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I am not sure if this is a bug in mail.app, or a configuration I just can't find. It might also be a strange sideffect of GPGmail.

Mail.app correctly displays all e-mails on my IMAP server, except for the e-mails in my "Sent Messages" folder. In the sent messages folder it messes up åäö, in typical quoted-printable with wrong char-set fashion. They become ‰ˆ.

When looking at the source of the e-mails it seems like the header generated by mail.app is correct:

Message-Id: <>
From: 
To: 
In-Reply-To: <>
Content-Type: multipart/signed; protocol="application/pgp-signature";
    micalg=pgp-sha1; boundary="Apple-Mail-4--741321197"
X-Smtp-Server: smtp.example.com
Content-Transfer-Encoding: 7bit
Mime-Version: 1.0 (Apple Message framework v936)
Subject: Example subject
Date: Fri, 26 Mar 2010 10:14:14 +0100
References: <>
X-Pgp-Agent: GPGMail 1.2.0 (v56)

This is an OpenPGP/MIME signed message (RFC 2440 and 3156)
--Apple-Mail-4--741321197
Content-Type: text/plain; charset=ISO-8859-1; format=flowed; delsp=yes
Content-Transfer-Encoding: quoted-printable

<Text here with =E5=E4=F6>

--Apple-Mail-4--741321197
content-type: application/pgp-signature; x-mac-type=70674453;
    name=PGP.sig
content-description: This is a digitally signed message part
content-disposition: inline; filename=PGP.sig
content-transfer-encoding: 7bit

-----BEGIN PGP SIGNATURE-----
Version: GnuPG/MacGPG2 v2.0.12 (Darwin)

iEYEARECAAYFAkus62kACgkQlIRLofxhDjYnnwCcDmCXuMGsKlh3a418s12coJgn
36sAoKMdkP3+g/OMK+Ps7AbjQq4Nbqzv
=XMko
-----END PGP SIGNATURE-----

--Apple-Mail-4--741321197--

How can I get mail.app to use the correct charset?

Some more test results:

  • Thunderbird has no problem displaying the messages.
  • When I send a message to myself it displays correctly in the Inbox, but incorrectly in the Sent folder. But: moving the message from Sent to Inbox does not change the erroneous formatting.
  • Turning off signatures makes the messages display correctly in the Sent folder as well. The only difference I can see (beyond headers added in transfer), is the This is an OpenPGP/MIME signed message (RFC 2440 and 3156) line added before the first mime block.
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1  
Indeed it's very likely that Mail doesn't like the PGP things. To be sure: what if you send a message without using PGP? (Like: send a message through webmail?) What if you send a PGP-signed message to yourself, does it really display fine in the Inbox? –  Arjan Mar 29 '10 at 8:29
    
When I send a message to myself it displays correctly in the inbox, but incorrectly in the sent messages folder. Turning off signatures makes the messages display correctly in the sent messages folder. The only difference I can see (beyond headers added in transfer), is the "This is an OpenPGP/MIME signed message (RFC 2440 and 3156)" line added before the first mime block. –  pehrs Mar 29 '10 at 8:50
1  
Hmmm. First, Mail.app moves the message to Sent, and then tells IMAP the message is there (this would be different when using smtp.gmail.com). Hence, it could also be a combination of Mail and the IMAP server. (Some Thunderbird IMAP madness at superuser.com/questions/42009/…, just as an aside.) Maybe manually moving messages from Sent into the Inbox can give you more insight if Mail handles the two mailboxes differently, or if the server converts it? –  Arjan Mar 29 '10 at 9:36
    
It seems that moving the mail from sent to inbox does not change the formating. In other word, the moved mail is still displayed incorrectly... –  pehrs Mar 29 '10 at 10:44
    
When sending yourself a message, can you see any difference in its source in Sent versus Inbox? (Odd that the mail server might actually be fixing something here, it seems. That might also be the reason Thunderbird has no problems displaying sent messages, as those have gone through the IMAP route. Maybe peeking into the source for Sent in Mail.app versus Thunderbird can give you some insight too...) –  Arjan Mar 29 '10 at 14:59

2 Answers 2

up vote 0 down vote accepted

The 10.6.3 update mentions:

Mail fixes and improvements provided for:

  • [..]
  • signing and encrypting messages, such as when using an Entrust PKI (Public Key Infrastructure).
  • [..]

Any luck for you?

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Still no luck. I have settled for living with this bug and posted it to the developer of GPGmail to see if they know anything about it. –  pehrs Apr 14 '10 at 8:20

I have a similar problem. Often, if I move the message to a "Temporary" folder, rebuild, empty the trash, restart mail.app (it "compacts" the mailboxes then), repeat, and then move the message back, it can be restored.

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