I realized that suspend/resume is not supported yet on GNU/Linux: https://anonscm.debian.org/cgit/pcsclite/PCSC.git/tree/TODO#n7
So, I can't test myself.
Here is an attempt to improve:

It looks like SCardGetStatusChange doesn't return failure after wake up.
Here, what we need is catching the event of wake up, which requires reset of the card.
I think that we can check by the dwEventState field.
I'll try on GNU/Linux environment, then ask you to try.

@werner there had to be some mix up, as the log snippet is not mine.

This seems to be the relevant part of the log:

2017-11-18 07:45:15 scdaemon[8918] DBG: ccid-driver: CCID: card inactive/removed
2017-11-18 07:45:15 scdaemon[8918] ccid open error: skip
2017-11-18 07:45:15 scdaemon[8918] pcsc_establish_context failed: no service (0x8010001d)
2017-11-18 07:45:15 scdaemon[8918] DBG: ccid-driver: CCID: interrupt callback 0
2017-11-18 07:45:15 scdaemon[8918] DBG: ccid-driver: CCID: card removed

Tested with Gpg4win-3.0.0-beta17 with GpgOL-2.0.2-beta8 on Windows 10 (64bit) with Outlook 2016.

Jochen could you please test this on one of our test VM's again and resolve this then?

I am closing this bug report, as I can't get feedback to fix something.

gniibe: Can you check the status?

Please try this patch:

GpgEX is now also compiled with ASLR + DEP. I still have to check some other binaries of Gpg4win before I close this task but I no longer see it as blocking a 3.0 release where I wanted to have this included.

I tested with the GnuPG version 2.0.30 (GPG4WIn) as well as the current 2.1.16
Windows binaries. SCdaemon was running but was unable to get exclusive card access.
Why?
The Cisco Network Manager as well as Cisco Anyconnect VPN did both gain shared
card access (they were not told to do so!). I needed both programs to get access
to the university network.

Uninstalling both Programs and restarting did resolve the issue. To find the
two offenders I used Process Explorer (Processes for all users) and used the
Find Handle or DLL functon with the search term "SCARD". All crosschecked all
Processes (except for scdaemon which sould access the card) and Services
(svchost) to be only scdaemon aswell as the services to be Windows internal.
To determine the inital issue I used
https://sourceforge.net/projects/pcsctracker/ which told me the status of my
Yubikey (as Present,InUse -> Shared Access).

As a suggestion I like to see the experimental option to change the accessmode
from exclusive to shared on the commandline (If for example the other
application cannot be uninstalled).

Which version of GnuPG are you using? Do you have scdaemon?

I've just announced a new 3.0 beta that contains the updated GpgOL

http://lists.wald.intevation.org/pipermail/gpg4win-devel/2016-November/001659.html

Please let me know if it still crashes for you with that version.

Thanks a lot. I will test as soon as you release the test build.

I've tried this again with the current development version after a very large
refactoring how we handle mails. The bug appears to be gone. I've tested 10
times to send a file with closed / open outlook and with and without encryption
active.

If I install gpg4win-2.3.3 on the same system / setup the crash is reliably
reproducible.

It's still likely that we made a reference counting error internally in code
that was changed / fixed now. And Outlook released the Mail object too early and
crashed.

Kaspersky probably had some similar error in their code.

I'll upload a new Gpg4win beta with the new gpgol next. I'll ping in this issue
once thats done so you could ideally confirm that its fixed now.

Fixed with commit df08a0c. Thanks.

That's awesome aheinecke! Honestly wasn't sure if this issue would ever get much
attention. Thanks for the effort in making Gpg4win a more secure product!

GpgOL is built with DEP and and ASLR now. Need to enable this for GpgEX and some
other parts of Gpg4win, too. So not yet fully resolved but I keep it in mind.

I run in the same issue as PRab whenever I suspend or hibernate my machine. The
machine as Broadcom BCM5880 with a smart-card reader, so I cannot unplug it.
Quickest workaround is to kill/restart scdaemon.

Is there/could there be a command that could be sent to scdaemon via the agent
so a reset could be triggered? It should be easy enough to line that up as part
of the resume scripts.

Interesting...

The Kaspersky issue is about Outlook 2007... Is that supposed bug really already
THAT old?!

This could be a nasty one. The crash occurs after the data structure of the mail
was unloaded in outlook and GpgOL already completely detached it's event
handlers from the object and frees up the memory. GpgOL is not executing any
code when the crash occurs. That outlook blames GpgOL is likely because it jumps
into an invalid memory region that was allocated for GpgOL but is no longer
valid. This shouldn't happen though as we have already successfully unregistered
all our callbacks.

So I currently think that somehow when using send from explorer outlook through
some side effect / bug does a callback into GpgOL's event handling code which
was already destroyed. I'll try to confirm that theory on monday by keeping the
event handlers around after the unload event occurred.

Also does not appear that we are the first ones with that problem:
https://forum.kaspersky.com/index.php?showtopic=225375

:-/

Thanks! :-)

Thanks for the report. I am able to reproduce the problem.

Looking into it.

To make it clear: I'm not even trying to sign or encrypt, just send a plaintext
message with attachment also in the clear.

Gpg4win 2.3.1 and 2.3.2 included 64 bit versions of gpgol.

Duplicate of T2171

You can now. Thus is not a bug but a feature request.

Note that we do not use Microsoft compilers but use gcc and in cross build
environment.

Actually we are working on a 64 bit version.

Thanks for testing 2.1 and for reporting the results.
Good to know that it works now.

I have good news : gpg 2.1 rocks !
Problem solved and here is the solution :

As Sijie said, the "smartcard compatible" pageant was loading the SIG key and
the AUTH key.

Unfortunately, under gpg 2.0.x, when you export a public key and use gpg2ssh,
the output is the ssh key for the SIG key (and not the auth).

So when using gpg-agent, it was waiting for putty to request the AUTH key and
not the SIG key (as it should !). The "smartcard enabled" pageant was sending
the SIG key so it was working with it.

Now for the good part : with gpg 2.1, we can now natively use --export-ssh-key,
and this command export the AUTH key, so in the end, it works :)

Thank you everyone for the help, and I hope it can helps other people too !

Can we close this bug please ?

Regards

For history purpose, and trying to maximize information, I have been asked to post some part of the discussion I have
on the mailing list about this problem. Here it is :

I tried older version (of gpg4win) (which, at the time, worked for people with the
same setup as myself), but I can try new version too of course.

That is helpful, because development right now is concentrating more
on Gpg4win 3 with the new GnuPG 2.1 (to become 2.2) and this is where
gpg-agent and pinentry is handled slightly differently. So making sure that
it works with the new version is better for the future.

Ok, I installed gpg4win 3.0.0 BETA 128.
The problem stay the same, no pin is asked.

In the mean time, I tried this tool : http://smartcard-auth.de/ssh-en.html
It replace the pageant.exe that ships with putty. And it works. When I
log on the server with putty, I got asked for the PIN. So I think this
is not a problem with the smartcard or with keys. It seems that it's
only that gpg-agent doesn't trigger the pinentry.

I tried witht gpg-agent on another computer (fresh install) running Windows 7 x64, and
with another smartcard, same problem : no pinentry asked.

Yes gpg-agent is started before, I can see it in the process list (and even the scdaemon process).

In fact, pageant can't be started at the same time as gpg-agent (I suppose it share the same mutex because it
says "pageant is already running" when I try to start pageant while gpg-agent is already running).

Did you start gpg-agent before putty or pageant?

and there is no w64 version of 1.4

We won't fix such things for 1.4 (Windows)

I believe I have also seen this issue (or something very similar) on my Windows
7 64bit machine. I am running gpg 2.1.11. I hope this isn't redundant, but it
seems that I need to restart scdaemon anytime I unplug/replug my yubikey or
suspend/resume my computer.

Sometimes it doesn't recover even after restarting scdaemon. In those cases, I
am able to fix it by stopping scdaemon, removing the yubikey, starting scdaemon,
and finally reinserting the yubikey.

Thank you again.

It is likely that the token itself doesn't work well after wakeup from sleep
mode. In this case, all that we can do is re-inserting the token manually.

I'm not sure how PC/SC service handles USB reset after wakeup.

Sorry to say, but mapping the error to "no reader" doesn't help. The first
reset event doesn't get handled. Later it trys to remove the reader but it's
not getting correctly resetted/reinserted again.

I've attached the debug log again

Thank you for further testing.
I think that current code doesn't handle the case when card goes inactive/reset
while reader keeps working. Current code only goes to the reset sequence for a
card again when it detects reader failure. So, although the concept is
different, I think mapping PSCS_W_CARD_RESET to SW_HOST_NO_READER (for now) will
work. Given the situation we don't yet support multiple cards, this workaround
would be OK for a while.

Nope. Neither mapping the "reset card" event to SW_HOST_CARD_INACTIVE or
SW_HOST_NO_CARD helps. It seems that somewhere in the code the return code
SW error codes are not being handled correctly and the card doesn't get
resetted.

I've attached a small log where you can see that pcsc returns the error
reason "reset card" which then gets remapped to "Card reset required" (was
general error before). I also can see that the error is getting mapped to
GPG_ERR_CARD_RESET (because of the error message "Card reset required")
leaving the daemon around with no working card and reporting general errors
again (0x100b).

Additional Info: This bug only happens when you put your computer/laptop
into sleep mode while the smartcard/reader (yubikey) is plugged in. If I
remove the reader before putting it to sleep and attaching it after getting
out of the sleep mode, the scdaemon works fine.

D338: 740_0002-scd-map-card-reset-event.patch

Maybe it's more appropriate to map the PSCS_W_CARD_RESET event to the
SW_HOST_CARD_INACTIVE error code which later gets mapped to GPG_ERR_CARD_RESET
error code.

I've attached the patch file. It would make sense to backport this mapping as
well. Right now it's not yet tested.

I found another problem with the smartcard service under windows. Putting
the system into sleep mode and waking it up again creates an 0x80100068
error code (aka PCSC_W_RESET_CARD).

I'll test if it helps to map the RESET_CARD event to the same REMOVE_CARD
event to get the card reactivated after sleep mode.

Logfile:
2015-12-21 22:16:57 scdaemon[10040] DBG: send apdu: c=00 i=CA p1=00 p2=C4
lc=-1 le=256 em=0
2015-12-21 22:16:57 scdaemon[10040] DBG: PCSC_data: 00 CA 00 C4 00
2015-12-21 22:16:57 scdaemon[10040] pcsc_transmit failed: reset card
(0x80100068)
2015-12-21 22:16:57 scdaemon[10040] apdu_send_simple(0) failed: general
error

Thank you for your testing.

Your change is pushed with my comment:
http://git.gnupg.org/cgi-bin/gitweb.cgi?p=gnupg.git;a=commit;h=d1a97585c5e73fbc7d4cf90e38f76ffc5aea305f

I'll backport this to GnuPG 2.0.

Here's the logfile with all the errors (guru debug level) vanilla 2.1.10

After some time spending fighting with the build tools of gnupg (cross compile
for windows under debian) I managed to build the installer with my patched
file.

Most important: The most common error thrown is the 0x8010001e
(E_SERVICE_STOPPED) This is the important one. The other error 0x8010001d
(E_NO_SERVICE) is only thrown in the transition from ok to stopped. So only
sometimes.

This was my process:

git clone git://git.gnupg.org/gnupg.git
cd gnupg
git checkout tags/gnupg-2.1.10
./autogen.sh
cat ../0001-scd-Fix-removal-of-unplugged-usb-readers.patch | patch -p1
sed -i -e 's/^SELFCHECK=1/SELFCHECK=0/' build-aux/speedo.mk
make -f build-aux/speedo.mk w32-installer

I've created new logfiles (vanilla 2.1.10 und patched 2.1.10) to show the
difference and confirm that it'S actually working now :-)

I'm okay with signing off the commit. I can test this for Windows 8.1 or 10,
my only problem is that I'm not able to compile gpg for windows right now. Or
are there instructions somewhere on how to achieve this?

Thank you again.

I think that Windows 8 (and later) changed the PC/SC service. The service is
only available when smartcard is there, and after the removal, it returns
PCSC_E_NO_SERVICE error. This is not expected for current code.

I'm applying your patch with my comment like above. Do you agree to put the
line in the commit log?:

   Signed-off-by: Daniel Hoffend <dh@dotlan.net>

I don't have Windows 8 machine. So, I leave this issue as testing.