Re: [gpgtools-users] Mail does not validate my own signatures

2011-02-03 Thread Cutler James R
Header is wrapped on my system with caching enabled in mail. [10.6.6 up to date]

On Feb 3, 2011, at 4:09 AM, Raphaël “Kena” Poss wrote:

> Hi Alex
> 
> On Thu, 03 Feb 2011 07:53 +0100, "Alexander Willner" 
> wrote:
>> On 03.02.2011, at 03:37, Raphael 'kena' Poss wrote:
>>> I checked with GPGMail disabled (not in the Bundles directory), and I see 
>>> that Mail.app still breaks the content header with GPGMail disabled. So 
>>> this behavior seems not specific to GPGMail.
>> 
>> Neither it seems to be specific to Apple Mail since I cannot reproduce
>> this issue (see below). Not sure why your message gets modified - maybe
>> you've using slightly different mail servers in Mail and Thunderbird?
>> Does it help to rename Library/Preferences/com.apple.mail.plist and
>> reconfigure Mail.app?
> 
> The mail server is the same in Mail and Thunderbird. As another data
> point, I sniffed the IMAP traffic between Mail and the server, and I
> also confirm that the content header is on a single line at the point it
> comes from IMAP into Mail.app.
> 
> (btw, all these tests are made with Mail 4.4 build 1082.)
> 
> However you were on the right track. I think I found where the issue
> lies. Here is the path through the experiment:
> 
> I tried with another Mac running 10.6.6 and the same Mail build. I
> configured the same mail server, once over SSL and once over plain IMAP.
> In both cases, the content header is wrapped. 
> 
> Then I created a blank OS X user account on that other Mac with a virgin
> Mail install (as you suggested) and there the content header is still
> wrapped.
> 
> Then I checked your idea to use a different mail server. I redirected
> the message to a different e-mail account and I downloaded it using that
> different account's server on the 2nd Mac. Surprise! Then the header is
> *not* wrapped. Then I install GPGMail and the signature does validate
> properly.
> 
> So I got back to the 1st Mac with GPGMail and I connect to this 2nd
> e-mail server. Alas, then the header is wrapped again!
> 
> To summarize:
> 
> Mac 1Mac 2
> Server 1 broken   broken
> Server 2 broken   OK
> 
> Now, I tried to make another blank OS X user account, and I tried again.
> And then it was, the header was not wrapped in either server 1 nor
> server 2!
> 
> That got me thinking and I browsed through the differences between my
> first test account above and this new one. They were both identical,
> except for *one* option: "do not keep copies of the messages nor
> attachments" in Mail's account preferences. 
> 
> I checked all my previous experiments and I can confirm this: in all my
> situations the content header is wrapped if and only if caching is
> disabled.
> 
> Now what to do with that? I certainly don't want to enable caching of my
> main inbox on any computer. 
> 
> Thanks in advance for any comments or suggestions.
> -- 
> Raphaël “Kena” Poss
> 
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James R. Cutler
james.cut...@consultant.com




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Re: [gpgtools-users] Mail does not validate my own signatures

2011-02-03 Thread Alexander Willner

> Well as Bob notes maybe there is something to do on GPGMail's side as
> well. Would that also happen?

If someone wants to work on this[1] issue, yes. I think it would not be a huge 
code change. But our "team" is surprisingly small - so I wouldn't expect to see 
a fix any time soon.
But I've the feeling that you would be able to help here ;)

Best regards, Alex

[1] http://gpgtools.lighthouseapp.com/projects/65764/tickets/125

On 03.02.2011, at 12:24, Raphaël “Kena” Poss wrote:

> 
> 
> On Thu, 03 Feb 2011 11:09 +0100, "Alexander Willner" 
> wrote:
>> Confirmed your issue. Let see what Apple says. I guess: nothing.
> 
> Well as Bob notes maybe there is something to do on GPGMail's side as
> well. Would that also happen?
> -- 
> Raphaël “Kena” Poss
> 
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Re: [gpgtools-users] Mail does not validate my own signatures

2011-02-03 Thread Raphaël “Kena” Poss


On Thu, 03 Feb 2011 11:09 +0100, "Alexander Willner" 
wrote:
> Confirmed your issue. Let see what Apple says. I guess: nothing.

Well as Bob notes maybe there is something to do on GPGMail's side as
well. Would that also happen?
-- 
Raphaël “Kena” Poss

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Re: [gpgtools-users] Mail does not validate my own signatures

2011-02-03 Thread Bob Bishop
Hi,

I wrote:

> Nothing wrong with that (see RFC 2822). [etc]

RFC 2822 is obsolete and I should of course have referenced RFC 5322 which says 
exactly the same thing. Apologies

--
Bob Bishop
r...@gid.co.uk




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Re: [gpgtools-users] Mail does not validate my own signatures

2011-02-03 Thread Alexander Willner

On 03.02.2011, at 11:01, Raphael 'kena' Poss wrote:
>  If I download the messages, then both signatures verify. At least for your 
> example e-mails.

Confirmed your issue. Let see what Apple says. I guess: nothing.

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Re: [gpgtools-users] Mail does not validate my own signatures

2011-02-03 Thread Bob Bishop
Hi,

On 3 Feb 2011, at 02:37, Raphael 'kena' Poss wrote:

> Hi again,
> 
> I think I nailed this bug. Basically, Mail.app improperly changes the MIME 
> content headers upon receiving from the mail server. In particular, the 
> following in the signed message body:
> 
> """
> Content-Type: text/plain; charset=us-ascii
> """
> 
> gets changed to:
> 
> """
> Content-Type: text/plain;
>   charset=us-ascii
> """
> 
> i.e. "charset=..." gets moved to the next line, with a TAB character. [etc]

Nothing wrong with that (see RFC 2822). However, the RFC also says:
"Each header field should be treated in its unfolded form for further syntactic 
and semantic evaluation."

ie GPGMail should unfold headers before processing further.

--
Bob Bishop  +44 (0)118 940 1243
r...@gid.co.ukfax +44 (0)118 940 1295
 mobile +44 (0)783 626 4518





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Re: [gpgtools-users] Mail does not validate my own signatures

2011-02-03 Thread Raphael 'kena' Poss
-BEGIN PGP SIGNED MESSAGE-
Hash: RIPEMD160


Op 3 feb 2011, om 10:59 heeft Raphael 'kena' Poss het volgende geschreven:
>> 2. Working?: someone else composes a mail -> signs it -> sends it -> you 
>> download this message -> you can validate it (e.g. this mail)
> 
> This mail (PGP inline), yes.
> 
> The other mail (OpenPGP), no.

To clarify: if I leave the message on the server, then PGP inline works and 
OpenPGP does not. If I download the messages, then both signatures verify. At 
least for your example e-mails.

- -- 
k
-BEGIN PGP SIGNATURE-
Version: GnuPG/MacGPG2 v2.0.17 (Darwin)
Comment: 
https://www.biglumber.com/x/web?pk=9B3290AB2972C92BBAFAB69C236E4E505024FAE3

iEYEAREDAAYFAk1KfN0ACgkQRoOteLWdVhqvtACfclqrLRfp4pQqFtUau9UC03DY
0gsAn0CSBU1OvaCe+IFGJdbDKNqdB7ng
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Re: [gpgtools-users] Mail does not validate my own signatures

2011-02-03 Thread Raphael 'kena' Poss

Op 3 feb 2011, om 10:21 heeft Alexander Willner het volgende geschreven:
> So I guess the workflows are:
> 1. Working: composing mail -> signing it -> sending it -> others can validate 
> it
> 2. Working?: someone else composes a mail -> signs it -> sends it -> you 
> download this message -> you can validate it (e.g. this mail)

This mail (PGP inline), yes.

The other mail (OpenPGP), no.

> 3. Problem: composing mail -> signing it -> sending it -> download your own 
> message -> you can validate it

yes

> 
> I case that (2) is working I cannot see why (3) doesn't. Assuming you're not 
> using any filters to modify your own mails I guess this might worth a bug 
> report to Apple.
> 
> Btw: could you sign your reply once?

sure.

-- 
k

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Re: [gpgtools-users] Mail does not validate my own signatures

2011-02-03 Thread Alexander Willner
(and again using PGP/MIME)

Hi Raphaël,

tough issue.

On 03.02.2011, at 10:09, Raphaël “Kena” Poss wrote:
> I also confirm that the content header is on a single line at the point it 
> comes from IMAP into Mail.app.
and
> the content header is wrapped if and only if caching is disabled.

So I guess the workflows are:
1. Working: composing mail -> signing it -> sending it -> others can validate it
2. Working?: someone else composes a mail -> signs it -> sends it -> you 
download this message -> you can validate it (e.g. this mail)
3. Problem: composing mail -> signing it -> sending it -> download your own 
message -> you can validate it

I case that (2) is working I cannot see why (3) doesn't. Assuming you're not 
using any filters to modify your own mails I guess this might worth a bug 
report to Apple.

Btw: could you sign your reply once?

Best regards, Alex




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Re: [gpgtools-users] Mail does not validate my own signatures

2011-02-03 Thread Alexander Willner
-BEGIN PGP SIGNED MESSAGE-
Hash: SHA1

Hi Raphaël,

tough issue.

On 03.02.2011, at 10:09, Raphaël “Kena” Poss wrote:
> I also confirm that the content header is on a single line at the point it 
> comes from IMAP into Mail.app.

and
> the content header is wrapped if and only if caching is disabled.

So I guess the workflows are:
 1. Working: composing mail -> signing it -> sending it -> others can validate 
it
 2. Working?: someone else composes a mail -> signs it -> sends it -> you 
download this message -> you can validate it (e.g. this mail)
 3. Problem: composing mail -> signing it -> sending it -> download your own 
message -> you can validate it

I case that (2) is working I cannot see why (3) doesn't. Assuming you're not 
using any filters to modify your own mails I guess this might worth a bug 
report to Apple.

Btw: could you sign your reply once?

Best regards, Alex


-BEGIN PGP SIGNATURE-
Version: GnuPG/MacGPG2 v2.0.17 (Darwin)
Comment: GPGTools - http://gpgtools.org

iEYEARECAAYFAk1Kc5sACgkQ3RyQelD+nTIosACgzCvXTHOP4ZFk17ZP39Ib+35C
5dcAn3CxajAoBcKoYb1Xq2HYnhWREUK1
=h95Q
-END PGP SIGNATURE-

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Re: [gpgtools-users] Mail does not validate my own signatures

2011-02-03 Thread Raphaël “Kena” Poss
Hi Alex

On Thu, 03 Feb 2011 07:53 +0100, "Alexander Willner" 
wrote:
> On 03.02.2011, at 03:37, Raphael 'kena' Poss wrote:
> > I checked with GPGMail disabled (not in the Bundles directory), and I see 
> > that Mail.app still breaks the content header with GPGMail disabled. So 
> > this behavior seems not specific to GPGMail.
> 
> Neither it seems to be specific to Apple Mail since I cannot reproduce
> this issue (see below). Not sure why your message gets modified - maybe
> you've using slightly different mail servers in Mail and Thunderbird?
> Does it help to rename Library/Preferences/com.apple.mail.plist and
> reconfigure Mail.app?

The mail server is the same in Mail and Thunderbird. As another data
point, I sniffed the IMAP traffic between Mail and the server, and I
also confirm that the content header is on a single line at the point it
comes from IMAP into Mail.app.

(btw, all these tests are made with Mail 4.4 build 1082.)

However you were on the right track. I think I found where the issue
lies. Here is the path through the experiment:

I tried with another Mac running 10.6.6 and the same Mail build. I
configured the same mail server, once over SSL and once over plain IMAP.
In both cases, the content header is wrapped. 

Then I created a blank OS X user account on that other Mac with a virgin
Mail install (as you suggested) and there the content header is still
wrapped.

Then I checked your idea to use a different mail server. I redirected
the message to a different e-mail account and I downloaded it using that
different account's server on the 2nd Mac. Surprise! Then the header is
*not* wrapped. Then I install GPGMail and the signature does validate
properly.

So I got back to the 1st Mac with GPGMail and I connect to this 2nd
e-mail server. Alas, then the header is wrapped again!

To summarize:

 Mac 1Mac 2
Server 1 broken   broken
Server 2 broken   OK

Now, I tried to make another blank OS X user account, and I tried again.
And then it was, the header was not wrapped in either server 1 nor
server 2!

That got me thinking and I browsed through the differences between my
first test account above and this new one. They were both identical,
except for *one* option: "do not keep copies of the messages nor
attachments" in Mail's account preferences. 

I checked all my previous experiments and I can confirm this: in all my
situations the content header is wrapped if and only if caching is
disabled.

Now what to do with that? I certainly don't want to enable caching of my
main inbox on any computer. 

Thanks in advance for any comments or suggestions.
-- 
Raphaël “Kena” Poss

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Re: [gpgtools-users] Mail does not validate my own signatures

2011-02-02 Thread Alexander Willner
Hi Raphael,

thank you for digging through the code.

On 03.02.2011, at 03:37, Raphael 'kena' Poss wrote:
> I checked with GPGMail disabled (not in the Bundles directory), and I see 
> that Mail.app still breaks the content header with GPGMail disabled. So this 
> behavior seems not specific to GPGMail.

Neither it seems to be specific to Apple Mail since I cannot reproduce this 
issue (see below). Not sure why your message gets modified - maybe you've using 
slightly different mail servers in Mail and Thunderbird? Does it help to rename 
Library/Preferences/com.apple.mail.plist and reconfigure Mail.app?

Best regards, Alex

=
This is an OpenPGP/MIME signed message (RFC 2440 and 3156)
--Apple-Mail-2-580498424
Content-Transfer-Encoding: 7bit
Content-Type: text/plain; charset=us-ascii

qsdfqsdfs q

--Apple-Mail-2-580498424
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 v2.0.17 (Darwin)
Comment: GPGTools - http://gpgtools.org

iEYEARECAAYFAk1KTg4ACgkQ3RyQelD+nTKPfQCfVl08b6E379D/HlSJr/zCQD+4
s3MAn2Hluan1R+mflg+IZYaKCQqwbnYP
=kRnX
-END PGP SIGNATURE-

--Apple-Mail-2-580498424--
=

smime.p7s
Description: S/MIME cryptographic signature


PGP.sig
Description: This is a digitally signed message part
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Re: [gpgtools-users] Mail does not validate my own signatures

2011-02-02 Thread Raphael 'kena' Poss
Hi again,

I think I nailed this bug. Basically, Mail.app improperly changes the MIME 
content headers upon receiving from the mail server. In particular, the 
following in the signed message body:

"""
Content-Type: text/plain; charset=us-ascii
"""

gets changed to:

"""
Content-Type: text/plain;
charset=us-ascii
"""

i.e. "charset=..." gets moved to the next line, with a TAB character. 

Since the signature was generated with the content-type header on a single 
line, this change invalidates the signature. I found this out by looking at the 
detailed log from GPGME, see the bottom of this  mail for a copy. Basically 
this shows that the mail was generated/sent with the header on a single line, 
which I can also confirm by looking at the e-mail on the IMAP server directly 
(using a different client). Strangely when keeping the mails on the IMAP 
server, the header is modified on the local copy but not on the server. 
Thunderbird/Enigmail also leaves the header untouched, that's why the signature 
verifies with it.

I checked with GPGMail disabled (not in the Bundles directory), and I see that 
Mail.app still breaks the content header with GPGMail disabled. So this 
behavior seems not specific to GPGMail.

Now that said, I hear that some other people using Mail.app can actually 
validate my sigs. Is there a setting in Mail.app to prevent this handling of 
content headers? Also, could we work around this in GPGMail by trying (once) to 
re-format the content headers the first time signature verification fails?


Thanks


Output from GPGME:

- Log data when generating the sig:

GPGME 2011-02-03 03:17:53 <0x7fff7020eca0>  _gpgme_io_write: check: 
436f6e74656e742d 5472616e73666572 Content-Transfer
GPGME 2011-02-03 03:17:53 <0x7fff7020eca0>  _gpgme_io_write: check: 
2d456e636f64696e 673a20376269740d -Encoding: 7bit.
GPGME 2011-02-03 03:17:53 <0x7fff7020eca0>  _gpgme_io_write: check: 
0a436f6e74656e74 2d547970653a2074 .Content-Type: t
GPGME 2011-02-03 03:17:53 <0x7fff7020eca0>  _gpgme_io_write: check: 
6578742f706c6169 6e3b206368617273 ext/plain; chars
GPGME 2011-02-03 03:17:53 <0x7fff7020eca0>  _gpgme_io_write: check: 
65743d75732d6173 6369690d0a0d0a66 et=us-asciif
GPGME 2011-02-03 03:17:53 <0x7fff7020eca0>  _gpgme_io_write: check: 
6f6f0d0a0d0a626c 61680d0a0d0a ooblah
...
GPGME 2011-02-03 03:17:59 <0x7fff7020eca0>  _gpgme_io_read: check: 
2d2d2d2d2d424547 494e205047502053 -BEGIN PGP S
GPGME 2011-02-03 03:17:59 <0x7fff7020eca0>  _gpgme_io_read: check: 
49474e4154555245 2d2d2d2d2d0a5665 IGNATURE-.Ve
GPGME 2011-02-03 03:17:59 <0x7fff7020eca0>  _gpgme_io_read: check: 
7273696f6e3a2047 6e7550472f4d6163 rsion: GnuPG/Mac
GPGME 2011-02-03 03:17:59 <0x7fff7020eca0>  _gpgme_io_read: check: 
475047322076322e 302e313720284461 GPG2 v2.0.17 (Da
GPGME 2011-02-03 03:17:59 <0x7fff7020eca0>  _gpgme_io_read: check: 
7277696e290a436f 6d6d656e743a2068 rwin).Comment: h
GPGME 2011-02-03 03:17:59 <0x7fff7020eca0>  _gpgme_io_read: check: 
747470733a2f2f77 2e6269676c75 ttps://www.biglu
GPGME 2011-02-03 03:17:59 <0x7fff7020eca0>  _gpgme_io_read: check: 
6d6265722e636f6d 2f782f7765623f70 mber.com/x/web?p
GPGME 2011-02-03 03:17:59 <0x7fff7020eca0>  _gpgme_io_read: check: 
6b3d394233323930 4142323937324339 k=9B3290AB2972C9
GPGME 2011-02-03 03:17:59 <0x7fff7020eca0>  _gpgme_io_read: check: 
3242424146414236 3943323336453445 2BBAFAB69C236E4E
GPGME 2011-02-03 03:17:59 <0x7fff7020eca0>  _gpgme_io_read: check: 
3530353032344641 45330a0a69455945 505024FAE3..iEYE
GPGME 2011-02-03 03:17:59 <0x7fff7020eca0>  _gpgme_io_read: check: 
4152454441415946 416b314b45466341 AREDAAYFAk1KEFcA
GPGME 2011-02-03 03:17:59 <0x7fff7020eca0>  _gpgme_io_read: check: 
43676b51526f4f74 654c576456686f6b CgkQRoOteLWdVhok
GPGME 2011-02-03 03:17:59 <0x7fff7020eca0>  _gpgme_io_read: check: 
55774366644f584e 4236347762745245 UwCfdOXNB64wbtRE
GPGME 2011-02-03 03:17:59 <0x7fff7020eca0>  _gpgme_io_read: check: 
5070727043456767 557675460a663467 PprpCEggUvuF.f4g
GPGME 2011-02-03 03:17:59 <0x7fff7020eca0>  _gpgme_io_read: check: 
416e5242444d4741 5271794743704731 AnRBDMGARqyGCpG1
GPGME 2011-02-03 03:17:59 <0x7fff7020eca0>  _gpgme_io_read: check: 
2b6e62546a495148 72493459530a3d52 +nbTjIQHrI4YS.=R
GPGME 2011-02-03 03:17:59 <0x7fff7020eca0>  _gpgme_io_read: check: 
434e550a2d2d2d2d 2d454e4420504750 CNU.-END PGP
GPGME 2011-02-03 03:17:59 <0x7fff7020eca0>  _gpgme_io_read: check: 
205349474e415455 52452d2d2d2d2d0a  SIGNATURE-.

- Log data when validating the sig:

GPGME 2011-02-03 03:18:38 <0x7fff7020eca0>  _gpgme_io_write: check: 
2d2d2d2d2d424547 494e205047502053 -BEGIN PGP S
GPGME 2011-02-03 03:18:38 <0x7fff7020eca0>  _gpgme_io_write: check: 
49474e4154555245 2d2d2d2d2d0d0a56 IGNATURE-..V
GPGME 2011-02-03 03:18:38 <0x7fff7020eca0>  _gpgme_io_write: check: 
657273696f6e3a20 476e7550472f4d61 ersion: GnuPG/Ma
GPGME 2011-02-03 03:18:38 <0x7fff7020eca0>  _gpgme_io_write: check: 
6347504732207632 2e302e3137202844 cGPG2 v2.0.17 (D
GPGME 2