--- /dev/null
+# $OpenBSD: Makefile,v 1.1 2021/02/16 21:39:17 jan Exp $
+
+# Copyright (c) 2021 Jan Klemkow <j.klemkow@wemelug.de>
+#
+# Permission to use, copy, modify, and distribute this software for any
+# purpose with or without fee is hereby granted, provided that the above
+# copyright notice and this permission notice appear in all copies.
+#
+# THE SOFTWARE IS PROVIDED "AS IS" AND THE AUTHOR DISCLAIMS ALL WARRANTIES
+# WITH REGARD TO THIS SOFTWARE INCLUDING ALL IMPLIED WARRANTIES OF
+# MERCHANTABILITY AND FITNESS. IN NO EVENT SHALL THE AUTHOR BE LIABLE FOR
+# ANY SPECIAL, DIRECT, INDIRECT, OR CONSEQUENTIAL DAMAGES OR ANY DAMAGES
+# WHATSOEVER RESULTING FROM LOSS OF USE, DATA OR PROFITS, WHETHER IN AN
+# ACTION OF CONTRACT, NEGLIGENCE OR OTHER TORTIOUS ACTION, ARISING OUT OF
+# OR IN CONNECTION WITH THE USE OR PERFORMANCE OF THIS SOFTWARE.
+
+# This regression test is based on manual test descriptions from:
+# https://github.com/noxxi/libressl-tests
+
+# The following port must be installed for the regression tests:
+# p5-IO-Socket-SSL perl interface to SSL sockets
+
+PERL = perl
+OPENSSL ?= openssl
+
+PKG_REQUIRE != pkg_info -e 'p5-IO-Socket-SSL-*'
+.if empty (PKG_REQUIRE)
+regress:
+ @echo "missing package p5-IO-Socket-SSL"
+ @echo SKIPPED
+.endif
+
+REGRESS_TARGETS += test-inlabel-wildcard-cert-no-CA-client
+REGRESS_TARGETS += test-inlabel-wildcard-cert-CA-client
+REGRESS_TARGETS += test-common-wildcard-cert-no-CA-client
+REGRESS_TARGETS += test-common-wildcard-cert-CA-client
+REGRESS_TARGETS += test-verify-unusual-wildcard-cert
+REGRESS_TARGETS += test-openssl-verify-common-wildcard-cert
+REGRESS_TARGETS += test-chain-certificates-s_server
+REGRESS_TARGETS += test-alternative-chain
+REGRESS_CLEANUP = cleanup-ssl
+REGRESS_SETUP_ONCE = create-libressl-test-certs
+
+REGRESS_EXPECTED_FAILURES += test-unusual-wildcard-cert-no-CA-client
+REGRESS_EXPECTED_FAILURES += test-common-wildcard-cert-no-CA-client
+REGRESS_EXPECTED_FAILURES += test-common-wildcard-cert-CA-client
+REGRESS_EXPECTED_FAILURES += test-verify-unusual-wildcard-cert
+
+create-libressl-test-certs: create-libressl-test-certs.pl
+ ${PERL} ${.CURDIR}/$@.pl
+
+cleanup-ssl:
+ rm *.pem *.key
+
+test-inlabel-wildcard-cert-no-CA-client:
+ # unusual wildcard cert, no CA given to client
+ # start server
+ ${OPENSSL} s_server -cert server-unusual-wildcard.pem \
+ -key server-unusual-wildcard.pem & \
+ timeout=$$(($$(date +%s) + 5)); \
+ while fstat -p $$! | ! grep -q 'tcp .* \*:4433$$'; \
+ do test $$(date +%s) -lt $$timeout || exit 1; done
+ # start client
+ echo "Q" | ${OPENSSL} s_client -verify_return_error \
+ | grep "Verify return code: 21"
+
+test-inlabel-wildcard-cert-CA-client:
+ # unusual wildcard cert, CA given to client
+ # start server
+ ${OPENSSL} s_server -cert server-unusual-wildcard.pem \
+ -key server-unusual-wildcard.pem & \
+ timeout=$$(($$(date +%s) + 5)); \
+ while fstat -p $$! | ! grep -q 'tcp .* \*:4433$$'; \
+ do test $$(date +%s) -lt $$timeout || exit 1; done
+ # start client
+ echo "Q" | ${OPENSSL} s_client -CAfile caR.pem \
+ | grep "Verify return code: 0"
+
+test-common-wildcard-cert-no-CA-client:
+ # common wildcard cert, no CA given to client
+ # start server
+ ${OPENSSL} s_server -cert server-common-wildcard.pem \
+ -key server-common-wildcard.pem & \
+ timeout=$$(($$(date +%s) + 5)); \
+ while fstat -p $$! | ! grep -q 'tcp .* \*:4433$$'; \
+ do test $$(date +%s) -lt $$timeout || exit 1; done
+ # start client
+ echo "Q" | ${OPENSSL} s_client \
+ | grep "Verify return code: 21"
+
+test-common-wildcard-cert-CA-client:
+ # common wildcard cert, CA given to client
+ # start server
+ ${OPENSSL} s_server -cert server-unusual-wildcard.pem \
+ -key server-unusual-wildcard.pem & \
+ timeout=$$(($$(date +%s) + 5)); \
+ while fstat -p $$! | ! grep -q 'tcp .* \*:4433$$'; \
+ do test $$(date +%s) -lt $$timeout || exit 1; done
+ # start client
+ echo "Q" | ${OPENSSL} s_client -CAfile caR.pem \
+ | grep "Verify return code: 21"
+
+test-verify-unusual-wildcard-cert:
+ # openssl verify, unusual wildcard cert
+ ${OPENSSL} verify -CAfile caR.pem server-unusual-wildcard.pem \
+ | grep "server-unusual-wildcard.pem: OK"
+
+test-openssl-verify-common-wildcard-cert:
+ # openssl verify, common wildcard cert
+ ${OPENSSL} verify -CAfile caR.pem server-common-wildcard.pem \
+ | grep "server-common-wildcard.pem: OK"
+
+test-chain-certificates-s_server:
+ # Not all chain certificates are sent in s_server
+ # start server
+ # ${OPENSSL} s_server -cert server-subca.pem -CAfile subcaR.pem
+ ${OPENSSL} s_server -cert server-subca-chainS.pem -CAfile subcaR.pem & \
+ timeout=$$(($$(date +%s) + 5)); \
+ while fstat -p $$! | ! grep -q 'tcp .* \*:4433$$'; \
+ do test $$(date +%s) -lt $$timeout || exit 1; done
+ # start client
+ ${OPENSSL} s_client -CAfile caR.pem | grep "Verify return code: 0"
+
+test-alternative-chain:
+ # alternative chain not found
+ ${OPENSSL} verify -verbose -trusted caR.pem -untrusted chainSX.pem \
+ server-subca.pem | grep "server-subca.pem: OK"
+
+.include <bsd.regress.mk>
--- /dev/null
+#!/usr/bin/perl
+
+# Copyright (c) 2021 Steffen Ullrich <sullr@cpan.org>
+# Public Domain
+
+use strict;
+use warnings;
+use IO::Socket::SSL::Utils;
+
+# primitive CA - ROOT
+my @ca = cert(
+ CA => 1,
+ subject => { CN => 'ROOT' }
+);
+out('caR.pem', pem(crt => $ca[0]));
+out('caR.key', pem(key => $ca[1]));
+
+# server certificate where SAN contains in-label wildcards, which a
+# client MAY choose to accept as per RFC 6125 section 6.4.3.
+my @leafcert = cert(
+ issuer => \@ca,
+ purpose => 'server',
+ subject => { CN => 'server.local' },
+ subjectAltNames => [
+ [ DNS => 'bar.server.local' ],
+ [ DNS => 'www*.server.local'],
+ [ DNS => '*.www.server.local'],
+ [ DNS => 'foo.server.local' ],
+ [ DNS => 'server.local' ],
+ ]
+);
+out('server-unusual-wildcard.pem', pem(@leafcert));
+
+@leafcert = cert(
+ issuer => \@ca,
+ purpose => 'server',
+ subject => { CN => 'server.local' },
+ subjectAltNames => [
+ [ DNS => 'bar.server.local' ],
+ [ DNS => '*.www.server.local'],
+ [ DNS => 'foo.server.local' ],
+ [ DNS => 'server.local' ],
+ ]
+);
+out('server-common-wildcard.pem', pem(@leafcert));
+
+# alternative CA - OLD_ROOT
+my @caO = cert(
+ CA => 1,
+ subject => { CN => 'OLD_ROOT' }
+);
+out('caO.pem', pem(crt => $caO[0]));
+out('caO.key', pem(key => $caO[1]));
+
+# alternative ROOT CA, signed by OLD_ROOT, same key as other ROOT CA
+my @caX = cert(
+ issuer => \@caO,
+ CA => 1,
+ subject => { CN => 'ROOT' },
+ key => $ca[1],
+);
+out('caX.pem', pem(crt => $caX[0]));
+out('caX.key', pem(key => $caX[1]));
+
+# subCA below ROOT
+my @subcaR = cert(
+ issuer => \@ca,
+ CA => 1,
+ subject => { CN => 'SubCA.of.ROOT' }
+);
+out('subcaR.pem', pem(crt => $subcaR[0]));
+out('subcaR.key', pem(key => $subcaR[1]));
+out('chainSX.pem', pem($subcaR[0]), pem($caX[0]));
+
+@leafcert = cert(
+ issuer => \@subcaR,
+ purpose => 'server',
+ subject => { CN => 'server.subca.local' },
+ subjectAltNames => [
+ [ DNS => 'server.subca.local' ],
+ ]
+);
+out('server-subca.pem', pem(@leafcert));
+out('server-subca-chainSX.pem', pem(@leafcert, $subcaR[0], $caX[0]));
+out('server-subca-chainS.pem', pem(@leafcert, $subcaR[0]));
+
+
+sub cert { CERT_create(not_after => 10*365*86400+time(), @_) }
+sub pem {
+ my @default = qw(crt key);
+ my %m = (key => \&PEM_key2string, crt => \&PEM_cert2string);
+ my $result = '';
+ while (my $f = shift(@_)) {
+ my $v;
+ if ($f =~m{^(key|crt)$}) {
+ $v = shift(@_);
+ } else {
+ $v = $f;
+ $f = shift(@default) || 'crt';
+ }
+ $f = $m{$f} || die "wrong key $f";
+ $result .= $f->($v);
+ }
+ return $result;
+}
+
+sub out {
+ my $file = shift;
+ open(my $fh,'>',"$file") or die "failed to create $file: $!";
+ print $fh @_
+}