PGP Encrypted mail with Gpg4win and Kopano from Outlook

[aheinecke]

Thank you very much for the confirmation. This is exactly the problem my reporter had and which I describe above.

[Sebastian]

To shed some light on this: several conversions happen. This is related to how Outlook over ActiveSync and Kopano (MAPI) work.

When you send an email via OL+KOE a mime message (RFC2822) is generated by Outlook and sent to the server (z-push) via ActiveSync.
We cannot directly send this email, because it has to pass the MAPI layer of Kopano, so this mime message is converted into a mapi message (via libvmime/im2mapi), placed in the users Outbox as MAPI message, picked up by the kopano-spooler, converted back into a mime message (again via libvmime) and then sent via SMTP.

@umgfoin could you post the mime message received by Z-Push (printed in wbxml log) when sending the mail from Outlook?
I guess that this one is still correct, but in the following two conversions break it.

[umgfoin]

@sebastian said:

@umgfoin could you post the mime message received by Z-Push (printed in wbxml log) …?

Yes, of course - I’ll post the log-info asap, but I’m off till Friday.
++umgfoin.

[umgfoin]

Hi @sebastian,
sent you a pm with link to wbxml log.
++umgfoin.

[aheinecke]

What are the next steps here?
Should we move to a ticket? I’m not sure into which category this falls.

As you support S/MIME somehow I think it might not be such a huge step to support OpenPGP in a similar way. GpgOL’s whole MIME support is based on “faking to be S/MIME” ;-)

Btw. would it help If I would ask my reporter to report this issue somehow as a customer?

[fbartels]

@aheinecke said in PGP Encrypted mail with Gpg4win and Kopano from Outlook:

Btw. would it help If I would ask my reporter to report this issue somehow as a customer?

If you want something to get a higher priority this always helps.

[GeeGee]

I hope this will be solved soon.

[fbartels]

Hi @aheinecke ,

I just remembered this thread, did your customer get in contact with our support?

[umgfoin]

Hello all / @aheinecke,

recent changes seem to have solved above problems for encryption - gpg-signatures still are broken:

Gpg4win + Outlook + Kopano OL + Z-Push + Kopano-core + Kopano-webapp produces valid output for GpgOL generated mails.

Tested 2018-06-19 15:17 CEST with :

core kc-git-master 8.6.80.1128
webapp git-master 3.4.15final.221-ga3347f1
z-push 2.4.3.beta1+6
GpgOL 2.06
KOE 3.0.305
Outlook 16.0.4639

WebApp received representation of a mail composed in Outlook with GpgOL as below:
++umgfoin

-----BEGIN PGP MESSAGE-----

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=P78E
-----END PGP MESSAGE-----

[umgfoin]

Malheureusement, the above said is valid for gpg-encryption, only.
If the mail ist gpg-signed, too or only, the mail arrives with an attachment unknown_content_type.bin containing either the pgp-signature, or the string Version: 1. Additionally, the decrypted body contains MIME-tags.

[fbartels]

@umgfoin said in PGP Encrypted mail with Gpg4win and Kopano from Outlook:

Malheureusement, the above said is valid for gpg-encryption, only.
If the mail ist gpg-signed, too or only, the mail arrives with an attachment unknown_content_type.bin …

Yes, that is what I also was able to observe.

[umgfoin]

…and now the good better news:

gpg-encryption & signature works as expected for PGP/Inline-messages with GpgOL v2.2.0, which is part of recent Gpg4win 3.1.2 .

It still fails with wrongly constructed/ parsed MIME-multipart elements (unknown_content_type.bin), unencrypted attachments etc. as soon as Content-Type: multipart/mixed MIME-structures are involved.

++umgfoin.

[rolf]

This post is deleted!

[rolf]

Hi,

how is the actual state of this point? Is it solved?

I’m wondering if this problem maybe could be a problem of gpb4win and not kopano: there is a alternative gpg plugin existing for outlook 2016 (and other versions) called gpg4o that works perfectly with outlook and kopano.

If you need further data, please let me know…

Kind regards

Rolf

[fbartels]

@rolf as you can see in the reply from @umgfoin it seems to work now (that is what I also experienced when I tried it the last time)

[rolf]

@fbartels thats unfortunately just 50%.

• It still doesnt work when sending crypted (and optionally signed) messages with attachments.
• with attachments it just works when receive
• the way to use pgp/inline is just a workaround and NOT a solution.

sorry, but the bug is still existing and prevents the usage of a lot of pgp usecases.

is there the possibility that this may be solved this year? That’ll be great :-)

Kind regards

Rolf

[fbartels]

@rolf said in PGP Encrypted mail with Gpg4win and Kopano from Outlook:

thats unfortunately just 50%.

Ah, I wasn’t aware since I just briefly tried it out myself.

@rolf said in PGP Encrypted mail with Gpg4win and Kopano from Outlook:

is there the possibility that this may be solved this year? That’ll be great :-)

PGP currently isn’t a priority for us at Kopano. If an external developer want to dive into this then patches are welcome.

[robgnu]

Hello,
I just want to ask if there are any news on this topic. I have a client who licensed a new Kopano subscription (30 Users). My client has the same problems as described above. The use of GPG/PGP encryption is a must have in this case.

I hope we can find a solution on this topic?

[fbartels]

@robgnu unfortunately our own priorities have not changed since my last reply.

[robgnu]

@fbartels Thank you for your quick reply. That are very sad news for me.

I have done some tests this morning and I can confirm, that the KOE is not affecting this problem. I created a new ActiveSync account on Outlook 2016 without KOE installed. The problems are exact the same as described above:

• Sending encrypted/signed mails does not work.
• Sending encrypted/signed mails with attachments does not work.
• Fallback to PGP/Inline works without attachments.
• Receiving all kind of E-Mails with Outlook/GpgOL works. So only outgoing mails are affected.

All my tests where on Outlook 2016/GpgOL-Extension connected via ActiveSync to Kopano. The test-receiver was an external IMAP-Account with Thunderbird/Enigmail.

My client has a subscription. So I will contact the support on Tuesday. I hope there will be a solution with a higher priority than before.

Regards, Robert.