#! /usr/bin/perl use strict; use warnings; use POSIX; use File::Spec::Functions qw/catfile/; use File::Compare qw/compare_text/; use OpenSSL::Test qw/:DEFAULT srctop_dir srctop_file/; use OpenSSL::Test::Utils; setup("test_cms"); plan skip_all => "CMS is not supported by this OpenSSL build" if disabled("cms"); my $smdir = srctop_dir("test", "smime-certs"); my $smcont = srctop_file("test", "smcont.txt"); my ($no_des, $no_dh, $no_dsa, $no_ec, $no_ec2m, $no_rc2, $no_zlib) = disabled qw/des dh dsa ec ec2m rc2 zlib/; plan tests => 4; my @smime_pkcs7_tests = ( [ "signed content DER format, RSA key", [ "-sign", "-in", $smcont, "-outform", "DER", "-nodetach", "-certfile", catfile($smdir, "smroot.pem"), "-signer", catfile($smdir, "smrsa1.pem"), "-out", "test.cms" ], [ "-verify", "-in", "test.cms", "-inform", "DER", "-CAfile", catfile($smdir, "smroot.pem"), "-out", "smtst.txt" ] ], [ "signed detached content DER format, RSA key", [ "-sign", "-in", $smcont, "-outform", "DER", "-signer", catfile($smdir, "smrsa1.pem"), "-out", "test.cms" ], [ "-verify", "-in", "test.cms", "-inform", "DER", "-CAfile", catfile($smdir, "smroot.pem"), "-out", "smtst.txt", "-content", $smcont ] ], [ "signed content test streaming BER format, RSA", [ "-sign", "-in", $smcont, "-outform", "DER", "-nodetach", "-stream", "-signer", catfile($smdir, "smrsa1.pem"), "-out", "test.cms" ], [ "-verify", "-in", "test.cms", "-inform", "DER", "-CAfile", catfile($smdir, "smroot.pem"), "-out", "smtst.txt" ] ], [ "signed content DER format, DSA key", [ "-sign", "-in", $smcont, "-outform", "DER", "-nodetach", "-signer", catfile($smdir, "smdsa1.pem"), "-out", "test.cms" ], [ "-verify", "-in", "test.cms", "-inform", "DER", "-CAfile", catfile($smdir, "smroot.pem"), "-out", "smtst.txt" ] ], [ "signed detached content DER format, DSA key", [ "-sign", "-in", $smcont, "-outform", "DER", "-signer", catfile($smdir, "smdsa1.pem"), "-out", "test.cms" ], [ "-verify", "-in", "test.cms", "-inform", "DER", "-CAfile", catfile($smdir, "smroot.pem"), "-out", "smtst.txt", "-content", $smcont ] ], [ "signed detached content DER format, add RSA signer (with DSA existing)", [ "-resign", "-inform", "DER", "-in", "test.cms", "-outform", "DER", "-signer", catfile($smdir, "smrsa1.pem"), "-out", "test2.cms" ], [ "-verify", "-in", "test2.cms", "-inform", "DER", "-CAfile", catfile($smdir, "smroot.pem"), "-out", "smtst.txt", "-content", $smcont ] ], [ "signed content test streaming BER format, DSA key", [ "-sign", "-in", $smcont, "-outform", "DER", "-nodetach", "-stream", "-signer", catfile($smdir, "smdsa1.pem"), "-out", "test.cms" ], [ "-verify", "-in", "test.cms", "-inform", "DER", "-CAfile", catfile($smdir, "smroot.pem"), "-out", "smtst.txt" ] ], [ "signed content test streaming BER format, 2 DSA and 2 RSA keys", [ "-sign", "-in", $smcont, "-outform", "DER", "-nodetach", "-signer", catfile($smdir, "smrsa1.pem"), "-signer", catfile($smdir, "smrsa2.pem"), "-signer", catfile($smdir, "smdsa1.pem"), "-signer", catfile($smdir, "smdsa2.pem"), "-stream", "-out", "test.cms" ], [ "-verify", "-in", "test.cms", "-inform", "DER", "-CAfile", catfile($smdir, "smroot.pem"), "-out", "smtst.txt" ] ], [ "signed content test streaming BER format, 2 DSA and 2 RSA keys, no attributes", [ "-sign", "-in", $smcont, "-outform", "DER", "-noattr", "-nodetach", "-signer", catfile($smdir, "smrsa1.pem"), "-signer", catfile($smdir, "smrsa2.pem"), "-signer", catfile($smdir, "smdsa1.pem"), "-signer", catfile($smdir, "smdsa2.pem"), "-stream", "-out", "test.cms" ], [ "-verify", "-in", "test.cms", "-inform", "DER", "-CAfile", catfile($smdir, "smroot.pem"), "-out", "smtst.txt" ] ], [ "signed content test streaming S/MIME format, 2 DSA and 2 RSA keys", [ "-sign", "-in", $smcont, "-nodetach", "-signer", catfile($smdir, "smrsa1.pem"), "-signer", catfile($smdir, "smrsa2.pem"), "-signer", catfile($smdir, "smdsa1.pem"), "-signer", catfile($smdir, "smdsa2.pem"), "-stream", "-out", "test.cms" ], [ "-verify", "-in", "test.cms", "-CAfile", catfile($smdir, "smroot.pem"), "-out", "smtst.txt" ] ], [ "signed content test streaming multipart S/MIME format, 2 DSA and 2 RSA keys", [ "-sign", "-in", $smcont, "-signer", catfile($smdir, "smrsa1.pem"), "-signer", catfile($smdir, "smrsa2.pem"), "-signer", catfile($smdir, "smdsa1.pem"), "-signer", catfile($smdir, "smdsa2.pem"), "-stream", "-out", "test.cms" ], [ "-verify", "-in", "test.cms", "-CAfile", catfile($smdir, "smroot.pem"), "-out", "smtst.txt" ] ], [ "enveloped content test streaming S/MIME format, DES, 3 recipients", [ "-encrypt", "-in", $smcont, "-stream", "-out", "test.cms", catfile($smdir, "smrsa1.pem"), catfile($smdir, "smrsa2.pem"), catfile($smdir, "smrsa3.pem") ], [ "-decrypt", "-recip", catfile($smdir, "smrsa1.pem"), "-in", "test.cms", "-out", "smtst.txt" ] ], [ "enveloped content test streaming S/MIME format, DES, 3 recipients, 3rd used", [ "-encrypt", "-in", $smcont, "-stream", "-out", "test.cms", catfile($smdir, "smrsa1.pem"), catfile($smdir, "smrsa2.pem"), catfile($smdir, "smrsa3.pem") ], [ "-decrypt", "-recip", catfile($smdir, "smrsa3.pem"), "-in", "test.cms", "-out", "smtst.txt" ] ], [ "enveloped content test streaming S/MIME format, DES, 3 recipients, key only used", [ "-encrypt", "-in", $smcont, "-stream", "-out", "test.cms", catfile($smdir, "smrsa1.pem"), catfile($smdir, "smrsa2.pem"), catfile($smdir, "smrsa3.pem") ], [ "-decrypt", "-inkey", catfile($smdir, "smrsa3.pem"), "-in", "test.cms", "-out", "smtst.txt" ] ], [ "enveloped content test streaming S/MIME format, AES-256 cipher, 3 recipients", [ "-encrypt", "-in", $smcont, "-aes256", "-stream", "-out", "test.cms", catfile($smdir, "smrsa1.pem"), catfile($smdir, "smrsa2.pem"), catfile($smdir, "smrsa3.pem") ], [ "-decrypt", "-recip", catfile($smdir, "smrsa1.pem"), "-in", "test.cms", "-out", "smtst.txt" ] ], ); my @smime_cms_tests = ( [ "signed content test streaming BER format, 2 DSA and 2 RSA keys, keyid", [ "-sign", "-in", $smcont, "-outform", "DER", "-nodetach", "-keyid", "-signer", catfile($smdir, "smrsa1.pem"), "-signer", catfile($smdir, "smrsa2.pem"), "-signer", catfile($smdir, "smdsa1.pem"), "-signer", catfile($smdir, "smdsa2.pem"), "-stream", "-out", "test.cms" ], [ "-verify", "-in", "test.cms", "-inform", "DER", "-CAfile", catfile($smdir, "smroot.pem"), "-out", "smtst.txt" ] ], [ "signed content test streaming PEM format, 2 DSA and 2 RSA keys", [ "-sign", "-in", $smcont, "-outform", "PEM", "-nodetach", "-signer", catfile($smdir, "smrsa1.pem"), "-signer", catfile($smdir, "smrsa2.pem"), "-signer", catfile($smdir, "smdsa1.pem"), "-signer", catfile($smdir, "smdsa2.pem"), "-stream", "-out", "test.cms" ], [ "-verify", "-in", "test.cms", "-inform", "PEM", "-CAfile", catfile($smdir, "smroot.pem"), "-out", "smtst.txt" ] ], [ "signed content MIME format, RSA key, signed receipt request", [ "-sign", "-in", $smcont, "-signer", catfile($smdir, "smrsa1.pem"), "-nodetach", "-receipt_request_to", "test\@openssl.org", "-receipt_request_all", "-out", "test.cms" ], [ "-verify", "-in", "test.cms", "-CAfile", catfile($smdir, "smroot.pem"), "-out", "smtst.txt" ] ], [ "signed receipt MIME format, RSA key", [ "-sign_receipt", "-in", "test.cms", "-signer", catfile($smdir, "smrsa2.pem"), "-out", "test2.cms" ], [ "-verify_receipt", "test2.cms", "-in", "test.cms", "-CAfile", catfile($smdir, "smroot.pem") ] ], [ "enveloped content test streaming S/MIME format, DES, 3 recipients, keyid", [ "-encrypt", "-in", $smcont, "-stream", "-out", "test.cms", "-keyid", catfile($smdir, "smrsa1.pem"), catfile($smdir, "smrsa2.pem"), catfile($smdir, "smrsa3.pem") ], [ "-decrypt", "-recip", catfile($smdir, "smrsa1.pem"), "-in", "test.cms", "-out", "smtst.txt" ] ], [ "enveloped content test streaming PEM format, KEK", [ "-encrypt", "-in", $smcont, "-outform", "PEM", "-aes128", "-stream", "-out", "test.cms", "-secretkey", "000102030405060708090A0B0C0D0E0F", "-secretkeyid", "C0FEE0" ], [ "-decrypt", "-in", "test.cms", "-out", "smtst.txt", "-inform", "PEM", "-secretkey", "000102030405060708090A0B0C0D0E0F", "-secretkeyid", "C0FEE0" ] ], [ "enveloped content test streaming PEM format, KEK, key only", [ "-encrypt", "-in", $smcont, "-outform", "PEM", "-aes128", "-stream", "-out", "test.cms", "-secretkey", "000102030405060708090A0B0C0D0E0F", "-secretkeyid", "C0FEE0" ], [ "-decrypt", "-in", "test.cms", "-out", "smtst.txt", "-inform", "PEM", "-secretkey", "000102030405060708090A0B0C0D0E0F" ] ], [ "data content test streaming PEM format", [ "-data_create", "-in", $smcont, "-outform", "PEM", "-nodetach", "-stream", "-out", "test.cms" ], [ "-data_out", "-in", "test.cms", "-inform", "PEM", "-out", "smtst.txt" ] ], [ "encrypted content test streaming PEM format, 128 bit RC2 key", [ "-EncryptedData_encrypt", "-in", $smcont, "-outform", "PEM", "-rc2", "-secretkey", "000102030405060708090A0B0C0D0E0F", "-stream", "-out", "test.cms" ], [ "-EncryptedData_decrypt", "-in", "test.cms", "-inform", "PEM", "-secretkey", "000102030405060708090A0B0C0D0E0F", "-out", "smtst.txt" ] ], [ "encrypted content test streaming PEM format, 40 bit RC2 key", [ "-EncryptedData_encrypt", "-in", $smcont, "-outform", "PEM", "-rc2", "-secretkey", "0001020304", "-stream", "-out", "test.cms" ], [ "-EncryptedData_decrypt", "-in", "test.cms", "-inform", "PEM", "-secretkey", "0001020304", "-out", "smtst.txt" ] ], [ "encrypted content test streaming PEM format, triple DES key", [ "-EncryptedData_encrypt", "-in", $smcont, "-outform", "PEM", "-des3", "-secretkey", "000102030405060708090A0B0C0D0E0F1011121314151617", "-stream", "-out", "test.cms" ], [ "-EncryptedData_decrypt", "-in", "test.cms", "-inform", "PEM", "-secretkey", "000102030405060708090A0B0C0D0E0F1011121314151617", "-out", "smtst.txt" ] ], [ "encrypted content test streaming PEM format, 128 bit AES key", [ "-EncryptedData_encrypt", "-in", $smcont, "-outform", "PEM", "-aes128", "-secretkey", "000102030405060708090A0B0C0D0E0F", "-stream", "-out", "test.cms" ], [ "-EncryptedData_decrypt", "-in", "test.cms", "-inform", "PEM", "-secretkey", "000102030405060708090A0B0C0D0E0F", "-out", "smtst.txt" ] ], ); my @smime_cms_comp_tests = ( [ "compressed content test streaming PEM format", [ "-compress", "-in", $smcont, "-outform", "PEM", "-nodetach", "-stream", "-out", "test.cms" ], [ "-uncompress", "-in", "test.cms", "-inform", "PEM", "-out", "smtst.txt" ] ] ); my @smime_cms_param_tests = ( [ "signed content test streaming PEM format, RSA keys, PSS signature", [ "-sign", "-in", $smcont, "-outform", "PEM", "-nodetach", "-signer", catfile($smdir, "smrsa1.pem"), "-keyopt", "rsa_padding_mode:pss", "-out", "test.cms" ], [ "-verify", "-in", "test.cms", "-inform", "PEM", "-CAfile", catfile($smdir, "smroot.pem"), "-out", "smtst.txt" ] ], [ "signed content test streaming PEM format, RSA keys, PSS signature, no attributes", [ "-sign", "-in", $smcont, "-outform", "PEM", "-nodetach", "-noattr", "-signer", catfile($smdir, "smrsa1.pem"), "-keyopt", "rsa_padding_mode:pss", "-out", "test.cms" ], [ "-verify", "-in", "test.cms", "-inform", "PEM", "-CAfile", catfile($smdir, "smroot.pem"), "-out", "smtst.txt" ] ], [ "signed content test streaming PEM format, RSA keys, PSS signature, SHA384 MGF1", [ "-sign", "-in", $smcont, "-outform", "PEM", "-nodetach", "-signer", catfile($smdir, "smrsa1.pem"), "-keyopt", "rsa_padding_mode:pss", "-keyopt", "rsa_mgf1_md:sha384", "-out", "test.cms" ], [ "-verify", "-in", "test.cms", "-inform", "PEM", "-CAfile", catfile($smdir, "smroot.pem"), "-out", "smtst.txt" ] ], [ "enveloped content test streaming S/MIME format, DES, OAEP default parameters", [ "-encrypt", "-in", $smcont, "-stream", "-out", "test.cms", "-recip", catfile($smdir, "smrsa1.pem"), "-keyopt", "rsa_padding_mode:oaep" ], [ "-decrypt", "-recip", catfile($smdir, "smrsa1.pem"), "-in", "test.cms", "-out", "smtst.txt" ] ], [ "enveloped content test streaming S/MIME format, DES, OAEP SHA256", [ "-encrypt", "-in", $smcont, "-stream", "-out", "test.cms", "-recip", catfile($smdir, "smrsa1.pem"), "-keyopt", "rsa_padding_mode:oaep", "-keyopt", "rsa_oaep_md:sha256" ], [ "-decrypt", "-recip", catfile($smdir, "smrsa1.pem"), "-in", "test.cms", "-out", "smtst.txt" ] ], [ "enveloped content test streaming S/MIME format, DES, ECDH", [ "-encrypt", "-in", $smcont, "-stream", "-out", "test.cms", "-recip", catfile($smdir, "smec1.pem") ], [ "-decrypt", "-recip", catfile($smdir, "smec1.pem"), "-in", "test.cms", "-out", "smtst.txt" ] ], [ "enveloped content test streaming S/MIME format, ECDH, DES, key identifier", [ "-encrypt", "-keyid", "-in", $smcont, "-stream", "-out", "test.cms", "-recip", catfile($smdir, "smec1.pem") ], [ "-decrypt", "-recip", catfile($smdir, "smec1.pem"), "-in", "test.cms", "-out", "smtst.txt" ] ], [ "enveloped content test streaming S/MIME format, ECDH, AES128, SHA256 KDF", [ "-encrypt", "-in", $smcont, "-stream", "-out", "test.cms", "-recip", catfile($smdir, "smec1.pem"), "-aes128", "-keyopt", "ecdh_kdf_md:sha256" ], [ "-decrypt", "-recip", catfile($smdir, "smec1.pem"), "-in", "test.cms", "-out", "smtst.txt" ] ], [ "enveloped content test streaming S/MIME format, ECDH, K-283, cofactor DH", [ "-encrypt", "-in", $smcont, "-stream", "-out", "test.cms", "-recip", catfile($smdir, "smec2.pem"), "-aes128", "-keyopt", "ecdh_kdf_md:sha256", "-keyopt", "ecdh_cofactor_mode:1" ], [ "-decrypt", "-recip", catfile($smdir, "smec2.pem"), "-in", "test.cms", "-out", "smtst.txt" ] ], [ "enveloped content test streaming S/MIME format, X9.42 DH", [ "-encrypt", "-in", $smcont, "-stream", "-out", "test.cms", "-recip", catfile($smdir, "smdh.pem"), "-aes128" ], [ "-decrypt", "-recip", catfile($smdir, "smdh.pem"), "-in", "test.cms", "-out", "smtst.txt" ] ] ); subtest "CMS => PKCS#7 compatibility tests\n" => sub { plan tests => scalar @smime_pkcs7_tests; foreach (@smime_pkcs7_tests) { SKIP: { my $skip_reason = check_availability($$_[0]); skip $skip_reason, 1 if $skip_reason; ok(run(app(["openssl", "cms", @{$$_[1]}])) && run(app(["openssl", "smime", @{$$_[2]}])) && compare_text($smcont, "smtst.txt") == 0, $$_[0]); } } }; subtest "CMS <= PKCS#7 compatibility tests\n" => sub { plan tests => scalar @smime_pkcs7_tests; foreach (@smime_pkcs7_tests) { SKIP: { my $skip_reason = check_availability($$_[0]); skip $skip_reason, 1 if $skip_reason; ok(run(app(["openssl", "smime", @{$$_[1]}])) && run(app(["openssl", "cms", @{$$_[2]}])) && compare_text($smcont, "smtst.txt") == 0, $$_[0]); } } }; subtest "CMS <=> CMS consistency tests\n" => sub { plan tests => (scalar @smime_pkcs7_tests) + (scalar @smime_cms_tests); foreach (@smime_pkcs7_tests) { SKIP: { my $skip_reason = check_availability($$_[0]); skip $skip_reason, 1 if $skip_reason; ok(run(app(["openssl", "cms", @{$$_[1]}])) && run(app(["openssl", "cms", @{$$_[2]}])) && compare_text($smcont, "smtst.txt") == 0, $$_[0]); } } foreach (@smime_cms_tests) { SKIP: { my $skip_reason = check_availability($$_[0]); skip $skip_reason, 1 if $skip_reason; ok(run(app(["openssl", "cms", @{$$_[1]}])) && run(app(["openssl", "cms", @{$$_[2]}])) && compare_text($smcont, "smtst.txt") == 0, $$_[0]); } } }; subtest "CMS <=> CMS consistency tests, modified key parameters\n" => sub { plan tests => (scalar @smime_cms_param_tests) + (scalar @smime_cms_comp_tests); foreach (@smime_cms_param_tests) { SKIP: { my $skip_reason = check_availability($$_[0]); skip $skip_reason, 1 if $skip_reason; ok(run(app(["openssl", "cms", @{$$_[1]}])) && run(app(["openssl", "cms", @{$$_[2]}])) && compare_text($smcont, "smtst.txt") == 0, $$_[0]); } } SKIP: { skip("Zlib not supported: compression tests skipped", scalar @smime_cms_comp_tests) if $no_zlib; foreach (@smime_cms_comp_tests) { SKIP: { my $skip_reason = check_availability($$_[0]); skip $skip_reason, 1 if $skip_reason; ok(run(app(["openssl", "cms", @{$$_[1]}])) && run(app(["openssl", "cms", @{$$_[2]}])) && compare_text($smcont, "smtst.txt") == 0, $$_[0]); } } } }; unlink "test.cms"; unlink "test2.cms"; unlink "smtst.txt"; sub check_availability { my $tnam = shift; return "$tnam: skipped, EC disabled\n" if ($no_ec && $tnam =~ /ECDH/); return "$tnam: skipped, ECDH disabled\n" if ($no_ec && $tnam =~ /ECDH/); return "$tnam: skipped, EC2M disabled\n" if ($no_ec2m && $tnam =~ /K-283/); return "$tnam: skipped, DH disabled\n" if ($no_dh && $tnam =~ /X9\.42/); return "$tnam: skipped, RC2 disabled\n" if ($no_rc2 && $tnam =~ /RC2/); return "$tnam: skipped, DES disabled\n" if ($no_des && $tnam =~ /DES/); return "$tnam: skipped, DSA disabled\n" if ($no_dsa && $tnam =~ / DSA/); return ""; }