How do I send an s/mime e-mail using x509v3?

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Joakim Olesen - 19 Aug 2004 16:11 GMT

Hi

I'm about to develop an application that sends/receives e-mails encrypted
and signed using x509v3 certificates. The asymmetric encryption algorithm
will be RSA. I don't want to buy any third-party tools, but using unmanaged
COM-objects is OK.

Do you have good links on this?
What classes should I use?

I've read about using CryptoAPI via CAPICOM, is this the way to go? (
http://msdn.microsoft.com/library/default.asp?url=/library/en-us/dncapi/html/enc
ryptdecrypt2a.asp )

I'm quite new to this, so help on getting me going is appreciated!

Thanks in advance.

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Joe Kaplan \(MVP - ADSI\) - 19 Aug 2004 17:23 GMT

Mitch's stuff is always very good. Also, there is a sample here that shows
some of the S/MIME part for the actual email implementation using CDO:

http://support.microsoft.com/default.aspx?scid=kb;en-us;280391

This sample shows signing, but I think there is one for encrypted/enveloped
messages as well.

Joe K.

> Hi
>
[quoted text clipped - 7 lines]
>
> I've read about using CryptoAPI via CAPICOM, is this the way to go? (

http://msdn.microsoft.com/library/default.asp?url=/library/en-us/dncapi/html/enc
ryptdecrypt2a.asp )

> I'm quite new to this, so help on getting me going is appreciated!
>
> Thanks in advance.

Reply to this Message

Michel Gallant - 19 Aug 2004 18:43 GMT

also, check out the CAPICOM 2.0.0.3 VB sample which shows some of
the S/MIME logic:
<capicom-install-dir>\CAPICOM\samples\vb\SMIME
- Mitch

"Joe Kaplan (MVP - ADSI)" <joseph.e.kaplan@removethis.accenture.com> wrote in message news:%23XrTejghEHA.556@TK2MSFTNGP10.phx.gbl...

> Mitch's stuff is always very good. Also, there is a sample here that shows
> some of the S/MIME part for the actual email implementation using CDO:
[quoted text clipped - 24 lines]
> >
> > Thanks in advance.

Reply to this Message

Joakim Olesen - 20 Aug 2004 13:02 GMT

Thanks for your answers. I've read more on this now, and I realize the
coding will take me quite some time, so I guess buying a third party tool
with a simpler API might be a better solution. Do you know a good (not very
expensive) third party tool to send/receive encrypted/signed s/mime
messages? I've searched google and found an s/mime tool made by Chilkat wich
looks promising (It has easy-to-use methods, handles the certificates on the
local computer for me etc.), but I'd like to know what tool you can
recommend?

> Hi
>
[quoted text clipped - 7 lines]
>
> I've read about using CryptoAPI via CAPICOM, is this the way to go? (

http://msdn.microsoft.com/library/default.asp?url=/library/en-us/dncapi/html/enc
ryptdecrypt2a.asp )

> I'm quite new to this, so help on getting me going is appreciated!
>
> Thanks in advance.

Reply to this Message

Joe Kaplan \(MVP - ADSI\) - 20 Aug 2004 16:04 GMT

We've used Chilkat in production on one of our boxes. I'm not really
thrilled with their API as it doesn't really integrate with the Framework at
all (it uses its own certificate class instead of the built-in .NET for
example) and we had horrible problems with resources leaks at first, but I
think they implement IDisposable now and things are better.

The hardest part with sending encrypted mail in my opinion is locating the
correct certificates for the recipients. In our environment, this involves
a lookup to AD and some crypto API calls to determine which cert is the
encryption cert and which one is the signing cert since the .NET
X509Certificate class conveniently ignores the KeyUsages field and doesn't
have a property for this.

Hopefully you'll have a good solution for the certificates issue.

Joe K.

> Thanks for your answers. I've read more on this now, and I realize the
> coding will take me quite some time, so I guess buying a third party tool
[quoted text clipped - 17 lines]
> >
> > I've read about using CryptoAPI via CAPICOM, is this the way to go? (

http://msdn.microsoft.com/library/default.asp?url=/library/en-us/dncapi/html/enc
ryptdecrypt2a.asp )

> > I'm quite new to this, so help on getting me going is appreciated!
> >
> > Thanks in advance.

Reply to this Message

Eugene Mayevski - 21 Aug 2004 00:26 GMT

Hello!
You wrote on Fri, 20 Aug 2004 14:02:56 +0200:

JO> Thanks for your answers. I've read more on this now, and I realize the
JO> coding will take me quite some time, so I guess buying a third party
JO> tool with a simpler API might be a better solution. Do you know a good
JO> (not very expensive) third party tool to send/receive encrypted/signed
JO> s/mime messages?

You might want to check SecureBlackbox
(http://www.secureblackbox.com/description-sec-mimeblackbox.html) for this.
SecureBlackbox offers PKI support and MIME + S/MIME support (PGP/MIME to be
avaialble later).

With best regards,
Eugene Mayevski

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How do I send an s/mime e-mail using x509v3?

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