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Asked: 2026-05-12T14:47:10+00:00

I am trying to make a fake CA and sign a certificate with it

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I am trying to make a fake CA and sign a certificate with it to use with stunnel (which just seems to be calling OpenSSL routines, so you probably don’t need to know the program to help :). However, stunnel keeps rejecting my certificate saying that it isn’t signed with the right key!

This is how I’m generating my keys and certs with OpenSSL:

openssl genrsa -out ca_key.pem 1024

openssl req -config ./root2.cfg -new -sha1 -x509 -key ca_key.pem -out ca_cert.pem -subj "/CN=blah.blah.com/OU=Dev blah CA/C=CA/ST=blah/L=blah/O=Blah Software"

openssl genrsa -out MPS_key.pem 1024

openssl req -config ./MPS2.cfg -new -sha1 -key MPS_key.pem -out MPS_cert_req.pem -subj "/CN=blah.blah.com/OU=blah Certificate/C=CA/ST=blah/L=blah/O=Blah Software"

openssl x509 -req -in MPS_cert_req.pem -signkey ca_key.pem -out MPS_cert.pem -extensions MPS_ext

Then my stunnel.conf has these entries:

CAfile = ca_cert.pem
key = MPS_key.pem
cert = MPS_cert.pem

When I try and start stunnel I get the generic OpenSSL “key doesn’t match certificate” error:

2009.09.09 16:36:04 LOG3[492:172]: SSL_CTX_use_RSAPrivateKey_file: B080074: error:0B080074:x509 certificate routines:X509_check_private_key:key values mismatch

Did I do something wrong in generating my files?

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1 Answer

  1. Editorial Team

    I’ll summarize what you have setup:

    1. You have a “CA” certificate, which is self-signed.
    2. You have MPS_cert, which is self-signed.
    3. You signed MPS_cert using the CA key.

    If you read the reference for OpenSSL’s x509 command (http://openssl.org/docs/apps/x509.html) you’ll see that the -signkey parameter instructs OpenSSL to self-sign the supplied certificate with the given private key. This is not what you want.

    What you want to do is create a self-signed CA and then use that to sign your CSR and generate a valid certificate.

    openssl verify ca_cert.pem
ca_cert.pem: /CN=blah.blah.com/OU=Dev blah CA/C=CA/ST=blah/L=blah/O=Blah Software
error 18 at 0 depth lookup:self signed certificate
OK

openssl verify MPS_cert.pem
MPS_cert.pem: /CN=blah.blah.com/OU=blah Certificate/C=CA/ST=blah/L=blah/O=Blah Software
error 18 at 0 depth lookup:self signed certificate
OK

    The relevant options are -CA, -CAkey, and -set_serial

    openssl x509 -CA ca_cert.pem -CAkey ca_key.pem -set_serial 1 -req -in MPS_cert_req.pem -out MPS_cert2.pem -days 365

    This should result in a certificate which is signed by your CA, which is itself self-signed.

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