Gpg4Win 3.0.2 hangs if replying to an encrypted message in Outlook 2010
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Description

In Outlook 2010 / Windows 7, I can send and receive encrypted messages.
But replying to an encrypted message leaves the message windows open and don't send it.
The message appears in the "Drafts" folder and remains there for ever.
Resending the message from there fails, too.
I've added the gpgol.log file (names of reveiver are changed to XXXXX) of such a trial.

For insurance, I also applied "Beta/gpgol/2.0.4-beta22_x64" dlls, but same behavior.

hs created this task.Dec 12 2017, 4:35 PM
hs renamed this task from Gpg4Win 3.0.2 hangs is replying to an encrypted message in Outlook 2010 to Gpg4Win 3.0.2 hangs if replying to an encrypted message in Outlook 2010.Dec 12 2017, 4:44 PM
aheinecke triaged this task as High priority.Dec 13 2017, 10:39 AM
aheinecke added a subscriber: aheinecke.

Thanks for the report and the log.
I see the problem. In your case of a reply outlook does not give us the SMTP address for the recipient but an Exchange DN

15:22:41/7292/message.cpp:get_recipients: `/O=XXXXXX/OU=EXCHANGE ADMINISTRATIVE GROUP (FYDIBOHF23SPDLT)/CN=RECIPIENTS/CN=XXXX XXXX7F5'

This is sent to Kleopatra which fails because it can't parse the recipient.

I could somewhat reproduce this problem when I disconnected the connection to Exchange from my Outlook and then tried to respond to an exchange mail. Although for me Outlook did not Hang and an error message (with a General Error) showed up.

I have some ideas to add more fallbacks for the Exchange address to SMTP Address resolution.
Using PR_EMS_AB_PROXY_ADDRESS form the address entry: https://social.msdn.microsoft.com/Forums/office/en-US/94db4502-8888-4e88-a03f-a329540a7add/premsabproxyaddresses-not-working-in-offline-mode?forum=outlookdev

And Recipient->AddressEntry->GetExchangeUser->PrimarySmtpAddress

But both these fallbacks also failed in my offline scenario, but should work in a usual online scenario. For offline I don't have a working fallback, yet. But at least we should check for an Exchange style address and error out properly.

@hs could you please retest with 2.0.6-beta8 http://files.gpg4win.org/Beta/gpgol/ and attach the log file again.

I did a blind fix, meaning that I could not reproduce the problem but I now added some different code and fallbacks to other documented ways to look up the SMTP Address of the recipient. At least the log should now tell me more.

Hopefully it already works, but no promises ;-)

Thank you very much.

aheinecke lowered the priority of this task from High to Normal.Jan 15 2018, 8:52 AM
aheinecke added a project: Info Needed.

For the 3.0.3 I tested more with Microsoft Exchange Online, an Exchange 2012 Server and could not reproduce such problems. So I'm lowering the priority to normal as I don't think many users are affected.

Info Needed as to further debug this I would need more information or a way to reproduce it.