#! /usr/bin/env perl # Copyright 2015-2023 The OpenSSL Project Authors. All Rights Reserved. # # Licensed under the Apache License 2.0 (the "License"). You may not use # this file except in compliance with the License. You can obtain a copy # in the file LICENSE in the source distribution or at # https://www.openssl.org/source/license.html use strict; use warnings; use POSIX; use File::Spec::Functions qw/catfile/; use File::Compare qw/compare_text compare/; use OpenSSL::Test qw/:DEFAULT srctop_dir srctop_file bldtop_dir bldtop_file with data_file/; use OpenSSL::Test::Utils; BEGIN { setup("test_cms"); } use lib srctop_dir('Configurations'); use lib bldtop_dir('.'); my $no_fips = disabled('fips') || ($ENV{NO_FIPS} // 0); plan skip_all => "CMS is not supported by this OpenSSL build" if disabled("cms"); my $provpath = bldtop_dir("providers"); # Some tests require legacy algorithms to be included. my @legacyprov = ("-provider-path", $provpath, "-provider", "default", "-provider", "legacy" ); my @defaultprov = ("-provider-path", $provpath, "-provider", "default"); my @config = ( ); my $provname = 'default'; my $datadir = srctop_dir("test", "recipes", "80-test_cms_data"); my $smdir = srctop_dir("test", "smime-certs"); my $smcont = srctop_file("test", "smcont.txt"); my $smcont_zero = srctop_file("test", "smcont_zero.txt"); my ($no_des, $no_dh, $no_dsa, $no_ec, $no_ec2m, $no_rc2, $no_zlib) = disabled qw/des dh dsa ec ec2m rc2 zlib/; $no_rc2 = 1 if disabled("legacy"); plan tests => 18; ok(run(test(["pkcs7_test"])), "test pkcs7"); unless ($no_fips) { @config = ( "-config", srctop_file("test", "fips-and-base.cnf") ); $provname = 'fips'; } $ENV{OPENSSL_TEST_LIBCTX} = "1"; my @prov = ("-provider-path", $provpath, @config, "-provider", $provname); my $smrsa1024 = catfile($smdir, "smrsa1024.pem"); my $smrsa1 = catfile($smdir, "smrsa1.pem"); my $smroot = catfile($smdir, "smroot.pem"); my @smime_pkcs7_tests = ( [ "signed content DER format, RSA key", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "DER", "-nodetach", "-certfile", $smroot, "-signer", $smrsa1, "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "DER", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "signed detached content DER format, RSA key", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "DER", "-signer", $smrsa1, "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "DER", "-CAfile", $smroot, "-out", "{output}.txt", "-content", $smcont ], \&final_compare ], [ "signed content test streaming BER format, RSA", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "DER", "-nodetach", "-stream", "-signer", $smrsa1, "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "DER", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "signed content DER format, DSA key", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "DER", "-nodetach", "-signer", catfile($smdir, "smdsa1.pem"), "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "DER", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "signed detached content DER format, DSA key", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "DER", "-signer", catfile($smdir, "smdsa1.pem"), "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "DER", "-CAfile", $smroot, "-out", "{output}.txt", "-content", $smcont ], \&final_compare ], [ "signed detached content DER format, add RSA signer (with DSA existing)", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "DER", "-signer", catfile($smdir, "smdsa1.pem"), "-out", "{output}.cms" ], [ "{cmd1}", @prov, "-resign", "-in", "{output}.cms", "-inform", "DER", "-outform", "DER", "-signer", $smrsa1, "-out", "{output}2.cms" ], [ "{cmd2}", @prov, "-verify", "-in", "{output}2.cms", "-inform", "DER", "-CAfile", $smroot, "-out", "{output}.txt", "-content", $smcont ], \&final_compare ], [ "signed content test streaming BER format, DSA key", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "DER", "-nodetach", "-stream", "-signer", catfile($smdir, "smdsa1.pem"), "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "DER", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "signed content test streaming BER format, 2 DSA and 2 RSA keys", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "DER", "-nodetach", "-stream", "-signer", $smrsa1, "-signer", catfile($smdir, "smrsa2.pem"), "-signer", catfile($smdir, "smdsa1.pem"), "-signer", catfile($smdir, "smdsa2.pem"), "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "DER", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "signed content test streaming BER format, 2 DSA and 2 RSA keys, no attributes", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "DER", "-noattr", "-nodetach", "-stream", "-signer", $smrsa1, "-signer", catfile($smdir, "smrsa2.pem"), "-signer", catfile($smdir, "smdsa1.pem"), "-signer", catfile($smdir, "smdsa2.pem"), "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "DER", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "signed content S/MIME format, RSA key SHA1", [ "{cmd1}", @defaultprov, "-sign", "-in", $smcont, "-md", "sha1", "-certfile", $smroot, "-signer", $smrsa1, "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "signed zero-length content S/MIME format, RSA key SHA1", [ "{cmd1}", @defaultprov, "-sign", "-in", $smcont_zero, "-md", "sha1", "-certfile", $smroot, "-signer", $smrsa1, "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-CAfile", $smroot, "-out", "{output}.txt" ], \&zero_compare ], [ "signed content test streaming S/MIME format, 2 DSA and 2 RSA keys", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-nodetach", "-signer", $smrsa1, "-signer", catfile($smdir, "smrsa2.pem"), "-signer", catfile($smdir, "smdsa1.pem"), "-signer", catfile($smdir, "smdsa2.pem"), "-stream", "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "signed content test streaming multipart S/MIME format, 2 DSA and 2 RSA keys", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-signer", $smrsa1, "-signer", catfile($smdir, "smrsa2.pem"), "-signer", catfile($smdir, "smdsa1.pem"), "-signer", catfile($smdir, "smdsa2.pem"), "-stream", "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "enveloped content test streaming S/MIME format, DES, 3 recipients", [ "{cmd1}", @defaultprov, "-encrypt", "-in", $smcont, "-stream", "-out", "{output}.cms", $smrsa1, catfile($smdir, "smrsa2.pem"), catfile($smdir, "smrsa3.pem") ], [ "{cmd2}", @defaultprov, "-decrypt", "-recip", $smrsa1, "-in", "{output}.cms", "-out", "{output}.txt" ], \&final_compare ], [ "enveloped content test streaming S/MIME format, DES, 3 recipients, 3rd used", [ "{cmd1}", @defaultprov, "-encrypt", "-in", $smcont, "-stream", "-out", "{output}.cms", $smrsa1, catfile($smdir, "smrsa2.pem"), catfile($smdir, "smrsa3.pem") ], [ "{cmd2}", @defaultprov, "-decrypt", "-recip", catfile($smdir, "smrsa3.pem"), "-in", "{output}.cms", "-out", "{output}.txt" ], \&final_compare ], [ "enveloped content test streaming S/MIME format, DES, 3 recipients, key only used", [ "{cmd1}", @defaultprov, "-encrypt", "-in", $smcont, "-stream", "-out", "{output}.cms", $smrsa1, catfile($smdir, "smrsa2.pem"), catfile($smdir, "smrsa3.pem") ], [ "{cmd2}", @defaultprov, "-decrypt", "-inkey", catfile($smdir, "smrsa3.pem"), "-in", "{output}.cms", "-out", "{output}.txt" ], \&final_compare ], [ "enveloped content test streaming S/MIME format, AES-256 cipher, 3 recipients", [ "{cmd1}", @prov, "-encrypt", "-in", $smcont, "-aes256", "-stream", "-out", "{output}.cms", $smrsa1, catfile($smdir, "smrsa2.pem"), catfile($smdir, "smrsa3.pem") ], [ "{cmd2}", @prov, "-decrypt", "-recip", $smrsa1, "-in", "{output}.cms", "-out", "{output}.txt" ], \&final_compare ], ); my @smime_cms_tests = ( [ "signed content test streaming BER format, 2 DSA and 2 RSA keys, keyid", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "DER", "-nodetach", "-keyid", "-signer", $smrsa1, "-signer", catfile($smdir, "smrsa2.pem"), "-signer", catfile($smdir, "smdsa1.pem"), "-signer", catfile($smdir, "smdsa2.pem"), "-stream", "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "DER", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "signed content test streaming PEM format, 2 DSA and 2 RSA keys", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "PEM", "-nodetach", "-signer", $smrsa1, "-signer", catfile($smdir, "smrsa2.pem"), "-signer", catfile($smdir, "smdsa1.pem"), "-signer", catfile($smdir, "smdsa2.pem"), "-stream", "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "PEM", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "signed content MIME format, RSA key, signed receipt request", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-nodetach", "-signer", $smrsa1, "-receipt_request_to", "test\@openssl.org", "-receipt_request_all", "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "signed receipt MIME format, RSA key", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-nodetach", "-signer", $smrsa1, "-receipt_request_to", "test\@openssl.org", "-receipt_request_all", "-out", "{output}.cms" ], [ "{cmd1}", @prov, "-sign_receipt", "-in", "{output}.cms", "-signer", catfile($smdir, "smrsa2.pem"), "-out", "{output}2.cms" ], [ "{cmd2}", @prov, "-verify_receipt", "{output}2.cms", "-in", "{output}.cms", "-CAfile", $smroot ] ], [ "enveloped content test streaming S/MIME format, DES, 3 recipients, keyid", [ "{cmd1}", @defaultprov, "-encrypt", "-in", $smcont, "-stream", "-out", "{output}.cms", "-keyid", $smrsa1, catfile($smdir, "smrsa2.pem"), catfile($smdir, "smrsa3.pem") ], [ "{cmd2}", @defaultprov, "-decrypt", "-recip", $smrsa1, "-in", "{output}.cms", "-out", "{output}.txt" ], \&final_compare ], [ "enveloped content test streaming PEM format, AES-256-CBC cipher, KEK", [ "{cmd1}", @prov, "-encrypt", "-in", $smcont, "-outform", "PEM", "-aes128", "-stream", "-out", "{output}.cms", "-secretkey", "000102030405060708090A0B0C0D0E0F", "-secretkeyid", "C0FEE0" ], [ "{cmd2}", @prov, "-decrypt", "-in", "{output}.cms", "-out", "{output}.txt", "-inform", "PEM", "-secretkey", "000102030405060708090A0B0C0D0E0F", "-secretkeyid", "C0FEE0" ], \&final_compare ], [ "enveloped content test streaming PEM format, AES-256-GCM cipher, KEK", [ "{cmd1}", @prov, "-encrypt", "-in", $smcont, "-outform", "PEM", "-aes-128-gcm", "-stream", "-out", "{output}.cms", "-secretkey", "000102030405060708090A0B0C0D0E0F", "-secretkeyid", "C0FEE0" ], [ "{cmd2}", "-decrypt", "-in", "{output}.cms", "-out", "{output}.txt", "-inform", "PEM", "-secretkey", "000102030405060708090A0B0C0D0E0F", "-secretkeyid", "C0FEE0" ], \&final_compare ], [ "enveloped content test streaming PEM format, KEK, key only", [ "{cmd1}", @prov, "-encrypt", "-in", $smcont, "-outform", "PEM", "-aes128", "-stream", "-out", "{output}.cms", "-secretkey", "000102030405060708090A0B0C0D0E0F", "-secretkeyid", "C0FEE0" ], [ "{cmd2}", @prov, "-decrypt", "-in", "{output}.cms", "-out", "{output}.txt", "-inform", "PEM", "-secretkey", "000102030405060708090A0B0C0D0E0F" ], \&final_compare ], [ "data content test streaming PEM format", [ "{cmd1}", @prov, "-data_create", "-in", $smcont, "-outform", "PEM", "-nodetach", "-stream", "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-data_out", "-in", "{output}.cms", "-inform", "PEM", "-out", "{output}.txt" ], \&final_compare ], [ "encrypted content test streaming PEM format, 128 bit RC2 key", [ "{cmd1}", @legacyprov, "-EncryptedData_encrypt", "-in", $smcont, "-outform", "PEM", "-rc2", "-secretkey", "000102030405060708090A0B0C0D0E0F", "-stream", "-out", "{output}.cms" ], [ "{cmd2}", @legacyprov, "-EncryptedData_decrypt", "-in", "{output}.cms", "-inform", "PEM", "-secretkey", "000102030405060708090A0B0C0D0E0F", "-out", "{output}.txt" ], \&final_compare ], [ "encrypted content test streaming PEM format, 40 bit RC2 key", [ "{cmd1}", @legacyprov, "-EncryptedData_encrypt", "-in", $smcont, "-outform", "PEM", "-rc2", "-secretkey", "0001020304", "-stream", "-out", "{output}.cms" ], [ "{cmd2}", @legacyprov, "-EncryptedData_decrypt", "-in", "{output}.cms", "-inform", "PEM", "-secretkey", "0001020304", "-out", "{output}.txt" ], \&final_compare ], [ "encrypted content test streaming PEM format, triple DES key", [ "{cmd1}", @prov, "-EncryptedData_encrypt", "-in", $smcont, "-outform", "PEM", "-des3", "-secretkey", "000102030405060708090A0B0C0D0E0F1011121314151617", "-stream", "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-EncryptedData_decrypt", "-in", "{output}.cms", "-inform", "PEM", "-secretkey", "000102030405060708090A0B0C0D0E0F1011121314151617", "-out", "{output}.txt" ], \&final_compare ], [ "encrypted content test streaming PEM format, 128 bit AES key", [ "{cmd1}", @prov, "-EncryptedData_encrypt", "-in", $smcont, "-outform", "PEM", "-aes128", "-secretkey", "000102030405060708090A0B0C0D0E0F", "-stream", "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-EncryptedData_decrypt", "-in", "{output}.cms", "-inform", "PEM", "-secretkey", "000102030405060708090A0B0C0D0E0F", "-out", "{output}.txt" ], \&final_compare ], ); my @smime_cms_cades_tests = ( [ "signed content DER format, RSA key, CAdES-BES compatible", [ "{cmd1}", @prov, "-sign", "-cades", "-in", $smcont, "-outform", "DER", "-nodetach", "-certfile", $smroot, "-signer", $smrsa1, "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-cades", "-in", "{output}.cms", "-inform", "DER", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "signed content DER format, RSA key, SHA256 md, CAdES-BES compatible", [ "{cmd1}", @prov, "-sign", "-cades", "-md", "sha256", "-in", $smcont, "-outform", "DER", "-nodetach", "-certfile", $smroot, "-signer", $smrsa1, "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-cades", "-in", "{output}.cms", "-inform", "DER", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "signed content DER format, RSA key, SHA512 md, CAdES-BES compatible", [ "{cmd1}", @prov, "-sign", "-cades", "-md", "sha512", "-in", $smcont, "-outform", "DER", "-nodetach", "-certfile", $smroot, "-signer", $smrsa1, "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-cades", "-in", "{output}.cms", "-inform", "DER", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "signed content DER format, RSA key, SHA256 md, CAdES-BES compatible", [ "{cmd1}", @prov, "-sign", "-cades", "-binary", "-nodetach", "-nosmimecap", "-md", "sha256", "-in", $smcont, "-outform", "DER", "-certfile", $smroot, "-signer", $smrsa1, "-outform", "DER", "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-cades", "-in", "{output}.cms", "-inform", "DER", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "resigned content DER format, RSA key, SHA256 md, CAdES-BES compatible", [ "{cmd1}", @prov, "-sign", "-cades", "-binary", "-nodetach", "-nosmimecap", "-md", "sha256", "-in", $smcont, "-outform", "DER", "-certfile", $smroot, "-signer", $smrsa1, "-outform", "DER", "-out", "{output}.cms" ], [ "{cmd1}", @prov, "-resign", "-cades", "-binary", "-nodetach", "-nosmimecap", "-md", "sha256", "-inform", "DER", "-in", "{output}.cms", "-certfile", $smroot, "-signer", catfile($smdir, "smrsa2.pem"), "-outform", "DER", "-out", "{output}2.cms" ], [ "{cmd2}", @prov, "-verify", "-cades", "-in", "{output}2.cms", "-inform", "DER", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], ); my @smime_cms_cades_ko_tests = ( [ "sign content DER format, RSA key, not CAdES-BES compatible", [ @prov, "-sign", "-in", $smcont, "-outform", "DER", "-nodetach", "-certfile", $smroot, "-signer", $smrsa1, "-out", "{output}.cms" ], "fail to verify token since requiring CAdES-BES compatibility", [ @prov, "-verify", "-cades", "-in", "{output}.cms", "-inform", "DER", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ] ); # cades options test - check that some combinations are rejected my @smime_cms_cades_invalid_option_tests = ( [ [ "-cades", "-noattr" ], ],[ [ "-verify", "-cades", "-noattr" ], ],[ [ "-verify", "-cades", "-noverify" ], ], ); my @smime_cms_comp_tests = ( [ "compressed content test streaming PEM format", [ "{cmd1}", @prov, "-compress", "-in", $smcont, "-outform", "PEM", "-nodetach", "-stream", "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-uncompress", "-in", "{output}.cms", "-inform", "PEM", "-out", "{output}.txt" ], \&final_compare ] ); my @smime_cms_param_tests = ( [ "signed content test streaming PEM format, RSA keys, PSS signature", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "PEM", "-nodetach", "-signer", $smrsa1, "-keyopt", "rsa_padding_mode:pss", "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "PEM", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "signed content test streaming PEM format, RSA keys, PSS signature, saltlen=max", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "PEM", "-nodetach", "-signer", $smrsa1, "-keyopt", "rsa_padding_mode:pss", "-keyopt", "rsa_pss_saltlen:max", "-out", "{output}.cms" ], sub { my %opts = @_; rsapssSaltlen("$opts{output}.cms") == 222; }, [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "PEM", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "signed content test streaming PEM format, RSA keys, PSS signature, no attributes", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "PEM", "-nodetach", "-noattr", "-signer", $smrsa1, "-keyopt", "rsa_padding_mode:pss", "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "PEM", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "signed content test streaming PEM format, RSA keys, PSS signature, SHA384 MGF1", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "PEM", "-nodetach", "-signer", $smrsa1, "-keyopt", "rsa_padding_mode:pss", "-keyopt", "rsa_mgf1_md:sha384", "-out", "{output}.cms" ], [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "PEM", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "signed content test streaming PEM format, RSA keys, PSS signature, saltlen=16", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "PEM", "-nodetach", "-signer", $smrsa1, "-md", "sha256", "-keyopt", "rsa_padding_mode:pss", "-keyopt", "rsa_pss_saltlen:16", "-out", "{output}.cms" ], sub { my %opts = @_; rsapssSaltlen("$opts{output}.cms") == 16; }, [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "PEM", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "signed content test streaming PEM format, RSA keys, PSS signature, saltlen=digest", [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "PEM", "-nodetach", "-signer", $smrsa1, "-md", "sha256", "-keyopt", "rsa_padding_mode:pss", "-keyopt", "rsa_pss_saltlen:digest", "-out", "{output}.cms" ], # digest is SHA-256, which produces 32 bytes of output sub { my %opts = @_; rsapssSaltlen("$opts{output}.cms") == 32; }, [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "PEM", "-CAfile", $smroot, "-out", "{output}.txt" ], \&final_compare ], [ "enveloped content test streaming S/MIME format, DES, OAEP default parameters", [ "{cmd1}", @defaultprov, "-encrypt", "-in", $smcont, "-stream", "-out", "{output}.cms", "-recip", $smrsa1, "-keyopt", "rsa_padding_mode:oaep" ], [ "{cmd2}", @defaultprov, "-decrypt", "-recip", $smrsa1, "-in", "{output}.cms", "-out", "{output}.txt" ], \&final_compare ], [ "enveloped content test streaming S/MIME format, DES, OAEP SHA256", [ "{cmd1}", @defaultprov, "-encrypt", "-in", $smcont, "-stream", "-out", "{output}.cms", "-recip", $smrsa1, "-keyopt", "rsa_padding_mode:oaep", "-keyopt", "rsa_oaep_md:sha256" ], [ "{cmd2}", @defaultprov, "-decrypt", "-recip", $smrsa1, "-in", "{output}.cms", "-out", "{output}.txt" ], \&final_compare ], [ "enveloped content test streaming S/MIME format, DES, ECDH", [ "{cmd1}", @defaultprov, "-encrypt", "-in", $smcont, "-stream", "-out", "{output}.cms", "-recip", catfile($smdir, "smec1.pem") ], [ "{cmd2}", @defaultprov, "-decrypt", "-recip", catfile($smdir, "smec1.pem"), "-in", "{output}.cms", "-out", "{output}.txt" ], \&final_compare ], [ "enveloped content test streaming S/MIME format, DES, ECDH, 2 recipients, key only used", [ "{cmd1}", @defaultprov, "-encrypt", "-in", $smcont, "-stream", "-out", "{output}.cms", catfile($smdir, "smec1.pem"), catfile($smdir, "smec3.pem") ], [ "{cmd2}", @defaultprov, "-decrypt", "-inkey", catfile($smdir, "smec3.pem"), "-in", "{output}.cms", "-out", "{output}.txt" ], \&final_compare ], [ "enveloped content test streaming S/MIME format, ECDH, DES, key identifier", [ "{cmd1}", @defaultprov, "-encrypt", "-keyid", "-in", $smcont, "-stream", "-out", "{output}.cms", "-recip", catfile($smdir, "smec1.pem") ], [ "{cmd2}", @defaultprov, "-decrypt", "-recip", catfile($smdir, "smec1.pem"), "-in", "{output}.cms", "-out", "{output}.txt" ], \&final_compare ], [ "enveloped content test streaming S/MIME format, ECDH, AES-128-CBC, SHA256 KDF", [ "{cmd1}", @prov, "-encrypt", "-in", $smcont, "-stream", "-out", "{output}.cms", "-recip", catfile($smdir, "smec1.pem"), "-aes128", "-keyopt", "ecdh_kdf_md:sha256" ], [ "{cmd2}", @prov, "-decrypt", "-recip", catfile($smdir, "smec1.pem"), "-in", "{output}.cms", "-out", "{output}.txt" ], \&final_compare ], [ "enveloped content test streaming S/MIME format, ECDH, AES-128-GCM cipher, SHA256 KDF", [ "{cmd1}", @prov, "-encrypt", "-in", $smcont, "-stream", "-out", "{output}.cms", "-recip", catfile($smdir, "smec1.pem"), "-aes-128-gcm", "-keyopt", "ecdh_kdf_md:sha256" ], [ "{cmd2}", "-decrypt", "-recip", catfile($smdir, "smec1.pem"), "-in", "{output}.cms", "-out", "{output}.txt" ], \&final_compare ], [ "enveloped content test streaming S/MIME format, ECDH, K-283, cofactor DH", [ "{cmd1}", @prov, "-encrypt", "-in", $smcont, "-stream", "-out", "{output}.cms", "-recip", catfile($smdir, "smec2.pem"), "-aes128", "-keyopt", "ecdh_kdf_md:sha256", "-keyopt", "ecdh_cofactor_mode:1" ], [ "{cmd2}", @prov, "-decrypt", "-recip", catfile($smdir, "smec2.pem"), "-in", "{output}.cms", "-out", "{output}.txt" ], \&final_compare ], [ "enveloped content test streaming S/MIME format, X9.42 DH", [ "{cmd1}", @prov, "-encrypt", "-in", $smcont, "-stream", "-out", "{output}.cms", "-recip", catfile($smdir, "smdh.pem"), "-aes128" ], [ "{cmd2}", @prov, "-decrypt", "-recip", catfile($smdir, "smdh.pem"), "-in", "{output}.cms", "-out", "{output}.txt" ], \&final_compare ] ); my @contenttype_cms_test = ( [ "signed content test - check that content type is added to additional signerinfo, RSA keys", [ "{cmd1}", @prov, "-sign", "-binary", "-nodetach", "-stream", "-in", $smcont, "-outform", "DER", "-signer", $smrsa1, "-md", "SHA256", "-out", "{output}.cms" ], [ "{cmd1}", @prov, "-resign", "-binary", "-nodetach", "-in", "{output}.cms", "-inform", "DER", "-outform", "DER", "-signer", catfile($smdir, "smrsa2.pem"), "-md", "SHA256", "-out", "{output}2.cms" ], sub { my %opts = @_; contentType_matches("$opts{output}2.cms") == 2; }, [ "{cmd2}", @prov, "-verify", "-in", "{output}2.cms", "-inform", "DER", "-CAfile", $smroot, "-out", "{output}.txt" ] ], ); my @incorrect_attribute_cms_test = ( "bad_signtime_attr.cms", "no_ct_attr.cms", "no_md_attr.cms", "ct_multiple_attr.cms" ); # Runs a standard loop on the input array sub runner_loop { my %opts = ( @_ ); my $cnt1 = 0; foreach (@{$opts{tests}}) { $cnt1++; $opts{output} = "$opts{prefix}-$cnt1"; SKIP: { my $skip_reason = check_availability($$_[0]); skip $skip_reason, 1 if $skip_reason; my $ok = 1; 1 while unlink "$opts{output}.txt"; foreach (@$_[1..$#$_]) { if (ref $_ eq 'CODE') { $ok &&= $_->(%opts); } else { my @cmd = map { my $x = $_; while ($x =~ /\{([^\}]+)\}/) { $x = $`.$opts{$1}.$' if exists $opts{$1}; } $x; } @$_; diag "CMD: openssl ", join(" ", @cmd); $ok &&= run(app(["openssl", @cmd])); $opts{input} = $opts{output}; } } ok($ok, $$_[0]); } } } sub final_compare { my %opts = @_; diag "Comparing $smcont with $opts{output}.txt"; return compare_text($smcont, "$opts{output}.txt") == 0; } sub zero_compare { my %opts = @_; diag "Checking for zero-length file"; return (-e "$opts{output}.txt" && -z "$opts{output}.txt"); } subtest "CMS => PKCS#7 compatibility tests\n" => sub { plan tests => scalar @smime_pkcs7_tests; runner_loop(prefix => 'cms2pkcs7', cmd1 => 'cms', cmd2 => 'smime', tests => [ @smime_pkcs7_tests ]); }; subtest "CMS <= PKCS#7 compatibility tests\n" => sub { plan tests => scalar @smime_pkcs7_tests; runner_loop(prefix => 'pkcs72cms', cmd1 => 'smime', cmd2 => 'cms', tests => [ @smime_pkcs7_tests ]); }; subtest "CMS <=> CMS consistency tests\n" => sub { plan tests => (scalar @smime_pkcs7_tests) + (scalar @smime_cms_tests); runner_loop(prefix => 'cms2cms-1', cmd1 => 'cms', cmd2 => 'cms', tests => [ @smime_pkcs7_tests ]); runner_loop(prefix => 'cms2cms-2', cmd1 => 'cms', cmd2 => 'cms', tests => [ @smime_cms_tests ]); }; subtest "CMS <=> CMS consistency tests, modified key parameters\n" => sub { plan tests => (scalar @smime_cms_param_tests) + (scalar @smime_cms_comp_tests); runner_loop(prefix => 'cms2cms-mod', cmd1 => 'cms', cmd2 => 'cms', tests => [ @smime_cms_param_tests ]); SKIP: { skip("Zlib not supported: compression tests skipped", scalar @smime_cms_comp_tests) if $no_zlib; runner_loop(prefix => 'cms2cms-comp', cmd1 => 'cms', cmd2 => 'cms', tests => [ @smime_cms_comp_tests ]); } }; # Returns the number of matches of a Content Type Attribute in a binary file. sub contentType_matches { # Read in a binary file my ($in) = @_; open (HEX_IN, "$in") or die("open failed for $in : $!"); binmode(HEX_IN); local $/; my $str = ; # Find ASN1 data for a Content Type Attribute (with a OID of PKCS7 data) my @c = $str =~ /\x30\x18\x06\x09\x2A\x86\x48\x86\xF7\x0D\x01\x09\x03\x31\x0B\x06\x09\x2A\x86\x48\x86\xF7\x0D\x01\x07\x01/gs; close(HEX_IN); return scalar(@c); } sub rsapssSaltlen { my ($in) = @_; my $exit = 0; my @asn1parse = run(app(["openssl", "asn1parse", "-in", $in, "-dump"]), capture => 1, statusvar => $exit); return -1 if $exit != 0; my $pssparam_offset = -1; while ($_ = shift @asn1parse) { chomp; next unless /:rsassaPss/; # This line contains :rsassaPss, the next line contains a raw dump of the # RSA_PSS_PARAMS sequence; obtain its offset $_ = shift @asn1parse; if (/^\s*(\d+):/) { $pssparam_offset = int($1); } } if ($pssparam_offset == -1) { note "Failed to determine RSA_PSS_PARAM offset in CMS. " + "Was the file correctly signed with RSASSA-PSS?"; return -1; } my @pssparam = run(app(["openssl", "asn1parse", "-in", $in, "-strparse", $pssparam_offset]), capture => 1, statusvar => $exit); return -1 if $exit != 0; my $saltlen = -1; # Can't use asn1parse -item RSA_PSS_PARAMS here, because that's deprecated. # This assumes the salt length is the last field, which may possibly be # incorrect if there is a non-standard trailer field, but there almost never # is in PSS. if ($pssparam[-1] =~ /prim:\s+INTEGER\s+:([A-Fa-f0-9]+)/) { $saltlen = hex($1); } if ($saltlen == -1) { note "Failed to determine salt length from RSA_PSS_PARAM struct. " + "Was the file correctly signed with RSASSA-PSS?"; return -1; } return $saltlen; } subtest "CMS Check the content type attribute is added for additional signers\n" => sub { plan tests => (scalar @contenttype_cms_test); runner_loop(prefix => 'cms2cms-added', cmd1 => 'cms', cmd2 => 'cms', tests => [ @contenttype_cms_test ]); }; subtest "CMS Check that bad attributes fail when verifying signers\n" => sub { plan tests => (scalar @incorrect_attribute_cms_test); my $cnt = 0; foreach my $name (@incorrect_attribute_cms_test) { my $out = "incorrect-$cnt.txt"; ok(!run(app(["openssl", "cms", @prov, "-verify", "-in", catfile($datadir, $name), "-inform", "DER", "-CAfile", $smroot, "-out", $out ])), $name); } }; subtest "CMS Check that bad encryption algorithm fails\n" => sub { plan tests => 1; SKIP: { skip "DES or Legacy isn't supported in this build", 1 if disabled("des") || disabled("legacy"); my $out = "smtst.txt"; ok(!run(app(["openssl", "cms", @legacyprov, "-encrypt", "-in", $smcont, "-stream", "-recip", $smrsa1, "-des-ede3", "-out", $out ])), "Decrypt message from OpenSSL 1.1.1"); } }; subtest "CMS Decrypt message encrypted with OpenSSL 1.1.1\n" => sub { plan tests => 1; SKIP: { skip "EC or DES isn't supported in this build", 1 if disabled("ec") || disabled("des"); my $out = "smtst.txt"; ok(run(app(["openssl", "cms", @defaultprov, "-decrypt", "-inkey", catfile($smdir, "smec3.pem"), "-in", catfile($datadir, "ciphertext_from_1_1_1.cms"), "-out", $out ])) && compare_text($smcont, $out) == 0, "Decrypt message from OpenSSL 1.1.1"); } }; subtest "CAdES <=> CAdES consistency tests\n" => sub { plan tests => (scalar @smime_cms_cades_tests); runner_loop(prefix => 'cms-cades', cmd1 => 'cms', cmd2 => 'cms', tests => [ @smime_cms_cades_tests ]); }; subtest "CAdES; cms incompatible arguments tests\n" => sub { plan tests => (scalar @smime_cms_cades_invalid_option_tests); foreach (@smime_cms_cades_invalid_option_tests) { ok(!run(app(["openssl", "cms", @{$$_[0]} ] ))); } }; subtest "CAdES ko tests\n" => sub { plan tests => 2 * scalar @smime_cms_cades_ko_tests; foreach (@smime_cms_cades_ko_tests) { SKIP: { my $skip_reason = check_availability($$_[0]); skip $skip_reason, 1 if $skip_reason; ok(run(app(["openssl", "cms", @{$$_[1]}])), $$_[0]); ok(!run(app(["openssl", "cms", @{$$_[3]}])), $$_[2]); } } }; subtest "CMS binary input tests\n" => sub { my $input = srctop_file("test", "smcont.bin"); my $signed = "smcont.signed"; my $verified = "smcont.verified"; plan tests => 11; ok(run(app(["openssl", "cms", "-sign", "-md", "sha256", "-signer", $smrsa1, "-binary", "-in", $input, "-out", $signed])), "sign binary input with -binary"); ok(run(app(["openssl", "cms", "-verify", "-CAfile", $smroot, "-binary", "-in", $signed, "-out", $verified])), "verify binary input with -binary"); is(compare($input, $verified), 0, "binary input retained with -binary"); ok(run(app(["openssl", "cms", "-sign", "-md", "sha256", "-signer", $smrsa1, "-in", $input, "-out", $signed.".nobin"])), "sign binary input without -binary"); ok(run(app(["openssl", "cms", "-verify", "-CAfile", $smroot, "-in", $signed.".nobin", "-out", $verified.".nobin"])), "verify binary input without -binary"); is(compare($input, $verified.".nobin"), 1, "binary input not retained without -binary"); ok(!run(app(["openssl", "cms", "-verify", "-CAfile", $smroot, "-crlfeol", "-binary", "-in", $signed, "-out", $verified.".crlfeol"])), "verify binary input wrong crlfeol"); ok(run(app(["openssl", "cms", "-sign", "-md", "sha256", "-signer", $smrsa1, "-crlfeol", "-binary", "-in", $input, "-out", $signed.".crlf"])), "sign binary input with -binary -crlfeol"); ok(run(app(["openssl", "cms", "-verify", "-CAfile", $smroot, "-crlfeol", "-binary", "-in", $signed.".crlf", "-out", $verified.".crlf"])), "verify binary input with -binary -crlfeol"); is(compare($input, $verified.".crlf"), 0, "binary input retained with -binary -crlfeol"); ok(!run(app(["openssl", "cms", "-verify", "-CAfile", $smroot, "-binary", "-in", $signed.".crlf", "-out", $verified.".crlf2"])), "verify binary input with -binary missing -crlfeol"); }; # Test case for missing MD algorithm (must not segfault) with({ exit_checker => sub { return shift == 4; } }, sub { ok(run(app(['openssl', 'smime', '-verify', '-noverify', '-inform', 'PEM', '-in', data_file("pkcs7-md4.pem"), ])), "Check failure of EVP_DigestInit is handled correctly"); }); 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 ""; } # Test case for the locking problem reported in #19643. # This will fail if the fix is in and deadlock on Windows (and possibly # other platforms) if not. ok(!run(app(['openssl', 'cms', '-verify', '-CAfile', srctop_file("test/certs", "pkitsta.pem"), '-policy', 'anyPolicy', '-in', srctop_file("test/smime-eml", "SignedInvalidMappingFromanyPolicyTest7.eml") ])), "issue#19643"); # Check that we get the expected failure return code with({ exit_checker => sub { return shift == 6; } }, sub { ok(run(app(['openssl', 'cms', '-encrypt', '-in', srctop_file("test", "smcont.txt"), '-aes128', '-stream', '-recip', srctop_file("test/smime-certs", "badrsa.pem"), ])), "Check failure during BIO setup with -stream is handled correctly"); }); # Test case for return value mis-check reported in #21986 with({ exit_checker => sub { return shift == 3; } }, sub { SKIP: { skip "DSA is not supported in this build", 1 if $no_dsa; ok(run(app(['openssl', 'cms', '-sign', '-in', srctop_file("test", "smcont.txt"), '-signer', srctop_file("test/smime-certs", "smdsa1.pem"), '-md', 'SHAKE256'])), "issue#21986"); } }); # Test for problem reported in #22225 with({ exit_checker => sub { return shift == 3; } }, sub { ok(run(app(['openssl', 'cms', '-encrypt', '-in', srctop_file("test", "smcont.txt"), '-aes-256-ctr', '-recip', catfile($smdir, "smec1.pem"), ])), "Check for failure when cipher does not have an assigned OID (issue#22225)"); });