On Sat, Feb 13, 2021 at 03:53:48PM +0100, Theo Buehler wrote:
> On Sat, Feb 13, 2021 at 11:58:04AM +0100, Jan Klemkow wrote:
> > A coworker of mine has made tests with LibreSSL [1] and found some
> > regressions.  I took his test descriptions and created the following
> > automated regression test.  In the repository he described his findings
> > in detail.  I kept the numbers of the files and subtests in the target
> > names for now.  So, its easier to match it with his files.
> > 
> > I don't know how to handle the result of "test-01-ssl".  Thats why its
> > just a comment.  Someone may have an idea to handle this properly.
> > 
> > Any comments, wishes or OK's?
> > 
> > [1]: https://github.com/noxxi/libressl-tests
> 
> First of all thanks for the effort!
> 
> The perl script and probably also the Makefile should have a license.
> 
> Please add a check that tests whether the required perl modules are
> installed (p5-IO-Socket-SSL and p5-Net-SSLeay) and otherwise prints
> SKIPPED and their names, so I can install them if they're not present.
> I never remember their exact capitalization and hyphenation...
> 
> Various comments inline, and a patch for openssl(1) at the end that may
> simplify some things.

This is an updated version of the test including comments and wishes
from tb@ and bluhm@.

OK?

Thanks,
Jan

Index: regress/lib/libcrypto/validate/Makefile
===================================================================
RCS file: regress/lib/libcrypto/validate/Makefile
diff -N regress/lib/libcrypto/validate/Makefile
--- /dev/null   1 Jan 1970 00:00:00 -0000
+++ regress/lib/libcrypto/validate/Makefile     15 Feb 2021 13:38:22 -0000
@@ -0,0 +1,133 @@
+# $OpenBSD$
+
+# Copyright (c) 2021 Jan Klemkow <j.klem...@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
+
+PERL_REQUIRE !=        perl -Mstrict -Mwarnings -e ' \
+    eval { require IO::Socket::SSL } or print $@; \
+'
+.if ! empty (PERL_REQUIRE)
+regress:
+       @echo "${PERL_REQUIRE}"
+       @echo install these perl packages for additional tests
+       @echo SKIPPED
+.endif
+
+REGRESS_TARGETS +=     test-unusual-wildcard-cert-no-CA-client
+REGRESS_TARGETS +=     test-unusual-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
+REGRESS_EXPECTED_FAILURES +=   test-alternative-chain
+
+create-libressl-test-certs: create-libressl-test-certs.pl
+       ${PERL} ${.CURDIR}/$@.pl
+
+cleanup-ssl:
+       rm *.pem *.key
+
+test-unusual-wildcard-cert-no-CA-client:
+       # unusual wildcard cert, no CA given to client
+       # start client
+       ${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-unusual-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>
Index: regress/lib/libcrypto/validate/create-libressl-test-certs.pl
===================================================================
RCS file: regress/lib/libcrypto/validate/create-libressl-test-certs.pl
diff -N regress/lib/libcrypto/validate/create-libressl-test-certs.pl
--- /dev/null   1 Jan 1970 00:00:00 -0000
+++ regress/lib/libcrypto/validate/create-libressl-test-certs.pl        15 Feb 
2021 12:54:58 -0000
@@ -0,0 +1,111 @@
+#!/usr/bin/perl
+
+# Copyright (c) 2021 Steffen Ullrich <su...@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 are allowed by
+# RFC 6125
+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 @_
+}

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