2 * Written by Dr Stephen N Henson (steve@openssl.org) for the OpenSSL
5 /* ====================================================================
6 * Copyright (c) 1999-2004 The OpenSSL Project. All rights reserved.
8 * Redistribution and use in source and binary forms, with or without
9 * modification, are permitted provided that the following conditions
12 * 1. Redistributions of source code must retain the above copyright
13 * notice, this list of conditions and the following disclaimer.
15 * 2. Redistributions in binary form must reproduce the above copyright
16 * notice, this list of conditions and the following disclaimer in
17 * the documentation and/or other materials provided with the
20 * 3. All advertising materials mentioning features or use of this
21 * software must display the following acknowledgment:
22 * "This product includes software developed by the OpenSSL Project
23 * for use in the OpenSSL Toolkit. (http://www.OpenSSL.org/)"
25 * 4. The names "OpenSSL Toolkit" and "OpenSSL Project" must not be used to
26 * endorse or promote products derived from this software without
27 * prior written permission. For written permission, please contact
28 * licensing@OpenSSL.org.
30 * 5. Products derived from this software may not be called "OpenSSL"
31 * nor may "OpenSSL" appear in their names without prior written
32 * permission of the OpenSSL Project.
34 * 6. Redistributions of any form whatsoever must retain the following
36 * "This product includes software developed by the OpenSSL Project
37 * for use in the OpenSSL Toolkit (http://www.OpenSSL.org/)"
39 * THIS SOFTWARE IS PROVIDED BY THE OpenSSL PROJECT ``AS IS'' AND ANY
40 * EXPRESSED OR IMPLIED WARRANTIES, INCLUDING, BUT NOT LIMITED TO, THE
41 * IMPLIED WARRANTIES OF MERCHANTABILITY AND FITNESS FOR A PARTICULAR
42 * PURPOSE ARE DISCLAIMED. IN NO EVENT SHALL THE OpenSSL PROJECT OR
43 * ITS CONTRIBUTORS BE LIABLE FOR ANY DIRECT, INDIRECT, INCIDENTAL,
44 * SPECIAL, EXEMPLARY, OR CONSEQUENTIAL DAMAGES (INCLUDING, BUT
45 * NOT LIMITED TO, PROCUREMENT OF SUBSTITUTE GOODS OR SERVICES;
46 * LOSS OF USE, DATA, OR PROFITS; OR BUSINESS INTERRUPTION)
47 * HOWEVER CAUSED AND ON ANY THEORY OF LIABILITY, WHETHER IN CONTRACT,
48 * STRICT LIABILITY, OR TORT (INCLUDING NEGLIGENCE OR OTHERWISE)
49 * ARISING IN ANY WAY OUT OF THE USE OF THIS SOFTWARE, EVEN IF ADVISED
50 * OF THE POSSIBILITY OF SUCH DAMAGE.
51 * ====================================================================
53 * This product includes cryptographic software written by Eric Young
54 * (eay@cryptsoft.com). This product includes software written by Tim
55 * Hudson (tjh@cryptsoft.com).
59 /* S/MIME utility function */
64 #include <openssl/crypto.h>
65 #include <openssl/pem.h>
66 #include <openssl/err.h>
67 #include <openssl/x509_vfy.h>
68 #include <openssl/x509v3.h>
70 static int save_certs(char *signerfile, STACK_OF(X509) *signers);
71 static int smime_cb(int ok, X509_STORE_CTX *ctx);
75 #define SMIME_SIGNERS 0x40
76 #define SMIME_ENCRYPT (1 | SMIME_OP)
77 #define SMIME_DECRYPT (2 | SMIME_IP)
78 #define SMIME_SIGN (3 | SMIME_OP | SMIME_SIGNERS)
79 #define SMIME_VERIFY (4 | SMIME_IP)
80 #define SMIME_PK7OUT (5 | SMIME_IP | SMIME_OP)
81 #define SMIME_RESIGN (6 | SMIME_IP | SMIME_OP | SMIME_SIGNERS)
83 typedef enum OPTION_choice {
84 OPT_ERR = -1, OPT_EOF = 0, OPT_HELP,
85 OPT_ENCRYPT, OPT_DECRYPT, OPT_SIGN, OPT_RESIGN, OPT_VERIFY,
86 OPT_PK7OUT, OPT_TEXT, OPT_NOINTERN, OPT_NOVERIFY, OPT_NOCHAIN,
87 OPT_NOCERTS, OPT_NOATTR, OPT_NODETACH, OPT_NOSMIMECAP,
88 OPT_BINARY, OPT_NOSIGS, OPT_STREAM, OPT_INDEF, OPT_NOINDEF,
89 OPT_NOOLDMIME, OPT_CRLFEOL, OPT_RAND, OPT_ENGINE, OPT_PASSIN,
90 OPT_TO, OPT_FROM, OPT_SUBJECT, OPT_SIGNER, OPT_RECIP, OPT_MD,
91 OPT_CIPHER, OPT_INKEY, OPT_KEYFORM, OPT_CERTFILE, OPT_CAFILE,
93 OPT_CAPATH, OPT_IN, OPT_INFORM, OPT_OUT, OPT_OUTFORM, OPT_CONTENT
96 OPTIONS smime_options[] = {
97 {OPT_HELP_STR, 1, '-', "Usage: %s [options] cert.pem...\n"},
98 {OPT_HELP_STR, 1, '-',
99 " cert.pem... recipient certs for encryption\n"},
100 {OPT_HELP_STR, 1, '-', "Valid options are:\n"},
101 {"help", OPT_HELP, '-', "Display this summary"},
102 {"encrypt", OPT_ENCRYPT, '-', "Encrypt message"},
103 {"decrypt", OPT_DECRYPT, '-', "Decrypt encrypted message"},
104 {"sign", OPT_SIGN, '-', "Sign message"},
105 {"verify", OPT_VERIFY, '-', "Verify signed message"},
106 {"pk7out", OPT_PK7OUT, '-', "Output PKCS#7 structure"},
107 {"nointern", OPT_NOINTERN, '-',
108 "Don't search certificates in message for signer"},
109 {"nosigs", OPT_NOSIGS, '-', "Don't verify message signature"},
110 {"noverify", OPT_NOVERIFY, '-', "Don't verify signers certificate"},
111 {"nocerts", OPT_NOCERTS, '-',
112 "Don't include signers certificate when signing"},
113 {"nodetach", OPT_NODETACH, '-', "Use opaque signing"},
114 {"noattr", OPT_NOATTR, '-', "Don't include any signed attributes"},
115 {"binary", OPT_BINARY, '-', "Don't translate message to text"},
116 {"certfile", OPT_CERTFILE, '<', "Other certificates file"},
117 {"signer", OPT_SIGNER, '<', "Signer certificate file"},
118 {"recip", OPT_RECIP, '<', "Recipient certificate file for decryption"},
119 {"in", OPT_IN, '<', "Input file"},
120 {"inform", OPT_INFORM, 'F', "Input format SMIME (default), PEM or DER"},
121 {"inkey", OPT_INKEY, '<',
122 "Input private key (if not signer or recipient)"},
123 {"keyform", OPT_KEYFORM, 'f', "Input private key format (PEM or ENGINE)"},
124 {"out", OPT_OUT, '>', "Output file"},
125 {"outform", OPT_OUTFORM, 'F',
126 "Output format SMIME (default), PEM or DER"},
127 {"content", OPT_CONTENT, '<',
128 "Supply or override content for detached signature"},
129 {"to", OPT_TO, 's', "To address"},
130 {"from", OPT_FROM, 's', "From address"},
131 {"subject", OPT_SUBJECT, 's', "Subject"},
132 {"text", OPT_TEXT, '-', "Include or delete text MIME headers"},
133 {"CApath", OPT_CAPATH, '/', "Trusted certificates directory"},
134 {"CAfile", OPT_CAFILE, '<', "Trusted certificates file"},
135 {"resign", OPT_RESIGN, '-'},
136 {"nochain", OPT_NOCHAIN, '-'},
137 {"nosmimecap", OPT_NOSMIMECAP, '-'},
138 {"stream", OPT_STREAM, '-'},
139 {"indef", OPT_INDEF, '-'},
140 {"noindef", OPT_NOINDEF, '-'},
141 {"nooldmime", OPT_NOOLDMIME, '-'},
142 {"crlfeol", OPT_CRLFEOL, '-'},
143 {"rand", OPT_RAND, 's',
144 "Load the file(s) into the random number generator"},
145 {"passin", OPT_PASSIN, 's', "Input file pass phrase source"},
147 {"", OPT_CIPHER, '-', "Any supported cipher"},
149 #ifndef OPENSSL_NO_ENGINE
150 {"engine", OPT_ENGINE, 's', "Use engine, possibly a hardware device"},
155 int smime_main(int argc, char **argv)
157 BIO *in = NULL, *out = NULL, *indata = NULL;
158 EVP_PKEY *key = NULL;
160 STACK_OF(OPENSSL_STRING) *sksigners = NULL, *skkeys = NULL;
161 STACK_OF(X509) *encerts = NULL, *other = NULL;
162 X509 *cert = NULL, *recip = NULL, *signer = NULL;
163 X509_STORE *store = NULL;
164 X509_VERIFY_PARAM *vpm = NULL;
165 const EVP_CIPHER *cipher = NULL;
166 const EVP_MD *sign_md = NULL;
167 char *CAfile = NULL, *CApath = NULL, *inrand = NULL;
168 char *certfile = NULL, *keyfile = NULL, *contfile = NULL, *prog;
169 char *infile = NULL, *outfile = NULL, *signerfile = NULL, *recipfile =
171 char *passinarg = NULL, *passin = NULL, *to = NULL, *from =
172 NULL, *subject = NULL;
173 const char *inmode = "r", *outmode = "w";
175 int flags = PKCS7_DETACHED, operation = 0, ret = 0, need_rand = 0, indef =
177 int informat = FORMAT_SMIME, outformat = FORMAT_SMIME, keyform =
179 int vpmtouched = 0, rv = 0;
182 if ((vpm = X509_VERIFY_PARAM_new()) == NULL)
185 prog = opt_init(argc, argv, smime_options);
186 while ((o = opt_next()) != OPT_EOF) {
191 BIO_printf(bio_err, "%s: Use -help for summary.\n", prog);
194 opt_help(smime_options);
198 if (!opt_format(opt_arg(), OPT_FMT_PEMDER, &informat))
205 if (!opt_format(opt_arg(), OPT_FMT_PEMDER, &outformat))
212 operation = SMIME_ENCRYPT;
215 operation = SMIME_DECRYPT;
218 operation = SMIME_SIGN;
221 operation = SMIME_RESIGN;
224 operation = SMIME_VERIFY;
227 operation = SMIME_PK7OUT;
233 flags |= PKCS7_NOINTERN;
236 flags |= PKCS7_NOVERIFY;
239 flags |= PKCS7_NOCHAIN;
242 flags |= PKCS7_NOCERTS;
245 flags |= PKCS7_NOATTR;
248 flags &= ~PKCS7_DETACHED;
251 flags |= PKCS7_NOSMIMECAP;
254 flags |= PKCS7_BINARY;
257 flags |= PKCS7_NOSIGS;
267 flags |= PKCS7_NOOLDMIMETYPE;
270 flags |= PKCS7_CRLFEOL;
277 e = setup_engine(opt_arg(), 0);
280 passinarg = opt_arg();
292 /* If previous -signer argument add signer to list */
294 if (sksigners == NULL
295 && (sksigners = sk_OPENSSL_STRING_new_null()) == NULL)
297 sk_OPENSSL_STRING_push(sksigners, signerfile);
299 keyfile = signerfile;
301 && (skkeys = sk_OPENSSL_STRING_new_null()) == NULL)
303 sk_OPENSSL_STRING_push(skkeys, keyfile);
306 signerfile = opt_arg();
309 recipfile = opt_arg();
312 if (!opt_md(opt_arg(), &sign_md))
316 if (!opt_cipher(opt_unknown(), &cipher))
320 /* If previous -inkey arument add signer to list */
322 if (signerfile == NULL) {
324 "%s: Must have -signer before -inkey\n", prog);
327 if (sksigners == NULL
328 && (sksigners = sk_OPENSSL_STRING_new_null()) == NULL)
330 sk_OPENSSL_STRING_push(sksigners, signerfile);
333 && (skkeys = sk_OPENSSL_STRING_new_null()) == NULL)
335 sk_OPENSSL_STRING_push(skkeys, keyfile);
340 if (!opt_format(opt_arg(), OPT_FMT_ANY, &keyform))
344 certfile = opt_arg();
353 contfile = opt_arg();
356 if (!opt_verify(o, vpm))
362 argc = opt_num_rest();
365 if (!(operation & SMIME_SIGNERS) && (skkeys || sksigners)) {
366 BIO_puts(bio_err, "Multiple signers or keys not allowed\n");
370 if (operation & SMIME_SIGNERS) {
371 /* Check to see if any final signer needs to be appended */
372 if (keyfile && !signerfile) {
373 BIO_puts(bio_err, "Illegal -inkey without -signer\n");
378 && (sksigners = sk_OPENSSL_STRING_new_null()) == NULL)
380 sk_OPENSSL_STRING_push(sksigners, signerfile);
381 if (!skkeys && (skkeys = sk_OPENSSL_STRING_new_null()) == NULL)
384 keyfile = signerfile;
385 sk_OPENSSL_STRING_push(skkeys, keyfile);
388 BIO_printf(bio_err, "No signer certificate specified\n");
394 } else if (operation == SMIME_DECRYPT) {
395 if (!recipfile && !keyfile) {
397 "No recipient certificate or key specified\n");
400 } else if (operation == SMIME_ENCRYPT) {
402 BIO_printf(bio_err, "No recipient(s) certificate(s) specified\n");
406 } else if (!operation)
409 if (!app_passwd(passinarg, NULL, &passin, NULL)) {
410 BIO_printf(bio_err, "Error getting password\n");
415 app_RAND_load_file(NULL, (inrand != NULL));
417 BIO_printf(bio_err, "%ld semi-random bytes loaded\n",
418 app_RAND_load_files(inrand));
423 if (!(operation & SMIME_SIGNERS))
424 flags &= ~PKCS7_DETACHED;
426 if (operation & SMIME_OP) {
427 if (outformat == FORMAT_ASN1)
430 if (flags & PKCS7_BINARY)
434 if (operation & SMIME_IP) {
435 if (informat == FORMAT_ASN1)
438 if (flags & PKCS7_BINARY)
442 if (operation == SMIME_ENCRYPT) {
444 #ifndef OPENSSL_NO_DES
445 cipher = EVP_des_ede3_cbc();
447 BIO_printf(bio_err, "No cipher selected\n");
451 encerts = sk_X509_new_null();
455 cert = load_cert(*argv, FORMAT_PEM,
456 NULL, e, "recipient certificate file");
459 sk_X509_push(encerts, cert);
466 if (!(other = load_certs(certfile, FORMAT_PEM, NULL,
467 e, "certificate file"))) {
468 ERR_print_errors(bio_err);
473 if (recipfile && (operation == SMIME_DECRYPT)) {
474 if (!(recip = load_cert(recipfile, FORMAT_PEM, NULL,
475 e, "recipient certificate file"))) {
476 ERR_print_errors(bio_err);
481 if (operation == SMIME_DECRYPT) {
484 } else if (operation == SMIME_SIGN) {
486 keyfile = signerfile;
491 key = load_key(keyfile, keyform, 0, passin, e, "signing key file");
496 in = bio_open_default(infile, inmode);
500 if (operation & SMIME_IP) {
501 if (informat == FORMAT_SMIME)
502 p7 = SMIME_read_PKCS7(in, &indata);
503 else if (informat == FORMAT_PEM)
504 p7 = PEM_read_bio_PKCS7(in, NULL, NULL, NULL);
505 else if (informat == FORMAT_ASN1)
506 p7 = d2i_PKCS7_bio(in, NULL);
508 BIO_printf(bio_err, "Bad input format for PKCS#7 file\n");
513 BIO_printf(bio_err, "Error reading S/MIME message\n");
518 if (!(indata = BIO_new_file(contfile, "rb"))) {
519 BIO_printf(bio_err, "Can't read content file %s\n", contfile);
525 out = bio_open_default(outfile, outmode);
529 if (operation == SMIME_VERIFY) {
530 if (!(store = setup_verify(CAfile, CApath)))
532 X509_STORE_set_verify_cb(store, smime_cb);
534 X509_STORE_set1_param(store, vpm);
539 if (operation == SMIME_ENCRYPT) {
541 flags |= PKCS7_STREAM;
542 p7 = PKCS7_encrypt(encerts, in, cipher, flags);
543 } else if (operation & SMIME_SIGNERS) {
546 * If detached data content we only enable streaming if S/MIME output
549 if (operation == SMIME_SIGN) {
550 if (flags & PKCS7_DETACHED) {
551 if (outformat == FORMAT_SMIME)
552 flags |= PKCS7_STREAM;
554 flags |= PKCS7_STREAM;
555 flags |= PKCS7_PARTIAL;
556 p7 = PKCS7_sign(NULL, NULL, other, in, flags);
559 if (flags & PKCS7_NOCERTS) {
560 for (i = 0; i < sk_X509_num(other); i++) {
561 X509 *x = sk_X509_value(other, i);
562 PKCS7_add_certificate(p7, x);
566 flags |= PKCS7_REUSE_DIGEST;
567 for (i = 0; i < sk_OPENSSL_STRING_num(sksigners); i++) {
568 signerfile = sk_OPENSSL_STRING_value(sksigners, i);
569 keyfile = sk_OPENSSL_STRING_value(skkeys, i);
570 signer = load_cert(signerfile, FORMAT_PEM, NULL,
571 e, "signer certificate");
574 key = load_key(keyfile, keyform, 0, passin, e, "signing key file");
577 if (!PKCS7_sign_add_signer(p7, signer, key, sign_md, flags))
584 /* If not streaming or resigning finalize structure */
585 if ((operation == SMIME_SIGN) && !(flags & PKCS7_STREAM)) {
586 if (!PKCS7_final(p7, in, flags))
592 BIO_printf(bio_err, "Error creating PKCS#7 structure\n");
597 if (operation == SMIME_DECRYPT) {
598 if (!PKCS7_decrypt(p7, key, recip, out, flags)) {
599 BIO_printf(bio_err, "Error decrypting PKCS#7 structure\n");
602 } else if (operation == SMIME_VERIFY) {
603 STACK_OF(X509) *signers;
604 if (PKCS7_verify(p7, other, store, indata, out, flags))
605 BIO_printf(bio_err, "Verification successful\n");
607 BIO_printf(bio_err, "Verification failure\n");
610 signers = PKCS7_get0_signers(p7, other, flags);
611 if (!save_certs(signerfile, signers)) {
612 BIO_printf(bio_err, "Error writing signers to %s\n", signerfile);
616 sk_X509_free(signers);
617 } else if (operation == SMIME_PK7OUT)
618 PEM_write_bio_PKCS7(out, p7);
621 BIO_printf(out, "To: %s\n", to);
623 BIO_printf(out, "From: %s\n", from);
625 BIO_printf(out, "Subject: %s\n", subject);
626 if (outformat == FORMAT_SMIME) {
627 if (operation == SMIME_RESIGN)
628 rv = SMIME_write_PKCS7(out, p7, indata, flags);
630 rv = SMIME_write_PKCS7(out, p7, in, flags);
631 } else if (outformat == FORMAT_PEM)
632 rv = PEM_write_bio_PKCS7_stream(out, p7, in, flags);
633 else if (outformat == FORMAT_ASN1)
634 rv = i2d_PKCS7_bio_stream(out, p7, in, flags);
636 BIO_printf(bio_err, "Bad output format for PKCS#7 file\n");
640 BIO_printf(bio_err, "Error writing output\n");
648 app_RAND_write_file(NULL);
650 ERR_print_errors(bio_err);
651 sk_X509_pop_free(encerts, X509_free);
652 sk_X509_pop_free(other, X509_free);
653 X509_VERIFY_PARAM_free(vpm);
655 sk_OPENSSL_STRING_free(sksigners);
657 sk_OPENSSL_STRING_free(skkeys);
658 X509_STORE_free(store);
668 OPENSSL_free(passin);
672 static int save_certs(char *signerfile, STACK_OF(X509) *signers)
678 tmp = BIO_new_file(signerfile, "w");
681 for (i = 0; i < sk_X509_num(signers); i++)
682 PEM_write_bio_X509(tmp, sk_X509_value(signers, i));
687 /* Minimal callback just to output policy info (if any) */
689 static int smime_cb(int ok, X509_STORE_CTX *ctx)
693 error = X509_STORE_CTX_get_error(ctx);
695 if ((error != X509_V_ERR_NO_EXPLICIT_POLICY)
696 && ((error != X509_V_OK) || (ok != 2)))