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      1 /*
      2  * Copyright 1999-2025 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 /* S/MIME utility function */
     11 
     12 #include <stdio.h>
     13 #include <string.h>
     14 #include "apps.h"
     15 #include "progs.h"
     16 #include <openssl/crypto.h>
     17 #include <openssl/pem.h>
     18 #include <openssl/err.h>
     19 #include <openssl/x509_vfy.h>
     20 #include <openssl/x509v3.h>
     21 
     22 static int save_certs(char *signerfile, STACK_OF(X509) *signers);
     23 static int smime_cb(int ok, X509_STORE_CTX *ctx);
     24 
     25 #define SMIME_OP        0x10
     26 #define SMIME_IP        0x20
     27 #define SMIME_SIGNERS   0x40
     28 #define SMIME_ENCRYPT   (1 | SMIME_OP)
     29 #define SMIME_DECRYPT   (2 | SMIME_IP)
     30 #define SMIME_SIGN      (3 | SMIME_OP | SMIME_SIGNERS)
     31 #define SMIME_VERIFY    (4 | SMIME_IP)
     32 #define SMIME_PK7OUT    (5 | SMIME_IP | SMIME_OP)
     33 #define SMIME_RESIGN    (6 | SMIME_IP | SMIME_OP | SMIME_SIGNERS)
     34 
     35 typedef enum OPTION_choice {
     36     OPT_COMMON,
     37     OPT_ENCRYPT, OPT_DECRYPT, OPT_SIGN, OPT_RESIGN, OPT_VERIFY,
     38     OPT_PK7OUT, OPT_TEXT, OPT_NOINTERN, OPT_NOVERIFY, OPT_NOCHAIN,
     39     OPT_NOCERTS, OPT_NOATTR, OPT_NODETACH, OPT_NOSMIMECAP,
     40     OPT_BINARY, OPT_NOSIGS, OPT_STREAM, OPT_INDEF, OPT_NOINDEF,
     41     OPT_CRLFEOL, OPT_ENGINE, OPT_PASSIN,
     42     OPT_TO, OPT_FROM, OPT_SUBJECT, OPT_SIGNER, OPT_RECIP, OPT_MD,
     43     OPT_CIPHER, OPT_INKEY, OPT_KEYFORM, OPT_CERTFILE, OPT_CAFILE,
     44     OPT_CAPATH, OPT_CASTORE, OPT_NOCAFILE, OPT_NOCAPATH, OPT_NOCASTORE,
     45     OPT_R_ENUM, OPT_PROV_ENUM, OPT_CONFIG,
     46     OPT_V_ENUM,
     47     OPT_IN, OPT_INFORM, OPT_OUT,
     48     OPT_OUTFORM, OPT_CONTENT
     49 } OPTION_CHOICE;
     50 
     51 const OPTIONS smime_options[] = {
     52     {OPT_HELP_STR, 1, '-', "Usage: %s [options] [cert...]\n"},
     53 
     54     OPT_SECTION("General"),
     55     {"help", OPT_HELP, '-', "Display this summary"},
     56     {"in", OPT_IN, '<', "Input file"},
     57     {"inform", OPT_INFORM, 'c', "Input format SMIME (default), PEM or DER"},
     58     {"out", OPT_OUT, '>', "Output file"},
     59     {"outform", OPT_OUTFORM, 'c',
     60      "Output format SMIME (default), PEM or DER"},
     61     {"inkey", OPT_INKEY, 's',
     62      "Input private key (if not signer or recipient)"},
     63     {"keyform", OPT_KEYFORM, 'f', "Input private key format (ENGINE, other values ignored)"},
     64 #ifndef OPENSSL_NO_ENGINE
     65     {"engine", OPT_ENGINE, 's', "Use engine, possibly a hardware device"},
     66 #endif
     67     {"stream", OPT_STREAM, '-', "Enable CMS streaming" },
     68     {"indef", OPT_INDEF, '-', "Same as -stream" },
     69     {"noindef", OPT_NOINDEF, '-', "Disable CMS streaming"},
     70     OPT_CONFIG_OPTION,
     71 
     72     OPT_SECTION("Action"),
     73     {"encrypt", OPT_ENCRYPT, '-', "Encrypt message"},
     74     {"decrypt", OPT_DECRYPT, '-', "Decrypt encrypted message"},
     75     {"sign", OPT_SIGN, '-', "Sign message"},
     76     {"resign", OPT_RESIGN, '-', "Resign a signed message"},
     77     {"verify", OPT_VERIFY, '-', "Verify signed message"},
     78 
     79     OPT_SECTION("Signing/Encryption"),
     80     {"passin", OPT_PASSIN, 's', "Input file pass phrase source"},
     81     {"md", OPT_MD, 's', "Digest algorithm to use when signing or resigning"},
     82     {"", OPT_CIPHER, '-', "Any supported cipher"},
     83     {"pk7out", OPT_PK7OUT, '-', "Output PKCS#7 structure"},
     84     {"nointern", OPT_NOINTERN, '-',
     85      "Don't search certificates in message for signer"},
     86     {"nodetach", OPT_NODETACH, '-', "Use opaque signing"},
     87     {"noattr", OPT_NOATTR, '-', "Don't include any signed attributes"},
     88     {"binary", OPT_BINARY, '-', "Don't translate message to text"},
     89     {"signer", OPT_SIGNER, 's', "Signer certificate file"},
     90     {"content", OPT_CONTENT, '<',
     91      "Supply or override content for detached signature"},
     92     {"nocerts", OPT_NOCERTS, '-',
     93      "Don't include signers certificate when signing"},
     94 
     95     OPT_SECTION("Verification/Decryption"),
     96     {"nosigs", OPT_NOSIGS, '-', "Don't verify message signature"},
     97     {"noverify", OPT_NOVERIFY, '-', "Don't verify signers certificate"},
     98 
     99     {"certfile", OPT_CERTFILE, '<', "Other certificates file"},
    100     {"recip", OPT_RECIP, '<', "Recipient certificate file for decryption"},
    101 
    102     OPT_SECTION("Email"),
    103     {"to", OPT_TO, 's', "To address"},
    104     {"from", OPT_FROM, 's', "From address"},
    105     {"subject", OPT_SUBJECT, 's', "Subject"},
    106     {"text", OPT_TEXT, '-', "Include or delete text MIME headers"},
    107     {"nosmimecap", OPT_NOSMIMECAP, '-', "Omit the SMIMECapabilities attribute"},
    108 
    109     OPT_SECTION("Certificate chain"),
    110     {"CApath", OPT_CAPATH, '/', "Trusted certificates directory"},
    111     {"CAfile", OPT_CAFILE, '<', "Trusted certificates file"},
    112     {"CAstore", OPT_CASTORE, ':', "Trusted certificates store URI"},
    113     {"no-CAfile", OPT_NOCAFILE, '-',
    114      "Do not load the default certificates file"},
    115     {"no-CApath", OPT_NOCAPATH, '-',
    116      "Do not load certificates from the default certificates directory"},
    117     {"no-CAstore", OPT_NOCASTORE, '-',
    118      "Do not load certificates from the default certificates store"},
    119     {"nochain", OPT_NOCHAIN, '-',
    120      "set PKCS7_NOCHAIN so certificates contained in the message are not used as untrusted CAs" },
    121     {"crlfeol", OPT_CRLFEOL, '-', "Use CRLF as EOL termination instead of LF only"},
    122 
    123     OPT_R_OPTIONS,
    124     OPT_V_OPTIONS,
    125     OPT_PROV_OPTIONS,
    126 
    127     OPT_PARAMETERS(),
    128     {"cert", 0, 0, "Recipient certs, used when encrypting"},
    129     {NULL}
    130 };
    131 
    132 int smime_main(int argc, char **argv)
    133 {
    134     CONF *conf = NULL;
    135     BIO *in = NULL, *out = NULL, *indata = NULL;
    136     EVP_PKEY *key = NULL;
    137     PKCS7 *p7 = NULL;
    138     STACK_OF(OPENSSL_STRING) *sksigners = NULL, *skkeys = NULL;
    139     STACK_OF(X509) *encerts = NULL, *other = NULL;
    140     X509 *cert = NULL, *recip = NULL, *signer = NULL;
    141     X509_STORE *store = NULL;
    142     X509_VERIFY_PARAM *vpm = NULL;
    143     EVP_CIPHER *cipher = NULL;
    144     EVP_MD *sign_md = NULL;
    145     const char *CAfile = NULL, *CApath = NULL, *CAstore = NULL, *prog = NULL;
    146     char *certfile = NULL, *keyfile = NULL, *contfile = NULL;
    147     char *infile = NULL, *outfile = NULL, *signerfile = NULL, *recipfile = NULL;
    148     char *passinarg = NULL, *passin = NULL, *to = NULL, *from = NULL;
    149     char *subject = NULL, *digestname = NULL, *ciphername = NULL;
    150     OPTION_CHOICE o;
    151     int noCApath = 0, noCAfile = 0, noCAstore = 0;
    152     int flags = PKCS7_DETACHED, operation = 0, ret = 0, indef = 0;
    153     int informat = FORMAT_SMIME, outformat = FORMAT_SMIME, keyform =
    154         FORMAT_UNDEF;
    155     int vpmtouched = 0, rv = 0;
    156     ENGINE *e = NULL;
    157     const char *mime_eol = "\n";
    158     OSSL_LIB_CTX *libctx = app_get0_libctx();
    159 
    160     if ((vpm = X509_VERIFY_PARAM_new()) == NULL)
    161         return 1;
    162 
    163     prog = opt_init(argc, argv, smime_options);
    164     while ((o = opt_next()) != OPT_EOF) {
    165         switch (o) {
    166         case OPT_EOF:
    167         case OPT_ERR:
    168  opthelp:
    169             BIO_printf(bio_err, "%s: Use -help for summary.\n", prog);
    170             goto end;
    171         case OPT_HELP:
    172             opt_help(smime_options);
    173             ret = 0;
    174             goto end;
    175         case OPT_INFORM:
    176             if (!opt_format(opt_arg(), OPT_FMT_PDS, &informat))
    177                 goto opthelp;
    178             break;
    179         case OPT_IN:
    180             infile = opt_arg();
    181             break;
    182         case OPT_OUTFORM:
    183             if (!opt_format(opt_arg(), OPT_FMT_PDS, &outformat))
    184                 goto opthelp;
    185             break;
    186         case OPT_OUT:
    187             outfile = opt_arg();
    188             break;
    189         case OPT_ENCRYPT:
    190             operation = SMIME_ENCRYPT;
    191             break;
    192         case OPT_DECRYPT:
    193             operation = SMIME_DECRYPT;
    194             break;
    195         case OPT_SIGN:
    196             operation = SMIME_SIGN;
    197             break;
    198         case OPT_RESIGN:
    199             operation = SMIME_RESIGN;
    200             break;
    201         case OPT_VERIFY:
    202             operation = SMIME_VERIFY;
    203             break;
    204         case OPT_PK7OUT:
    205             operation = SMIME_PK7OUT;
    206             break;
    207         case OPT_TEXT:
    208             flags |= PKCS7_TEXT;
    209             break;
    210         case OPT_NOINTERN:
    211             flags |= PKCS7_NOINTERN;
    212             break;
    213         case OPT_NOVERIFY:
    214             flags |= PKCS7_NOVERIFY;
    215             break;
    216         case OPT_NOCHAIN:
    217             flags |= PKCS7_NOCHAIN;
    218             break;
    219         case OPT_NOCERTS:
    220             flags |= PKCS7_NOCERTS;
    221             break;
    222         case OPT_NOATTR:
    223             flags |= PKCS7_NOATTR;
    224             break;
    225         case OPT_NODETACH:
    226             flags &= ~PKCS7_DETACHED;
    227             break;
    228         case OPT_NOSMIMECAP:
    229             flags |= PKCS7_NOSMIMECAP;
    230             break;
    231         case OPT_BINARY:
    232             flags |= PKCS7_BINARY;
    233             break;
    234         case OPT_NOSIGS:
    235             flags |= PKCS7_NOSIGS;
    236             break;
    237         case OPT_STREAM:
    238         case OPT_INDEF:
    239             indef = 1;
    240             break;
    241         case OPT_NOINDEF:
    242             indef = 0;
    243             break;
    244         case OPT_CRLFEOL:
    245             flags |= PKCS7_CRLFEOL;
    246             mime_eol = "\r\n";
    247             break;
    248         case OPT_R_CASES:
    249             if (!opt_rand(o))
    250                 goto end;
    251             break;
    252         case OPT_PROV_CASES:
    253             if (!opt_provider(o))
    254                 goto end;
    255             break;
    256         case OPT_CONFIG:
    257             conf = app_load_config_modules(opt_arg());
    258             if (conf == NULL)
    259                 goto end;
    260             break;
    261         case OPT_ENGINE:
    262             e = setup_engine(opt_arg(), 0);
    263             break;
    264         case OPT_PASSIN:
    265             passinarg = opt_arg();
    266             break;
    267         case OPT_TO:
    268             to = opt_arg();
    269             break;
    270         case OPT_FROM:
    271             from = opt_arg();
    272             break;
    273         case OPT_SUBJECT:
    274             subject = opt_arg();
    275             break;
    276         case OPT_SIGNER:
    277             /* If previous -signer argument add signer to list */
    278             if (signerfile != NULL) {
    279                 if (sksigners == NULL
    280                     && (sksigners = sk_OPENSSL_STRING_new_null()) == NULL)
    281                     goto end;
    282                 if (sk_OPENSSL_STRING_push(sksigners, signerfile) <= 0)
    283                     goto end;
    284                 if (keyfile == NULL)
    285                     keyfile = signerfile;
    286                 if (skkeys == NULL
    287                     && (skkeys = sk_OPENSSL_STRING_new_null()) == NULL)
    288                     goto end;
    289                 if (sk_OPENSSL_STRING_push(skkeys, keyfile) <= 0)
    290                     goto end;
    291                 keyfile = NULL;
    292             }
    293             signerfile = opt_arg();
    294             break;
    295         case OPT_RECIP:
    296             recipfile = opt_arg();
    297             break;
    298         case OPT_MD:
    299             digestname = opt_arg();
    300             break;
    301         case OPT_CIPHER:
    302             ciphername = opt_unknown();
    303             break;
    304         case OPT_INKEY:
    305             /* If previous -inkey argument add signer to list */
    306             if (keyfile != NULL) {
    307                 if (signerfile == NULL) {
    308                     BIO_printf(bio_err,
    309                                "%s: Must have -signer before -inkey\n", prog);
    310                     goto opthelp;
    311                 }
    312                 if (sksigners == NULL
    313                     && (sksigners = sk_OPENSSL_STRING_new_null()) == NULL)
    314                     goto end;
    315                 if (sk_OPENSSL_STRING_push(sksigners, signerfile) <= 0)
    316                     goto end;
    317                 signerfile = NULL;
    318                 if (skkeys == NULL
    319                     && (skkeys = sk_OPENSSL_STRING_new_null()) == NULL)
    320                     goto end;
    321                 if (sk_OPENSSL_STRING_push(skkeys, keyfile) <= 0)
    322                     goto end;
    323             }
    324             keyfile = opt_arg();
    325             break;
    326         case OPT_KEYFORM:
    327             if (!opt_format(opt_arg(), OPT_FMT_ANY, &keyform))
    328                 goto opthelp;
    329             break;
    330         case OPT_CERTFILE:
    331             certfile = opt_arg();
    332             break;
    333         case OPT_CAFILE:
    334             CAfile = opt_arg();
    335             break;
    336         case OPT_CAPATH:
    337             CApath = opt_arg();
    338             break;
    339         case OPT_CASTORE:
    340             CAstore = opt_arg();
    341             break;
    342         case OPT_NOCAFILE:
    343             noCAfile = 1;
    344             break;
    345         case OPT_NOCAPATH:
    346             noCApath = 1;
    347             break;
    348         case OPT_NOCASTORE:
    349             noCAstore = 1;
    350             break;
    351         case OPT_CONTENT:
    352             contfile = opt_arg();
    353             break;
    354         case OPT_V_CASES:
    355             if (!opt_verify(o, vpm))
    356                 goto opthelp;
    357             vpmtouched++;
    358             break;
    359         }
    360     }
    361 
    362     /* Extra arguments are files with recipient keys. */
    363     argc = opt_num_rest();
    364     argv = opt_rest();
    365 
    366     if (!app_RAND_load())
    367         goto end;
    368 
    369     if (digestname != NULL) {
    370         if (!opt_md(digestname, &sign_md))
    371             goto opthelp;
    372     }
    373     if (ciphername != NULL) {
    374         if (!opt_cipher_any(ciphername, &cipher))
    375             goto opthelp;
    376     }
    377     if (!(operation & SMIME_SIGNERS) && (skkeys != NULL || sksigners != NULL)) {
    378         BIO_puts(bio_err, "Multiple signers or keys not allowed\n");
    379         goto opthelp;
    380     }
    381     if (!operation) {
    382         BIO_puts(bio_err,
    383                 "No operation (-encrypt|-sign|...) specified\n");
    384         goto opthelp;
    385     }
    386 
    387     if (operation & SMIME_SIGNERS) {
    388         /* Check to see if any final signer needs to be appended */
    389         if (keyfile && !signerfile) {
    390             BIO_puts(bio_err, "Illegal -inkey without -signer\n");
    391             goto opthelp;
    392         }
    393         if (signerfile != NULL) {
    394             if (sksigners == NULL
    395                 && (sksigners = sk_OPENSSL_STRING_new_null()) == NULL)
    396                 goto end;
    397             if (sk_OPENSSL_STRING_push(sksigners, signerfile) <= 0)
    398                 goto end;
    399             if (!skkeys && (skkeys = sk_OPENSSL_STRING_new_null()) == NULL)
    400                 goto end;
    401             if (!keyfile)
    402                 keyfile = signerfile;
    403             if (sk_OPENSSL_STRING_push(skkeys, keyfile) <= 0)
    404                 goto end;
    405         }
    406         if (sksigners == NULL) {
    407             BIO_printf(bio_err, "No signer certificate specified\n");
    408             goto opthelp;
    409         }
    410         signerfile = NULL;
    411         keyfile = NULL;
    412     } else if (operation == SMIME_DECRYPT) {
    413         if (recipfile == NULL && keyfile == NULL) {
    414             BIO_printf(bio_err,
    415                        "No recipient certificate or key specified\n");
    416             goto opthelp;
    417         }
    418     } else if (operation == SMIME_ENCRYPT) {
    419         if (argc == 0) {
    420             BIO_printf(bio_err, "No recipient(s) certificate(s) specified\n");
    421             goto opthelp;
    422         }
    423     }
    424 
    425     if (!app_passwd(passinarg, NULL, &passin, NULL)) {
    426         BIO_printf(bio_err, "Error getting password\n");
    427         goto end;
    428     }
    429 
    430     ret = 2;
    431 
    432     if (!(operation & SMIME_SIGNERS))
    433         flags &= ~PKCS7_DETACHED;
    434 
    435     if (!(operation & SMIME_OP)) {
    436         if (flags & PKCS7_BINARY)
    437             outformat = FORMAT_BINARY;
    438     }
    439 
    440     if (!(operation & SMIME_IP)) {
    441         if (flags & PKCS7_BINARY)
    442             informat = FORMAT_BINARY;
    443     }
    444 
    445     if (operation == SMIME_ENCRYPT) {
    446         if (cipher == NULL) {
    447 #ifndef OPENSSL_NO_DES
    448             cipher = (EVP_CIPHER *)EVP_des_ede3_cbc();
    449 #else
    450             BIO_printf(bio_err, "No cipher selected\n");
    451             goto end;
    452 #endif
    453         }
    454         encerts = sk_X509_new_null();
    455         if (encerts == NULL)
    456             goto end;
    457         while (*argv != NULL) {
    458             cert = load_cert(*argv, FORMAT_UNDEF,
    459                              "recipient certificate file");
    460             if (cert == NULL)
    461                 goto end;
    462             if (!sk_X509_push(encerts, cert))
    463                 goto end;
    464             cert = NULL;
    465             argv++;
    466         }
    467     }
    468 
    469     if (certfile != NULL) {
    470         if (!load_certs(certfile, 0, &other, NULL, "certificates")) {
    471             ERR_print_errors(bio_err);
    472             goto end;
    473         }
    474     }
    475 
    476     if (recipfile != NULL && (operation == SMIME_DECRYPT)) {
    477         if ((recip = load_cert(recipfile, FORMAT_UNDEF,
    478                                "recipient certificate file")) == NULL) {
    479             ERR_print_errors(bio_err);
    480             goto end;
    481         }
    482     }
    483 
    484     if (operation == SMIME_DECRYPT) {
    485         if (keyfile == NULL)
    486             keyfile = recipfile;
    487     } else if (operation == SMIME_SIGN) {
    488         if (keyfile == NULL)
    489             keyfile = signerfile;
    490     } else {
    491         keyfile = NULL;
    492     }
    493 
    494     if (keyfile != NULL) {
    495         key = load_key(keyfile, keyform, 0, passin, e, "signing key");
    496         if (key == NULL)
    497             goto end;
    498     }
    499 
    500     in = bio_open_default(infile, 'r', informat);
    501     if (in == NULL)
    502         goto end;
    503 
    504     if (operation & SMIME_IP) {
    505         PKCS7 *p7_in = NULL;
    506 
    507         p7 = PKCS7_new_ex(libctx, app_get0_propq());
    508         if (p7 == NULL) {
    509             BIO_printf(bio_err, "Error allocating PKCS7 object\n");
    510             goto end;
    511         }
    512         if (informat == FORMAT_SMIME) {
    513             p7_in = SMIME_read_PKCS7_ex(in, &indata, &p7);
    514         } else if (informat == FORMAT_PEM) {
    515             p7_in = PEM_read_bio_PKCS7(in, &p7, NULL, NULL);
    516         } else if (informat == FORMAT_ASN1) {
    517             p7_in = d2i_PKCS7_bio(in, &p7);
    518         } else {
    519             BIO_printf(bio_err, "Bad input format for PKCS#7 file\n");
    520             goto end;
    521         }
    522 
    523         if (p7_in == NULL) {
    524             BIO_printf(bio_err, "Error reading S/MIME message\n");
    525             goto end;
    526         }
    527         if (contfile != NULL) {
    528             BIO_free(indata);
    529             if ((indata = BIO_new_file(contfile, "rb")) == NULL) {
    530                 BIO_printf(bio_err, "Can't read content file %s\n", contfile);
    531                 goto end;
    532             }
    533         }
    534     }
    535 
    536     out = bio_open_default(outfile, 'w', outformat);
    537     if (out == NULL)
    538         goto end;
    539 
    540     if (operation == SMIME_VERIFY) {
    541         if ((store = setup_verify(CAfile, noCAfile, CApath, noCApath,
    542                                   CAstore, noCAstore)) == NULL)
    543             goto end;
    544         X509_STORE_set_verify_cb(store, smime_cb);
    545         if (vpmtouched)
    546             X509_STORE_set1_param(store, vpm);
    547     }
    548 
    549     ret = 3;
    550 
    551     if (operation == SMIME_ENCRYPT) {
    552         if (indef)
    553             flags |= PKCS7_STREAM;
    554         p7 = PKCS7_encrypt_ex(encerts, in, cipher, flags, libctx, app_get0_propq());
    555     } else if (operation & SMIME_SIGNERS) {
    556         int i;
    557         /*
    558          * If detached data content we only enable streaming if S/MIME output
    559          * format.
    560          */
    561         if (operation == SMIME_SIGN) {
    562             if (flags & PKCS7_DETACHED) {
    563                 if (outformat == FORMAT_SMIME)
    564                     flags |= PKCS7_STREAM;
    565             } else if (indef) {
    566                 flags |= PKCS7_STREAM;
    567             }
    568             flags |= PKCS7_PARTIAL;
    569             p7 = PKCS7_sign_ex(NULL, NULL, other, in, flags, libctx, app_get0_propq());
    570             if (p7 == NULL)
    571                 goto end;
    572             if (flags & PKCS7_NOCERTS) {
    573                 for (i = 0; i < sk_X509_num(other); i++) {
    574                     X509 *x = sk_X509_value(other, i);
    575                     PKCS7_add_certificate(p7, x);
    576                 }
    577             }
    578         } else {
    579             flags |= PKCS7_REUSE_DIGEST;
    580         }
    581         for (i = 0; i < sk_OPENSSL_STRING_num(sksigners); i++) {
    582             signerfile = sk_OPENSSL_STRING_value(sksigners, i);
    583             keyfile = sk_OPENSSL_STRING_value(skkeys, i);
    584             signer = load_cert(signerfile, FORMAT_UNDEF, "signer certificate");
    585             if (signer == NULL)
    586                 goto end;
    587             key = load_key(keyfile, keyform, 0, passin, e, "signing key");
    588             if (key == NULL)
    589                 goto end;
    590 
    591             if (!PKCS7_sign_add_signer(p7, signer, key, sign_md, flags))
    592                 goto end;
    593             X509_free(signer);
    594             signer = NULL;
    595             EVP_PKEY_free(key);
    596             key = NULL;
    597         }
    598         /* If not streaming or resigning finalize structure */
    599         if ((operation == SMIME_SIGN) && !(flags & PKCS7_STREAM)) {
    600             if (!PKCS7_final(p7, in, flags))
    601                 goto end;
    602         }
    603     }
    604 
    605     if (p7 == NULL) {
    606         BIO_printf(bio_err, "Error creating PKCS#7 structure\n");
    607         goto end;
    608     }
    609 
    610     ret = 4;
    611     if (operation == SMIME_DECRYPT) {
    612         if (!PKCS7_decrypt(p7, key, recip, out, flags)) {
    613             BIO_printf(bio_err, "Error decrypting PKCS#7 structure\n");
    614             goto end;
    615         }
    616     } else if (operation == SMIME_VERIFY) {
    617         STACK_OF(X509) *signers;
    618         if (PKCS7_verify(p7, other, store, indata, out, flags))
    619             BIO_printf(bio_err, "Verification successful\n");
    620         else {
    621             BIO_printf(bio_err, "Verification failure\n");
    622             goto end;
    623         }
    624         signers = PKCS7_get0_signers(p7, other, flags);
    625         if (!save_certs(signerfile, signers)) {
    626             BIO_printf(bio_err, "Error writing signers to %s\n", signerfile);
    627             ret = 5;
    628             goto end;
    629         }
    630         sk_X509_free(signers);
    631     } else if (operation == SMIME_PK7OUT) {
    632         PEM_write_bio_PKCS7(out, p7);
    633     } else {
    634         if (to)
    635             BIO_printf(out, "To: %s%s", to, mime_eol);
    636         if (from)
    637             BIO_printf(out, "From: %s%s", from, mime_eol);
    638         if (subject)
    639             BIO_printf(out, "Subject: %s%s", subject, mime_eol);
    640         if (outformat == FORMAT_SMIME) {
    641             if (operation == SMIME_RESIGN)
    642                 rv = SMIME_write_PKCS7(out, p7, indata, flags);
    643             else
    644                 rv = SMIME_write_PKCS7(out, p7, in, flags);
    645         } else if (outformat == FORMAT_PEM) {
    646             rv = PEM_write_bio_PKCS7_stream(out, p7, in, flags);
    647         } else if (outformat == FORMAT_ASN1) {
    648             rv = i2d_PKCS7_bio_stream(out, p7, in, flags);
    649         } else {
    650             BIO_printf(bio_err, "Bad output format for PKCS#7 file\n");
    651             goto end;
    652         }
    653         if (rv == 0) {
    654             BIO_printf(bio_err, "Error writing output\n");
    655             ret = 3;
    656             goto end;
    657         }
    658     }
    659     ret = 0;
    660  end:
    661     if (ret)
    662         ERR_print_errors(bio_err);
    663     sk_X509_pop_free(encerts, X509_free);
    664     sk_X509_pop_free(other, X509_free);
    665     X509_VERIFY_PARAM_free(vpm);
    666     sk_OPENSSL_STRING_free(sksigners);
    667     sk_OPENSSL_STRING_free(skkeys);
    668     X509_STORE_free(store);
    669     X509_free(cert);
    670     X509_free(recip);
    671     X509_free(signer);
    672     EVP_PKEY_free(key);
    673     EVP_MD_free(sign_md);
    674     EVP_CIPHER_free(cipher);
    675     PKCS7_free(p7);
    676     release_engine(e);
    677     BIO_free(in);
    678     BIO_free(indata);
    679     BIO_free_all(out);
    680     OPENSSL_free(passin);
    681     NCONF_free(conf);
    682     return ret;
    683 }
    684 
    685 static int save_certs(char *signerfile, STACK_OF(X509) *signers)
    686 {
    687     int i;
    688     BIO *tmp;
    689 
    690     if (signerfile == NULL)
    691         return 1;
    692     tmp = BIO_new_file(signerfile, "w");
    693     if (tmp == NULL)
    694         return 0;
    695     for (i = 0; i < sk_X509_num(signers); i++)
    696         PEM_write_bio_X509(tmp, sk_X509_value(signers, i));
    697     BIO_free(tmp);
    698     return 1;
    699 }
    700 
    701 /* Minimal callback just to output policy info (if any) */
    702 
    703 static int smime_cb(int ok, X509_STORE_CTX *ctx)
    704 {
    705     int error;
    706 
    707     error = X509_STORE_CTX_get_error(ctx);
    708 
    709     if ((error != X509_V_ERR_NO_EXPLICIT_POLICY)
    710         && ((error != X509_V_OK) || (ok != 2)))
    711         return ok;
    712 
    713     policies_print(ctx);
    714 
    715     return ok;
    716 }
    717