2 * Copyright 1999-2016 The OpenSSL Project Authors. All Rights Reserved.
4 * Licensed under the OpenSSL license (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
10 /* S/MIME utility function */
15 #include <openssl/crypto.h>
16 #include <openssl/pem.h>
17 #include <openssl/err.h>
18 #include <openssl/x509_vfy.h>
19 #include <openssl/x509v3.h>
21 static int save_certs(char *signerfile, STACK_OF(X509) *signers);
22 static int smime_cb(int ok, X509_STORE_CTX *ctx);
26 #define SMIME_SIGNERS 0x40
27 #define SMIME_ENCRYPT (1 | SMIME_OP)
28 #define SMIME_DECRYPT (2 | SMIME_IP)
29 #define SMIME_SIGN (3 | SMIME_OP | SMIME_SIGNERS)
30 #define SMIME_VERIFY (4 | SMIME_IP)
31 #define SMIME_PK7OUT (5 | SMIME_IP | SMIME_OP)
32 #define SMIME_RESIGN (6 | SMIME_IP | SMIME_OP | SMIME_SIGNERS)
34 typedef enum OPTION_choice {
35 OPT_ERR = -1, OPT_EOF = 0, OPT_HELP,
36 OPT_ENCRYPT, OPT_DECRYPT, OPT_SIGN, OPT_RESIGN, OPT_VERIFY,
37 OPT_PK7OUT, OPT_TEXT, OPT_NOINTERN, OPT_NOVERIFY, OPT_NOCHAIN,
38 OPT_NOCERTS, OPT_NOATTR, OPT_NODETACH, OPT_NOSMIMECAP,
39 OPT_BINARY, OPT_NOSIGS, OPT_STREAM, OPT_INDEF, OPT_NOINDEF,
40 OPT_NOOLDMIME, OPT_CRLFEOL, OPT_RAND, OPT_ENGINE, OPT_PASSIN,
41 OPT_TO, OPT_FROM, OPT_SUBJECT, OPT_SIGNER, OPT_RECIP, OPT_MD,
42 OPT_CIPHER, OPT_INKEY, OPT_KEYFORM, OPT_CERTFILE, OPT_CAFILE,
44 OPT_CAPATH, OPT_NOCAFILE, OPT_NOCAPATH, OPT_IN, OPT_INFORM, OPT_OUT,
45 OPT_OUTFORM, OPT_CONTENT
48 OPTIONS smime_options[] = {
49 {OPT_HELP_STR, 1, '-', "Usage: %s [options] cert.pem...\n"},
50 {OPT_HELP_STR, 1, '-',
51 " cert.pem... recipient certs for encryption\n"},
52 {OPT_HELP_STR, 1, '-', "Valid options are:\n"},
53 {"help", OPT_HELP, '-', "Display this summary"},
54 {"encrypt", OPT_ENCRYPT, '-', "Encrypt message"},
55 {"decrypt", OPT_DECRYPT, '-', "Decrypt encrypted message"},
56 {"sign", OPT_SIGN, '-', "Sign message"},
57 {"verify", OPT_VERIFY, '-', "Verify signed message"},
58 {"pk7out", OPT_PK7OUT, '-', "Output PKCS#7 structure"},
59 {"nointern", OPT_NOINTERN, '-',
60 "Don't search certificates in message for signer"},
61 {"nosigs", OPT_NOSIGS, '-', "Don't verify message signature"},
62 {"noverify", OPT_NOVERIFY, '-', "Don't verify signers certificate"},
63 {"nocerts", OPT_NOCERTS, '-',
64 "Don't include signers certificate when signing"},
65 {"nodetach", OPT_NODETACH, '-', "Use opaque signing"},
66 {"noattr", OPT_NOATTR, '-', "Don't include any signed attributes"},
67 {"binary", OPT_BINARY, '-', "Don't translate message to text"},
68 {"certfile", OPT_CERTFILE, '<', "Other certificates file"},
69 {"signer", OPT_SIGNER, 's', "Signer certificate file"},
70 {"recip", OPT_RECIP, '<', "Recipient certificate file for decryption"},
71 {"in", OPT_IN, '<', "Input file"},
72 {"inform", OPT_INFORM, 'c', "Input format SMIME (default), PEM or DER"},
73 {"inkey", OPT_INKEY, '<',
74 "Input private key (if not signer or recipient)"},
75 {"keyform", OPT_KEYFORM, 'f', "Input private key format (PEM or ENGINE)"},
76 {"out", OPT_OUT, '>', "Output file"},
77 {"outform", OPT_OUTFORM, 'c',
78 "Output format SMIME (default), PEM or DER"},
79 {"content", OPT_CONTENT, '<',
80 "Supply or override content for detached signature"},
81 {"to", OPT_TO, 's', "To address"},
82 {"from", OPT_FROM, 's', "From address"},
83 {"subject", OPT_SUBJECT, 's', "Subject"},
84 {"text", OPT_TEXT, '-', "Include or delete text MIME headers"},
85 {"CApath", OPT_CAPATH, '/', "Trusted certificates directory"},
86 {"CAfile", OPT_CAFILE, '<', "Trusted certificates file"},
87 {"no-CAfile", OPT_NOCAFILE, '-',
88 "Do not load the default certificates file"},
89 {"no-CApath", OPT_NOCAPATH, '-',
90 "Do not load certificates from the default certificates directory"},
91 {"resign", OPT_RESIGN, '-'},
92 {"nochain", OPT_NOCHAIN, '-'},
93 {"nosmimecap", OPT_NOSMIMECAP, '-'},
94 {"stream", OPT_STREAM, '-'},
95 {"indef", OPT_INDEF, '-'},
96 {"noindef", OPT_NOINDEF, '-'},
97 {"nooldmime", OPT_NOOLDMIME, '-'},
98 {"crlfeol", OPT_CRLFEOL, '-'},
99 {"rand", OPT_RAND, 's',
100 "Load the file(s) into the random number generator"},
101 {"passin", OPT_PASSIN, 's', "Input file pass phrase source"},
102 {"md", OPT_MD, 's', "Digest algorithm to use when signing or resigning"},
103 {"", OPT_CIPHER, '-', "Any supported cipher"},
105 #ifndef OPENSSL_NO_ENGINE
106 {"engine", OPT_ENGINE, 's', "Use engine, possibly a hardware device"},
111 int smime_main(int argc, char **argv)
113 BIO *in = NULL, *out = NULL, *indata = NULL;
114 EVP_PKEY *key = NULL;
116 STACK_OF(OPENSSL_STRING) *sksigners = NULL, *skkeys = NULL;
117 STACK_OF(X509) *encerts = NULL, *other = NULL;
118 X509 *cert = NULL, *recip = NULL, *signer = NULL;
119 X509_STORE *store = NULL;
120 X509_VERIFY_PARAM *vpm = NULL;
121 const EVP_CIPHER *cipher = NULL;
122 const EVP_MD *sign_md = NULL;
123 char *CAfile = NULL, *CApath = NULL, *inrand = NULL;
124 char *certfile = NULL, *keyfile = NULL, *contfile = NULL, *prog;
125 char *infile = NULL, *outfile = NULL, *signerfile = NULL, *recipfile =
127 char *passinarg = NULL, *passin = NULL, *to = NULL, *from =
128 NULL, *subject = NULL;
130 int noCApath = 0, noCAfile = 0;
131 int flags = PKCS7_DETACHED, operation = 0, ret = 0, need_rand = 0, indef =
133 int informat = FORMAT_SMIME, outformat = FORMAT_SMIME, keyform =
135 int vpmtouched = 0, rv = 0;
137 const char *mime_eol = "\n";
139 if ((vpm = X509_VERIFY_PARAM_new()) == NULL)
142 prog = opt_init(argc, argv, smime_options);
143 while ((o = opt_next()) != OPT_EOF) {
148 BIO_printf(bio_err, "%s: Use -help for summary.\n", prog);
151 opt_help(smime_options);
155 if (!opt_format(opt_arg(), OPT_FMT_PDS, &informat))
162 if (!opt_format(opt_arg(), OPT_FMT_PDS, &outformat))
169 operation = SMIME_ENCRYPT;
172 operation = SMIME_DECRYPT;
175 operation = SMIME_SIGN;
178 operation = SMIME_RESIGN;
181 operation = SMIME_VERIFY;
184 operation = SMIME_PK7OUT;
190 flags |= PKCS7_NOINTERN;
193 flags |= PKCS7_NOVERIFY;
196 flags |= PKCS7_NOCHAIN;
199 flags |= PKCS7_NOCERTS;
202 flags |= PKCS7_NOATTR;
205 flags &= ~PKCS7_DETACHED;
208 flags |= PKCS7_NOSMIMECAP;
211 flags |= PKCS7_BINARY;
214 flags |= PKCS7_NOSIGS;
224 flags |= PKCS7_NOOLDMIMETYPE;
227 flags |= PKCS7_CRLFEOL;
235 e = setup_engine(opt_arg(), 0);
238 passinarg = opt_arg();
250 /* If previous -signer argument add signer to list */
252 if (sksigners == NULL
253 && (sksigners = sk_OPENSSL_STRING_new_null()) == NULL)
255 sk_OPENSSL_STRING_push(sksigners, signerfile);
257 keyfile = signerfile;
259 && (skkeys = sk_OPENSSL_STRING_new_null()) == NULL)
261 sk_OPENSSL_STRING_push(skkeys, keyfile);
264 signerfile = opt_arg();
267 recipfile = opt_arg();
270 if (!opt_md(opt_arg(), &sign_md))
274 if (!opt_cipher(opt_unknown(), &cipher))
278 /* If previous -inkey arument add signer to list */
280 if (signerfile == NULL) {
282 "%s: Must have -signer before -inkey\n", prog);
285 if (sksigners == NULL
286 && (sksigners = sk_OPENSSL_STRING_new_null()) == NULL)
288 sk_OPENSSL_STRING_push(sksigners, signerfile);
291 && (skkeys = sk_OPENSSL_STRING_new_null()) == NULL)
293 sk_OPENSSL_STRING_push(skkeys, keyfile);
298 if (!opt_format(opt_arg(), OPT_FMT_ANY, &keyform))
302 certfile = opt_arg();
317 contfile = opt_arg();
320 if (!opt_verify(o, vpm))
326 argc = opt_num_rest();
329 if (!(operation & SMIME_SIGNERS) && (skkeys || sksigners)) {
330 BIO_puts(bio_err, "Multiple signers or keys not allowed\n");
334 if (operation & SMIME_SIGNERS) {
335 /* Check to see if any final signer needs to be appended */
336 if (keyfile && !signerfile) {
337 BIO_puts(bio_err, "Illegal -inkey without -signer\n");
342 && (sksigners = sk_OPENSSL_STRING_new_null()) == NULL)
344 sk_OPENSSL_STRING_push(sksigners, signerfile);
345 if (!skkeys && (skkeys = sk_OPENSSL_STRING_new_null()) == NULL)
348 keyfile = signerfile;
349 sk_OPENSSL_STRING_push(skkeys, keyfile);
352 BIO_printf(bio_err, "No signer certificate specified\n");
358 } else if (operation == SMIME_DECRYPT) {
359 if (!recipfile && !keyfile) {
361 "No recipient certificate or key specified\n");
364 } else if (operation == SMIME_ENCRYPT) {
366 BIO_printf(bio_err, "No recipient(s) certificate(s) specified\n");
370 } else if (!operation)
373 if (!app_passwd(passinarg, NULL, &passin, NULL)) {
374 BIO_printf(bio_err, "Error getting password\n");
379 app_RAND_load_file(NULL, (inrand != NULL));
381 BIO_printf(bio_err, "%ld semi-random bytes loaded\n",
382 app_RAND_load_files(inrand));
387 if (!(operation & SMIME_SIGNERS))
388 flags &= ~PKCS7_DETACHED;
390 if (!(operation & SMIME_OP)) {
391 if (flags & PKCS7_BINARY)
392 outformat = FORMAT_BINARY;
395 if (!(operation & SMIME_IP)) {
396 if (flags & PKCS7_BINARY)
397 informat = FORMAT_BINARY;
400 if (operation == SMIME_ENCRYPT) {
402 #ifndef OPENSSL_NO_DES
403 cipher = EVP_des_ede3_cbc();
405 BIO_printf(bio_err, "No cipher selected\n");
409 encerts = sk_X509_new_null();
413 cert = load_cert(*argv, FORMAT_PEM,
414 "recipient certificate file");
417 sk_X509_push(encerts, cert);
424 if (!load_certs(certfile, &other, FORMAT_PEM, NULL,
425 "certificate file")) {
426 ERR_print_errors(bio_err);
431 if (recipfile && (operation == SMIME_DECRYPT)) {
432 if ((recip = load_cert(recipfile, FORMAT_PEM,
433 "recipient certificate file")) == NULL) {
434 ERR_print_errors(bio_err);
439 if (operation == SMIME_DECRYPT) {
442 } else if (operation == SMIME_SIGN) {
444 keyfile = signerfile;
449 key = load_key(keyfile, keyform, 0, passin, e, "signing key file");
454 in = bio_open_default(infile, 'r', informat);
458 if (operation & SMIME_IP) {
459 if (informat == FORMAT_SMIME)
460 p7 = SMIME_read_PKCS7(in, &indata);
461 else if (informat == FORMAT_PEM)
462 p7 = PEM_read_bio_PKCS7(in, NULL, NULL, NULL);
463 else if (informat == FORMAT_ASN1)
464 p7 = d2i_PKCS7_bio(in, NULL);
466 BIO_printf(bio_err, "Bad input format for PKCS#7 file\n");
471 BIO_printf(bio_err, "Error reading S/MIME message\n");
476 if ((indata = BIO_new_file(contfile, "rb")) == NULL) {
477 BIO_printf(bio_err, "Can't read content file %s\n", contfile);
483 out = bio_open_default(outfile, 'w', outformat);
487 if (operation == SMIME_VERIFY) {
488 if ((store = setup_verify(CAfile, CApath, noCAfile, noCApath)) == NULL)
490 X509_STORE_set_verify_cb(store, smime_cb);
492 X509_STORE_set1_param(store, vpm);
497 if (operation == SMIME_ENCRYPT) {
499 flags |= PKCS7_STREAM;
500 p7 = PKCS7_encrypt(encerts, in, cipher, flags);
501 } else if (operation & SMIME_SIGNERS) {
504 * If detached data content we only enable streaming if S/MIME output
507 if (operation == SMIME_SIGN) {
508 if (flags & PKCS7_DETACHED) {
509 if (outformat == FORMAT_SMIME)
510 flags |= PKCS7_STREAM;
512 flags |= PKCS7_STREAM;
513 flags |= PKCS7_PARTIAL;
514 p7 = PKCS7_sign(NULL, NULL, other, in, flags);
517 if (flags & PKCS7_NOCERTS) {
518 for (i = 0; i < sk_X509_num(other); i++) {
519 X509 *x = sk_X509_value(other, i);
520 PKCS7_add_certificate(p7, x);
524 flags |= PKCS7_REUSE_DIGEST;
525 for (i = 0; i < sk_OPENSSL_STRING_num(sksigners); i++) {
526 signerfile = sk_OPENSSL_STRING_value(sksigners, i);
527 keyfile = sk_OPENSSL_STRING_value(skkeys, i);
528 signer = load_cert(signerfile, FORMAT_PEM,
529 "signer certificate");
532 key = load_key(keyfile, keyform, 0, passin, e, "signing key file");
535 if (!PKCS7_sign_add_signer(p7, signer, key, sign_md, flags))
542 /* If not streaming or resigning finalize structure */
543 if ((operation == SMIME_SIGN) && !(flags & PKCS7_STREAM)) {
544 if (!PKCS7_final(p7, in, flags))
550 BIO_printf(bio_err, "Error creating PKCS#7 structure\n");
555 if (operation == SMIME_DECRYPT) {
556 if (!PKCS7_decrypt(p7, key, recip, out, flags)) {
557 BIO_printf(bio_err, "Error decrypting PKCS#7 structure\n");
560 } else if (operation == SMIME_VERIFY) {
561 STACK_OF(X509) *signers;
562 if (PKCS7_verify(p7, other, store, indata, out, flags))
563 BIO_printf(bio_err, "Verification successful\n");
565 BIO_printf(bio_err, "Verification failure\n");
568 signers = PKCS7_get0_signers(p7, other, flags);
569 if (!save_certs(signerfile, signers)) {
570 BIO_printf(bio_err, "Error writing signers to %s\n", signerfile);
574 sk_X509_free(signers);
575 } else if (operation == SMIME_PK7OUT)
576 PEM_write_bio_PKCS7(out, p7);
579 BIO_printf(out, "To: %s%s", to, mime_eol);
581 BIO_printf(out, "From: %s%s", from, mime_eol);
583 BIO_printf(out, "Subject: %s%s", subject, mime_eol);
584 if (outformat == FORMAT_SMIME) {
585 if (operation == SMIME_RESIGN)
586 rv = SMIME_write_PKCS7(out, p7, indata, flags);
588 rv = SMIME_write_PKCS7(out, p7, in, flags);
589 } else if (outformat == FORMAT_PEM)
590 rv = PEM_write_bio_PKCS7_stream(out, p7, in, flags);
591 else if (outformat == FORMAT_ASN1)
592 rv = i2d_PKCS7_bio_stream(out, p7, in, flags);
594 BIO_printf(bio_err, "Bad output format for PKCS#7 file\n");
598 BIO_printf(bio_err, "Error writing output\n");
606 app_RAND_write_file(NULL);
608 ERR_print_errors(bio_err);
609 sk_X509_pop_free(encerts, X509_free);
610 sk_X509_pop_free(other, X509_free);
611 X509_VERIFY_PARAM_free(vpm);
612 sk_OPENSSL_STRING_free(sksigners);
613 sk_OPENSSL_STRING_free(skkeys);
614 X509_STORE_free(store);
623 OPENSSL_free(passin);
627 static int save_certs(char *signerfile, STACK_OF(X509) *signers)
633 tmp = BIO_new_file(signerfile, "w");
636 for (i = 0; i < sk_X509_num(signers); i++)
637 PEM_write_bio_X509(tmp, sk_X509_value(signers, i));
642 /* Minimal callback just to output policy info (if any) */
644 static int smime_cb(int ok, X509_STORE_CTX *ctx)
648 error = X509_STORE_CTX_get_error(ctx);
650 if ((error != X509_V_ERR_NO_EXPLICIT_POLICY)
651 && ((error != X509_V_OK) || (ok != 2)))