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Outlook Express and OpenPGP/MIME

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Tristan Miller

unread,
Mar 22, 2006, 10:59:39 PM3/22/06
to
Greetings.

I tend to sign my outgoing mail via OpenPGP/MIME, resulting in messages
with a Content-Type of
multipart/signed(text/plain,application/pgp-signature). I've had reports
from users of Microsoft Outlook Express that such messages are displayed
as a blank e-mail with both the text/plain and application/pgp-signature
parts shown as attachments.

My questions are as follows, then:

1) Is there some patch or simple plugin which fixes this issue to which I
can refer these people? (Some of them refuse or are unable to switch to a
different e-mail program such as Thunderbird.)

2) Is there anything I can do to make my signed mails friendlier to Outlook
Express? I have seen a report (see
<nntp://news.gmane.org/gmane.mail.mutt.user/20060226111...@leela.local.dossen.dk>
or <http://comments.gmane.org/gmane.mail.mutt.user/23765>) that sending
messages as
multipart/signed(multipart/mixed(text/plain,text/plain),application/pgp-signature)
might work. However, I don't think this option will work for me, since
AFAIK my mail client (KMail) doesn't allow one to filter outgoing mail
before it is signed.

Regards,
Tristan

--
_
_V.-o Tristan Miller [en,(fr,de,ia)] >< Space is limited
/ |`-' -=-=-=-=-=-=-=-=-=-=-=-=-=-=-= <> In a haiku, so it's hard
(7_\\ http://www.nothingisreal.com/ >< To finish what you

Sam

unread,
Mar 23, 2006, 7:02:19 AM3/23/06
to
Tristan Miller writes:

> Greetings.
>
> I tend to sign my outgoing mail via OpenPGP/MIME, resulting in messages
> with a Content-Type of
> multipart/signed(text/plain,application/pgp-signature). I've had reports
> from users of Microsoft Outlook Express that such messages are displayed
> as a blank e-mail with both the text/plain and application/pgp-signature
> parts shown as attachments.

Known bug in Microsoft shitware. Prepare to get a bunch of Outlook luser
claim that this is your problem, and not theirs.

> My questions are as follows, then:
>
> 1) Is there some patch or simple plugin which fixes this issue to which I
> can refer these people? (Some of them refuse or are unable to switch to a
> different e-mail program such as Thunderbird.)

Yes. Refer them to install the following patch:
http://www.mozilla.com/thunderbird/

> 2) Is there anything I can do to make my signed mails friendlier to Outlook
> Express?

No. Proper compatibility with non-proprietary, open Internet standards is
not a priority for Microsoft.


Frank Slootweg

unread,
Mar 23, 2006, 10:09:42 AM3/23/06
to
Tristan Miller <psych...@nothingisreal.com> wrote:
> Greetings.
>
> I tend to sign my outgoing mail via OpenPGP/MIME, resulting in messages
> with a Content-Type of
> multipart/signed(text/plain,application/pgp-signature). I've had reports
> from users of Microsoft Outlook Express that such messages are displayed
> as a blank e-mail with both the text/plain and application/pgp-signature
> parts shown as attachments.

No help, but just to let you know that this is indeed true. At least,
assuming that Sam's (Usenet) *article* is structured the same as your
(e-mail) *messages*, Outlook Express displays Sam's article exactly the
way you described: A .dat signature file and a .txt file containing the
body of Sam's post.

Probably stupid suggestion: You can't persuade the recipients, to just
open the .txt attachment? Perhaps if the know the message is from a safe
sender and you say so in the "Subject:"?

[deleted]

Frank Slootweg

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Mar 23, 2006, 10:14:28 AM3/23/06
to
Sam <s...@email-scan.com> wrote:
[deleted]

> Known bug in Microsoft shitware. Prepare to get a bunch of Outlook luser
> claim that this is your problem, and not theirs.

Minor, but important nit: Note that Outlook Express is not the same as
"Outlook". While it is quite possible, and even likely, that "Outlook"
(i.e. any Outlook version *other* than "Express") is also broken, it
isn't realistic to expect consistency from Microsoft, now is it? :-)

[deleted]

Tristan Miller

unread,
Mar 23, 2006, 1:00:43 PM3/23/06
to
Greetings.

In article <4422ba35$0$8303$dbd4...@news.wanadoo.nl>, Frank Slootweg
wrote:


>> I tend to sign my outgoing mail via OpenPGP/MIME, resulting in messages
>> with a Content-Type of
>> multipart/signed(text/plain,application/pgp-signature). I've had
>> reports from users of Microsoft Outlook Express that such messages are
>> displayed as a blank e-mail with both the text/plain and
>> application/pgp-signature parts shown as attachments.
>

> Probably stupid suggestion: You can't persuade the recipients, to just
> open the .txt attachment?

Oh, they're not afraid to open the text attachment. They're just confused
that they have to do so in order to read my e-mail. Another disadvantage
is that inline URLs are not hyperlinked, so people get annoyed that they
have to copy the URL and paste it in their web browser rather than simply
click on it as they do in non-signed e-mails.

Jem Berkes

unread,
Mar 23, 2006, 1:36:29 PM3/23/06
to
> I tend to sign my outgoing mail via OpenPGP/MIME, resulting in
> messages with a Content-Type of
> multipart/signed(text/plain,application/pgp-signature). I've had
> reports from users of Microsoft Outlook Express that such messages are
> displayed as a blank e-mail with both the text/plain and
> application/pgp-signature parts shown as attachments.

Do you know what software the Outlook people are using for the PGP plugin?
Straying off topic, but the reason I ask is that I'm trying to convince
friends to use PGP or GnuPG and they are asking me what free software will
allow them to easily do PGP within Outlook.

--
Jem Berkes
Software design for Windows and Linux/Unix-like systems
http://www.sysdesign.ca/

Peter Peters

unread,
Mar 24, 2006, 3:16:27 AM3/24/06
to
On Thu, 23 Mar 2006 18:00:43 +0000, Tristan Miller
<psych...@nothingisreal.com> wrote:

>Oh, they're not afraid to open the text attachment. They're just confused
>that they have to do so in order to read my e-mail. Another disadvantage
>is that inline URLs are not hyperlinked, so people get annoyed that they
>have to copy the URL and paste it in their web browser rather than simply
>click on it as they do in non-signed e-mails.

Tell them it is a security measure to prevent accidental klicking on
suspect URL's.

--
Peter Peters, senior netwerkbeheerder
Dienst Informatietechnologie, Bibliotheek en Educatie (ITBE)
Universiteit Twente, Postbus 217, 7500 AE Enschede
telefoon: 053 - 489 2301, fax: 053 - 489 2383, http://www.utwente.nl/itbe

Matt Westfall

unread,
Apr 21, 2006, 9:19:11 AM4/21/06
to
-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA1

stop using PGP/MIME use Inline Signature / Encryption

Then they will only be annoyed by the top two lines of your message
saying it's signed.
Matt Westfall
Owner / Operator
FiftyPounds Internet
http://www.fiftypounds.com

This message is digitally signed with Pretty Good Privacy (PGP)
Info: http://en.wikipedia.org/wiki/Pretty_Good_Privacy

Tristan Miller wrote:
> Greetings.
>
> I tend to sign my outgoing mail via OpenPGP/MIME, resulting in messages
> with a Content-Type of
> multipart/signed(text/plain,application/pgp-signature). I've had reports
> from users of Microsoft Outlook Express that such messages are displayed
> as a blank e-mail with both the text/plain and application/pgp-signature
> parts shown as attachments.
>
> My questions are as follows, then:
>
> 1) Is there some patch or simple plugin which fixes this issue to which I
> can refer these people? (Some of them refuse or are unable to switch to a
> different e-mail program such as Thunderbird.)
>
> 2) Is there anything I can do to make my signed mails friendlier to Outlook
> Express? I have seen a report (see
> <nntp://news.gmane.org/gmane.mail.mutt.user/20060226111...@leela.local.dossen.dk>
> or <http://comments.gmane.org/gmane.mail.mutt.user/23765>) that sending
> messages as
> multipart/signed(multipart/mixed(text/plain,text/plain),application/pgp-signature)
> might work. However, I don't think this option will work for me, since
> AFAIK my mail client (KMail) doesn't allow one to filter outgoing mail
> before it is signed.
>
> Regards,
> Tristan
>

-----BEGIN PGP SIGNATURE-----
Version: GnuPG v1.4.3 (MingW32)

iD8DBQFESNvPb/8X6V5MpAURAn26AKC0qHj3HbjChmcDNaBqhSY0c+HCEQCfTB37
cRUF7CSt/EXtaMk0qGCVHp0=
=LRwA
-----END PGP SIGNATURE-----

Matt Westfall

unread,
Apr 21, 2006, 9:41:32 AM4/21/06
to
-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA1

The G-DATA Plugin is supposed to accomplish it,

It doesn't work for me, all it did was add a toolbar button to open GPA,
lol.


Matt Westfall
Owner / Operator
FiftyPounds Internet
http://www.fiftypounds.com

This message is digitally signed with Pretty Good Privacy (PGP)
Info: http://en.wikipedia.org/wiki/Pretty_Good_Privacy

Jem Berkes wrote:
>> I tend to sign my outgoing mail via OpenPGP/MIME, resulting in
>> messages with a Content-Type of
>> multipart/signed(text/plain,application/pgp-signature). I've had
>> reports from users of Microsoft Outlook Express that such messages are
>> displayed as a blank e-mail with both the text/plain and
>> application/pgp-signature parts shown as attachments.
>
> Do you know what software the Outlook people are using for the PGP plugin?
> Straying off topic, but the reason I ask is that I'm trying to convince
> friends to use PGP or GnuPG and they are asking me what free software will
> allow them to easily do PGP within Outlook.
>

-----BEGIN PGP SIGNATURE-----
Version: GnuPG v1.4.3 (MingW32)

iD8DBQFESOEMb/8X6V5MpAURAi9BAJwIyzjDS0hP9W3N0CHG7HCEY4/DEgCeJpIK
vQxedmkOwhYfRSQrvq2lDMI=
=NXYw
-----END PGP SIGNATURE-----

David F. Skoll

unread,
Apr 21, 2006, 9:28:46 PM4/21/06
to
Matt Westfall wrote:

> stop using PGP/MIME use Inline Signature / Encryption

Why? Why should people accomodate those who use
broken software?

--
David.

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