test/recipes/80-test_cms.t

   1 #! /usr/bin/env perl
   2 # Copyright 2015-2023 The OpenSSL Project Authors. All Rights Reserved.
   3 #
   4 # Licensed under the Apache License 2.0 (the "License").  You may not use
   5 # this file except in compliance with the License.  You can obtain a copy
   6 # in the file LICENSE in the source distribution or at
   7 # https://www.openssl.org/source/license.html
   8
   9
  10 use strict;
  11 use warnings;
  12
  13 use POSIX;
  14 use File::Spec::Functions qw/catfile/;
  15 use File::Compare qw/compare_text compare/;
  16 use OpenSSL::Test qw/:DEFAULT srctop_dir srctop_file bldtop_dir bldtop_file with data_file/;
  17
  18 use OpenSSL::Test::Utils;
  19
  20 BEGIN {
  21     setup("test_cms");
  22 }
  23
  24 use lib srctop_dir('Configurations');
  25 use lib bldtop_dir('.');
  26
  27 my $no_fips = disabled('fips') || ($ENV{NO_FIPS} // 0);
  28
  29 plan skip_all => "CMS is not supported by this OpenSSL build"
  30     if disabled("cms");
  31
  32 my $provpath = bldtop_dir("providers");
  33
  34 # Some tests require legacy algorithms to be included.
  35 my @legacyprov = ("-provider-path", $provpath,
  36                   "-provider", "default",
  37                   "-provider", "legacy" );
  38 my @defaultprov = ("-provider-path", $provpath,
  39                    "-provider", "default");
  40
  41 my @config = ( );
  42 my $provname = 'default';
  43
  44 my $datadir = srctop_dir("test", "recipes", "80-test_cms_data");
  45 my $smdir    = srctop_dir("test", "smime-certs");
  46 my $smcont   = srctop_file("test", "smcont.txt");
  47 my $smcont_zero = srctop_file("test", "smcont_zero.txt");
  48 my ($no_des, $no_dh, $no_dsa, $no_ec, $no_ec2m, $no_rc2, $no_zlib)
  49     = disabled qw/des dh dsa ec ec2m rc2 zlib/;
  50
  51 $no_rc2 = 1 if disabled("legacy");
  52
  53 plan tests => 23;
  54
  55 ok(run(test(["pkcs7_test"])), "test pkcs7");
  56
  57 unless ($no_fips) {
  58     @config = ( "-config", srctop_file("test", "fips-and-base.cnf") );
  59     $provname = 'fips';
  60 }
  61
  62 $ENV{OPENSSL_TEST_LIBCTX} = "1";
  63 my @prov = ("-provider-path", $provpath,
  64             @config,
  65             "-provider", $provname);
  66
  67 my $smrsa1024 = catfile($smdir, "smrsa1024.pem");
  68 my $smrsa1 = catfile($smdir, "smrsa1.pem");
  69 my $smroot = catfile($smdir, "smroot.pem");
  70
  71 my @smime_pkcs7_tests = (
  72
  73     [ "signed content DER format, RSA key",
  74       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "DER", "-nodetach",
  75         "-certfile", $smroot, "-signer", $smrsa1, "-out", "{output}.cms" ],
  76       [ "{cmd2}",  @prov, "-verify", "-in", "{output}.cms", "-inform", "DER",
  77         "-CAfile", $smroot, "-out", "{output}.txt" ],
  78       \&final_compare
  79     ],
  80
  81     [ "signed detached content DER format, RSA key",
  82       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "DER",
  83         "-signer", $smrsa1, "-out", "{output}.cms" ],
  84       [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "DER",
  85         "-CAfile", $smroot, "-out", "{output}.txt",
  86         "-content", $smcont ],
  87       \&final_compare
  88     ],
  89
  90     [ "signed content test streaming BER format, RSA",
  91       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "DER", "-nodetach",
  92         "-stream",
  93         "-signer", $smrsa1, "-out", "{output}.cms" ],
  94       [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "DER",
  95         "-CAfile", $smroot, "-out", "{output}.txt" ],
  96       \&final_compare
  97     ],
  98
  99     [ "signed content DER format, DSA key",
 100       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "DER", "-nodetach",
 101         "-signer", catfile($smdir, "smdsa1.pem"), "-out", "{output}.cms" ],
 102       [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "DER",
 103         "-CAfile", $smroot, "-out", "{output}.txt" ],
 104       \&final_compare
 105     ],
 106
 107     [ "signed detached content DER format, DSA key",
 108       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "DER",
 109         "-signer", catfile($smdir, "smdsa1.pem"), "-out", "{output}.cms" ],
 110       [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "DER",
 111         "-CAfile", $smroot, "-out", "{output}.txt",
 112         "-content", $smcont ],
 113       \&final_compare
 114     ],
 115
 116     [ "signed detached content DER format, add RSA signer (with DSA existing)",
 117       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "DER",
 118         "-signer", catfile($smdir, "smdsa1.pem"), "-out", "{output}.cms" ],
 119       [ "{cmd1}", @prov, "-resign", "-in", "{output}.cms", "-inform", "DER", "-outform", "DER",
 120         "-signer", $smrsa1, "-out", "{output}2.cms" ],
 121       [ "{cmd2}", @prov, "-verify", "-in", "{output}2.cms", "-inform", "DER",
 122         "-CAfile", $smroot, "-out", "{output}.txt",
 123         "-content", $smcont ],
 124       \&final_compare
 125     ],
 126
 127     [ "signed content test streaming BER format, DSA key",
 128       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "DER",
 129         "-nodetach", "-stream",
 130         "-signer", catfile($smdir, "smdsa1.pem"), "-out", "{output}.cms" ],
 131       [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "DER",
 132         "-CAfile", $smroot, "-out", "{output}.txt" ],
 133       \&final_compare
 134     ],
 135
 136     [ "signed content test streaming BER format, 2 DSA and 2 RSA keys",
 137       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "DER",
 138         "-nodetach", "-stream",
 139         "-signer", $smrsa1,
 140         "-signer", catfile($smdir, "smrsa2.pem"),
 141         "-signer", catfile($smdir, "smdsa1.pem"),
 142         "-signer", catfile($smdir, "smdsa2.pem"),
 143         "-out", "{output}.cms" ],
 144       [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "DER",
 145         "-CAfile", $smroot, "-out", "{output}.txt" ],
 146       \&final_compare
 147     ],
 148
 149     [ "signed content test streaming BER format, 2 DSA and 2 RSA keys, no attributes",
 150       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "DER",
 151         "-noattr", "-nodetach", "-stream",
 152         "-signer", $smrsa1,
 153         "-signer", catfile($smdir, "smrsa2.pem"),
 154         "-signer", catfile($smdir, "smdsa1.pem"),
 155         "-signer", catfile($smdir, "smdsa2.pem"),
 156         "-out", "{output}.cms" ],
 157       [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "DER",
 158         "-CAfile", $smroot, "-out", "{output}.txt" ],
 159       \&final_compare
 160     ],
 161
 162     [ "signed content S/MIME format, RSA key SHA1",
 163       [ "{cmd1}", @defaultprov, "-sign", "-in", $smcont, "-md", "sha1",
 164         "-certfile", $smroot,
 165         "-signer", $smrsa1, "-out", "{output}.cms" ],
 166       [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms",
 167         "-CAfile", $smroot, "-out", "{output}.txt" ],
 168       \&final_compare
 169     ],
 170
 171     [ "signed zero-length content S/MIME format, RSA key SHA1",
 172       [ "{cmd1}", @defaultprov, "-sign", "-in", $smcont_zero, "-md", "sha1",
 173         "-certfile", $smroot, "-signer", $smrsa1, "-out", "{output}.cms" ],
 174       [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms",
 175         "-CAfile", $smroot, "-out", "{output}.txt" ],
 176       \&zero_compare
 177     ],
 178
 179     [ "signed content test streaming S/MIME format, 2 DSA and 2 RSA keys",
 180       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-nodetach",
 181         "-signer", $smrsa1,
 182         "-signer", catfile($smdir, "smrsa2.pem"),
 183         "-signer", catfile($smdir, "smdsa1.pem"),
 184         "-signer", catfile($smdir, "smdsa2.pem"),
 185         "-stream", "-out", "{output}.cms" ],
 186       [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms",
 187         "-CAfile", $smroot, "-out", "{output}.txt" ],
 188       \&final_compare
 189     ],
 190
 191     [ "signed content test streaming multipart S/MIME format, 2 DSA and 2 RSA keys",
 192       [ "{cmd1}", @prov, "-sign", "-in", $smcont,
 193         "-signer", $smrsa1,
 194         "-signer", catfile($smdir, "smrsa2.pem"),
 195         "-signer", catfile($smdir, "smdsa1.pem"),
 196         "-signer", catfile($smdir, "smdsa2.pem"),
 197         "-stream", "-out", "{output}.cms" ],
 198       [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms",
 199         "-CAfile", $smroot, "-out", "{output}.txt" ],
 200       \&final_compare
 201     ],
 202
 203     [ "enveloped content test streaming S/MIME format, DES, 3 recipients",
 204       [ "{cmd1}", @defaultprov, "-encrypt", "-in", $smcont,
 205         "-stream", "-out", "{output}.cms",
 206         $smrsa1,
 207         catfile($smdir, "smrsa2.pem"),
 208         catfile($smdir, "smrsa3.pem") ],
 209       [ "{cmd2}", @defaultprov, "-decrypt", "-recip", $smrsa1,
 210         "-in", "{output}.cms", "-out", "{output}.txt" ],
 211       \&final_compare
 212     ],
 213
 214     [ "enveloped content test streaming S/MIME format, DES, 3 recipients, 3rd used",
 215       [ "{cmd1}", @defaultprov, "-encrypt", "-in", $smcont,
 216         "-stream", "-out", "{output}.cms",
 217         $smrsa1,
 218         catfile($smdir, "smrsa2.pem"),
 219         catfile($smdir, "smrsa3.pem") ],
 220       [ "{cmd2}", @defaultprov, "-decrypt", "-recip", catfile($smdir, "smrsa3.pem"),
 221         "-in", "{output}.cms", "-out", "{output}.txt" ],
 222       \&final_compare
 223     ],
 224
 225     [ "enveloped content test streaming S/MIME format, DES, 3 recipients, cert and key files used",
 226       [ "{cmd1}", @defaultprov, "-encrypt", "-in", $smcont,
 227         "-stream", "-out", "{output}.cms",
 228         $smrsa1,
 229         catfile($smdir, "smrsa2.pem"),
 230         catfile($smdir, "smrsa3-cert.pem") ],
 231       [ "{cmd2}", @defaultprov, "-decrypt",
 232         "-recip", catfile($smdir, "smrsa3-cert.pem"),
 233         "-inkey", catfile($smdir, "smrsa3-key.pem"),
 234         "-in", "{output}.cms", "-out", "{output}.txt" ],
 235       \&final_compare
 236     ],
 237
 238     [ "enveloped content test streaming S/MIME format, AES-256 cipher, 3 recipients",
 239       [ "{cmd1}", @prov, "-encrypt", "-in", $smcont,
 240         "-aes256", "-stream", "-out", "{output}.cms",
 241         $smrsa1,
 242         catfile($smdir, "smrsa2.pem"),
 243         catfile($smdir, "smrsa3.pem") ],
 244       [ "{cmd2}", @prov, "-decrypt", "-recip", $smrsa1,
 245         "-in", "{output}.cms", "-out", "{output}.txt" ],
 246       \&final_compare
 247     ],
 248
 249 );
 250
 251 my @smime_cms_tests = (
 252
 253     [ "signed content test streaming BER format, 2 DSA and 2 RSA keys, keyid",
 254       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "DER",
 255         "-nodetach", "-keyid",
 256         "-signer", $smrsa1,
 257         "-signer", catfile($smdir, "smrsa2.pem"),
 258         "-signer", catfile($smdir, "smdsa1.pem"),
 259         "-signer", catfile($smdir, "smdsa2.pem"),
 260         "-stream", "-out", "{output}.cms" ],
 261       [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "DER",
 262         "-CAfile", $smroot, "-out", "{output}.txt" ],
 263       \&final_compare
 264     ],
 265
 266     [ "signed content test streaming PEM format, 2 DSA and 2 RSA keys",
 267       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "PEM", "-nodetach",
 268         "-signer", $smrsa1,
 269         "-signer", catfile($smdir, "smrsa2.pem"),
 270         "-signer", catfile($smdir, "smdsa1.pem"),
 271         "-signer", catfile($smdir, "smdsa2.pem"),
 272         "-stream", "-out", "{output}.cms" ],
 273       [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "PEM",
 274         "-CAfile", $smroot, "-out", "{output}.txt" ],
 275       \&final_compare
 276     ],
 277
 278     [ "signed content MIME format, RSA key, signed receipt request",
 279       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-nodetach",
 280         "-signer", $smrsa1,
 281         "-receipt_request_to", "test\@openssl.org", "-receipt_request_all",
 282         "-out", "{output}.cms" ],
 283       [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms",
 284         "-CAfile", $smroot, "-out", "{output}.txt" ],
 285       \&final_compare
 286     ],
 287
 288     [ "signed receipt MIME format, RSA key",
 289       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-nodetach",
 290         "-signer", $smrsa1,
 291         "-receipt_request_to", "test\@openssl.org", "-receipt_request_all",
 292         "-out", "{output}.cms" ],
 293       [ "{cmd1}", @prov, "-sign_receipt", "-in", "{output}.cms",
 294         "-signer", catfile($smdir, "smrsa2.pem"), "-out", "{output}2.cms" ],
 295       [ "{cmd2}", @prov, "-verify_receipt", "{output}2.cms", "-in", "{output}.cms",
 296         "-CAfile", $smroot ]
 297     ],
 298
 299     [ "enveloped content test streaming S/MIME format, DES, 3 recipients, keyid",
 300       [ "{cmd1}", @defaultprov, "-encrypt", "-in", $smcont,
 301         "-stream", "-out", "{output}.cms", "-keyid",
 302         $smrsa1,
 303         catfile($smdir, "smrsa2.pem"),
 304         catfile($smdir, "smrsa3.pem") ],
 305       [ "{cmd2}", @defaultprov, "-decrypt", "-recip", $smrsa1,
 306         "-in", "{output}.cms", "-out", "{output}.txt" ],
 307       \&final_compare
 308     ],
 309
 310     [ "enveloped content test streaming PEM format, AES-256-CBC cipher, KEK",
 311       [ "{cmd1}", @prov, "-encrypt", "-in", $smcont, "-outform", "PEM", "-aes128",
 312         "-stream", "-out", "{output}.cms",
 313         "-secretkey", "000102030405060708090A0B0C0D0E0F",
 314         "-secretkeyid", "C0FEE0" ],
 315       [ "{cmd2}", @prov, "-decrypt", "-in", "{output}.cms", "-out", "{output}.txt",
 316         "-inform", "PEM",
 317         "-secretkey", "000102030405060708090A0B0C0D0E0F",
 318         "-secretkeyid", "C0FEE0" ],
 319       \&final_compare
 320     ],
 321
 322     [ "enveloped content test streaming PEM format, AES-256-GCM cipher, KEK",
 323       [ "{cmd1}", @prov, "-encrypt", "-in", $smcont, "-outform", "PEM", "-aes-128-gcm",
 324         "-stream", "-out", "{output}.cms",
 325         "-secretkey", "000102030405060708090A0B0C0D0E0F",
 326         "-secretkeyid", "C0FEE0" ],
 327       [ "{cmd2}", "-decrypt", "-in", "{output}.cms", "-out", "{output}.txt",
 328         "-inform", "PEM",
 329         "-secretkey", "000102030405060708090A0B0C0D0E0F",
 330         "-secretkeyid", "C0FEE0" ],
 331       \&final_compare
 332     ],
 333
 334     [ "enveloped content test streaming PEM format, KEK, key only",
 335       [ "{cmd1}", @prov, "-encrypt", "-in", $smcont, "-outform", "PEM", "-aes128",
 336         "-stream", "-out", "{output}.cms",
 337         "-secretkey", "000102030405060708090A0B0C0D0E0F",
 338         "-secretkeyid", "C0FEE0" ],
 339       [ "{cmd2}", @prov, "-decrypt", "-in", "{output}.cms", "-out", "{output}.txt",
 340         "-inform", "PEM",
 341         "-secretkey", "000102030405060708090A0B0C0D0E0F" ],
 342       \&final_compare
 343     ],
 344
 345     [ "data content test streaming PEM format",
 346       [ "{cmd1}", @prov, "-data_create", "-in", $smcont, "-outform", "PEM",
 347         "-nodetach", "-stream", "-out", "{output}.cms" ],
 348       [ "{cmd2}", @prov, "-data_out", "-in", "{output}.cms", "-inform", "PEM",
 349         "-out", "{output}.txt" ],
 350       \&final_compare
 351     ],
 352
 353     [ "encrypted content test streaming PEM format, 128 bit RC2 key",
 354       [ "{cmd1}", @legacyprov, "-EncryptedData_encrypt",
 355         "-in", $smcont, "-outform", "PEM",
 356         "-rc2", "-secretkey", "000102030405060708090A0B0C0D0E0F",
 357         "-stream", "-out", "{output}.cms" ],
 358       [ "{cmd2}", @legacyprov, "-EncryptedData_decrypt", "-in", "{output}.cms",
 359         "-inform", "PEM",
 360         "-secretkey", "000102030405060708090A0B0C0D0E0F",
 361         "-out", "{output}.txt" ],
 362       \&final_compare
 363     ],
 364
 365     [ "encrypted content test streaming PEM format, 40 bit RC2 key",
 366       [ "{cmd1}", @legacyprov, "-EncryptedData_encrypt",
 367         "-in", $smcont, "-outform", "PEM",
 368         "-rc2", "-secretkey", "0001020304",
 369         "-stream", "-out", "{output}.cms" ],
 370       [ "{cmd2}", @legacyprov, "-EncryptedData_decrypt", "-in", "{output}.cms",
 371         "-inform", "PEM",
 372         "-secretkey", "0001020304", "-out", "{output}.txt" ],
 373       \&final_compare
 374     ],
 375
 376     [ "encrypted content test streaming PEM format, triple DES key",
 377       [ "{cmd1}", @prov, "-EncryptedData_encrypt", "-in", $smcont, "-outform", "PEM",
 378         "-des3", "-secretkey", "000102030405060708090A0B0C0D0E0F1011121314151617",
 379         "-stream", "-out", "{output}.cms" ],
 380       [ "{cmd2}", @prov, "-EncryptedData_decrypt", "-in", "{output}.cms",
 381         "-inform", "PEM",
 382         "-secretkey", "000102030405060708090A0B0C0D0E0F1011121314151617",
 383         "-out", "{output}.txt" ],
 384       \&final_compare
 385     ],
 386
 387     [ "encrypted content test streaming PEM format, 128 bit AES key",
 388       [ "{cmd1}", @prov, "-EncryptedData_encrypt", "-in", $smcont, "-outform", "PEM",
 389         "-aes128", "-secretkey", "000102030405060708090A0B0C0D0E0F",
 390         "-stream", "-out", "{output}.cms" ],
 391       [ "{cmd2}", @prov, "-EncryptedData_decrypt", "-in", "{output}.cms",
 392         "-inform", "PEM",
 393         "-secretkey", "000102030405060708090A0B0C0D0E0F",
 394         "-out", "{output}.txt" ],
 395       \&final_compare
 396     ],
 397
 398     [ "encrypted content test streaming PEM format -noout, 128 bit AES key",
 399       [ "{cmd1}", @prov, "-EncryptedData_encrypt", "-in", $smcont, "-outform", "PEM",
 400         "-aes128", "-secretkey", "000102030405060708090A0B0C0D0E0F",
 401         "-stream", "-noout" ],
 402       [ "{cmd2}", @prov, "-help" ]
 403     ],
 404 );
 405
 406 my @smime_cms_cades_tests = (
 407
 408     [ "signed content DER format, RSA key, CAdES-BES compatible",
 409       [ "{cmd1}", @prov, "-sign", "-cades", "-in", $smcont, "-outform", "DER",
 410          "-nodetach",
 411         "-certfile", $smroot, "-signer", $smrsa1, "-out", "{output}.cms" ],
 412       [ "{cmd2}", @prov, "-verify", "-cades", "-in", "{output}.cms", "-inform", "DER",
 413         "-CAfile", $smroot, "-out", "{output}.txt" ],
 414       \&final_compare
 415     ],
 416
 417     [ "signed content DER format, RSA key, SHA256 md, CAdES-BES compatible",
 418       [ "{cmd1}", @prov, "-sign", "-cades", "-md", "sha256", "-in", $smcont, "-outform",
 419         "DER", "-nodetach", "-certfile", $smroot,
 420         "-signer", $smrsa1, "-out", "{output}.cms" ],
 421       [ "{cmd2}", @prov, "-verify", "-cades", "-in", "{output}.cms", "-inform", "DER",
 422         "-CAfile", $smroot, "-out", "{output}.txt" ],
 423       \&final_compare
 424     ],
 425
 426     [ "signed content DER format, RSA key, SHA512 md, CAdES-BES compatible",
 427       [ "{cmd1}", @prov, "-sign", "-cades", "-md", "sha512", "-in", $smcont, "-outform",
 428         "DER", "-nodetach", "-certfile", $smroot,
 429         "-signer", $smrsa1, "-out", "{output}.cms" ],
 430       [ "{cmd2}", @prov, "-verify", "-cades", "-in", "{output}.cms", "-inform", "DER",
 431         "-CAfile", $smroot, "-out", "{output}.txt" ],
 432       \&final_compare
 433     ],
 434
 435     [ "signed content DER format, RSA key, SHA256 md, CAdES-BES compatible",
 436       [ "{cmd1}", @prov, "-sign", "-cades", "-binary",  "-nodetach", "-nosmimecap", "-md", "sha256",
 437         "-in", $smcont, "-outform", "DER",
 438         "-certfile", $smroot, "-signer", $smrsa1,
 439         "-outform", "DER", "-out", "{output}.cms"  ],
 440       [ "{cmd2}", @prov, "-verify", "-cades", "-in", "{output}.cms", "-inform", "DER",
 441         "-CAfile", $smroot, "-out", "{output}.txt" ],
 442       \&final_compare
 443     ],
 444
 445     [ "resigned content DER format, RSA key, SHA256 md, CAdES-BES compatible",
 446       [ "{cmd1}", @prov, "-sign", "-cades", "-binary",  "-nodetach", "-nosmimecap", "-md", "sha256",
 447         "-in", $smcont, "-outform", "DER",
 448         "-certfile", $smroot, "-signer", $smrsa1,
 449         "-outform", "DER", "-out", "{output}.cms"  ],
 450       [ "{cmd1}", @prov, "-resign", "-cades", "-binary", "-nodetach", "-nosmimecap", "-md", "sha256",
 451         "-inform", "DER", "-in", "{output}.cms",
 452         "-certfile", $smroot, "-signer", catfile($smdir, "smrsa2.pem"),
 453         "-outform", "DER", "-out", "{output}2.cms" ],
 454
 455       [ "{cmd2}", @prov, "-verify", "-cades", "-in", "{output}2.cms", "-inform", "DER",
 456         "-CAfile", $smroot, "-out", "{output}.txt" ],
 457       \&final_compare
 458     ],
 459 );
 460
 461 my @smime_cms_cades_ko_tests = (
 462     [ "sign content DER format, RSA key, not CAdES-BES compatible",
 463       [ @prov, "-sign", "-in", $smcont, "-outform", "DER", "-nodetach",
 464         "-certfile", $smroot, "-signer", $smrsa1, "-out", "cades-ko.cms" ],
 465       "fail to verify token since requiring CAdES-BES compatibility",
 466       [ @prov, "-verify", "-cades", "-in", "cades-ko.cms", "-inform", "DER",
 467         "-CAfile", $smroot, "-out", "cades-ko.txt" ],
 468       \&final_compare
 469     ]
 470 );
 471
 472 # cades options test - check that some combinations are rejected
 473 my @smime_cms_cades_invalid_option_tests = (
 474     [
 475         [ "-cades", "-noattr" ],
 476     ],[
 477         [ "-verify", "-cades", "-noattr" ],
 478     ],[
 479         [ "-verify", "-cades", "-noverify" ],
 480     ],
 481 );
 482
 483 my @smime_cms_comp_tests = (
 484
 485     [ "compressed content test streaming PEM format",
 486       [ "{cmd1}", @prov, "-compress", "-in", $smcont, "-outform", "PEM", "-nodetach",
 487         "-stream", "-out", "{output}.cms" ],
 488       [ "{cmd2}", @prov, "-uncompress", "-in", "{output}.cms", "-inform", "PEM",
 489         "-out", "{output}.txt" ],
 490       \&final_compare
 491     ]
 492
 493 );
 494
 495 my @smime_cms_param_tests = (
 496     [ "signed content test streaming PEM format, RSA keys, PSS signature",
 497       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "PEM", "-nodetach",
 498         "-signer", $smrsa1,
 499         "-keyopt", "rsa_padding_mode:pss",
 500         "-out", "{output}.cms" ],
 501       [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "PEM",
 502         "-CAfile", $smroot, "-out", "{output}.txt" ],
 503       \&final_compare
 504     ],
 505
 506     [ "signed content test streaming PEM format, RSA keys, PSS signature, saltlen=max",
 507       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "PEM", "-nodetach",
 508         "-signer", $smrsa1,
 509         "-keyopt", "rsa_padding_mode:pss", "-keyopt", "rsa_pss_saltlen:max",
 510         "-out", "{output}.cms" ],
 511       sub { my %opts = @_; rsapssSaltlen("$opts{output}.cms") == 222; },
 512       [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "PEM",
 513         "-CAfile", $smroot, "-out", "{output}.txt" ],
 514       \&final_compare
 515     ],
 516
 517     [ "signed content test streaming PEM format, RSA keys, PSS signature, no attributes",
 518       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "PEM", "-nodetach",
 519         "-noattr", "-signer", $smrsa1,
 520         "-keyopt", "rsa_padding_mode:pss",
 521         "-out", "{output}.cms" ],
 522       [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "PEM",
 523         "-CAfile", $smroot, "-out", "{output}.txt" ],
 524       \&final_compare
 525     ],
 526
 527     [ "signed content test streaming PEM format, RSA keys, PSS signature, SHA384 MGF1",
 528       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "PEM", "-nodetach",
 529         "-signer", $smrsa1,
 530         "-keyopt", "rsa_padding_mode:pss", "-keyopt", "rsa_mgf1_md:sha384",
 531         "-out", "{output}.cms" ],
 532       [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "PEM",
 533         "-CAfile", $smroot, "-out", "{output}.txt" ],
 534       \&final_compare
 535     ],
 536
 537     [ "signed content test streaming PEM format, RSA keys, PSS signature, saltlen=16",
 538       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "PEM", "-nodetach",
 539         "-signer", $smrsa1, "-md", "sha256",
 540         "-keyopt", "rsa_padding_mode:pss", "-keyopt", "rsa_pss_saltlen:16",
 541         "-out", "{output}.cms" ],
 542       sub { my %opts = @_; rsapssSaltlen("$opts{output}.cms") == 16; },
 543       [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "PEM",
 544         "-CAfile", $smroot, "-out", "{output}.txt" ],
 545       \&final_compare
 546     ],
 547
 548     [ "signed content test streaming PEM format, RSA keys, PSS signature, saltlen=digest",
 549       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "PEM", "-nodetach",
 550         "-signer", $smrsa1, "-md", "sha256",
 551         "-keyopt", "rsa_padding_mode:pss", "-keyopt", "rsa_pss_saltlen:digest",
 552         "-out", "{output}.cms" ],
 553       # digest is SHA-256, which produces 32 bytes of output
 554       sub { my %opts = @_; rsapssSaltlen("$opts{output}.cms") == 32; },
 555       [ "{cmd2}", @prov, "-verify", "-in", "{output}.cms", "-inform", "PEM",
 556         "-CAfile", $smroot, "-out", "{output}.txt" ],
 557       \&final_compare
 558     ],
 559
 560     [ "enveloped content test streaming S/MIME format, DES, OAEP default parameters",
 561       [ "{cmd1}", @defaultprov, "-encrypt", "-in", $smcont,
 562         "-stream", "-out", "{output}.cms",
 563         "-recip", $smrsa1,
 564         "-keyopt", "rsa_padding_mode:oaep" ],
 565       [ "{cmd2}", @defaultprov, "-decrypt", "-recip", $smrsa1,
 566         "-in", "{output}.cms", "-out", "{output}.txt" ],
 567       \&final_compare
 568     ],
 569
 570     [ "enveloped content test streaming S/MIME format, DES, OAEP SHA256",
 571       [ "{cmd1}", @defaultprov, "-encrypt", "-in", $smcont,
 572         "-stream", "-out", "{output}.cms",
 573         "-recip", $smrsa1,
 574         "-keyopt", "rsa_padding_mode:oaep",
 575         "-keyopt", "rsa_oaep_md:sha256" ],
 576       [ "{cmd2}", @defaultprov, "-decrypt", "-recip", $smrsa1,
 577         "-in", "{output}.cms", "-out", "{output}.txt" ],
 578       \&final_compare
 579     ],
 580
 581     [ "enveloped content test streaming S/MIME format, DES, ECDH",
 582       [ "{cmd1}", @defaultprov, "-encrypt", "-in", $smcont,
 583         "-stream", "-out", "{output}.cms",
 584         "-recip", catfile($smdir, "smec1.pem") ],
 585       [ "{cmd2}", @defaultprov, "-decrypt", "-recip", catfile($smdir, "smec1.pem"),
 586         "-in", "{output}.cms", "-out", "{output}.txt" ],
 587       \&final_compare
 588     ],
 589
 590     [ "enveloped content test streaming S/MIME format, DES, ECDH, 2 recipients, key only used",
 591       [ "{cmd1}", @defaultprov, "-encrypt", "-in", $smcont,
 592         "-stream", "-out", "{output}.cms",
 593         catfile($smdir, "smec1.pem"),
 594         catfile($smdir, "smec3.pem") ],
 595       [ "{cmd2}", @defaultprov, "-decrypt", "-inkey", catfile($smdir, "smec3.pem"),
 596         "-in", "{output}.cms", "-out", "{output}.txt" ],
 597       \&final_compare
 598     ],
 599
 600     [ "enveloped content test streaming S/MIME format, ECDH, DES, key identifier",
 601       [ "{cmd1}", @defaultprov, "-encrypt", "-keyid", "-in", $smcont,
 602         "-stream", "-out", "{output}.cms",
 603         "-recip", catfile($smdir, "smec1.pem") ],
 604       [ "{cmd2}", @defaultprov, "-decrypt", "-recip", catfile($smdir, "smec1.pem"),
 605         "-in", "{output}.cms", "-out", "{output}.txt" ],
 606       \&final_compare
 607     ],
 608
 609     [ "enveloped content test streaming S/MIME format, ECDH, AES-128-CBC, SHA256 KDF",
 610       [ "{cmd1}", @prov, "-encrypt", "-in", $smcont,
 611         "-stream", "-out", "{output}.cms",
 612         "-recip", catfile($smdir, "smec1.pem"), "-aes128",
 613         "-keyopt", "ecdh_kdf_md:sha256" ],
 614       [ "{cmd2}", @prov, "-decrypt", "-recip", catfile($smdir, "smec1.pem"),
 615         "-in", "{output}.cms", "-out", "{output}.txt" ],
 616       \&final_compare
 617     ],
 618
 619     [ "enveloped content test streaming S/MIME format, ECDH, AES-128-GCM cipher, SHA256 KDF",
 620       [ "{cmd1}", @prov, "-encrypt", "-in", $smcont,
 621         "-stream", "-out", "{output}.cms",
 622         "-recip", catfile($smdir, "smec1.pem"), "-aes-128-gcm", "-keyopt", "ecdh_kdf_md:sha256" ],
 623       [ "{cmd2}", "-decrypt", "-recip", catfile($smdir, "smec1.pem"),
 624         "-in", "{output}.cms", "-out", "{output}.txt" ],
 625       \&final_compare
 626     ],
 627
 628     [ "enveloped content test streaming S/MIME format, ECDH, K-283, cofactor DH",
 629       [ "{cmd1}", @prov, "-encrypt", "-in", $smcont,
 630         "-stream", "-out", "{output}.cms",
 631         "-recip", catfile($smdir, "smec2.pem"), "-aes128",
 632         "-keyopt", "ecdh_kdf_md:sha256", "-keyopt", "ecdh_cofactor_mode:1" ],
 633       [ "{cmd2}", @prov, "-decrypt", "-recip", catfile($smdir, "smec2.pem"),
 634         "-in", "{output}.cms", "-out", "{output}.txt" ],
 635       \&final_compare
 636     ],
 637
 638     [ "enveloped content test streaming S/MIME format, X9.42 DH",
 639       [ "{cmd1}", @prov, "-encrypt", "-in", $smcont,
 640         "-stream", "-out", "{output}.cms",
 641         "-recip", catfile($smdir, "smdh.pem"), "-aes128" ],
 642       [ "{cmd2}", @prov, "-decrypt", "-recip", catfile($smdir, "smdh.pem"),
 643         "-in", "{output}.cms", "-out", "{output}.txt" ],
 644       \&final_compare
 645     ]
 646 );
 647
 648 my @smime_cms_param_tests_autodigestmax = (
 649     [ "signed content test streaming PEM format, RSA keys, PSS signature, saltlen=auto-digestmax, digestsize < maximum salt length",
 650       [ "{cmd1}", @prov, "-sign", "-in", $smcont, "-outform", "PEM", "-nodetach",
 651         "-signer", $smrsa1, "-md", "sha256",
 652         "-keyopt", "rsa_padding_mode:pss", "-keyopt", "rsa_pss_saltlen:auto-digestmax",
 653         "-out", "{output}.cms" ],
 654       # digest is SHA-256, which produces 32, bytes of output
 655       sub { my %opts = @_; rsapssSaltlen("$opts{output}.cms") == 32; },
 656       [ "{cmd2}", @defaultprov, "-verify", "-in", "{output}.cms", "-inform", "PEM",
 657         "-CAfile", $smroot, "-out", "{output}.txt" ],
 658       \&final_compare
 659     ],
 660
 661     [ "signed content test streaming PEM format, RSA keys, PSS signature, saltlen=auto-digestmax, digestsize > maximum salt length",
 662       [ "{cmd1}", @defaultprov, "-sign", "-in", $smcont, "-outform", "PEM", "-nodetach",
 663         "-signer", $smrsa1024, "-md", "sha512",
 664         "-keyopt", "rsa_padding_mode:pss", "-keyopt", "rsa_pss_saltlen:auto-digestmax",
 665         "-out", "{output}.cms" ],
 666       # digest is SHA-512, which produces 64, bytes of output, but an RSA-PSS
 667       # signature with a 1024 bit RSA key can only accommodate 62
 668       sub { my %opts = @_; rsapssSaltlen("$opts{output}.cms") == 62; },
 669       [ "{cmd2}", @defaultprov, "-verify", "-in", "{output}.cms", "-inform", "PEM",
 670         "-CAfile", $smroot, "-out", "{output}.txt" ],
 671       \&final_compare
 672     ]
 673 );
 674
 675
 676 my @contenttype_cms_test = (
 677     [ "signed content test - check that content type is added to additional signerinfo, RSA keys",
 678       [ "{cmd1}", @prov, "-sign", "-binary", "-nodetach", "-stream", "-in", $smcont,
 679         "-outform", "DER", "-signer", $smrsa1, "-md", "SHA256",
 680         "-out", "{output}.cms" ],
 681       [ "{cmd1}", @prov, "-resign", "-binary", "-nodetach", "-in", "{output}.cms",
 682         "-inform", "DER", "-outform", "DER",
 683         "-signer", catfile($smdir, "smrsa2.pem"), "-md", "SHA256",
 684         "-out", "{output}2.cms" ],
 685       sub { my %opts = @_; contentType_matches("$opts{output}2.cms") == 2; },
 686       [ "{cmd2}", @prov, "-verify", "-in", "{output}2.cms", "-inform", "DER",
 687         "-CAfile", $smroot, "-out", "{output}.txt" ]
 688     ],
 689 );
 690
 691 my @incorrect_attribute_cms_test = (
 692     "bad_signtime_attr.cms",
 693     "no_ct_attr.cms",
 694     "no_md_attr.cms",
 695     "ct_multiple_attr.cms"
 696 );
 697
 698 # Runs a standard loop on the input array
 699 sub runner_loop {
 700     my %opts = ( @_ );
 701     my $cnt1 = 0;
 702
 703     foreach (@{$opts{tests}}) {
 704         $cnt1++;
 705         $opts{output} = "$opts{prefix}-$cnt1";
 706       SKIP: {
 707           my $skip_reason = check_availability($$_[0]);
 708           skip $skip_reason, 1 if $skip_reason;
 709           my $ok = 1;
 710           1 while unlink "$opts{output}.txt";
 711
 712           foreach (@$_[1..$#$_]) {
 713               if (ref $_ eq 'CODE') {
 714                   $ok &&= $_->(%opts);
 715               } else {
 716                   my @cmd = map {
 717                       my $x = $_;
 718                       while ($x =~ /\{([^\}]+)\}/) {
 719                           $x = $`.$opts{$1}.$' if exists $opts{$1};
 720                       }
 721                       $x;
 722                   } @$_;
 723
 724                   diag "CMD: openssl ", join(" ", @cmd);
 725                   $ok &&= run(app(["openssl", @cmd]));
 726                   $opts{input} = $opts{output};
 727               }
 728           }
 729
 730           ok($ok, $$_[0]);
 731         }
 732     }
 733 }
 734
 735 sub final_compare {
 736     my %opts = @_;
 737
 738     diag "Comparing $smcont with $opts{output}.txt";
 739     return compare_text($smcont, "$opts{output}.txt") == 0;
 740 }
 741
 742 sub zero_compare {
 743     my %opts = @_;
 744
 745     diag "Checking for zero-length file";
 746     return (-e "$opts{output}.txt" && -z "$opts{output}.txt");
 747 }
 748
 749 subtest "CMS => PKCS#7 compatibility tests\n" => sub {
 750     plan tests => scalar @smime_pkcs7_tests;
 751
 752     runner_loop(prefix => 'cms2pkcs7', cmd1 => 'cms', cmd2 => 'smime',
 753                 tests => [ @smime_pkcs7_tests ]);
 754 };
 755 subtest "CMS <= PKCS#7 compatibility tests\n" => sub {
 756     plan tests => scalar @smime_pkcs7_tests;
 757
 758     runner_loop(prefix => 'pkcs72cms', cmd1 => 'smime', cmd2 => 'cms',
 759                 tests => [ @smime_pkcs7_tests ]);
 760 };
 761
 762 subtest "CMS <=> CMS consistency tests\n" => sub {
 763     plan tests => (scalar @smime_pkcs7_tests) + (scalar @smime_cms_tests);
 764
 765     runner_loop(prefix => 'cms2cms-1', cmd1 => 'cms', cmd2 => 'cms',
 766                 tests => [ @smime_pkcs7_tests ]);
 767     runner_loop(prefix => 'cms2cms-2', cmd1 => 'cms', cmd2 => 'cms',
 768                 tests => [ @smime_cms_tests ]);
 769 };
 770
 771 subtest "CMS <=> CMS consistency tests, modified key parameters\n" => sub {
 772     plan tests =>
 773         (scalar @smime_cms_param_tests) + (scalar @smime_cms_comp_tests) +
 774         (scalar @smime_cms_param_tests_autodigestmax) + 1;
 775
 776     ok(run(app(["openssl", "cms", @prov,
 777                 "-sign", "-in", $smcont,
 778                 "-outform", "PEM",
 779                 "-nodetach",
 780                 "-signer", $smrsa1,
 781                 "-keyopt", "rsa_padding_mode:pss",
 782                 "-keyopt", "rsa_pss_saltlen:auto-digestmax",
 783                 "-out", "digestmaxtest.cms"])));
 784     # Providers that do not support rsa_pss_saltlen:auto-digestmax will parse
 785     # it as 0
 786     my $no_autodigestmax = rsapssSaltlen("digestmaxtest.cms") == 0;
 787     1 while unlink "digestmaxtest.cms";
 788
 789     runner_loop(prefix => 'cms2cms-mod', cmd1 => 'cms', cmd2 => 'cms',
 790                 tests => [ @smime_cms_param_tests ]);
 791   SKIP: {
 792       skip("Zlib not supported: compression tests skipped",
 793            scalar @smime_cms_comp_tests)
 794           if $no_zlib;
 795
 796       runner_loop(prefix => 'cms2cms-comp', cmd1 => 'cms', cmd2 => 'cms',
 797                   tests => [ @smime_cms_comp_tests ]);
 798     }
 799
 800   SKIP: {
 801     skip("rsa_pss_saltlen:auto-digestmax not supported",
 802          scalar @smime_cms_param_tests_autodigestmax)
 803        if $no_autodigestmax;
 804
 805        runner_loop(prefix => 'cms2cms-comp', 'cmd1' => 'cms', cmd2 => 'cms',
 806                    tests => [ @smime_cms_param_tests_autodigestmax ]);
 807   }
 808 };
 809
 810 # Returns the number of matches of a Content Type Attribute in a binary file.
 811 sub contentType_matches {
 812   # Read in a binary file
 813   my ($in) = @_;
 814   open (HEX_IN, "$in") or die("open failed for $in : $!");
 815   binmode(HEX_IN);
 816   local $/;
 817   my $str = <HEX_IN>;
 818
 819   # Find ASN1 data for a Content Type Attribute (with a OID of PKCS7 data)
 820   my @c = $str =~ /\x30\x18\x06\x09\x2A\x86\x48\x86\xF7\x0D\x01\x09\x03\x31\x0B\x06\x09\x2A\x86\x48\x86\xF7\x0D\x01\x07\x01/gs;
 821
 822   close(HEX_IN);
 823   return scalar(@c);
 824 }
 825
 826 sub rsapssSaltlen {
 827   my ($in) = @_;
 828   my $exit = 0;
 829
 830   my @asn1parse = run(app(["openssl", "asn1parse", "-in", $in, "-dump"]),
 831                       capture => 1,
 832                       statusvar => $exit);
 833   return -1 if $exit != 0;
 834
 835   my $pssparam_offset = -1;
 836   while ($_ = shift @asn1parse) {
 837     chomp;
 838     next unless /:rsassaPss/;
 839     # This line contains :rsassaPss, the next line contains a raw dump of the
 840     # RSA_PSS_PARAMS sequence; obtain its offset
 841     $_ = shift @asn1parse;
 842     if (/^\s*(\d+):/) {
 843       $pssparam_offset = int($1);
 844     }
 845   }
 846
 847   if ($pssparam_offset == -1) {
 848     note "Failed to determine RSA_PSS_PARAM offset in CMS. " +
 849          "Was the file correctly signed with RSASSA-PSS?";
 850     return -1;
 851   }
 852
 853   my @pssparam = run(app(["openssl", "asn1parse", "-in", $in,
 854                           "-strparse", $pssparam_offset]),
 855                      capture => 1,
 856                      statusvar => $exit);
 857   return -1 if $exit != 0;
 858
 859   my $saltlen = -1;
 860   # Can't use asn1parse -item RSA_PSS_PARAMS here, because that's deprecated.
 861   # This assumes the salt length is the last field, which may possibly be
 862   # incorrect if there is a non-standard trailer field, but there almost never
 863   # is in PSS.
 864   if ($pssparam[-1] =~ /prim:\s+INTEGER\s+:([A-Fa-f0-9]+)/) {
 865     $saltlen = hex($1);
 866   }
 867
 868   if ($saltlen == -1) {
 869     note "Failed to determine salt length from RSA_PSS_PARAM struct. " +
 870          "Was the file correctly signed with RSASSA-PSS?";
 871     return -1;
 872   }
 873
 874   return $saltlen;
 875 }
 876
 877 subtest "CMS Check the content type attribute is added for additional signers\n" => sub {
 878     plan tests => (scalar @contenttype_cms_test);
 879
 880     runner_loop(prefix => 'cms2cms-added', cmd1 => 'cms', cmd2 => 'cms',
 881                 tests => [ @contenttype_cms_test ]);
 882 };
 883
 884 subtest "CMS Check that bad attributes fail when verifying signers\n" => sub {
 885     plan tests =>
 886         (scalar @incorrect_attribute_cms_test);
 887
 888     my $cnt = 0;
 889     foreach my $name (@incorrect_attribute_cms_test) {
 890         my $out = "incorrect-$cnt.txt";
 891
 892         ok(!run(app(["openssl", "cms", @prov, "-verify", "-in",
 893                      catfile($datadir, $name), "-inform", "DER", "-CAfile",
 894                      $smroot, "-out", $out ])),
 895             $name);
 896     }
 897 };
 898
 899 subtest "CMS Check that bad encryption algorithm fails\n" => sub {
 900     plan tests => 1;
 901
 902     SKIP: {
 903         skip "DES or Legacy isn't supported in this build", 1
 904             if disabled("des") || disabled("legacy");
 905
 906         my $out = "smtst.txt";
 907
 908         ok(!run(app(["openssl", "cms", @legacyprov, "-encrypt",
 909                     "-in", $smcont,
 910                     "-stream", "-recip", $smrsa1,
 911                     "-des-ede3",
 912                     "-out", $out ])),
 913            "Decrypt message from OpenSSL 1.1.1");
 914     }
 915 };
 916
 917 subtest "CMS Decrypt message encrypted with OpenSSL 1.1.1\n" => sub {
 918     plan tests => 1;
 919
 920     SKIP: {
 921         skip "EC or DES isn't supported in this build", 1
 922             if disabled("ec") || disabled("des");
 923
 924         my $out = "smtst.txt";
 925
 926         ok(run(app(["openssl", "cms", @defaultprov, "-decrypt",
 927                     "-inkey", catfile($smdir, "smec3.pem"),
 928                     "-in", catfile($datadir, "ciphertext_from_1_1_1.cms"),
 929                     "-out", $out ]))
 930            && compare_text($smcont, $out) == 0,
 931            "Decrypt message from OpenSSL 1.1.1");
 932     }
 933 };
 934
 935 subtest "CAdES <=> CAdES consistency tests\n" => sub {
 936     plan tests => (scalar @smime_cms_cades_tests);
 937
 938     runner_loop(prefix => 'cms-cades', cmd1 => 'cms', cmd2 => 'cms',
 939                 tests => [ @smime_cms_cades_tests ]);
 940 };
 941
 942 subtest "CAdES; cms incompatible arguments tests\n" => sub {
 943     plan tests => (scalar @smime_cms_cades_invalid_option_tests);
 944
 945     foreach (@smime_cms_cades_invalid_option_tests) {
 946         ok(!run(app(["openssl", "cms", @{$$_[0]} ] )));
 947     }
 948 };
 949
 950 subtest "CAdES ko tests\n" => sub {
 951     plan tests => 2 * scalar @smime_cms_cades_ko_tests;
 952
 953     foreach (@smime_cms_cades_ko_tests) {
 954       SKIP: {
 955         my $skip_reason = check_availability($$_[0]);
 956         skip $skip_reason, 1 if $skip_reason;
 957         1 while unlink "cades-ko.txt";
 958
 959         ok(run(app(["openssl", "cms", @{$$_[1]}])), $$_[0]);
 960         ok(!run(app(["openssl", "cms", @{$$_[3]}])), $$_[2]);
 961         }
 962     }
 963 };
 964
 965 subtest "CMS binary input tests\n" => sub {
 966     my $input = srctop_file("test", "smcont.bin");
 967     my $signed = "smcont.signed";
 968     my $verified = "smcont.verified";
 969
 970     plan tests => 11;
 971
 972     ok(run(app(["openssl", "cms", "-sign", "-md", "sha256", "-signer", $smrsa1,
 973                 "-binary", "-in", $input, "-out", $signed])),
 974        "sign binary input with -binary");
 975     ok(run(app(["openssl", "cms", "-verify", "-CAfile", $smroot,
 976                 "-binary", "-in", $signed, "-out", $verified])),
 977        "verify binary input with -binary");
 978     is(compare($input, $verified), 0, "binary input retained with -binary");
 979
 980     ok(run(app(["openssl", "cms", "-sign", "-md", "sha256", "-signer", $smrsa1,
 981                 "-in", $input, "-out", $signed.".nobin"])),
 982        "sign binary input without -binary");
 983     ok(run(app(["openssl", "cms", "-verify", "-CAfile", $smroot,
 984                 "-in", $signed.".nobin", "-out", $verified.".nobin"])),
 985        "verify binary input without -binary");
 986     is(compare($input, $verified.".nobin"), 1, "binary input not retained without -binary");
 987     ok(!run(app(["openssl", "cms", "-verify", "-CAfile", $smroot, "-crlfeol",
 988                 "-binary", "-in", $signed, "-out", $verified.".crlfeol"])),
 989        "verify binary input wrong crlfeol");
 990
 991     ok(run(app(["openssl", "cms", "-sign", "-md", "sha256", "-signer", $smrsa1,
 992                 "-crlfeol",
 993                 "-binary", "-in", $input, "-out", $signed.".crlf"])),
 994        "sign binary input with -binary -crlfeol");
 995     ok(run(app(["openssl", "cms", "-verify", "-CAfile", $smroot, "-crlfeol",
 996                 "-binary", "-in", $signed.".crlf", "-out", $verified.".crlf"])),
 997        "verify binary input with -binary -crlfeol");
 998     is(compare($input, $verified.".crlf"), 0,
 999        "binary input retained with -binary -crlfeol");
1000     ok(!run(app(["openssl", "cms", "-verify", "-CAfile", $smroot,
1001                 "-binary", "-in", $signed.".crlf", "-out", $verified.".crlf2"])),
1002        "verify binary input with -binary missing -crlfeol");
1003 };
1004
1005 subtest "CMS signed digest, DER format" => sub {
1006     plan tests => 2;
1007
1008     # Pre-computed SHA256 digest of $smcont in hexadecimal form
1009     my $digest = "ff236ef61b396355f75a4cc6e1c306d4c309084ae271a9e2ad6888f10a101b32";
1010
1011     my $sig_file = "signature.der";
1012     ok(run(app(["openssl", "cms", @prov, "-sign", "-digest", $digest,
1013                     "-outform", "DER",
1014                     "-certfile", catfile($smdir, "smroot.pem"),
1015                     "-signer", catfile($smdir, "smrsa1.pem"),
1016                     "-out", $sig_file])),
1017         "CMS sign pre-computed digest, DER format");
1018
1019     ok(run(app(["openssl", "cms", @prov, "-verify", "-in", $sig_file,
1020                     "-inform", "DER",
1021                     "-CAfile", catfile($smdir, "smroot.pem"),
1022                     "-content", $smcont])),
1023        "Verify CMS signed digest, DER format");
1024 };
1025
1026 subtest "CMS signed digest, S/MIME format" => sub {
1027     plan tests => 2;
1028
1029     # Pre-computed SHA256 digest of $smcont in hexadecimal form
1030     my $digest = "ff236ef61b396355f75a4cc6e1c306d4c309084ae271a9e2ad6888f10a101b32";
1031
1032     my $sig_file = "signature.smime";
1033     ok(run(app(["openssl", "cms", @prov, "-sign", "-digest", $digest,
1034                     "-outform", "SMIME",
1035                     "-certfile", catfile($smdir, "smroot.pem"),
1036                     "-signer", catfile($smdir, "smrsa1.pem"),
1037                     "-out", $sig_file])),
1038         "CMS sign pre-computed digest, S/MIME format");
1039
1040     ok(run(app(["openssl", "cms", @prov, "-verify", "-in", $sig_file,
1041                     "-inform", "SMIME",
1042                     "-CAfile", catfile($smdir, "smroot.pem"),
1043                     "-content", $smcont])),
1044        "Verify CMS signed digest, S/MIME format");
1045 };
1046
1047 subtest "CMS code signing test" => sub {
1048     plan tests => 7;
1049     my $sig_file = "signature.p7s";
1050     ok(run(app(["openssl", "cms", @prov, "-sign", "-in", $smcont,
1051                    "-certfile", catfile($smdir, "smroot.pem"),
1052                    "-signer", catfile($smdir, "smrsa1.pem"),
1053                    "-out", $sig_file])),
1054        "accept perform CMS signature with smime certificate");
1055
1056     ok(run(app(["openssl", "cms", @prov, "-verify", "-in", $sig_file,
1057                     "-CAfile", catfile($smdir, "smroot.pem"),
1058                     "-content", $smcont])),
1059        "accept verify CMS signature with smime certificate");
1060
1061     ok(!run(app(["openssl", "cms", @prov, "-verify", "-in", $sig_file,
1062                     "-CAfile", catfile($smdir, "smroot.pem"),
1063                     "-purpose", "codesign",
1064                     "-content", $smcont])),
1065        "fail verify CMS signature with smime certificate for purpose code signing");
1066
1067     ok(!run(app(["openssl", "cms", @prov, "-verify", "-in", $sig_file,
1068                     "-CAfile", catfile($smdir, "smroot.pem"),
1069                     "-purpose", "football",
1070                     "-content", $smcont])),
1071        "fail verify CMS signature with invalid purpose argument");
1072
1073     ok(run(app(["openssl", "cms", @prov, "-sign", "-in", $smcont,
1074                    "-certfile", catfile($smdir, "smroot.pem"),
1075                    "-signer", catfile($smdir, "csrsa1.pem"),
1076                    "-out", $sig_file])),
1077         "accept perform CMS signature with code signing certificate");
1078
1079     ok(run(app(["openssl", "cms", @prov, "-verify", "-in", $sig_file,
1080                     "-CAfile", catfile($smdir, "smroot.pem"),
1081                     "-purpose", "codesign",
1082                     "-content", $smcont])),
1083        "accept verify CMS signature with code signing certificate for purpose code signing");
1084
1085     ok(!run(app(["openssl", "cms", @prov, "-verify", "-in", $sig_file,
1086                     "-CAfile", catfile($smdir, "smroot.pem"),
1087                     "-content", $smcont])),
1088        "fail verify CMS signature with code signing certificate for purpose smime_sign");
1089 };
1090
1091 # Test case for missing MD algorithm (must not segfault)
1092
1093 with({ exit_checker => sub { return shift == 4; } },
1094     sub {
1095         ok(run(app(['openssl', 'smime', '-verify', '-noverify',
1096                     '-inform', 'PEM',
1097                     '-in', data_file("pkcs7-md4.pem"),
1098                    ])),
1099             "Check failure of EVP_DigestInit in PKCS7 signed is handled");
1100
1101         ok(run(app(['openssl', 'smime', '-decrypt',
1102                     '-inform', 'PEM',
1103                     '-in', data_file("pkcs7-md4-encrypted.pem"),
1104                     '-recip', srctop_file("test", "certs", "ee-cert.pem"),
1105                     '-inkey', srctop_file("test", "certs", "ee-key.pem")
1106                    ])),
1107             "Check failure of EVP_DigestInit in PKCS7 signedAndEnveloped is handled");
1108     });
1109
1110 sub check_availability {
1111     my $tnam = shift;
1112
1113     return "$tnam: skipped, EC disabled\n"
1114         if ($no_ec && $tnam =~ /ECDH/);
1115     return "$tnam: skipped, ECDH disabled\n"
1116         if ($no_ec && $tnam =~ /ECDH/);
1117     return "$tnam: skipped, EC2M disabled\n"
1118         if ($no_ec2m && $tnam =~ /K-283/);
1119     return "$tnam: skipped, DH disabled\n"
1120         if ($no_dh && $tnam =~ /X9\.42/);
1121     return "$tnam: skipped, RC2 disabled\n"
1122         if ($no_rc2 && $tnam =~ /RC2/);
1123     return "$tnam: skipped, DES disabled\n"
1124         if ($no_des && $tnam =~ /DES/);
1125     return "$tnam: skipped, DSA disabled\n"
1126         if ($no_dsa && $tnam =~ / DSA/);
1127
1128     return "";
1129 }
1130
1131 # Test case for the locking problem reported in #19643.
1132 # This will fail if the fix is in and deadlock on Windows (and possibly
1133 # other platforms) if not.
1134 ok(!run(app(['openssl', 'cms', '-verify',
1135              '-CAfile', srctop_file("test/certs", "pkitsta.pem"),
1136              '-policy', 'anyPolicy',
1137              '-in', srctop_file("test/smime-eml",
1138                                 "SignedInvalidMappingFromanyPolicyTest7.eml")
1139             ])),
1140    "issue#19643");
1141
1142 # Check that we get the expected failure return code
1143 with({ exit_checker => sub { return shift == 6; } },
1144     sub {
1145         ok(run(app(['openssl', 'cms', '-encrypt',
1146                     '-in', srctop_file("test", "smcont.txt"),
1147                     '-aes128', '-stream', '-recip',
1148                     srctop_file("test/smime-certs", "badrsa.pem"),
1149                    ])),
1150             "Check failure during BIO setup with -stream is handled correctly");
1151     });
1152
1153 # Test case for return value mis-check reported in #21986
1154 with({ exit_checker => sub { return shift == 3; } },
1155     sub {
1156         SKIP: {
1157           skip "DSA is not supported in this build", 1 if $no_dsa;
1158
1159           ok(run(app(['openssl', 'cms', '-sign',
1160                       '-in', srctop_file("test", "smcont.txt"),
1161                       '-signer', srctop_file("test/smime-certs", "smdsa1.pem"),
1162                       '-md', 'SHAKE256'])),
1163             "issue#21986");
1164         }
1165     });
1166
1167 # Test for problem reported in #22225
1168 with({ exit_checker => sub { return shift == 3; } },
1169     sub {
1170         ok(run(app(['openssl', 'cms', '-encrypt',
1171                     '-in', srctop_file("test", "smcont.txt"),
1172                     '-aes-256-ctr', '-recip',
1173                     catfile($smdir, "smec1.pem"),
1174                    ])),
1175            "Check for failure when cipher does not have an assigned OID (issue#22225)");
1176      });
1177
1178 # Test encrypt to three recipients, and decrypt using key-only;
1179 # i.e. do not follow the recommended practice of providing the
1180 # recipient cert in the decrypt op.
1181 #
1182 # Use RSAES-OAEP for key-transport, not RSAES-PKCS-v1_5.
1183 #
1184 # Because the cert is not provided during decrypt, all RSA ciphertexts
1185 # are decrypted in turn, and when/if there is a valid decryption, it
1186 # is assumed the correct content-key has been recovered.
1187 #
1188 # That process may fail with RSAES-PKCS-v1_5 b/c there is a
1189 # non-negligible chance that decrypting a random input using
1190 # RSAES-PKCS-v1_5 can result in a valid plaintext (so two content-keys
1191 # could be recovered and the wrong one might be used).
1192 #
1193 # See https://github.com/openssl/project/issues/380
1194 subtest "encrypt to three recipients with RSA-OAEP, key only decrypt" => sub {
1195     plan tests => 3;
1196
1197     my $pt = srctop_file("test", "smcont.txt");
1198     my $ct = "smtst.cms";
1199     my $ptpt = "smtst.txt";
1200
1201     ok(run(app(['openssl', 'cms',
1202                 @defaultprov,
1203                 '-encrypt', '-aes128',
1204                 '-in', $pt,
1205                 '-out', $ct,
1206                 '-stream',
1207                 '-recip', catfile($smdir, "smrsa1.pem"),
1208                 '-keyopt', 'rsa_padding_mode:oaep',
1209                 '-recip', catfile($smdir, "smrsa2.pem"),
1210                 '-keyopt', 'rsa_padding_mode:oaep',
1211                 '-recip', catfile($smdir, "smrsa3-cert.pem"),
1212                 '-keyopt', 'rsa_padding_mode:oaep',
1213                ])),
1214        "encrypt to three recipients with RSA-OAEP (avoid openssl/project issue#380)");
1215     ok(run(app(['openssl', 'cms',
1216                 @defaultprov,
1217                 '-decrypt', '-aes128',
1218                 '-in', $ct,
1219                 '-out', $ptpt,
1220                 '-inkey', catfile($smdir, "smrsa3-key.pem"),
1221                ])),
1222        "decrypt with key only");
1223     is(compare($pt, $ptpt), 0, "compare original message with decrypted ciphertext");
1224 };