent in ASCII RADIX-64 format into "human" terms.
    Characters were stripped or merged (i.e., AE became "Æ" and so on).  As a
    consequence, the messages failed their checksums.
    
    	IMPACT: Communications are compromised by the Exchange MTA to the
    point that messages cannot be decrypted and must be re-sent by other
    means, wasting a lot of time and placing time-sensitive data at risk of
    becoming useless.  Another possible risk would be some users eventually
    abandoning use of encryption for sensitive communications and sending data
    in the clear.  (I didn't resort to that, but I'm stubborn that way.)  Even
    attempts at using another Microsoft product -- Internet Explorer -- as a
    workaround failed miserably.  When attempting to send encrypted_file.txt
    (using Apache v1.3.6 on the server side), Explorer also tried "interpreting"
    the PGP-encyrpted message and stripped out phrases like "=67", so the
    final line in the encrypted message ended up being changed from "=67Rg" to
    "gRg".  Once again, checksum failure.
    
    	SOLUTION: My personal feeling is that individuals and agencies
    that use PGP or GPG should use any other MTA but Microsoft Exchange. (I'll
    spare the gentle reader my views on Microsoft's Internet Explorer for
    now.)  However, I recognize that some folks are stuck with Microsoft
    Exchange and related products as an "institutional solution," (sic) so I
    alternatively recommend that said users not send PGP encrypted messages in
    ASCII RADIX-64 format to Outlook users, but instead encrypt them as binary
    files and send them as attachments.  Fortunately, Outlook doesn't seem to
    want to "interpret" attached binaries.
    
    	CAVEATS: I have not sought confirmation on whether this same sort
    of behavior occurs with the PGP v5.x/v6.x plug-in for Exchange from
    Network Associates (I somehow doubt it does).  While I do use PGP v6.x, I
    do so only to communicate via Eudora with technophobes who can't get along
    without a GUI.  (I do not trust PGP 5.x and higher for Windows as the
    SWAP attack alone leaves me cold.)  Additionally, I refuse to load and
    operate Microsoft Exchange on my Windows machine.
    
    - -Jay
    
       (                                                              ______
       ))   .--- "There's always time for a good cup of coffee" ---.   >===<--.
     C|~~| (>--- Jay D. Dyson - jdysonat_private ---<) |   = |-'
      `--'  `- Superman had Kryptonite, I have NT.  Life is real. -'  `-----'
    
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