That did it. I had originally set up the domain as internal. Eventually I
moved the Global settings to match in an attempt at troubleshooting. I
moved them both to external and the mail is now signed.

Outlook is showing "This message has been tampered with" which is an issue
I had when attempting to write a solution in Python, though I don't know
that this is a ciphermail issue.

Thanks for the assistance Martijn

On Thu, Jan 11, 2018 at 9:38 PM, Martijn Brinkers <mart...@ciphermail.com>
wrote:

> On 11-01-18 22:25, Craig Andrews wrote:
> >
> > Hi Martijn,
> >
> > I just sent this test email via the ciphermail web ui
> >
> > 11 Jan 2018 21:18:08 | INFO incoming; MailID:
> > acef2600-f6e3-4758-9d6e-b5c4e642c077; Recipients: [us...@domain.tld];
> > Originator: us...@domain.tld; Sender: <>; Remote address: 127.0.0.1;
> > Subject: test mail [sign]; Message-ID:
> > <477865062.0.1515705488493.javamail.tomc...@ciphermail.internal.tld>;
> > (mitm.application.djigzo.james.mailets.Log) [Spool Thread #0]
> > 11 Jan 2018 21:18:09 | INFO Subject filter is disabled for the sender;
> > MailID: acef2600-f6e3-4758-9d6e-b5c4e642c077; Recipients:
> > [us...@domain.tld] (mitm.application.djigzo.james.mailets.Default)
> > [Spool Thread #0]
> > 11 Jan 2018 21:18:09 | INFO To internal recipient(s); MailID:
> > acef2600-f6e3-4758-9d6e-b5c4e642c077; Recipients: [us...@domain.tld]
> > (mitm.application.djigzo.james.mailets.Default) [Spool Thread #0]
> > 11 Jan 2018 21:18:09 | INFO Message handling is finished. Sending to
> > final recipient(s); MailID: acef2600-f6e3-4758-9d6e-b5c4e642c077;
> > Recipients: [us...@domain.tld]; Originator: us...@domain.tld; Sender:
> > <>; Remote address: 127.0.0.1; Subject: test mail [sign]; Message-ID:
> > <477865062.0.1515705488493.javamail.tomc...@ciphermail.internal.tld>;
> > (mitm.application.djigzo.james.mailets.Log) [Spool Thread #0]
>
> The recipient is considered to be an internal user. Email sent to
> internal users follow the decryption pipeline and email sent to external
> recipient follow the encryption pipeline. You either configured the
> global settings, a domain or a user as being in internal users. This is
> normal for the domain you receive email for because those emails in
> typical setups need to be decrypted. All other user, the email addresses
> for which you want to sign and/or encrypt need to be external. So, you
> either sent a message to a valid internal recipient or you accidentally
> mis-configured the Locality of the global settings/domain or user.
>
> Kind regards,
>
> Martijn Brinkers
>
>
> > On Thu, Jan 11, 2018 at 6:15 PM, Martijn Brinkers via Users
> > <users@lists.djigzo.com <mailto:users@lists.djigzo.com>> wrote:
> >
> >     On 11-01-18 19:09, Craig Andrews via Users wrote:
> >     > Hello,
> >     > I have two test users, both with valid root, intermediate, and
> >     personal
> >     > certs with the correct usage entitlements. Both certificates have a
> >     > white, valid background,
> >     >
> >     > For the two users, I have their S/MIME certificates selected in
> their
> >     > profile for signing and encryption (though I'm only trying to get
> >     > signing to work at the moment). I have both forced signing via
> header
> >     > "X-Sign" and subject signing via the example in the documentation (
> >     > (?i)\[\s*sign\s*\] ). I am using this script to test both the
> subject
> >     > and header, and Thunderbird to test the subject by sending a mail
> via
> >     > ciphercrypt.
> >     >
> >     > #!/usr/bin/env python
> >     > import smtplib
> >     > from email.MIMEMultipart import MIMEMultipart
> >     > from email.MIMEText import MIMEText
> >     >
> >     >
> >     > fromaddr = "us...@domain.tld"
> >     > toaddr = "us...@domain.tld"
> >     > msg = MIMEMultipart()
> >     > msg['From'] = fromaddr
> >     > msg['To'] = toaddr
> >     > msg['Subject'] = "mail subject [sign]"
> >     > msg['X-Sign'] = ""
> >     >
> >     > body = "dummy body message"
> >     > msg.attach(MIMEText(body, 'plain'))
> >     >
> >     > server = smtplib.SMTP('ciphermail.domain.tld', 25)
> >     > server.ehlo('ciphermail.domain.tld')
> >     > text = msg.as_string()
> >     > server.sendmail(fromaddr, toaddr, text)
> >     > server.quit()
> >     >
> >     >
> >     > I receive the email in the destination inbox, however, it is never
> >     > signed. I can verify from the headers that the "X-Sign" header is
> >     > present in the email. Currently the MTA/MPA isn't giving a lot of
> >     > information to debug. I can see the mail passing through, but
> there is
> >     > no mention of an attempt for any extra processing. I was wondering
> >     what
> >     > options in logging I can turn on to help debug this issue.
> >
> >     Hi Craig,
> >
> >     Can you send the relevant lines from the MPA log? The easiest is to
> >     filter on the MailID value (which is shown as a green GUID, looking
> >     similar to MailID: 28dde42b-3de0-4d8e-bc99-e0b32c8a00b3). Every
> email
> >     gets an unique MailID value. This makes it easier to filter out the
> >     relevant lines for an email.
> >
> >     Kind regards,
> >
> >     Martijn Brinkers
> >
> >
> >     --
> >     CipherMail email encryption
> >
> >     Email encryption with support for S/MIME, OpenPGP, PDF encryption and
> >     secure webmail pull.
> >
> >     https://www.ciphermail.com
> >
> >     Twitter: http://twitter.com/CipherMail
> >
> >     _______________________________________________
> >     Users mailing list
> >     Users@lists.djigzo.com <mailto:Users@lists.djigzo.com>
> >     https://lists.djigzo.com/lists/listinfo/users
> >     <https://lists.djigzo.com/lists/listinfo/users>
> >
> >
>
>
> --
> CipherMail email encryption
>
> Email encryption with support for S/MIME, OpenPGP, PDF encryption and
> secure webmail pull.
>
> https://www.ciphermail.com
>
> Twitter: http://twitter.com/CipherMail
>
>
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