Re: Keysigning challenge policies/procedures

2006-07-07 Thread Ingo Klöcker
Am Freitag, 7. Juli 2006 06:31 schrieb Todd Zullinger:
 What I don't see in any of the links is more information about
 sending an email challenge before signing a key.  (My apologies if
 I'm overlooking it on your page or any of the others.)

 It's been discussed here before but I've not found any scripts or
 good details that I could point my fellow LUG members toward.

Try CA-Bot (http://cabot.alioth.debian.org/). I haven't used it myself 
because I'm using a self-written script for creating challenges with 
KMail. But I've been sent a few challenges generated by CA-Bot. Last 
time I received such a message, it said (at least IIRC) that CA-Bot 
couldn't handle signed and/or encrypted replies. So using CA-Bot you 
can only check whether the person you send the challenge to can decrypt 
the challenge, but you can't check whether he also controls the signing 
key.

 Isn't 
 it a good thing to send some random data to each UID on the key
 someone wishes you to sign and require that they send back that data
 signed by the key to prove they control both the key and the email
 address in the UID?

Where control the email address is different from is the owner of the 
email address. Anybody between you and the owner of the email address 
can intercept the challenge, sign it and send it back to you. This is 
especially a problem with email addresses which don't contain the name, 
but just some random alias, nickname or whatever. [EMAIL PROTECTED] could 
be anyone's email address.

Regards,
Ingo


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Re: Keysigning challenge policies/procedures

2006-07-07 Thread Marcus Frings
* Todd Zullinger [EMAIL PROTECTED] wrote:

 What I don't see in any of the links is more information about sending
 an email challenge before signing a key.  (My apologies if I'm
 overlooking it on your page or any of the others.)

Before I used a protocol to signing keys where I sent out random strings
as challenge response but it's not worth. There is no enhanced security
and only more work for signer and signee. If you send the signed UIDs
encrypted to each mail address separately it has the same effect in
security because if the mail address bounces or the person behind the
address doesn't have the private key your signed UIDs won't become
publicly available.

 It's been discussed here before but I've not found any scripts or good
 details that I could point my fellow LUG members toward.  Isn't it a
 good thing to send some random data to each UID on the key someone
 wishes you to sign and require that they send back that data signed by
 the key to prove they control both the key and the email address in
 the UID?

There are some scripts around but don't use CA-Bot as Ingo suggested. As
he has already said it has problems with so-called sign-only-keys and it
sends out broken mails. caff, from the same author, handles these keys
much better. It can be downloaded from the third link I
mentioned. Besides it is already available in Debian and FreeBSD.

Regards,
Marcus
-- 
This elevator serves me alone. I have complete control over
this entire level. With cameras as my eyes and nodes as my
hands, I rule here, insect.
 (Shodan in System Shock)


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Re: Keysigning challenge policies/procedures

2006-07-07 Thread Todd Zullinger
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Hash: SHA1

Ingo Klöcker wrote:
 Try CA-Bot (http://cabot.alioth.debian.org/).

Thanks Ingo.

 I haven't used it myself because I'm using a self-written script for
 creating challenges with KMail.

Could you elaborate a little on the procedure you use to generate the
challenges?  I'd love to have some examples of how other folks do
things to present to my fellow LUG members.

 But I've been sent a few challenges generated by CA-Bot. Last time I
 received such a message, it said (at least IIRC) that CA-Bot
 couldn't handle signed and/or encrypted replies. So using CA-Bot you
 can only check whether the person you send the challenge to can
 decrypt the challenge, but you can't check whether he also controls
 the signing key.

That's unfortunate, since the signature is more important than the
decryption, AFAIAC.  I'll take a look and see if CA-bot can't be
useful as a starting point for some scripts of my own.

 Isn't it a good thing to send some random data to each UID on the
 key someone wishes you to sign and require that they send back that
 data signed by the key to prove they control both the key and the
 email address in the UID?
 
 Where control the email address is different from is the owner of
 the email address. Anybody between you and the owner of the email
 address can intercept the challenge, sign it and send it back to
 you.

Of course, but they can't sign it with the key I've been asked to sign
and which I verified from the key fingerprint and other owner details,
unless they are the proper owner of that key.

 This is especially a problem with email addresses which don't
 contain the name, but just some random alias, nickname or whatever.
 [EMAIL PROTECTED] could be anyone's email address.

Right.  But if we met in person and I showed you acceptable ID,
provided you with the key fingerprint and other key data, then
returned a challenge from you signed using the key matching the
fingerprint that you verified in our meeting, you know that I am in
control of the key and that I can get mail at [EMAIL PROTECTED]
Obviously, others can read mail there too and that's why I'm using GPG
to ensure that I'm the only one that will be able to decipher mail
sent to that address and generate verifiable email from that address.

Thanks,

- -- 
ToddOpenPGP - KeyID: 0xD654075A | URL: www.pobox.com/~tmz/pgp
==
You will never find time for anything.  If you want time you must make
it.
-- Charles Buxton

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Re: Keysigning challenge policies/procedures

2006-07-07 Thread Todd Zullinger
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Hash: SHA1

Marcus Frings wrote:
 * Todd Zullinger [EMAIL PROTECTED] wrote:
 
 What I don't see in any of the links is more information about
 sending an email challenge before signing a key.  (My apologies if
 I'm overlooking it on your page or any of the others.)
 
 Before I used a protocol to signing keys where I sent out random
 strings as challenge response but it's not worth. There is no
 enhanced security and only more work for signer and signee. If
 you send the signed UIDs encrypted to each mail address separately
 it has the same effect in security because if the mail address
 bounces or the person behind the address doesn't have the private
 key your signed UIDs won't become publicly available.

But that does mean that you can't get a signed key to someone if the
key you've signed doesn't have any encryption capabilities, correct?
Unless, of course, you have told the signee that they must provide you
with a key which they wish to have the signed keys encrypted to.

Have you found in practice that you don't run into many sign-only
keys that you are asked to certify?

 There are some scripts around but don't use CA-Bot as Ingo
 suggested. As he has already said it has problems with so-called
 sign-only-keys and it sends out broken mails. caff, from the same
 author, handles these keys much better. It can be downloaded from
 the third link I mentioned. Besides it is already available in
 Debian and FreeBSD.

Thanks, I'll look closer at caff.  I didn't pull down the package and
play with it yet.

- -- 
ToddOpenPGP - KeyID: 0xD654075A | URL: www.pobox.com/~tmz/pgp
==
You're not drunk if you can lie on the floor without holding on.
-- Dean Martin

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Re: Keysigning challenge policies/procedures

2006-07-07 Thread Mark Kirchner
On Friday, July 7, 2006, 11:19:47 AM, Marcus wrote:
 * Todd Zullinger [EMAIL PROTECTED] wrote:

 What I don't see in any of the links is more information about sending
 an email challenge before signing a key.  (My apologies if I'm
 overlooking it on your page or any of the others.)

 Before I used a protocol to signing keys where I sent out random strings
 as challenge response but it's not worth. There is no enhanced security
 and only more work for signer and signee. If you send the signed UIDs
 encrypted to each mail address separately it has the same effect in
 security

I don't think that's true: Decryption is (usually) handled by the
encryption subkey and there's absolutely no guarantee that this subkey
is controlled by the same person as the primary/signing key. There may
even be valid reasons to split the two roles.

Since UIDs are attached to the primary key and the primary key is the
only one that can modify UIDs (and signing a key is all about UIDs)
this system can't prove what it's supposed to prove: The link between
the UID (better: the e-mail-address in it) and the person in control
of it.

Regards,
Mark Kirchner

-- 
_
Key (0x172C073C): http://www.mark-kirchner.de/keys/key-mk.asc

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Re: Keysigning challenge policies/procedures

2006-07-07 Thread Ingo Klöcker
On Friday 07 July 2006 16:56, Todd Zullinger wrote:
 Ingo Klöcker wrote:
  I haven't used it myself because I'm using a self-written script
  for creating challenges with KMail.

 Could you elaborate a little on the procedure you use to generate the
 challenges?  I'd love to have some examples of how other folks do
 things to present to my fellow LUG members.

My script does the following:
For each key id that's given on the command line it first determines all 
UIDs which are neither revoked nor expired nor have already been signed 
by me. Then for each UID a random string is generated. I use the 
command 
  head -c 18 /dev/urandom | mimencode
for this. (mimencode is part of metamail.) This challenge and the key id 
and the UID are then inserted into a text explaining what the receiver 
of the challenge has to do. This text is then encrypted with the key 
corresponding to the key id. The encrypted text is then prepended with 
another text explaining what the encrypted text is about. Finally the 
resulting text is given to KMail together with the email address 
(==UID). Now I only have to click on the Send button in KMail to send 
the message. (I could make KMail automatically send the messages, but I 
prefer to have a last look at them before I send them in order to check 
that everything worked correctly.)

I've attached the script.

  Isn't it a good thing to send some random data to each UID on the
  key someone wishes you to sign and require that they send back
  that data signed by the key to prove they control both the key and
  the email address in the UID?
 
  Where control the email address is different from is the owner
  of the email address. Anybody between you and the owner of the
  email address can intercept the challenge, sign it and send it back
  to you.

 Of course, but they can't sign it with the key I've been asked to
 sign and which I verified from the key fingerprint and other owner
 details, unless they are the proper owner of that key.

Yes, they can if it was them who asked you to sign their key. For 
example, I could create a key with my name and your email address, go 
to a key signing party and make everybody sign the fake user id. And if 
I can intercept your mail then I can even reply to challenges. Of 
course, such an attack probably doesn't make much sense because for 
what purpose should I want to make someone believe I have an email 
address I do in fact not own (but which I can intercept).

Regards,
Ingo


send-challenge-v1.1.pl
Description: Perl program


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Re: Keysigning challenge policies/procedures

2006-07-07 Thread Ingo Klöcker
On Friday 07 July 2006 17:09, Todd Zullinger wrote:
 Marcus Frings wrote:
  * Todd Zullinger [EMAIL PROTECTED] wrote:
  What I don't see in any of the links is more information about
  sending an email challenge before signing a key.  (My apologies if
  I'm overlooking it on your page or any of the others.)
 
  Before I used a protocol to signing keys where I sent out random
  strings as challenge response but it's not worth. There is no
  enhanced security and only more work for signer and signee. If
  you send the signed UIDs encrypted to each mail address separately
  it has the same effect in security because if the mail address
  bounces or the person behind the address doesn't have the private
  key your signed UIDs won't become publicly available.

 But that does mean that you can't get a signed key to someone if the
 key you've signed doesn't have any encryption capabilities, correct?

That's obviously correct. In this case you could give the key owner a 
piece of paper with a random string and ask him to send it in a signed 
message to your email address. Then you know that he can use this key 
for signing messages. Obviously, you can't check the validity of the 
email addresses belonging to this key (unless he's got an encryption 
key you can use for checking the addresses).

But in case of a certification-only key even that won't work.

 Unless, of course, you have told the signee that they must provide
 you with a key which they wish to have the signed keys encrypted to.

 Have you found in practice that you don't run into many sign-only
 keys that you are asked to certify?

Among a few hundreds keys I've signed so far only a handful were 
sign-only or certification-only keys. I did simply sign them with a 
lower verification level.

Regards,
Ingo


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Re: Keysigning challenge policies/procedures

2006-07-07 Thread Todd Zullinger
-BEGIN PGP SIGNED MESSAGE-
Hash: SHA1

Ingo Klöcker wrote:
 On Friday 07 July 2006 17:09, Todd Zullinger wrote:
[...]
 But that does mean that you can't get a signed key to someone if
 the key you've signed doesn't have any encryption capabilities,
 correct?
 
 That's obviously correct. In this case you could give the key owner
 a piece of paper with a random string and ask him to send it in a
 signed message to your email address. Then you know that he can use
 this key for signing messages. Obviously, you can't check the
 validity of the email addresses belonging to this key (unless he's
 got an encryption key you can use for checking the addresses).

Is it really necessary to encrypt the challenge?  If the key has
encryption capabilities, I would do so, but if it was a sign only key
and I could not do so, just what sort of attacks or weaknesses are
there in sending the challenge in the clear?  I've seen David Shaw
point out that it didn't gain you much.  I'm just trying to work
through the possible scenarios so I have them clear in my mind before
trying to present this to a larger group, who may well end up with
questions on this that I'd like to have better answers for than I do
now.

 Have you found in practice that you don't run into many sign-only
 keys that you are asked to certify?
 
 Among a few hundreds keys I've signed so far only a handful were
 sign-only or certification-only keys. I did simply sign them with a
 lower verification level.

Okay.  I would have guessed that you probably wouldn't run into
terribly many keys like this, but thank you for giving some practical
experience to support this.

- -- 
ToddOpenPGP - KeyID: 0xD654075A | URL: www.pobox.com/~tmz/pgp
==
...unfortunately, we can't control the actions of everyone.
-- Bill Clinton, April 20, 1993

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Re: Keysigning challenge policies/procedures

2006-07-07 Thread David Shaw
On Fri, Jul 07, 2006 at 11:19:47AM +0200, Marcus Frings wrote:
 * Todd Zullinger [EMAIL PROTECTED] wrote:
 
  What I don't see in any of the links is more information about sending
  an email challenge before signing a key.  (My apologies if I'm
  overlooking it on your page or any of the others.)
 
 Before I used a protocol to signing keys where I sent out random strings
 as challenge response but it's not worth. There is no enhanced security
 and only more work for signer and signee. If you send the signed UIDs
 encrypted to each mail address separately it has the same effect in
 security because if the mail address bounces or the person behind the
 address doesn't have the private key your signed UIDs won't become
 publicly available.

I've been away on vacation and only picked up this thread now.  This
statement is not correct.  Back in the PGP 2.x days, this might have
been true, but with OpenPGP, there is no particular requirement that
the ability to sign and the ability to decrypt are connected.  You can
have a shared key with separate capabilities.

Sending an signed key via encrypted mail does not ensure anything
about the key owner.

David

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Re: Keysigning challenge policies/procedures

2006-07-07 Thread David Shaw
On Fri, Jul 07, 2006 at 08:39:37PM +0200, Ingo Klöcker wrote:
 On Friday 07 July 2006 17:09, Todd Zullinger wrote:
  Marcus Frings wrote:
   * Todd Zullinger [EMAIL PROTECTED] wrote:
   What I don't see in any of the links is more information about
   sending an email challenge before signing a key.  (My apologies if
   I'm overlooking it on your page or any of the others.)
  
   Before I used a protocol to signing keys where I sent out random
   strings as challenge response but it's not worth. There is no
   enhanced security and only more work for signer and signee. If
   you send the signed UIDs encrypted to each mail address separately
   it has the same effect in security because if the mail address
   bounces or the person behind the address doesn't have the private
   key your signed UIDs won't become publicly available.
 
  But that does mean that you can't get a signed key to someone if the
  key you've signed doesn't have any encryption capabilities, correct?
 
 That's obviously correct. In this case you could give the key owner a 
 piece of paper with a random string and ask him to send it in a signed 
 message to your email address. Then you know that he can use this key 
 for signing messages. Obviously, you can't check the validity of the 
 email addresses belonging to this key (unless he's got an encryption 
 key you can use for checking the addresses).

Sure you can: just send the random string to the email address.  If
the person can return the string back to you, signed, then you know
that there is access to both the signing key and the email address.

David

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Re: Keysigning challenge policies/procedures

2006-07-07 Thread David Shaw
On Fri, Jul 07, 2006 at 04:15:03PM -0400, Todd Zullinger wrote:
 Ingo Klöcker wrote:
  On Friday 07 July 2006 17:09, Todd Zullinger wrote:
 [...]
  But that does mean that you can't get a signed key to someone if
  the key you've signed doesn't have any encryption capabilities,
  correct?
  
  That's obviously correct. In this case you could give the key owner
  a piece of paper with a random string and ask him to send it in a
  signed message to your email address. Then you know that he can use
  this key for signing messages. Obviously, you can't check the
  validity of the email addresses belonging to this key (unless he's
  got an encryption key you can use for checking the addresses).
 
 Is it really necessary to encrypt the challenge?  If the key has
 encryption capabilities, I would do so, but if it was a sign only key
 and I could not do so, just what sort of attacks or weaknesses are
 there in sending the challenge in the clear?  I've seen David Shaw
 point out that it didn't gain you much.  I'm just trying to work
 through the possible scenarios so I have them clear in my mind before
 trying to present this to a larger group, who may well end up with
 questions on this that I'd like to have better answers for than I do
 now.

There is no harm (and no real benefit either) in sending the challenge
NOT in the clear.  Either way, you're proving the same thing: whether
the email address goes anywhere and whether someone who has access to
the email also has access to the key.

David

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Re: Keysigning challenge policies/procedures

2006-07-07 Thread Marcus Frings
* Ingo Klöcker [EMAIL PROTECTED] wrote:
 On Friday 07 July 2006 17:09, Todd Zullinger wrote:

 Have you found in practice that you don't run into many sign-only
 keys that you are asked to certify?

 Among a few hundreds keys I've signed so far only a handful were 
 sign-only or certification-only keys. I did simply sign them with a 
 lower verification level.

Me, too. I just give these sign-only keys a level of 2 as explained in
my policy. I have been at several (large) keysigning parties and luckily
there are not so many sign-only keys around. I don't like them very much
but that's life ...

Regards,
Marcus
-- 
Paranoia - das heißt doch nur, die Wirklichkeit
realistischer zu sehen als andere.


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Re: Keysigning challenge policies/procedures

2006-07-07 Thread David Shaw
On Fri, Jul 07, 2006 at 07:22:40PM +0200, Mark Kirchner wrote:
 On Friday, July 7, 2006, 11:19:47 AM, Marcus wrote:
  * Todd Zullinger [EMAIL PROTECTED] wrote:
 
  What I don't see in any of the links is more information about sending
  an email challenge before signing a key.  (My apologies if I'm
  overlooking it on your page or any of the others.)
 
  Before I used a protocol to signing keys where I sent out random strings
  as challenge response but it's not worth. There is no enhanced security
  and only more work for signer and signee. If you send the signed UIDs
  encrypted to each mail address separately it has the same effect in
  security
 
 I don't think that's true: Decryption is (usually) handled by the
 encryption subkey and there's absolutely no guarantee that this subkey
 is controlled by the same person as the primary/signing key. There may
 even be valid reasons to split the two roles.
 
 Since UIDs are attached to the primary key and the primary key is the
 only one that can modify UIDs (and signing a key is all about UIDs)
 this system can't prove what it's supposed to prove: The link between
 the UID (better: the e-mail-address in it) and the person in control
 of it.

This is exactly correct.  The identity (for lack of a better word)
is the primary+UID.  Since that is what you are signing when you sign
someone's key, that is what you should be verifying before you make
the signature.

David

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Re: Keysigning challenge policies/procedures

2006-07-07 Thread Todd Zullinger
-BEGIN PGP SIGNED MESSAGE-
Hash: SHA1

Hi David,

David Shaw wrote:
 I've been away on vacation and only picked up this thread now.

Hope it was relaxing.  Welcome back seems like a negative thing to
say.  ;)

 This statement is not correct.  Back in the PGP 2.x days, this might
 have been true, but with OpenPGP, there is no particular requirement
 that the ability to sign and the ability to decrypt are connected.
 You can have a shared key with separate capabilities.
 
 Sending an signed key via encrypted mail does not ensure anything
 about the key owner.

Marcus and Ingo have very been helpful in providing pretty specific
procedures that they've used (and documented) for key signing.  I've
read with interest the comments that you've made over the years as the
topic of keysigning has come up and I'd be very appreciative if you
could share a basic outline of the procedure you take or recommend.

As I alluded to at the start of this thread, I've been volunteered to
give a talk on the process and reason behind key signing at an
upcoming meeting of my local LUG.  I've been trying to find as many
different peoples policies and procedures as I can prior to my
presentation to a) refresh my memory and b) prepare for potential
questions on why one might use a particular method.

I highly respect the methods you've outlined on this list and I think
the members of my local LUG could benefit greatly from being exposed
to the policy/procedure for handling keys the come across at a key
signing party.

Thanks much for your efforts on GnuPG.  Like OpenSSH, it's one of the
applications that I use every single day and would have a hard time
living without.

- -- 
ToddOpenPGP - KeyID: 0xD654075A | URL: www.pobox.com/~tmz/pgp
==
Life is the art of drawing without an eraser.
-- John Gardner

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