I am attempting to open a email that suppose to have a .doc attached with it that been encrypted by gpgmail on a Mac and I am trying to open it within a Outlook 2013 on a Windows 7 desktop. I can decypt the message and rename the file from encrypted.asc to encrypted.eml.asc and then decrypt it into a encrypted.eml format but when I open it, their no attachment even thought the body has the file name “test.doc”. Does anyone know how I can resolve this so I can open the email after decrypting and see the attachment.
Hi Mike,
in order to help you, we would need to know more about the structure of the
email that you have received. Can you post an excerpt of the “structure lines” (mail headers and mime “headers”) (make sure that you do not post any sensitive information)?
I don’t know if somebody uses gpgmail and could has test emails encrypted to one
of the public test certs of gnupg.
Best,
Bernhard
Do you need the email actual mail headers of the message details or the encrypted mail coding?
Their also just another file called PGP MIME IDENTIFICATION that just says “Version 1” in it.
Hi, if you were able to decryt something, paste the structure of this file here.
Is it a MIME body or something else?
The email itself is a apple email originally. It contained a microsoft word document within it.
Here the top part of the email itself message body:
–Apple-Mail=_8CB3199F-AB1C-435D-A023-BA24E7EE2324
Content-Type: multipart/mixed;
boundary=“Apple-Mail=_3B2888EA-8B5B-471E-8F0B-E----------”
–Apple-Mail=_3B2888EA-8B5B-471E-8F0B-E----------
Content-Transfer-Encoding: quoted-printable
Content-Type: text/plain;
charset=windows-1252
Here=92s a document, attached.
–Apple-Mail=_3B2888EA-8B5B-471E-8F0B-E----------
Content-Disposition: attachment;
filename=“test.doc”
Content-Type: application/msword;
x-mac-type=5738424E;
x-mac-creator=4D535744;
x-unix-mode=0644;
name=“test.doc”
Content-Transfer-Encoding: base64
and below that is the random encryption part of the email.
such as “0M8R4KGxGuEAAAAAAAAAAAAAAAAAAAAAPgADAP7/CQAGAAAAAAAAAAAAAAABAAAAUAAAAAAAAAAA
EAAAUgAAAAEAAAD” and so forth.
So when I got the email originally, I had a “encrypt.asc” file that I decrypted without a problem which then became a “encypt” without any extensions. If I save it as a EML or a MHT, i can read the email but not extract the attachment that suppose to be there.
Hi Mike,
good to see more information, they do not quite add up in my head yet. 
Asking from my limited understanding:
So you could save the test.doc file and open it? (as a regular doc file)
And then there was another attachment called “encrypt.asc”?
You could decrypt that file, how did it look? (If you open it up in an editor or hex-editor)
Best,
Bernhard
If I did a Windows > Windows email and encrypt the test.doc and just sent that, i could decrypt it without a problem.
The problem i had was that the Mac user encrypted a test.doc within a Mac email and sent that, the entire email and attachment is all attached within a single email and is encrypted so when I try to decrypt it, it decrypts it but I can’t read the attachments when I try to rename the email to .eml or .msg format.
As far as I know gpgtools on Mac send MIME mails by default. We are currently working on support for that in Outlook Version > 2010 but It’s not yet released as part of a stable version.
If you’d like you can help us test it by installing it from:
https://wiki.gnupg.org/GpgOL/Development/Testversions
And check if you can access the attachment with that version.
That might be it. Any other way for me to work around this issue? The Mac ujser isn’t a user that under my control as he my client’s client. My client on the window side needs to be able to somehow decrypt the email in the end if their anyway around it when he using pgptools on a mac, I need something for a windows format machine with Outlook.
Hi Mike,
if MIME really is your problem,then it means that there is a MIME structure( a body)
in the encrypted attachment.
If you do not want to wait 4 weeks until we bring out the new Gpg4win,
you could look for a small application or script that parses MIME bodies
or adds the missing email header lines so that Outlook can parse it again
for your customer.
Best Regards,
Bernhard
ps.: Flattr Gpg4win at https://flattr.com/thing/2053326,
if you appreciate this answer and my work within the Gpg4win Initiative.