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Thread: WLM handling of S/MIME when one party doesn't have a Digital ID

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WLM handling of S/MIME when one party doesn't have a Digital ID
Aaron Marks 02.07.2007 19:50:07
I have been puzzled for the last few releases of Outlook Express, Windows
Mail, and now Windows Live Mail Beta as to why a Digital ID is required by
default to reply to a message that was originally sent with a Digital ID.

I'm an IT Consultant and I send out most of my emails with my S/MIME
signature because many of my clients like to be able to send encrypted
messages back to me containing sensitive information (financial, passwords,
etc.). I think that this is a typical reason why people use S/MIME, but
obviously most people do not have a S/MIME certificate (Digital ID).

There is a KB article somewhere that states the workaround for this problem
in OE 6, and it is basically that after hitting send and receiving the
message, "To send a signed or encrypted message you must first obtain a
digital ID for this account.", you then need to press cancel and then
de-select the "Sign" button.

This seems incredibly foolish to me, because most users are not computer
savy and will never think to look up a KB article or to press cancel when
their intention is to SEND a message. In my experience, users always give up
at this point and will just compose a new email message.

It would make MUCH MORE SENSE for the deafult behavior to be:

1. User receives a message that has a digital signature
2. Reply button is pressed
3. WLM checks to see if the user's account has a S/MIME certificate
3a. If user's account has a S/MIME certificate then auto-sign the reply
3b. If user's account DOES NOT have a certificate then DO NOT auto-sign
the reply.

This would make the process seamless to most people who have no idea what
S/MIME is or why they would ever want to encrypt an email message. This is
actually the way that Outlook has handled S/MIME certificates for as long as
I can remember, and it would only make sense for Microsoft's other email
platform to behave the same.

Please let me know if/when this will be implemented, and if not... why?

Thank you,

Aaron Marks
Re: WLM handling of S/MIME when one party doesn't have a Digital ID
"Roland Bierlein" <robier[ at ]gmx.de> 02.07.2007 20:45:16
"Aaron Marks" <Aaron Marks[ at ]discussions.microsoft.com> schrieb:

[reply to a digitally signed email]
[Quoted Text]
> It would make MUCH MORE SENSE for the deafult behavior to be:
>
> 1. User receives a message that has a digital signature
> 2. Reply button is pressed
> 3. WLM checks to see if the user's account has a S/MIME certificate
> 3a. If user's account has a S/MIME certificate then auto-sign the reply
> 3b. If user's account DOES NOT have a certificate then DO NOT auto-sign
> the reply.

Thanks for bringing this issue to my attention, Aaron! I have filed a
suggestion for it in the beta program!

Saludos
Roland
--
Please reply to the newsgroup to give others a chance
to help, or to learn from your experience. Thank you!

Re: WLM handling of S/MIME when one party doesn't have a Digital ID
"gardenerstouch" <gardenerstouch[ at ]g*No_Spam_Please*mail.com> 03.07.2007 04:00:38
By the way, this is feature is NOT something I can ever get used to, as I
am just way too clumsy for it not to drive me to total distraction
(insanity).
--
LuDean Marvin, M.Sc.
Adjunct Professor of Botany
Division of Math, Engineering, Science & Health
Olympic College
Bremerton, Washington
-------
"Speech-recognition in use. It makes mistakes, I correct some."
-------

"Roland Bierlein" <robier[ at ]gmx.de> wrote in message
news:9A97FE13-D50B-4EAE-AE9F-42C7921D3DF7[ at ]microsoft.com...
[Quoted Text]
> "Aaron Marks" <Aaron Marks[ at ]discussions.microsoft.com> schrieb:
>
> [reply to a digitally signed email]
>> It would make MUCH MORE SENSE for the deafult behavior to be:
>>
>> 1. User receives a message that has a digital signature
>> 2. Reply button is pressed
>> 3. WLM checks to see if the user's account has a S/MIME certificate
>> 3a. If user's account has a S/MIME certificate then auto-sign the reply
>> 3b. If user's account DOES NOT have a certificate then DO NOT auto-sign
>> the reply.
>
> Thanks for bringing this issue to my attention, Aaron! I have filed a
> suggestion for it in the beta program!
>
> Saludos
> Roland
> --
> Please reply to the newsgroup to give others a chance
> to help, or to learn from your experience. Thank you!

Re: WLM handling of S/MIME when one party doesn't have a Digital ID
"Roland Bierlein" <robier[ at ]gmx.de> 03.07.2007 11:06:57
Buenas tardes: *gardenerstouch* escribió:

[reply to a signed message with a signed message by default]
[Quoted Text]
> By the way, this is feature is NOT something I can ever get used to, as I
> am just way too clumsy for it not to drive me to total distraction
> (insanity).

Too bad you aren't a member of the beta and can vote on it! ;-)

Saludos
Roland
--
Probleme mit OE? Hier gibt es die Lösungen: <http://oe-faq.de>!

"Was Du nicht willst, daß man Dir tu',
das füg' auch keinem andern zu!" (Sprichwort nach Tob 4,15 bzw. Mat 7,12)
Re: WLM handling of S/MIME when one party doesn't have a Digital I
Aaron Marks 12.07.2007 08:44:07
Roland, do you think that my suggestion will make it in by the final build?
Or... maybe even by one of the next betas?

This is a serious problem that stops many users from being able to accept
email with S/MIME. Since Outlook Express and Windows Mail are the default
mail apps in Windows, millions of people use them. I find that many people I
email just can't figure out how to reply to my signed messages.

Are there any plans to add Windows Live Mail to the Microsoft Updates for
Vista and XP as a Recommended Update that would replace either Windows Mail
or Outlook Express (depending on if the user had XP or Vista)?

Thanks!

"Roland Bierlein" wrote:

[Quoted Text]
> Buenas tardes: *gardenerstouch* escribió:
>
> [reply to a signed message with a signed message by default]
> > By the way, this is feature is NOT something I can ever get used to, as I
> > am just way too clumsy for it not to drive me to total distraction
> > (insanity).
>
> Too bad you aren't a member of the beta and can vote on it! ;-)
>
> Saludos
> Roland
> --
> Probleme mit OE? Hier gibt es die Lösungen: <http://oe-faq.de>!
>
> "Was Du nicht willst, daß man Dir tu',
> das füg' auch keinem andern zu!" (Sprichwort nach Tob 4,15 bzw. Mat 7,12)
>
Re: WLM handling of S/MIME when one party doesn't have a Digital I
"Roland Bierlein" <robier[ at ]gmx.de> 12.07.2007 12:12:10
"Aaron Marks" <AaronMarks[ at ]discussions.microsoft.com> schrieb:

[Quoted Text]
> Roland, do you think that my suggestion will make it in by the final
> build?
> Or... maybe even by one of the next betas?

I really can't say, Aaron, sorry. Have not received any response from MSFT
on this issue.

> This is a serious problem that stops many users from being able to accept
> email with S/MIME.

Well, I started using them again by default for all my email. People seem to
manage replying to me so far. The greatest problem for spreading digital
IDs, in my opinion, is the need to get one for yourself in the first place.
That seems to be too much for many users.

> Are there any plans to add Windows Live Mail to the Microsoft Updates for
> Vista and XP as a Recommended Update that would replace either Windows
> Mail
> or Outlook Express (depending on if the user had XP or Vista)?

Have nothing heard of that, either. Since updates for Windows Live Mail
Desktop Beta were supposed to appear through Microsoft Update I'd certainly
expect updates for Windows Live Mail to appear there, too. But whether WLM
itself is going to appear there for an initial install, I have no clue.

Saludos
Roland
--
Please reply to the newsgroup to give others a chance
to help, or to learn from your experience. Thank you!

Re: WLM handling of S/MIME when one party doesn't have a Digital I
Aaron Marks 12.07.2007 23:54:03
I would definitely agree with you. I also think that it is too much to ask
of most users to acquire a Digital ID, but I also think that most people who
would actually require something like this, likely have a competent IT
consultant or staff that can help them with something like this.

I'm saying though that the biggest problem is sending Signed emails out to
people who have no idea what a digital ID is. There are plenty of people who
are using Outlook Express and just simply think that is THE PROGRAM that you
use to check email. So most people think that I'm doing something wrong when
I send them an email and they can't reply back if they are using Outlook
Express.

I can understand their logic... most people think that email is incredibly
simple and they also assume that it is secure.

I'm saying though that the current problem with Windows Mail though and OE
is that it confuses this people and by confusing normal computer users, you
will always inhibit the adoption of any technology. (especially considering
that OE is probably the most widely used email client)

"Roland Bierlein" wrote:

[Quoted Text]
> "Aaron Marks" <AaronMarks[ at ]discussions.microsoft.com> schrieb:
>
> > Roland, do you think that my suggestion will make it in by the final
> > build?
> > Or... maybe even by one of the next betas?
>
> I really can't say, Aaron, sorry. Have not received any response from MSFT
> on this issue.
>
> > This is a serious problem that stops many users from being able to accept
> > email with S/MIME.
>
> Well, I started using them again by default for all my email. People seem to
> manage replying to me so far. The greatest problem for spreading digital
> IDs, in my opinion, is the need to get one for yourself in the first place.
> That seems to be too much for many users.
>
> > Are there any plans to add Windows Live Mail to the Microsoft Updates for
> > Vista and XP as a Recommended Update that would replace either Windows
> > Mail
> > or Outlook Express (depending on if the user had XP or Vista)?
>
> Have nothing heard of that, either. Since updates for Windows Live Mail
> Desktop Beta were supposed to appear through Microsoft Update I'd certainly
> expect updates for Windows Live Mail to appear there, too. But whether WLM
> itself is going to appear there for an initial install, I have no clue.
>
> Saludos
> Roland
> --
> Please reply to the newsgroup to give others a chance
> to help, or to learn from your experience. Thank you!
>

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