openssl x509 -x509toreq -extensions v3_req will not output version 3 even though input cert.pem is X509v3

Wed Apr 26 19:07:13 UTC 2023

On Wed, 2023-04-26 at 17:38 +0200, Jelle de Jong wrote:

> I do not see the CSR back in your suggestion.

Yes, because I thought you do not need it because you produce a
certificate before.
And where needed, for simplicity and consistency better derive it from
the certificate rather than creating it from scratch.

Concerning the problem you mentioned that openssl x509 -x509toreq (by
default) does not copy X509v3 extensions
(BTW, PKCS#10 version 1 does support X.509 v3 extensions), I added
support for this in OpenSSL 3.0, to use as follows:

openssl x509 -x509toreq -in cert.pem -signkey key.pem -copy_extensions copy

Even more straightforward would be to produce first a CSR, like this:

openssl req -new -key key.pem -out csr.pem -subj '/CN=test.example.lan' \
  -addext 'subjectAltName = DNS:test.example.lan' \
  -addext 'keyUsage = digitalSignature, keyEncipherment'

and then derive a certificate, using the extension copy feature I added
to this app as well in OpenSSL 3.0 as follows: 

openssl req -x509 -key key.pem -in csr.pem -copy_extensions copy 

Yet of course both approaches do not work for you as long as you are
stuck with OpenSSL 1.x.

> Sadly only Debian Testing is shipping openssl 3.0.8-1 and there is no 
> backports package and my other systems also did not ship with version
> 3 
> for testing. https://packages.debian.org/bullseye/openssl

I have the same issue with Debian 11 (bullseye).
Yet one can easily compile any OpenSSL version 3.x also on any recent
version of Debian.
There are nice tutorials how to do this, see for instance here.

> What I am doing is to create a working but self-signed certificate
> first 
> and then replacing it later with a certificate signed by the 
> organisation (which can take multiple weeks at this customer).
> 
> That is why I want to generate a CSR from a working certificate that
> I generated.

I understand.

> -days 3653

PKCS#10 CSRs (as opposed to CRMF CSRs) do not support a validity period
- 
this needs to be defined and set by the certificate issuer (usually, a
CA).

> -newkey rsa:2048
> 
> Is there a way without having to use the -extfile configuration file?

As I see in your below email, you meanwhile found (with the hints given
before) how to do this.

Kind regards,
 David

On Wed, 2023-04-26 at 18:45 +0200, Jelle de Jong wrote:
> On 4/26/23 12:24, Dirk-Willem van Gulik wrote:
> > On 26 Apr 2023, at 12:11, Jelle de Jong <jelledejong at powercraft.nl>
> > wrote:
> > > I am trying to generate a CSR with X509v3 from a working X509v3
> > > cert but the output generates a version 1 CSR without X509v3.
> > > 
> > > These are the steps to reproduce:
> > > 
> > > openssl req -utf8 -x509 -nodes -new -keyout key.pem -out cert.pem
> > > -days 3650 -subj '/CN=test.example.lan' -extensions v3_req -addext
> > > 'subjectAltName = DNS:test.example.lan'
> > > 
> > > openssl x509 -x509toreq -in cert.pem -signkey key.pem -out csr.pem
> > > -extensions v3_req -ext
> > > subjectAltName,keyUsage,basicConstraints,extendedKeyUsage,certific
> > > atePolicies
> > > 
> > > openssl req -in csr.pem -noout -verify
> > > 
> > > openssl req -in csr.pem -out csr.req
> > > 
> > > # show X509v3 Subject Alternative Name:
> > > openssl x509 -in cert.pem -text -noout
> > > 
> > > # does not show X509v3 Subject Alternative Name:
> > > openssl req -in csr.req -text -noout
> > > 
> > > Tried with the bollow two versions
> > > 
> > > $ openssl version
> > > OpenSSL 1.1.1n  15 Mar 2022
> > > 
> > > # openssl version
> > > OpenSSL 1.1.1k  FIPS 25 Mar 2021
> > > 
> > > Can someone, do I need a diffrent openssl x509 -x509toreq -
> > > extensions …
> > 
> > 
> > I’d expect your default openssl.cnf or something to be empty or
> > incomplete.
> > 
> > This should work:
> > 
> >         cat <<EOM > ext.cnf
> >         authorityKeyIdentifier=keyid,issuer
> >         basicConstraints=CA:FALSE
> >         keyUsage = digitalSignature, nonRepudiation,
> > keyEncipherment, dataEncipherment
> >         EOM
> > 
> >         openssl x509 -x509toreq -in cert.pem -signkey key.pem -out
> > csr.pem -extfile ./ext.cnf
> >         openssl req -in csr.req -text -noout
> > 
> > Dw.
> > 
> > 
> > % cat ext.cnf
> > authorityKeyIdentifier=keyid,issuer
> > basicConstraints=CA:FALSE
> > keyUsage = digitalSignature, nonRepudiation, keyEncipherment,
> > dataEncipherment
> > 
> > % openssl x509 -x509toreq -in cert.pem -signkey key.pem -extfile
> > ./ext.cnf | openssl req -text -noout
> > Certificate Request:
> >      Data:
> >          Version: 1 (0x0)
> >          Subject: CN = test.example.lan
> >          Subject Public Key Info:
> >              Public Key Algorithm: rsaEncryption
> >                  Public-Key: (2048 bit)
> >                  Modulus:
> > ...
> >                  Exponent: 65537 (0x10001)
> >          Attributes:
> >              Requested Extensions:
> >                  X509v3 Authority Key
> > Identifier:                      DirName:/CN=test.example.lan
> >                     
> > serial:39:87:74:CF:10:D6:65:50:B4:AF:45:3A:1D:87:98:7A:D3:B5:16:EF
> >                  X509v3 Basic Constraints:                     
> > CA:FALSE
> >                  X509v3 Key Usage:                      Digital
> > Signature, Non Repudiation, Key Encipherment, Data Encipherment
> >      Signature Algorithm: sha256WithRSAEncryption
> >      Signature Value:
> >          ac:8a:5a:14:61:2f:59:21:b3:60:02:80:a5:c5:62:19:33:22:
> > ...
> > 
> 
> Thank you Dirk-Willem for replying!
> 
> I found a workaround for -x509toreq I tried the above and it did not 
> generate the X509v3 extentions! Even after I catched the csr.pem vs 
> csr.req mistake in the example command.
> 
> If someone can get the x509toreq output the X509v3 as expected then I 
> would love to see this.
> 
> Sadly only Debian Testing is shipping openssl 3.0.8-1 and there is no 
> backports package and my other systems also did not ship with version
> 3 
> for testing. https://packages.debian.org/bullseye/openssl
> 
> I needed to be able to reuse the same private key so I used both yours
> and David example and came up with this:
> 
> openssl genrsa -out key.pem 4096
> 
> openssl req -utf8 -x509 -nodes -new -key key.pem -out cert.pem -days 
> 3653 -subj '/CN=test.example.lan' -addext 'subjectAltName = 
> DNS:test.example.lan' -addext 'keyUsage = digitalSignature,
> keyEncipherment'
> 
> openssl req -utf8 -nodes -new -key key.pem -out csr.pem -subj 
> '/CN=test.example.lan' -addext 'subjectAltName = DNS:test.example.lan'
> -addext 'keyUsage = digitalSignature, keyEncipherment'
> 
> openssl req -in csr.pem -noout -verify
> verify OK
> 
> openssl req -in csr.pem -text -noout
> Certificate Request:
>      Data:
>          Version: 1 (0x0)
>          Subject: CN = test.example.lan
>          Subject Public Key Info:
>              Public Key Algorithm: rsaEncryption
>                  RSA Public-Key: (4096 bit)
>                  Modulus:
> ...
>                  Exponent: 65537 (0x10001)
>          Attributes:
>          Requested Extensions:
>              X509v3 Subject Alternative Name:
>                  DNS:test.example.lan
>              X509v3 Key Usage:
>                  Digital Signature, Key Encipherment
>      Signature Algorithm: sha256WithRSAEncryption
> ...
> 
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