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Sending enc/signed mails does not work with Exchange
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Encryption seems to work according to kleopatra's message. But when sending the
email an error occurs. An excerpt of gpgol's log file contains the following error:

52281/2908/engine-assuan.c:noclose_finalize_handler: [status:0000056C] called
52281/4744/engine.c:engine_wait: in.lock released
52281/2908/engine-assuan.c:async_worker_thread: step 1 - scanning work queue
52281/4744/engine.c:engine_wait: filter 06B0DC58 ready: Success
52281/2908/engine-assuan.c:async_worker_thread: step 2 - 0 items in queue;
waiting for 0 items:
52281/4744/ERROR/mimemaker.c:finalize_message: SaveChanges(6) failed: hr=0x80004005
58921/4744/message-events.cpp:OnWriteComplete:406: UlRelease(06B05F34) had 3
58921/4744/message-events.cpp:OnWriteComplete:407: UlRelease(00198BD4) had 3
58921/4744/message-events.cpp:OnWriteComplete: received
58921/4744/message-events.cpp:OnWriteComplete: received
58921/4744/message-events.cpp:OnSubmitComplete: received
60531/4744/ext-commands.cpp:DoCommand: commandID=61536 (0xf060)
context=SendNoteMessage hwnd=00040AEA
60531/4744/ext-commands.cpp:DoCommand: command passed on
61796/4744/olflange.cpp:~GpgolExt: cleaning up GpgolExt object;
61812/4744/user-events.cpp:OnSelectionChange: received
61812/4744/user-events.cpp:OnSelectionChange: message class: IPM.Note



Event Timeline

Are you using a local account, IMAP or an Exchange based account?

I'm using an Exchange base account.

Sorry, as stated in the README this does not work. I need to find a bit of time
to play with Exchange to figure out the right way to order the MIME headers.
There is no guarantee that I will succeed, though.

I have changed the title to keep an bug on this open.

werner renamed this task from Sending of encrypted email fails with unknown system error to Sending enc/signed mails does not work with Exchange.Aug 18 2009, 11:09 AM

Note that issue#1019 states that encryption works with XP and OL2007 - There was
no change in the mIME stuff since then.

Note that
reported a recpient not found problem with OL2007, MS Exhange 2003 and

And airflow.2010 at reports
Microsoft Exchange 2007 + Microsoft Office Outlook 2007 + PGP/GPG.
two subproblems which are different depending on if it is an external
or an exchange internal address.

For the internal address, the email sending just does not work, the button
leaves the window open.

For an external address it first seems to work but after a while there is an
error from the exchange with:
"Ihre Nachricht hat einige oder alle Empfänger nicht erreicht.

Betreff:    WG: Mailsubject
Gesendet am:      17.08.2009 18:28

Folgende(r) Empfänger kann/können nicht erreicht werden:

'externe at' am 17.08.2009 18:28
      Diese Nachricht konnte nicht gesendet werden. Versuchen Sie es

später erneut, oder wenden Sie sich an den Netzwerkadministrator. Fehler:

Escchange does not work - that is as expected. GpgOL even tells about this
during its first startup.

Hmmm. I didn't notice the hint at the first startup.

It is only shown on the very first start. FWIW:


if ( ANNOUNCE_NUMBER > opt.announce_number )
    /* Note: If you want to change the announcment, you need to
       increment the ANNOUNCE_NUMBER above.  The number assures
       that a user will see this message only once.  */
       _("Welcome to GpgOL 1.0\n"
         "GpgOL adds integrated OpenPGP and S/MIME encryption "
         "and digital signing support to Outlook 2003 and 2007.\n"
         "Although we tested this software extensively, we can't "
         "give you any guarantee that it will work as expected. "
         "The programming interface we are using has not been properly "
         "documented by Microsoft and thus the functionality of GpgOL "
         "may cease to work with an update of your Windows system.\n"
         "There are some known problems, the most severe being "
         "that sending encrypted or signed mails using an Exchange "
         "based account does not work.  Using GpgOL along with "
         "other Outlook plugins may in some cases not work."
    /* Show this warning only once.  */
    opt.announce_number = ANNOUNCE_NUMBER;
    write_options ();
bernhard raised the priority of this task from Normal to High.Sep 10 2009, 2:41 PM

Werner needs to try something to make sending MIME emails with Exchange
for the first time.
(So this problem will still be in 2.0.1rc1.)

bernhard changed Version from 2.0.0 to 2.0.1.
emanuel changed Version from 2.0.1 to 1.1.1.
emanuel added a subscriber: emanuel.

Using SMTP with GpgOL and Exchange seems to be work:

Can anybody confirm this?

werner lowered the priority of this task from High to Normal.Feb 10 2011, 1:57 PM
werner removed a project: Bug Report.
werner added a project: Feature Request.
werner added a project: Info Needed.