@space88man I shared a link below with an example key/cert pair from an ephemeral VM. I can provide access to that VM for testing if needed as well.

https://drive.google.com/drive/folders/1255E1iSUKaKbElwDsC8o3qsh6YTN5jrJ?usp...

Sounds like the code path that is causing the error is not being run. Is that on Debian 12? Try with the following tls.cfg:

``` [server:default] method = TLSv1.2+ verify_certificate = yes require_certificate = yes private_key = /etc/ssl/private/dsiprouter-key.pem certificate = /etc/ssl/private/dsiprouter-cert.pem ca_list = /etc/ssl/certs/ca-certificates.crt ca_path = /etc/ssl/certs

[client:default] method = TLSv1.2+ verify_certificate = yes require_certificate = yes private_key = /etc/ssl/private/dsiprouter-key.pem certificate = /etc/ssl/private/dsiprouter-cert.pem ca_list = /etc/ssl/certs/ca-certificates.crt ca_path = /etc/ssl/certs ```

Leaving a reference to an unrelated issue that has the same error message but with a totally different platfom and triggering mechanism. https://github.com/openssl/openssl/issues/18113

Not sure if this helps but the cert/key was generated with:

``` penssl req -new -newkey rsa:4096 -x509 -sha256 -days 365 -nodes -out /etc/dsiprouter/certs/dsiprouter-cert.pem -keyout /etc/dsiprouter/certs/dsiprouter-key.pem -subj "/C=US/ST=MI/L=Detroit/O=dSIPRouter/CN=ec2-3-94-130-255.compute-1.amazonaws.com" ```

The openssl.cnf is vanilla default from the openssl package, doesn't look like any extra providers or fips is enabled. /etc/ssl/openssl.cnf:

``` # # OpenSSL example configuration file. # See doc/man5/config.pod for more info. # # This is mostly being used for generation of certificate requests, # but may be used for auto loading of providers

# Note that you can include other files from the main configuration # file using the .include directive. #.include filename

# This definition stops the following lines choking if HOME isn't # defined. HOME = .

# Use this in order to automatically load providers. openssl_conf = openssl_init

# Comment out the next line to ignore configuration errors config_diagnostics = 1

# Extra OBJECT IDENTIFIER info: # oid_file = $ENV::HOME/.oid oid_section = new_oids

# To use this configuration file with the "-extfile" option of the # "openssl x509" utility, name here the section containing the # X.509v3 extensions to use: # extensions = # (Alternatively, use a configuration file that has only # X.509v3 extensions in its main [= default] section.)

[ new_oids ] # We can add new OIDs in here for use by 'ca', 'req' and 'ts'. # Add a simple OID like this: # testoid1=1.2.3.4 # Or use config file substitution like this: # testoid2=${testoid1}.5.6

# Policies used by the TSA examples. tsa_policy1 = 1.2.3.4.1 tsa_policy2 = 1.2.3.4.5.6 tsa_policy3 = 1.2.3.4.5.7

# For FIPS # Optionally include a file that is generated by the OpenSSL fipsinstall # application. This file contains configuration data required by the OpenSSL # fips provider. It contains a named section e.g. [fips_sect] which is # referenced from the [provider_sect] below. # Refer to the OpenSSL security policy for more information. # .include fipsmodule.cnf

[openssl_init] # providers = provider_sect

# List of providers to load # [provider_sect] # default = default_sect # The fips section name should match the section name inside the # included fipsmodule.cnf. # fips = fips_sect

# If no providers are activated explicitly, the default one is activated implicitly. # See man 7 OSSL_PROVIDER-default for more details. # # If you add a section explicitly activating any other provider(s), you most # probably need to explicitly activate the default provider, otherwise it # becomes unavailable in openssl. As a consequence applications depending on # OpenSSL may not work correctly which could lead to significant system # problems including inability to remotely access the system. # [default_sect] # activate = 1

#################################################################### [ ca ] default_ca = CA_default # The default ca section

#################################################################### [ CA_default ]

dir = ./demoCA # Where everything is kept certs = $dir/certs # Where the issued certs are kept crl_dir = $dir/crl # Where the issued crl are kept database = $dir/index.txt # database index file. #unique_subject = no # Set to 'no' to allow creation of # several certs with same subject. new_certs_dir = $dir/newcerts # default place for new certs.

certificate = $dir/cacert.pem # The CA certificate serial = $dir/serial # The current serial number crlnumber = $dir/crlnumber # the current crl number # must be commented out to leave a V1 CRL crl = $dir/crl.pem # The current CRL private_key = $dir/private/cakey.pem# The private key

x509_extensions = usr_cert # The extensions to add to the cert

# Comment out the following two lines for the "traditional" # (and highly broken) format. name_opt = ca_default # Subject Name options cert_opt = ca_default # Certificate field options

# Extension copying option: use with caution. # copy_extensions = copy

# Extensions to add to a CRL. Note: Netscape communicator chokes on V2 CRLs # so this is commented out by default to leave a V1 CRL. # crlnumber must also be commented out to leave a V1 CRL. # crl_extensions = crl_ext

default_days = 365 # how long to certify for default_crl_days= 30 # how long before next CRL default_md = default # use public key default MD preserve = no # keep passed DN ordering

# A few difference way of specifying how similar the request should look # For type CA, the listed attributes must be the same, and the optional # and supplied fields are just that :-) policy = policy_match

# For the CA policy [ policy_match ] countryName = match stateOrProvinceName = match organizationName = match organizationalUnitName = optional commonName = supplied emailAddress = optional

# For the 'anything' policy # At this point in time, you must list all acceptable 'object' # types. [ policy_anything ] countryName = optional stateOrProvinceName = optional localityName = optional organizationName = optional organizationalUnitName = optional commonName = supplied emailAddress = optional

#################################################################### [ req ] default_bits = 2048 default_keyfile = privkey.pem distinguished_name = req_distinguished_name attributes = req_attributes x509_extensions = v3_ca # The extensions to add to the self signed cert

# Passwords for private keys if not present they will be prompted for # input_password = secret # output_password = secret

# This sets a mask for permitted string types. There are several options. # default: PrintableString, T61String, BMPString. # pkix : PrintableString, BMPString (PKIX recommendation before 2004) # utf8only: only UTF8Strings (PKIX recommendation after 2004). # nombstr : PrintableString, T61String (no BMPStrings or UTF8Strings). # MASK:XXXX a literal mask value. # WARNING: ancient versions of Netscape crash on BMPStrings or UTF8Strings. string_mask = utf8only

# req_extensions = v3_req # The extensions to add to a certificate request

[ req_distinguished_name ] countryName = Country Name (2 letter code) countryName_default = AU countryName_min = 2 countryName_max = 2

stateOrProvinceName = State or Province Name (full name) stateOrProvinceName_default = Some-State

localityName = Locality Name (eg, city)

0.organizationName = Organization Name (eg, company) 0.organizationName_default = Internet Widgits Pty Ltd

# we can do this but it is not needed normally :-) #1.organizationName = Second Organization Name (eg, company) #1.organizationName_default = World Wide Web Pty Ltd

organizationalUnitName = Organizational Unit Name (eg, section) #organizationalUnitName_default =

commonName = Common Name (e.g. server FQDN or YOUR name) commonName_max = 64

emailAddress = Email Address emailAddress_max = 64

# SET-ex3 = SET extension number 3

[ req_attributes ] challengePassword = A challenge password challengePassword_min = 4 challengePassword_max = 20

unstructuredName = An optional company name

[ usr_cert ]

# These extensions are added when 'ca' signs a request.

# This goes against PKIX guidelines but some CAs do it and some software # requires this to avoid interpreting an end user certificate as a CA.

basicConstraints=CA:FALSE

# This is typical in keyUsage for a client certificate. # keyUsage = nonRepudiation, digitalSignature, keyEncipherment

# PKIX recommendations harmless if included in all certificates. subjectKeyIdentifier=hash authorityKeyIdentifier=keyid,issuer

# This stuff is for subjectAltName and issuerAltname. # Import the email address. # subjectAltName=email:copy # An alternative to produce certificates that aren't # deprecated according to PKIX. # subjectAltName=email:move

# Copy subject details # issuerAltName=issuer:copy

# This is required for TSA certificates. # extendedKeyUsage = critical,timeStamping

[ v3_req ]

# Extensions to add to a certificate request

basicConstraints = CA:FALSE keyUsage = nonRepudiation, digitalSignature, keyEncipherment

[ v3_ca ]

# Extensions for a typical CA

# PKIX recommendation.

subjectKeyIdentifier=hash

authorityKeyIdentifier=keyid:always,issuer

basicConstraints = critical,CA:true

# Key usage: this is typical for a CA certificate. However since it will # prevent it being used as an test self-signed certificate it is best # left out by default. # keyUsage = cRLSign, keyCertSign

# Include email address in subject alt name: another PKIX recommendation # subjectAltName=email:copy # Copy issuer details # issuerAltName=issuer:copy

# DER hex encoding of an extension: beware experts only! # obj=DER:02:03 # Where 'obj' is a standard or added object # You can even override a supported extension: # basicConstraints= critical, DER:30:03:01:01:FF

[ crl_ext ]

# CRL extensions. # Only issuerAltName and authorityKeyIdentifier make any sense in a CRL.

# issuerAltName=issuer:copy authorityKeyIdentifier=keyid:always

[ proxy_cert_ext ] # These extensions should be added when creating a proxy certificate

# This goes against PKIX guidelines but some CAs do it and some software # requires this to avoid interpreting an end user certificate as a CA.

basicConstraints=CA:FALSE

# This is typical in keyUsage for a client certificate. # keyUsage = nonRepudiation, digitalSignature, keyEncipherment

# PKIX recommendations harmless if included in all certificates. subjectKeyIdentifier=hash authorityKeyIdentifier=keyid,issuer

# This stuff is for subjectAltName and issuerAltname. # Import the email address. # subjectAltName=email:copy # An alternative to produce certificates that aren't # deprecated according to PKIX. # subjectAltName=email:move

# Copy subject details # issuerAltName=issuer:copy

# This really needs to be in place for it to be a proxy certificate. proxyCertInfo=critical,language:id-ppl-anyLanguage,pathlen:3,policy:foo

#################################################################### [ tsa ]

default_tsa = tsa_config1 # the default TSA section

[ tsa_config1 ]

# These are used by the TSA reply generation only. dir = ./demoCA # TSA root directory serial = $dir/tsaserial # The current serial number (mandatory) crypto_device = builtin # OpenSSL engine to use for signing signer_cert = $dir/tsacert.pem # The TSA signing certificate # (optional) certs = $dir/cacert.pem # Certificate chain to include in reply # (optional) signer_key = $dir/private/tsakey.pem # The TSA private key (optional) signer_digest = sha256 # Signing digest to use. (Optional) default_policy = tsa_policy1 # Policy if request did not specify it # (optional) other_policies = tsa_policy2, tsa_policy3 # acceptable policies (optional) digests = sha1, sha256, sha384, sha512 # Acceptable message digests (mandatory) accuracy = secs:1, millisecs:500, microsecs:100 # (optional) clock_precision_digits = 0 # number of digits after dot. (optional) ordering = yes # Is ordering defined for timestamps? # (optional, default: no) tsa_name = yes # Must the TSA name be included in the reply? # (optional, default: no) ess_cert_id_chain = no # Must the ESS cert id chain be included? # (optional, default: no) ess_cert_id_alg = sha1 # algorithm to compute certificate # identifier (optional, default: sha1)

[insta] # CMP using Insta Demo CA # Message transfer server = pki.certificate.fi:8700 # proxy = # set this as far as needed, e.g., http://192.168.1.1:8080 # tls_use = 0 path = pkix/

# Server authentication recipient = "/C=FI/O=Insta Demo/CN=Insta Demo CA" # or set srvcert or issuer ignore_keyusage = 1 # potentially needed quirk unprotected_errors = 1 # potentially needed quirk extracertsout = insta.extracerts.pem

# Client authentication ref = 3078 # user identification secret = pass:insta # can be used for both client and server side

# Generic message options cmd = ir # default operation, can be overridden on cmd line with, e.g., kur

# Certificate enrollment subject = "/CN=openssl-cmp-test" newkey = insta.priv.pem out_trusted = apps/insta.ca.crt # does not include keyUsage digitalSignature certout = insta.cert.pem

[pbm] # Password-based protection for Insta CA # Server and client authentication ref = $insta::ref # 3078 secret = $insta::secret # pass:insta

[signature] # Signature-based protection for Insta CA # Server authentication trusted = $insta::out_trusted # apps/insta.ca.crt

# Client authentication secret = # disable PBM key = $insta::newkey # insta.priv.pem cert = $insta::certout # insta.cert.pem

[ir] cmd = ir

[cr] cmd = cr

[kur] # Certificate update cmd = kur oldcert = $insta::certout # insta.cert.pem

[rr] # Certificate revocation cmd = rr oldcert = $insta::certout # insta.cert.pem ```

Closed #3737 as completed.