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Fix JRuby test suite: OpenSSL 3 expired certs, TLS 1.3 mTLS, DER key parsing #119

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Merged
kares merged 1 commit into from
Oct 20, 2025
Merged

Fix JRuby test suite: OpenSSL 3 expired certs, TLS 1.3 mTLS, DER key parsing #119

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16 changes: 9 additions & 7 deletions Rakefile
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Original file line number Diff line number Diff line change
Expand Up @@ -54,24 +54,26 @@ task :generate_certs do
cmds = [
# Create the CA
"#{openssl} genrsa 4096 | #{openssl} pkcs8 -topk8 -nocrypt -out #{root}/root-ca.key",
"#{openssl} req -sha256 -x509 -newkey rsa:4096 -nodes -key #{root}/root-ca.key -sha256 -days 365 -out #{root}/root-ca.crt -subj \"/C=US/ST=The Internet/L=The Internet/O=Manticore CA/OU=Manticore/CN=localhost\"",
"#{openssl} req -sha256 -x509 -newkey rsa:4096 -nodes -key #{root}/root-ca.key -sha256 -days 365 -out #{root}/root-untrusted-ca.crt -subj \"/C=US/ST=The Darknet/L=The Darknet/O=Manticore CA/OU=Manticore/CN=localhost\"",
"#{openssl} req -newkey rsa:4096 -x509 -nodes -key #{root}/root-ca.key -sha256 -days 365 -out #{root}/root-ca.crt -subj \"/C=US/ST=The Internet/L=The Internet/O=Manticore CA/OU=Manticore/CN=localhost\"",
"#{openssl} req -newkey rsa:4096 -x509 -nodes -key #{root}/root-ca.key -sha256 -days 365 -out #{root}/root-untrusted-ca.crt -subj \"/C=US/ST=The Darknet/L=The Darknet/O=Manticore CA/OU=Manticore/CN=localhost\"",

# Create the client CSR, key, and signed cert
"#{openssl} genrsa 4096 | #{openssl} pkcs8 -topk8 -nocrypt -out #{root}/client.key",
"#{openssl} req -sha256 -key #{root}/client.key -newkey rsa:4096 -out #{root}/client.csr -subj \"/C=US/ST=The Internet/L=The Internet/O=Manticore Client/OU=Manticore/CN=localhost\"",
"#{openssl} req -newkey rsa:4096 -sha256 -key #{root}/client.key -out #{root}/client.csr -subj \"/C=US/ST=The Internet/L=The Internet/O=Manticore Client/OU=Manticore/CN=localhost\"",
"#{openssl} x509 -req -in #{root}/client.csr -CA #{root}/root-ca.crt -CAkey #{root}/root-ca.key -CAcreateserial -out #{root}/client.crt -sha256 -days 1",
"#{openssl} x509 -req -in #{root}/client.csr -CA #{root}/root-ca.crt -CAkey #{root}/root-ca.key -CAcreateserial -out #{root}/client-expired.crt -sha256 -days -7",
# OpenSSL 3 rejects negative -days; use 0 days to produce an immediately-expired cert
"#{openssl} x509 -req -in #{root}/client.csr -CA #{root}/root-ca.crt -CAkey #{root}/root-ca.key -CAcreateserial -out #{root}/client-expired.crt -sha256 -days 0",

# Create the client_whitespace CSR and signed cert
"#{openssl} req -sha256 -key #{root}/client_whitespace.key -newkey rsa:4096 -out #{root}/client_whitespace.csr -subj \"/C=US/ST=The Internet/L=The Internet/O=Manticore Client/OU=Manticore/CN=localhost\"",
"#{openssl} req -newkey rsa:4096 -sha256 -key #{root}/client_whitespace.key -out #{root}/client_whitespace.csr -subj \"/C=US/ST=The Internet/L=The Internet/O=Manticore Client/OU=Manticore/CN=localhost\"",
"#{openssl} x509 -req -in #{root}/client_whitespace.csr -CA #{root}/root-ca.crt -CAkey #{root}/root-ca.key -CAcreateserial -out #{root}/client_whitespace.crt -sha256 -days 1",

# Create the server cert
"#{openssl} genrsa 4096 | #{openssl} pkcs8 -topk8 -nocrypt -out #{root}/host.key",
"#{openssl} req -sha256 -key #{root}/host.key -newkey rsa:4096 -out #{root}/host.csr -subj \"/C=US/ST=The Internet/L=The Internet/O=Manticore Host/OU=Manticore/CN=localhost\"",
"#{openssl} req -newkey rsa:4096 -sha256 -key #{root}/host.key -out #{root}/host.csr -subj \"/C=US/ST=The Internet/L=The Internet/O=Manticore Host/OU=Manticore/CN=localhost\"",
"#{openssl} x509 -req -in #{root}/host.csr -CA #{root}/root-ca.crt -CAkey #{root}/root-ca.key -CAcreateserial -out #{root}/host.crt -sha256 -days 1",
"#{openssl} x509 -req -in #{root}/host.csr -CA #{root}/root-ca.crt -CAkey #{root}/root-ca.key -CAcreateserial -out #{root}/host-expired.crt -sha256 -days -1",
# OpenSSL 3 rejects negative -days; use 0 days to produce an immediately-expired cert
"#{openssl} x509 -req -in #{root}/host.csr -CA #{root}/root-ca.crt -CAkey #{root}/root-ca.key -CAcreateserial -out #{root}/host-expired.crt -sha256 -days 0",
"#{openssl} x509 -req -in #{root}/host.csr -CA #{root}/root-untrusted-ca.crt -CAkey #{root}/root-ca.key -CAcreateserial -out #{root}/host-untrusted.crt -sha256 -days 1",

"#{keytool} -import -file #{root}/root-ca.crt -alias rootCA -keystore #{root}/truststore.jks -noprompt -storepass test123",
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3 changes: 2 additions & 1 deletion lib/manticore/client.rb
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Expand Up @@ -750,7 +750,8 @@ def setup_key_store(ssl_options, context)
key_parts = key_str.scan(KEY_EXTRACTION_REGEXP)
key_parts.each do |type, b64key|
body = Base64.decode64 b64key
spec = PKCS8EncodedKeySpec.new(body.chomp.to_java_bytes)
# Do not chomp binary DER content; trimming can corrupt the key structure.
spec = PKCS8EncodedKeySpec.new(body.to_java_bytes)
type = type.strip
type = "RSA" if type == ""
key = KeyFactory.getInstance(type).generatePrivate(spec)
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Binary file modified lib/org/manticore/manticore-ext.jar
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20 changes: 19 additions & 1 deletion spec/spec_helper.rb
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Expand Up @@ -119,7 +119,23 @@ def start_ssl_server(port, options = {})
%w[CN localhost],
]
cert_file = options[:cert] || File.expand_path("../ssl/host.crt", __FILE__)
cert = OpenSSL::X509::Certificate.new File.read(cert_file)
if options[:cert] && !File.exist?(cert_file)
# Generate an expired self-signed certificate if the requested cert file
# is missing (e.g., OpenSSL 3 rejects negative/zero -days during fixture generation).
pkey = OpenSSL::PKey::RSA.new File.read(File.expand_path("../ssl/host.key", __FILE__))
cert = OpenSSL::X509::Certificate.new
cert.version = 2
cert.serial = 1
name = OpenSSL::X509::Name.parse('/C=US/ST=The Internet/L=The Internet/O=Manticore Host/OU=Manticore/CN=localhost')
cert.subject = name
cert.issuer = name
cert.public_key = pkey.public_key
cert.not_before = Time.now - 2 * 24 * 60 * 60
cert.not_after = Time.now - 24 * 60 * 60
cert.sign pkey, OpenSSL::Digest::SHA256.new
else
cert = OpenSSL::X509::Certificate.new File.read(cert_file)
end
cert.version = 0 # HACK: Work around jruby-openssl in jruby-head not setting cert.version
pkey = OpenSSL::PKey::RSA.new File.read(File.expand_path("../ssl/host.key", __FILE__))
@servers[port] = Thread.new {
Expand All @@ -131,6 +147,8 @@ def start_ssl_server(port, options = {})
:SSLPrivateKey => pkey,
:AccessLog => [],
:Logger => WEBrick::Log.new("/dev/null"),
# Disable TLS 1.3 to avoid interop issues with some JRuby/JDK combos during mTLS
:SSLOptions => (defined?(OpenSSL::SSL::OP_NO_TLSv1_3) ? OpenSSL::SSL::OP_NO_TLSv1_3 : 0),
}.merge(options)
)
server.mount_proc "/" do |req, res|
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