My openssl.cnf (I have tried `\` and `\\` and `/` directory separators): [ ca ] default_ca = testca [ testca ] dir = . certificate = $dir\\ca_certificate.pem database = $dir\\index.txt new_certs_dir = $dir\\certs private_key = $dir\\private\\ca_private_key.pem serial = $dir\\serial default_crl_days = 7 default_days = 365 default_md = sha256 policy = testca_policy x509_extensions = certificate_extensions [ testca_policy ] commonName = supplied stateOrProvinceName = optional countryName = optional emailAddress = optional organizationName = optional organizationalUnitName = optional domainComponent = optional [ certificate_extensions ] basicConstraints = CA:false [ req ] default_bits = 2048 default_keyfile = .\\private\\ca_private_key.pem default_md = sha256 prompt = yes distinguished_name = root_ca_distinguished_name x509_extensions = root_ca_extensions [ root_ca_distinguished_name ] commonName = hostname [ root_ca_extensions ] basicConstraints = CA:true keyUsage = keyCertSign, cRLSign [ client_ca_extensions ] basicConstraints = CA:false keyUsage = digitalSignature,keyEncipherment extendedKeyUsage = 1.3.6.1.5.5.7.3.2 [ server_ca_extensions ] basicConstraints = CA:false keyUsage = digitalSignature,keyEncipherment extendedKeyUsage = 1.3.6.1.5.5.7.3.1 -----Original Message----- From: openssl-users <openssl-users-bounces@xxxxxxxxxxx> On Behalf Of Michael Wojcik Sent: Saturday, August 21, 2021 1:22 PM To: openssl-users@xxxxxxxxxxx Subject: RE: Need some help signing a certificate request > From: openssl-users <openssl-users-bounces@xxxxxxxxxxx> On Behalf Of > rgordey@xxxxxxxxxxxxxxx > Sent: Saturday, 21 August, 2021 09:48 > Thanks for the comment. I have tried both `/` and `\` with no change. Most or all Windows APIs, and most programs, support the forward slash as a directory separator. The exceptions are mostly the cmd.exe built-ins. > On Sat, Aug 21, 2021 at 09:21 <mailto:rgordey@xxxxxxxxxxxxxxx> wrote > When I type ‘openssl ca -config .\openssl.cnf -in ../server/req.pem > -out We need to see the contents of openssl.cnf. It might also help to have the CSR (req.pem). Since a CSR doesn't contain the private key (the CA should never see the private key), this is safe to share. -- Michael Wojcik