Enable TLSv1.1 on httpd 2.4.56 running on Docker

I am trying to modernize the infrastructure of a HTTP web service. I want to update the web server to something more recent and secure, but I have to maintain compatibility with some legacy devices in the field that are unable to connect using TLSv1.2.

The web server I am using is httpd version 2.4.56 running on a Docker container with Alpine Linux (for reference the image is httpd:2.4.56-alpine3.17)

I tried enabling TLSv1.1 ciphers changing the default httpd-ssl.conf file with this lines:

SSLCipherSuite ALL:@SECLEVEL=1
SSLProxyCipherSuite ALL:@SECLEVEL=1

The SSLProtocol and SSLProxyProtocol directives are all -SSLv3.

After that I changed /etc/ssl/openssl.cnf by adding at the top

openssl_conf = default_conf

and

[default_conf]
ssl_conf = ssl_sect

[ssl_sect]
system_default = system_default_sect

[system_default_sect]
MinProtocol = TLSv1.1
CipherString = DEFAULT@SECLEVEL=1

[openssl_init]
providers = provider_sect

after the [ new_oids ] section.

After that i tested the result with the command nmap -script ssl-enum-ciphers -p 9443 localhost and obtained the following result:

PORT     STATE SERVICE
9443/tcp open  tungsten-https
| ssl-enum-ciphers: 
|   TLSv1.2: 
|     ciphers: 
|       TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384 (ecdh_x25519) - A
|       TLS_DHE_RSA_WITH_AES_256_GCM_SHA384 (dh 2048) - A
|       TLS_ECDHE_RSA_WITH_CHACHA20_POLY1305_SHA256 (ecdh_x25519) - A
|       TLS_DHE_RSA_WITH_CHACHA20_POLY1305_SHA256 (dh 2048) - A
|       TLS_DHE_RSA_WITH_AES_256_CCM_8 (dh 2048) - A
|       TLS_DHE_RSA_WITH_AES_256_CCM (dh 2048) - A
|       TLS_ECDHE_RSA_WITH_ARIA_256_GCM_SHA384 (ecdh_x25519) - A
|       TLS_DHE_RSA_WITH_ARIA_256_GCM_SHA384 (dh 2048) - A
|       TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 (ecdh_x25519) - A
|       TLS_DHE_RSA_WITH_AES_128_GCM_SHA256 (dh 2048) - A
|       TLS_DHE_RSA_WITH_AES_128_CCM_8 (dh 2048) - A
|       TLS_DHE_RSA_WITH_AES_128_CCM (dh 2048) - A
|       TLS_ECDHE_RSA_WITH_ARIA_128_GCM_SHA256 (ecdh_x25519) - A
|       TLS_DHE_RSA_WITH_ARIA_128_GCM_SHA256 (dh 2048) - A
|       TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384 (ecdh_x25519) - A
|       TLS_DHE_RSA_WITH_AES_256_CBC_SHA256 (dh 2048) - A
|       TLS_ECDHE_RSA_WITH_CAMELLIA_256_CBC_SHA384 (ecdh_x25519) - A
|       TLS_DHE_RSA_WITH_CAMELLIA_256_CBC_SHA256 (dh 2048) - A
|       TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256 (ecdh_x25519) - A
|       TLS_DHE_RSA_WITH_AES_128_CBC_SHA256 (dh 2048) - A
|       TLS_ECDHE_RSA_WITH_CAMELLIA_128_CBC_SHA256 (ecdh_x25519) - A
|       TLS_DHE_RSA_WITH_CAMELLIA_128_CBC_SHA256 (dh 2048) - A
|       TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA (ecdh_x25519) - A
|       TLS_DHE_RSA_WITH_AES_256_CBC_SHA (dh 2048) - A
|       TLS_DHE_RSA_WITH_CAMELLIA_256_CBC_SHA (dh 2048) - A
|       TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA (ecdh_x25519) - A
|       TLS_DHE_RSA_WITH_AES_128_CBC_SHA (dh 2048) - A
|       TLS_DHE_RSA_WITH_CAMELLIA_128_CBC_SHA (dh 2048) - A
|       TLS_RSA_WITH_AES_256_GCM_SHA384 (rsa 2048) - A
|       TLS_RSA_WITH_AES_256_CCM_8 (rsa 2048) - A
|       TLS_RSA_WITH_AES_256_CCM (rsa 2048) - A
|       TLS_RSA_WITH_ARIA_256_GCM_SHA384 (rsa 2048) - A
|       TLS_RSA_WITH_AES_128_GCM_SHA256 (rsa 2048) - A
|       TLS_RSA_WITH_AES_128_CCM_8 (rsa 2048) - A
|       TLS_RSA_WITH_AES_128_CCM (rsa 2048) - A
|       TLS_RSA_WITH_ARIA_128_GCM_SHA256 (rsa 2048) - A
|       TLS_RSA_WITH_AES_256_CBC_SHA256 (rsa 2048) - A
|       TLS_RSA_WITH_CAMELLIA_256_CBC_SHA256 (rsa 2048) - A
|       TLS_RSA_WITH_AES_128_CBC_SHA256 (rsa 2048) - A
|       TLS_RSA_WITH_CAMELLIA_128_CBC_SHA256 (rsa 2048) - A
|       TLS_RSA_WITH_AES_256_CBC_SHA (rsa 2048) - A
|       TLS_RSA_WITH_CAMELLIA_256_CBC_SHA (rsa 2048) - A
|       TLS_RSA_WITH_AES_128_CBC_SHA (rsa 2048) - A
|       TLS_RSA_WITH_CAMELLIA_128_CBC_SHA (rsa 2048) - A
|     compressors: 
|       NULL
|     cipher preference: server
|   TLSv1.3: 
|     ciphers: 
|       TLS_AKE_WITH_AES_256_GCM_SHA384 (ecdh_x25519) - A
|       TLS_AKE_WITH_CHACHA20_POLY1305_SHA256 (ecdh_x25519) - A
|       TLS_AKE_WITH_AES_128_GCM_SHA256 (ecdh_x25519) - A
|     cipher preference: server
|_  least strength: A

Nmap done: 1 IP address (1 host up) scanned in 0.41 seconds

so, clearly I am missing something, as I expected some TLSv1.1 ciphers to show up.

I also tried inserting some syntax errors to see if the openssl.cnf file is read correctly and it seems that the configuration is ignored even if i can find it browsing the container filesystem.

For reference these are the complete configuration files i changed:

/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
openssl_conf = default_conf
# 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
# === Enable TLS 1.1 ===
[default_conf]
ssl_conf = ssl_sect
[ssl_sect]
system_default = system_default_sect
[system_default_sect]
MinProtocol = TLSv1.1
CipherString = DEFAULT@SECLEVEL=1
[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 = insta.ca.crt
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.ca.crt # does not include keyUsage digitalSignature
# 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

/usr/local/apache2/conf/extra/httpd-ssl.conf:

#
# This is the Apache server configuration file providing SSL support.
# It contains the configuration directives to instruct the server how to
# serve pages over an https connection. For detailed information about these
# directives see <URL:http://httpd.apache.org/docs/2.4/mod/mod_ssl.html>
#
# Do NOT simply read the instructions in here without understanding
# what they do.  They're here only as hints or reminders.  If you are unsure
# consult the online docs. You have been warned.
#
# Required modules: mod_log_config, mod_setenvif, mod_ssl,
#          socache_shmcb_module (for default value of SSLSessionCache)
#
# Pseudo Random Number Generator (PRNG):
# Configure one or more sources to seed the PRNG of the SSL library.
# The seed data should be of good random quality.
# WARNING! On some platforms /dev/random blocks if not enough entropy
# is available. This means you then cannot use the /dev/random device
# because it would lead to very long connection times (as long as
# it requires to make more entropy available). But usually those
# platforms additionally provide a /dev/urandom device which doesn't
# block. So, if available, use this one instead. Read the mod_ssl User
# Manual for more details.
#
#SSLRandomSeed startup file:/dev/random  512
#SSLRandomSeed startup file:/dev/urandom 512
#SSLRandomSeed connect file:/dev/random  512
#SSLRandomSeed connect file:/dev/urandom 512
#
# When we also provide SSL we have to listen to the
# standard HTTP port (see above) and to the HTTPS port
#
Listen 443
##
##  SSL Global Context
##
##  All SSL configuration in this context applies both to
##  the main server and all SSL-enabled virtual hosts.
##
#   SSL Cipher Suite:
#   List the ciphers that the client is permitted to negotiate,
#   and that httpd will negotiate as the client of a proxied server.
#   See the OpenSSL documentation for a complete list of ciphers, and
#   ensure these follow appropriate best practices for this deployment.
#   httpd 2.2.30, 2.4.13 and later force-disable aNULL, eNULL and EXP ciphers,
#   while OpenSSL disabled these by default in 0.9.8zf/1.0.0r/1.0.1m/1.0.2a.
#SSLCipherSuite HIGH:MEDIUM:!MD5:!RC4:!3DES
#SSLProxyCipherSuite HIGH:MEDIUM:!MD5:!RC4:!3DES
SSLCipherSuite ALL:@SECLEVEL=1
SSLProxyCipherSuite ALL:@SECLEVEL=1
#  By the end of 2016, only TLSv1.2 ciphers should remain in use.
#  Older ciphers should be disallowed as soon as possible, while the
#  kRSA ciphers do not offer forward secrecy.  These changes inhibit
#  older clients (such as IE6 SP2 or IE8 on Windows XP, or other legacy
#  non-browser tooling) from successfully connecting.
#
#  To restrict mod_ssl to use only TLSv1.2 ciphers, and disable
#  those protocols which do not support forward secrecy, replace
#  the SSLCipherSuite and SSLProxyCipherSuite directives above with
#  the following two directives, as soon as practical.
# SSLCipherSuite HIGH:MEDIUM:!SSLv3:!kRSA
# SSLProxyCipherSuite HIGH:MEDIUM:!SSLv3:!kRSA
#   User agents such as web browsers are not configured for the user's
#   own preference of either security or performance, therefore this
#   must be the prerogative of the web server administrator who manages
#   cpu load versus confidentiality, so enforce the server's cipher order.
SSLHonorCipherOrder on
#   SSL Protocol support:
#   List the protocol versions which clients are allowed to connect with.
#   Disable SSLv3 by default (cf. RFC 7525 3.1.1).  TLSv1 (1.0) should be
#   disabled as quickly as practical.  By the end of 2016, only the TLSv1.2
#   protocol or later should remain in use.
SSLProtocol all -SSLv3
SSLProxyProtocol all -SSLv3
#   Pass Phrase Dialog:
#   Configure the pass phrase gathering process.
#   The filtering dialog program (`builtin' is an internal
#   terminal dialog) has to provide the pass phrase on stdout.
SSLPassPhraseDialog  builtin
#   Inter-Process Session Cache:
#   Configure the SSL Session Cache: First the mechanism
#   to use and second the expiring timeout (in seconds).
#SSLSessionCache         "dbm:/usr/local/apache2/logs/ssl_scache"
SSLSessionCache        "shmcb:/usr/local/apache2/logs/ssl_scache(512000)"
SSLSessionCacheTimeout  300
#   OCSP Stapling (requires OpenSSL 0.9.8h or later)
#
#   This feature is disabled by default and requires at least
#   the two directives SSLUseStapling and SSLStaplingCache.
#   Refer to the documentation on OCSP Stapling in the SSL/TLS
#   How-To for more information.
#
#   Enable stapling for all SSL-enabled servers:
#SSLUseStapling On
#   Define a relatively small cache for OCSP Stapling using
#   the same mechanism that is used for the SSL session cache
#   above.  If stapling is used with more than a few certificates,
#   the size may need to be increased.  (AH01929 will be logged.)
#SSLStaplingCache "shmcb:/usr/local/apache2/logs/ssl_stapling(32768)"
#   Seconds before valid OCSP responses are expired from the cache
#SSLStaplingStandardCacheTimeout 3600
#   Seconds before invalid OCSP responses are expired from the cache
#SSLStaplingErrorCacheTimeout 600

I've the same problem, and the only working solution I've found is to downgrade Apache to version to 2.4.54 that uses OpenSSL v1.1 instead of v3.

By now I Don't know if there's another way to solve it.

ADDED april 9 2023:
It looks that @SECLEVEL=0 does the trick with SSL v3. I've tested it works with apache 2.4.56.