It's fixed in master by T3465: --pinentry-mode loopback with --delete-secret-keys, with new confirmation interaction.
For 2.2, you can use --batch and --yes, see T4667: "gpg: deleting secret key failed: No pinentry" when in --batch mode with --pinentry=loopback.

This is caused by the encoding of file in windows. If we directly redirect the stdout to file, windows encodes the file as CRLF+UCSE LE BOM but linux encodes it as LF+UTF-8. To make the file work, I just need to run dos2unix to convert the encoding. Hope it help someone having similar issue.

There is no way for us to fix. It is a shell issue.

No longer happens when the good old ldapwrapper is used.

Still happens. There are also "BER" errors that seem random.

IIRC, I red some hints on using a powershell module to switch the output to binary. I tries to find that mode, or weel its source or scrip) but to no success. It seems to be a common problem with powershell because it is not a real shell as we are used to (where many commands have a /b switch but that switching could also be done using setmode() ).

I can reproduce the problem.

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?

No, I used the standard Windows command line

Thanks for testing. Did you try with a powershell?

Tried this on Windows 8.1 (x64) with GnuPG 2.2.1 (libgcrypt 1.8.1) and was not able to reproduce it.

I tried to replicate this but failed. Well, I am on Vista and standard cmd.exe. Can you please try your tests again on a standard cmd.exe shell?

Raising priority so that we have a chance to review this for the next 2.2 release.

Without more information, we can not act on this.

Given that 2.0 reaches EOL in 6 months and the bug has been here for ages, I won't backport it to 2.0 anymore.

No I don't recall any such problems, sorry.

@werner The backport to 2.0 didn't happen, I think. Is this still relevant. @justus Do you recall any more problems in the tests?

Indeed, the difference seems to be the --output versus the stdout to a file.

The difference is the use of the --output option versus redirecting stdout to a file. A first guess would be that setmode (O_BINARY) has not been done, but in that case the -a exports would still work.

Found the problem and fixed it. The Problem is described in the commit. Basically glib always assumed it gets UTF-8 Encoded filenames even if they were provided in system locale through double click / open with / command line / drag & drop.

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.

Talked to Werner about this. He still has concerns that this is wrong because an application should not do globbing itself and only changing this in gpg.exe is inconsistent. It also might be a security problem as most users won't use the double dash to seperate arguments from filenames.

Added this to 3.0 because I don't want to release any known crashes.

I just commited the fix I had in gpg4win 2e71bf3. I don't see how this is objectionable as it changes the behavior back to what we had before we switched to building on jessie and is a minor ifdef.

Fixed in 6f02133bb07726afa6950e5b4685e75621276e60 by backporting a fix from
gpg-error.

After testing on Windows this problem is not resolved for Windows (I agree that
it's resolved for posix).

The issue there that I see now is not that it's a race between changing the
setting and immediately reading it again but that sometimes the communication
between gpgme and gpgconf fails.

See attached file no-read.txt for some debugging on this. GPGME writes a changed
option to gpgconf but gpgconf does not read it. I've used OutputDebugString and
DbgView to have syncronized debug output over process borders.

Not 100% reproducible but on my test system it fails very often.

Fixed in 0e242278dfaa64ce31a45b72f5fa0806a3dba898.

Actually we do not need that function on Windows. It is on Unix called at
startup to get a list of files not to close. On Windows we do not need to close
the files before a CreateProcess and thus close_all_fds is a dummy anyway.

I removed calling this function under Windows. To go into 2.1.18.

On Windows we copy the new file; on Unix we link-rename it. It might be worth
to change that old code to use estream and the same method for file updates as
we use elsewhere.

D401: 931_0001-qt-Add-test-for-CryptoConfig.patch

Can you repeat this also with GPA, which uses the gpgconf for ages?

Yes, It's even more visible in GPA because according to the gpgme log GPA does a
list options right after the change. So e.g. If you check "quiet" in the gpg
options then hit apply the check box gets unselected after apply although the
config is changed. Log is similar to the ones attached. Change options is
visible but afterwards the list-options still returns the old value.

On Linux I could not reproduce it with gpa, but as I think it's a timing issue
that might be expected. Attached is a patch that adds a Qt test which exposes
the problem on Linux. I can translate that to plain C if it helps. But I think
the attached Logs are already obvious that there is an issue.

Can you repeat this also with GPA, which uses the gpgconf for ages?

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?

In general, parallel operations aren't great, but I find that such bad
performance surprising.

If you update a key, only that key's effective policy is rechecked, not all
keys. But, the effective policy of conflicting keys is always rechecked.

While testing with tofu enabled I sometimes see that some actions take very
long. (>1minute)

Like importing a key in Kleopatra where Kleopatra does an import and starts a
keylist afterwards / in parallel.

I'll try to reproduce this on the command line. Just doing a simple import on
the command line is quick.

Do you have any hint what can take so long?
Like a trigger that would cause a rechecks for cross signatures?

Fixed in 2.1.11 and 2.0.30.

On Windows especially the initial keylist is very slow, subsequent keylists are
okish (less then 10 seconds) I don't think it's as big a problem anymore.
Listing a specific key is ~100ms. And that is with a large keyring (~18mb) on a
VM with a fairly slow harddisk.

For me this would be good enough to use tofu on windows. So it can be resolved
if you do not think the performance (especially of the initial listing) can be
improved or should have been better.

PS C:\Users\aheinecke> Measure-Command -Expression { gpg --no-auto-check-trustdb
--with-colons --trust-model tofu --list-keys --with-colons > $null }
gpg: NOTE: THIS IS A DEVELOPMENT VERSION!
gpg: It is only intended for test purposes and should NOT be
gpg: used in a production environment or with production keys!
gpg: please do a --check-trustdb
gpg: public key 60041E4EC03449C4 is 39 seconds newer than the signature
gpg: public key 60041E4EC03449C4 is 39 seconds newer than the signature

Days : 0
Hours : 0
Minutes : 1
Seconds : 14
Milliseconds : 785
Ticks : 747854659
TotalDays : 0.000865572521990741
TotalHours : 0.0207737405277778
TotalMinutes : 1.24642443166667
TotalSeconds : 74.7854659
TotalMilliseconds : 74785.4659

PS C:\Users\aheinecke> Measure-Command -Expression { gpg --no-auto-check-trustdb
--with-colons --trust-model tofu --list-keys --with-colons > $null }
gpg: NOTE: THIS IS A DEVELOPMENT VERSION!
gpg: It is only intended for test purposes and should NOT be
gpg: used in a production environment or with production keys!
gpg: please do a --check-trustdb
gpg: public key 60041E4EC03449C4 is 39 seconds newer than the signature

Days : 0
Hours : 0
Minutes : 0
Seconds : 7
Milliseconds : 812
Ticks : 78128420
TotalDays : 9.0426412037037E-05
TotalHours : 0.00217023388888889
TotalMinutes : 0.130214033333333
TotalSeconds : 7.812842
TotalMilliseconds : 7812.842

PS C:\Users\aheinecke> Measure-Command -Expression { gpg --no-auto-check-trustdb
--with-colons --trust-model pgp --list-keys --with-colons > $null }
gpg: NOTE: THIS IS A DEVELOPMENT VERSION!
gpg: It is only intended for test purposes and should NOT be
gpg: used in a production environment or with production keys!
gpg: public key 60041E4EC03449C4 is 39 seconds newer than the signature

Days : 0
Hours : 0
Minutes : 0
Seconds : 1
Milliseconds : 369
Ticks : 13697177
TotalDays : 1.58532141203704E-05
TotalHours : 0.000380477138888889
TotalMinutes : 0.0228286283333333
TotalSeconds : 1.3697177
TotalMilliseconds : 1369.7177

PS C:\Users\aheinecke> gpg --version
gpg (GnuPG) 2.1.17-beta30
libgcrypt 1.7.3

Home: C:/Users/aheinecke/AppData/Roaming/gnupg
Supported algorithms:
Pubkey: RSA, ELG, DSA, ECDH, ECDSA, EDDSA
Cipher: IDEA, 3DES, CAST5, BLOWFISH, AES, AES192, AES256, TWOFISH,

CAMELLIA128, CAMELLIA192, CAMELLIA256

Hash: SHA1, RIPEMD160, SHA256, SHA384, SHA512, SHA224
Compression: Uncompressed, ZIP, ZLIB, BZIP2

Fixed in 03a65a5. The time for doing a tofu --with-tofu-info --with-colons
listing is now similar to doing a pgp listing.

Please reopen if there are still unresolved issues.

$ time gpg2 --with-tofu-info --with-colons --no-auto-check-trustdb
--no-default-keyring --keyring /usr/share/keyrings/debian-keyring.gpg
--trust-model pgp -k >/dev/null
gpg: Note: signatures using the MD5 algorithm are rejected

real 0m1.972s
user 0m1.940s
sys 0m0.028s
$ time gpg2 --with-tofu-info --with-colons --no-auto-check-trustdb
--no-default-keyring --keyring /usr/share/keyrings/debian-keyring.gpg
--trust-model tofu -k >/dev/null
gpg: Note: signatures using the MD5 algorithm are rejected

real 0m2.252s
user 0m2.172s
sys 0m0.020s

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.

1.25 has been released.