GnuPG to create CSR

Ali Hassan Hamed Al Ajmi (eChannels) AliAjmi at
Tue Jan 31 13:05:45 CET 2017


Thanks for your response,

I have successfully created the CSR and send it to internal CA (Microsoft CA) team. They sent me the certificate. I have used Kleopatra UI to import the created certificate after save it in a file (attaching sample file). Using same Kleopatra UI, I have also imported root & intermediate certificates for the CA. looks like attached img(kleopatra.png):
We I tried to encrypt or sign any file, it shows this error (attached error.png)

Is there anything wrong I have done?
Or it is just because Kleopatra does not support X.509 certificate created by Microsoft CA?

-----Original Message-----
From: Daniel Kahn Gillmor [mailto:dkg at]
Sent: Saturday, January 14, 2017 1:41 AM
To: Ali Hassan Hamed Al Ajmi (eChannels) <AliAjmi at>; gnupg-users at
Subject: Re: GnuPG to create CSR

On Thu 2017-01-12 06:14:06 -0500, Ali Hassan Hamed Al Ajmi (eChannels) wrote:
> Hi,
> We are using GPG4win as files encryption tool which utilize "GnuPG"
> crypto engine. One of our requirements is to have certificate signed
> by our internal CA. since we have Microsoft CA, we need to create
> certification request that is compatible with Microsoft CA . Via
> gpg4win GUI, we are able to generate a X.509 keys CR (p10) that does
> not seem compatible with Microsoft CA.

When you say "does not seem compatible with Microsoft CA", i don't know what that means.  Is there a specific Microsoft CA product that you're using?  can you provide pointers to it?

can you provide error messages, warnings, or behaviors that indicate that the CSR you generated is incompatible?  What specific steps did you take with the Gpg4win gui to generate the CSR?

> Does "GnuPG" support creating CR (CSR) that is compatible with Microsoft CA (from command line/ other tools with GUI)?
> If Yes, how to generate a certification request that is compatible with Microsoft CA (CSR)?
> Can you please guide us to a manual /documentation where we will find such information.

If you want to use a command-line part of the GnuPG suite to create an
X.509 CSR, the tool "gpgsm" should be capable of doing it.


   gpgsm --gen-key

and follow the prompts.

If it asks you "Create self-signed certificate? (y/N)", you want to answer "N" (no) because you want the csr instead.

For example (this is not on windows, this is on a GNU/Linux machine, but it should look similar to what you see in the windows cmd.exe shell:

0 dkg at alice:~$ gpgsm --gen-key
gpgsm (GnuPG) 2.1.17; Copyright (C) 2016 Free Software Foundation, Inc.
This is free software: you are free to change and redistribute it.
There is NO WARRANTY, to the extent permitted by law.

Please select what kind of key you want:
   (1) RSA
   (2) Existing key
   (3) Existing key from card
Your selection? 1
What keysize do you want? (2048)
Requested keysize is 2048 bits
Possible actions for a RSA key:
   (1) sign, encrypt
   (2) sign
   (3) encrypt
Your selection? 1
Enter the X.509 subject name: CN=bananas.example Enter email addresses (end with an empty line):
Enter DNS names (optional; end with an empty line):
> bananas.example
> www.bananas.example
Enter URIs (optional; end with an empty line):
Create self-signed certificate? (y/N)
These parameters are used:
    Key-Type: RSA
    Key-Length: 2048
    Key-Usage: sign, encrypt
    Name-DN: CN=bananas.example
    Name-DNS: bananas.example
    Name-DNS: www.bananas.example

Proceed with creation? (y/N) y
Now creating certificate request.  This may take a while ...
gpgsm: about to sign the CSR for key: &C6962BE32BF3CA7C3207BCECC0FC1CD3C24CC2E7
gpgsm: certificate request created
Ready.  You should now send this request to your CA.
0 dkg at alice:$

Then you'd copy/paste the stuff between the "-----BEGIN CERTIFICATE REQUEST-----" and "-----END CERTIFICATE REQUEST-----" lines (including those lines as
well) into a file that you can import into your CA.

make sense?


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