From 6ae4596101d4f88c04fc02271c3c0786a4007fbf Mon Sep 17 00:00:00 2001 From: jan Date: Tue, 16 Feb 2021 21:39:17 +0000 Subject: [PATCH] Add x509 certificate validation regression tests The validation tests are originaly createtd by Steffen Ullrich. OK tb@ No objection jsing@ --- regress/usr.bin/openssl/Makefile | 4 +- regress/usr.bin/openssl/x509/Makefile | 129 ++++++++++++++++++ .../x509/create-libressl-test-certs.pl | 111 +++++++++++++++ 3 files changed, 242 insertions(+), 2 deletions(-) create mode 100644 regress/usr.bin/openssl/x509/Makefile create mode 100755 regress/usr.bin/openssl/x509/create-libressl-test-certs.pl diff --git a/regress/usr.bin/openssl/Makefile b/regress/usr.bin/openssl/Makefile index 0ef7928ea4f..d41b65a3f43 100644 --- a/regress/usr.bin/openssl/Makefile +++ b/regress/usr.bin/openssl/Makefile @@ -1,6 +1,6 @@ -# $OpenBSD: Makefile,v 1.6 2018/03/19 03:41:40 beck Exp $ +# $OpenBSD: Makefile,v 1.7 2021/02/16 21:39:17 jan Exp $ -SUBDIR= options +SUBDIR= options x509 CLEANFILES+= testdsa.key testdsa.pem rsakey.pem rsacert.pem dsa512.pem CLEANFILES+= appstest_dir diff --git a/regress/usr.bin/openssl/x509/Makefile b/regress/usr.bin/openssl/x509/Makefile new file mode 100644 index 00000000000..b20cb1d9bdd --- /dev/null +++ b/regress/usr.bin/openssl/x509/Makefile @@ -0,0 +1,129 @@ +# $OpenBSD: Makefile,v 1.1 2021/02/16 21:39:17 jan Exp $ + +# Copyright (c) 2021 Jan Klemkow +# +# 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 diff --git a/regress/usr.bin/openssl/x509/create-libressl-test-certs.pl b/regress/usr.bin/openssl/x509/create-libressl-test-certs.pl new file mode 100755 index 00000000000..fdb718aadcd --- /dev/null +++ b/regress/usr.bin/openssl/x509/create-libressl-test-certs.pl @@ -0,0 +1,111 @@ +#!/usr/bin/perl + +# Copyright (c) 2021 Steffen Ullrich +# 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 @_ +} -- 2.20.1