Kleopatra: Export of multiple S/MIME certificates only exports one
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	• ebo
	Fri, Jan 9, 4:03 PM

Description

This is a regression, the export works in the VSD versions. It is already broken in 4win 4.4.1, though.

To reproduce: In Kleopatra mark several S/MIME certs and choose "Export" in the context menu.
Name the file anything.pem (or .der, makes no difference). The double click the file to import again.

It should show 2 considered and 2 unchanged, but it is "1" instead in both cases.
Opening the .pem file shows only one certificate block, as one would expect given the import information.

Here is a gpgme log of the export of 3 S/MIME certificates:

2026-01-09_gpgme_log_exportMultipleSmime.txt1 MBDownload

On the command line, the following works as expected, two certificates blocks are printed:

gpgsm --export --armor Ted Berta

Details

Version: Gpg4win-5.0.0-beta479

Revisions and Commits

rG GnuPG
	rGc7770b0a7068 gpgsm: Make multiple search patterns work with keyboxd.

Related Objects

Mentioned In: T7996: Release GnuPG 2.5.17 (security)

Event Timeline

• ebo created this task.Fri, Jan 9, 4:03 PM

• ebo created this object with edit policy "Contributor (Project)".

• ebo added a project: Bug Report.Fri, Jan 9, 4:05 PM

• ebo triaged this task as High priority.Mon, Jan 12, 11:22 AM

• ikloecker claimed this task.Mon, Jan 12, 2:00 PM

• ikloecker moved this task from Backlog to WIP on the gpd5x board.

I can reproduce the issue only (!!!) with keyboxd (on Windows).

How I could reproduce it:

Remove %APPDATA%/gnupg
Start Kleopatra
Import (a file with) three S/MIME certificates
Select the three S/MIME certificates and export them

-> result: the file contains only one certificate

How I could NOT reproduce it:

Remove %APPDATA%/gnupg
Create %APPDATA%/gnupg
Create empty text file %APPDATA%/gnupg/common.conf
Start Kleopatra
Import (a file with) three S/MIME certificates
Select the three S/MIME certificates and export them

-> result: the file contains three (!!!) certificates

Conclusion: I don't know why but this looks suspiciously like a keyboxd-related problem.

I can reproduce this on the command line:

C:\Users\g10code>"c:\Program Files\GnuPG\bin\gpgsm.exe" --export --armor 579BAF3DF16AD462457BCC0897ADBC143D76EA7B 5A2B80F98F518D50891B1F0C7C6131AD107F9938 DB625D2BBBB5A3FD985C0233249B03090E85D402
Issuer ...: /CN=CA IVBB Deutsche Telekom AG 20/OU=Bund/O=PKI-1-Verwaltung/C=DE
Serial ...: 02195D190EBE34
Subject ..: /CN=iOS Test-Smartcard iostest01.sc/OU=BSI/O=Bund/C=DE/SerialNumber=2
    aka ..: iostest01.sc@bsi.bund.de
Keygrip ..: 527CE32FD0552D18479442EF90DD5E434C036329

-----BEGIN CERTIFICATE-----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ATAOBgNVHQ8BAf8EBAMCB4AwIgYDVR0lAQH/BBgwFgYIKwYBBQUHAwIGCisGAQQB
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dmJiLnRlbGVzZWMuZGUvb2NzcHIwDQYJKoZIhvcNAQENBQADggIBAIW+PpD1FT90
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d2AL1KAF5fNWLalSdzVtGt+3L7qglpKCGKie+Gjsy5OukvpiWGbqon71ldyEYePw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-----END CERTIFICATE-----

On the other hand, if I use a single pattern which matches the three certificates then I get three certificates:

C:\Users\g10code>"c:\Program Files\GnuPG\bin\gpgsm.exe" --export --armor ios
Issuer ...: /CN=CA IVBB Deutsche Telekom AG 20/OU=Bund/O=PKI-1-Verwaltung/C=DE
Serial ...: 0187E71E612C57
Subject ..: /CN=iOS Test-Smartcard iostest01.sc/OU=BSI/O=Bund/C=DE/SerialNumber=2
    aka ..: iostest01.sc@bsi.bund.de
Keygrip ..: C5F7C42C2233DB0AA2BA0427A43087DF793ABEDC

-----BEGIN CERTIFICATE-----
MIIFYDCCA0igAwIBAgIHAYfnHmEsVzANBgkqhkiG9w0BAQ0FADBgMQswCQYDVQQG
EwJERTEZMBcGA1UEChMQUEtJLTEtVmVyd2FsdHVuZzENMAsGA1UECxMEQnVuZDEn
MCUGA1UEAxMeQ0EgSVZCQiBEZXV0c2NoZSBUZWxla29tIEFHIDIwMB4XDTIzMTEx
NTEzMTAwM1oXDTI2MTExNTIzNTk1OVowYDELMAkGA1UEBhMCREUxDTALBgNVBAoT
BEJ1bmQxDDAKBgNVBAsTA0JTSTEoMCYGA1UEAxMfaU9TIFRlc3QtU21hcnRjYXJk
IGlvc3Rlc3QwMS5zYzEKMAgGA1UEBRMBMjBaMBQGByqGSM49AgEGCSskAwMCCAEB
BwNCAARH0m56eouD0s3APY7He95Y8+XjU/FCeC+POMtbF5fxd6cSrnaLbo2jp+wv
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MiAnybBpGhWHfcG9vkKhSqRIMEYxCzAJBgNVBAYTAkRFMRkwFwYDVQQKExBQS0kt
MS1WZXJ3YWx0dW5nMRwwGgYDVQQDExNQQ0EtMS1WZXJ3YWx0dW5nLTIwggQkqy5L
MCMGA1UdEQQcMBqBGGlvc3Rlc3QwMS5zY0Bic2kuYnVuZC5kZTCB4QYDVR0fBIHZ
MIHWMIHToIHQoIHNhm9sZGFwOi8veDUwMC5idW5kLmRlL0NOPUNBIElWQkIgRGV1
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iLENDvj48hBM0BqpUqdUBU23NphBhckF8lz8BcNRsRDkJH/GGpjthk6KlfUJEwL5
ue58L64KPX/hGruEGTQXD1vRaZDaTNNYJqmZf7oFLkvAzZ691PQ2LMFYsaY7Hx/v
IrUB8/uITifmEBhUWVuMjmsS/zwqgd26F0+F00gfCVxZL5cadNRzaKqgT9z5llf1
XNM4vcWfM8KCtwWgoVlwXmUYPl12PN5MRPcsK3uTjACVU0JHSHjqteOW6WwTta0R
g2G4rajiVrEjwdlTcQ0PBM3Kb11OUqCm4q49OAteg8o+1Azj4o/gPRsO71wGqPeh
bwCJgeFVhD0cEhtQs+bbuAM6xVrryt23LzzI8EJeFK+PNOFFnP5FqvpYOfPVg6WS
clCpS6GhFzYjmKrkxuvX6BJTN/sPZ+ecH5TNNBOB7rFbgsYYCpkrN1Q9haGmOd+R
taX1VfEsKRMxKroEUYQTHoz760Me2VjvXyaDvbwtmYiKxWQJ
-----END CERTIFICATE-----

Issuer ...: /CN=CA IVBB Deutsche Telekom AG 20/OU=Bund/O=PKI-1-Verwaltung/C=DE
Serial ...: 0303E0D8806D42
Subject ..: /CN=iOS Test-Smartcard iostest01.sc/OU=BSI/O=Bund/C=DE/SerialNumber=2
    aka ..: iostest01.sc@bsi.bund.de
Keygrip ..: 59C962C9DF6BF1339D0EB56C58916B3B4A00CB4C

-----BEGIN CERTIFICATE-----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MIHWMIHToIHQoIHNhm9sZGFwOi8veDUwMC5idW5kLmRlL0NOPUNBIElWQkIgRGV1
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ELdZb+o/e+AUqCbPzDpm4W5e2eYcLjovvsz04A7shDP0cyJ0tHrnQRqAf3mIcoSa
xSuKDdRMOYPSduuw+ssCvnEbGMQ6noA6HNdxX1T36Wk2BqytsqG+rwcERxBQ+fC5
aEFENvsg7wdOiC1j+/iGLVHiArh/iO4TV2KSjIPrvLviwTY4CkCil61xFaF2WmIb
rNthtgahnuxiLmKkX3m1iL2rFdxZTqowUxlr5KDqbeuvwNsD8NiFSj9Vce5HvF0k
7PDUlJE1J0frIxUSwL6bkEoOeRiJtJb6soe62H8z5JppK4tmd8dTlaeJ5UreLtZc
KJo8PXCVMvkE/07a0JAfh2sCI4Gc6ybuX5kUWVgvW0F1wUIV7V5ixUkf/o6cNpJZ
vVg1iykxhhP+gk2FiXpHuT/XwrlYvLOICP2y+55ei15TvsD6URgkycrDtA7ufa6G
CIgGwvfU4cDruSe69YlnHMLnZF0uuvV4UZ5phetcgpu/z0wv9ZB6JMupFwnkc+sJ
kfqrPWFyDQshGWr9IhBcqsUb2zBc8oVcRLdwhAa7gmv9I+gA
-----END CERTIFICATE-----

Issuer ...: /CN=CA IVBB Deutsche Telekom AG 20/OU=Bund/O=PKI-1-Verwaltung/C=DE
Serial ...: 02195D190EBE34
Subject ..: /CN=iOS Test-Smartcard iostest01.sc/OU=BSI/O=Bund/C=DE/SerialNumber=2
    aka ..: iostest01.sc@bsi.bund.de
Keygrip ..: 527CE32FD0552D18479442EF90DD5E434C036329

-----BEGIN CERTIFICATE-----
MIIFhDCCA2ygAwIBAgIHAhldGQ6+NDANBgkqhkiG9w0BAQ0FADBgMQswCQYDVQQG
EwJERTEZMBcGA1UEChMQUEtJLTEtVmVyd2FsdHVuZzENMAsGA1UECxMEQnVuZDEn
MCUGA1UEAxMeQ0EgSVZCQiBEZXV0c2NoZSBUZWxla29tIEFHIDIwMB4XDTIzMTEx
NTEzMTAwM1oXDTI2MTExNTIzNTk1OVowYDELMAkGA1UEBhMCREUxDTALBgNVBAoT
BEJ1bmQxDDAKBgNVBAsTA0JTSTEoMCYGA1UEAxMfaU9TIFRlc3QtU21hcnRjYXJk
IGlvc3Rlc3QwMS5zYzEKMAgGA1UEBRMBMjBaMBQGByqGSM49AgEGCSskAwMCCAEB
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MS1WZXJ3YWx0dW5nMRwwGgYDVQQDExNQQ0EtMS1WZXJ3YWx0dW5nLTIwggQkqy5L
MCMGA1UdEQQcMBqBGGlvc3Rlc3QwMS5zY0Bic2kuYnVuZC5kZTCB4QYDVR0fBIHZ
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ZWxla29tJTIwQUclMjAyMCZhdHRyPWNybDAWBgNVHSAEDzANMAsGCSsGAQQBvXQB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-----END CERTIFICATE-----

In fact, this has nothing to do with export:

C:\Users\g10code>"c:\Program Files\GnuPG\bin\gpgsm.exe" -k ios
[keyboxd]
---------
           ID: 0x3D76EA7B
          S/N: 0187E71E612C57
        (dec): 430901693590615
       Issuer: /CN=CA IVBB Deutsche Telekom AG 20/OU=Bund/O=PKI-1-Verwaltung/C=DE
      Subject: /CN=iOS Test-Smartcard iostest01.sc/OU=BSI/O=Bund/C=DE/SerialNumber=2
          aka: iostest01.sc@bsi.bund.de
     validity: 2023-11-15 13:10:03 through 2026-11-15 23:59:59
     key type: brainpoolP256r1
    key usage: keyAgreement
     policies: 1.3.6.1.4.1.7924.1.1:N:
     sha1 fpr: 57:9B:AF:3D:F1:6A:D4:62:45:7B:CC:08:97:AD:BC:14:3D:76:EA:7B
     sha2 fpr: 9C:96:A8:63:79:A2:D1:97:E3:D8:08:FF:84:9A:44:17:B8:14:E0:58:52:C2:D9:5D:C1:F2:82:6E:47:F7:94:9A

           ID: 0x107F9938
          S/N: 0303E0D8806D42
        (dec): 848689169984834
       Issuer: /CN=CA IVBB Deutsche Telekom AG 20/OU=Bund/O=PKI-1-Verwaltung/C=DE
      Subject: /CN=iOS Test-Smartcard iostest01.sc/OU=BSI/O=Bund/C=DE/SerialNumber=2
          aka: iostest01.sc@bsi.bund.de
     validity: 2023-11-15 13:10:03 through 2026-11-15 23:59:59
     key type: brainpoolP256r1
    key usage: nonRepudiation
     policies: 1.3.6.1.4.1.7924.1.1:N:
     sha1 fpr: 5A:2B:80:F9:8F:51:8D:50:89:1B:1F:0C:7C:61:31:AD:10:7F:99:38
     sha2 fpr: F0:6F:CC:53:5A:D3:B6:59:5F:3D:F2:B0:7D:73:0E:D5:04:BF:5B:29:AB:7C:DC:39:F6:09:84:75:CE:F5:82:E1

           ID: 0x0E85D402
          S/N: 02195D190EBE34
        (dec): 590837596470836
       Issuer: /CN=CA IVBB Deutsche Telekom AG 20/OU=Bund/O=PKI-1-Verwaltung/C=DE
      Subject: /CN=iOS Test-Smartcard iostest01.sc/OU=BSI/O=Bund/C=DE/SerialNumber=2
          aka: iostest01.sc@bsi.bund.de
     validity: 2023-11-15 13:10:03 through 2026-11-15 23:59:59
     key type: brainpoolP256r1
    key usage: digitalSignature
ext key usage: clientAuth, ms-smartcardLogon
     policies: 1.3.6.1.4.1.7924.1.1:N:
     sha1 fpr: DB:62:5D:2B:BB:B5:A3:FD:98:5C:02:33:24:9B:03:09:0E:85:D4:02
     sha2 fpr: A3:0A:8D:5E:0D:CA:47:E5:9A:41:C2:6A:C2:C8:CA:CC:C0:56:27:47:C9:E2:F1:8A:C1:BC:7C:F1:B1:98:4E:6E


C:\Users\g10code>"c:\Program Files\GnuPG\bin\gpgsm.exe" -k 579BAF3DF16AD462457BCC0897ADBC143D76EA7B 5A2B80F98F518D50891B1F0C7C6131AD107F9938 DB625D2BBBB5A3FD985C0233249B03090E85D402
[keyboxd]
---------
           ID: 0x0E85D402
          S/N: 02195D190EBE34
        (dec): 590837596470836
       Issuer: /CN=CA IVBB Deutsche Telekom AG 20/OU=Bund/O=PKI-1-Verwaltung/C=DE
      Subject: /CN=iOS Test-Smartcard iostest01.sc/OU=BSI/O=Bund/C=DE/SerialNumber=2
          aka: iostest01.sc@bsi.bund.de
     validity: 2023-11-15 13:10:03 through 2026-11-15 23:59:59
     key type: brainpoolP256r1
    key usage: digitalSignature
ext key usage: clientAuth, ms-smartcardLogon
     policies: 1.3.6.1.4.1.7924.1.1:N:
     sha1 fpr: DB:62:5D:2B:BB:B5:A3:FD:98:5C:02:33:24:9B:03:09:0E:85:D4:02
     sha2 fpr: A3:0A:8D:5E:0D:CA:47:E5:9A:41:C2:6A:C2:C8:CA:CC:C0:56:27:47:C9:E2:F1:8A:C1:BC:7C:F1:B1:98:4E:6E

Thanks Eva and Ingo. It seems 2.5.17 is not too far away.

• werner added a commit: rGc7770b0a7068: gpgsm: Make multiple search patterns work with keyboxd..Mon, Jan 12, 4:38 PM

• werner changed the task status from Open to Testing.Mon, Jan 12, 4:51 PM

• werner moved this task from Backlog to WIP on the gnupg26 board.

works in Gpg4win 5.0.1 with GnuPG 2.5.17

Test was to mark 3 S/MIME certificates in Kleopatra and then export them. The resulting file now has the expected 3 certificate blocks

• ebo closed this task as Resolved.Tue, Jan 27, 1:54 PM

• ebo moved this task from WIP to Done on the gpd5x board.

• ebo moved this task from Done to gpd-5.0.1 on the gpd5x board.Tue, Jan 27, 1:58 PM

• ebo edited projects, added gpd5x (gpd-5.0.1); removed gpd5x.

• werner mentioned this in T7996: Release GnuPG 2.5.17 (security).Tue, Jan 27, 3:44 PM