Outlook 2k + PGP 9.5 + Spampal

Hi all,
after a long time without using PGP (for this very problem), I'm trying to use it again.

The problem is that I already have Spampal (a freeware spam-filter) to act as proxy between Outlook and the mail servers and I don't know how to put PGP in the middle of it; of course removing Spampal is out of the question since I like it (otherwise I would already did it ). I considered gpg, but I never found a good automated plugin for Outlook (Gpg4Win has a plugin, but it is for Outlook 2003 and it doesn't work on 2k - at least not for me).

I'm using:
Outlook 2000 (9.0.0.6627)
Spampal 1.594
Stunnel 4.12
PGP 9.5
and I have 4 Gmail accounts plus 7 other mail accounts (circumstantial use ).

My current configuration (without PGP) is the following:
Outlook:
- all accounts have the pop3 and smtp address fields set to 127.0.0.1;
- all not-Gmail accounts have the 'Account name' field set to 'MyEmailAddresspop3address' format;
- all Gmail accounts have the 'Account name' field set to %27MyEmailAddress%40127.0.0.1">'MyEmailAddress127.0.0.1:1109' fomat;
- all the accounts have flagged on the option 'My server requires authentication' and inside its settings there is the account name/password of one of my Gmail account (since Gmail is my main e-mail provider, I'm using its SMTP server);
- all accounts have the default Outlook settings under the 'Advanced' tab.

Spampal:
- it catches all the incoming/outgoing traffic (since in Outlook I'm using 127.0.0.1 as POP3/SMTP addresses);
- it parses the 'Account name' fields to determine the real 'Account name' and the POP3 real address;
- for the not-Gmail account, it uses the above address to retreive the mail, analyze it, and pass it to Outlook;
- for the Gmail account, it try to retreive the mail from 127.0.0.1:1109 (Stunnel), analyze it, and pass it to Outlook;
- the outgoing e-mails (sent to 127.0.0.1) are redirected (after whitelisting the TO addresses) to 127.0.0.1:259 (stunnel).

Stunnel:
-it intercept the traffic to 127.0.0.1:1109 (POP3) - 127.0.0.1:259 (SMTP) and redirect it to the real Gmail's addresses. Basically it acts as SSL tunneler (Gmail require SSL communication for POP3 clients).

Now it come the PGP problem: what I want to do is to use PGP to sign(all)/encrypt(if I have the recipient's key) the outgoing e-mails and verify/decrypt the incoming e-mails; in theory I think (but I'm open to objections) it would be better to put it between Outlook and Spampal so it benefit from the filtered spam (in this case the outgoing e-mail would pass on PGP first and Spampal then, but I guess it is not a problem since Spampal simply record the recipient's e-mail address without modifying the e-mail body, so it should not break the sign/encrypt validity).

I tried to do this procedure myself, but I can't find how to cofigure Outlook and PGP (and eventually Spampal).

On the side note: PGP doesn't seems to automatically recognize the e-mail accounts and so it doesn't create the "services"; so far I disabled its mail proxy configuration since it's bloccking the whole communication.

Thanks in advance.

Di Fresco Marco
--
No virus found in this outgoing message.
Checked by AVG Free Edition.
Version: 7.1.407 / Virus Database: 268.13.0/465 - Release Date: 06/10/2006

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-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA256

Di Fresco Marco wrote:
> Hi all, after a long time without using PGP (for this very problem),
> I'm trying to use it again.
>
> The problem is that I already have Spampal (a freeware spam-filter)
> to act as proxy between Outlook and the mail servers and I don't know
> how to put PGP in the middle of it; of course removing Spampal is out
> of the question since I like it (otherwise I would already did it
> ). I considered gpg, but I never found a good automated plugin for
> Outlook (Gpg4Win has a plugin, but it is for Outlook 2003 and it
> doesn't work on 2k - at least not for me).
>
<snip>

Have a look at GPGrelay - <http://sourceforge.net/projects/gpgrelay/> -
I haven't used it but others on this list swear by it. It acts as a
filtering POP/IMAP/SMTP relay, so it should work with Spampal and Outlook.

- --
Alphax
Death to all fanatics!
Down with categorical imperative!
OpenPGP key: http://tinyurl.com/lvq4g
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-----BEGIN PGP SIGNED MESSAGE-----
Hash: RIPEMD160

In reply to Alphax's message sent 2006-10-08 00:36:

> Di Fresco Marco wrote:
&gt;
>>; Hi all, after a long time without using PGP (for this very
>> problem), I'm trying to use it again.
&gt;
>>; The problem is that I already have Spampal (a freeware spam-filter)
>>; to act as proxy between Outlook and the mail servers and I don't
>;> know how to put PGP in the middle of it; of course removing Spampal
&gt;> is out of the question since I like it (otherwise I would already
&gt;> did it ). I considered gpg, but I never found a good automated
>> plugin for Outlook (Gpg4Win has a plugin, but it is for Outlook
&gt;> 2003 and it doesn't work on 2k - at least not for me).
>
> <snip&gt;
>
&gt; Have a look at GPGrelay - <http://sourceforge.net/projects/gpgrelay/>
> - I haven't used it but others on this list swear by it. It acts as a
> filtering POP/IMAP/SMTP relay, so it should work with Spampal and
> Outlook.

GPGrelay is fantastic! I have GPGrelay sitting between external mail
servers and the local mail server with SpamBayes on its external face
just in case spammers start encrypting to addresses they scrape from pgp
keys.

MUA => *SpamBayes => local mail server => GPGrelay => ext. mail server

External POP3 <= GPGrelay <= SpamBayes <= local mail server <= MUA

*optionally used for SMTP based training

The local mail server receives from authorized senders only. The bulk of
inbound mail is retrieved via POP3 by the server for delivery to local
accounts (filtered by SpamBayes, and decrypted/verified by GPGrelay).

- --
List Moderator, PGP Encryption Help Team

Mike Daigle http://www.mikedaigle.ca
My PGP Key Send email with subject=pgpkey-request
Gossamer Spider Web of Trust http://www.gswot.org

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-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA1

Thanks to Alphax and Michael Daigle. GPGRelay is working for me (even if I was concerned at first, since it hasn't been updated since March, 31st 2005 --- I found it at SourceForge, isn't there a newer version?).

> MUA => *SpamBayes => local mail server => GPGrelay => ext. mail server
&gt;
> External POP3 <= GPGrelay <= SpamBayes <= local mail server <= MUA
>
> *optionally used for SMTP based training

I'm using the same scenario (since it matches what I wanted to do in the first place):
MUA <=> GPGRelay <=> Spampal <=> External mail server.

Di Fresco Marco
- --
No virus found in this outgoing message.
Checked by AVG Free Edition.
Version: 7.1.408 / Virus Database: 268.13.3/473 - Release Date: 12/10/2006

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Hi all,
as I said GPGRelay is working fine, except I noticed a side effect when it verifies signed e-mails.

Basically in the body of the e-mail I get the result of the verification of the signature (and it it is like I want), but the original body of the e-mail is moved to an attachment (and I would like to see in the body itself under the verification).

I checked the settings and under "Global Control&quot; - "Apparence of decrypted/verified mails"; and it is selected the option "Multipart, ASCII";; now, by what the tooltip says, this option should generate a view like I desire and the effect I actually get should belong to Forwarded, ASCII, but it isn't so.

It is not a major problem, but I would be grateful if you can help me in this issue too.

Thank in advance.

Di Fresco Marco
--
No virus found in this outgoing message.
Checked by AVG Free Edition.
Version: 7.1.408 / Virus Database: 268.13.3/473 - Release Date: 12/10/2006

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-----BEGIN PGP SIGNED MESSAGE-----
Hash: RIPEMD160

In reply to Di Fresco Marco's message sent 2006-10-13 18:55:

> as I said GPGRelay is working fine, except I noticed a side effect
&gt; when it verifies signed e-mails.
>
> Basically in the body of the e-mail I get the result of the
> verification of the signature (and it it is like I want), but the
> original body of the e-mail is moved to an attachment (and I would
>; like to see in the body itself under the verification).
>
> I checked the settings and under "Global Control&quot; - "Apparence of
> decrypted/verified mails"; and it is selected the option "Multipart,
>; ASCII";; now, by what the tooltip says, this option should generate a
> view like I desire and the effect I actually get should belong to
> Forwarded, ASCII, but it isn't so.

Actually, you've selected multi-part, which isn't really an attachment,
per se... but it *looks* the same as a message with attachment.

I don't like the clutter, so I use the headerfield option and have my
mail client label messages that were signed or encrypted according to
the GPGrelay header (for aesthetics I suppose, since my reply will be
encrypted by GPGrelay if a key is stored for the recipient regardless of
how the message arrived).

- --
List Moderator, PGP Encryption Help Team

Mike Daigle http://www.mikedaigle.ca
My PGP Key Send email with subject=pgpkey-request
Gossamer Spider Web of Trust http://www.gswot.org

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Comment: Mike Daigle Ontario, Canada www.mikedaigle.ca

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-----BEGIN PGP SIGNED MESSAGE-----
Hash: RIPEMD160

Michael Daigle wrote:

> I don't like the clutter, so I use the headerfield option and have my
> mail client label messages that were signed or encrypted according to
> the GPGrelay header

I just wondered how you accomplished the task of having the mail client
indicate that they were signed or encrypted. I take it your mail client
is Thunderbird?

- --
Jim
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