2 * Copyright 1999-2018 The OpenSSL Project Authors. All Rights Reserved.
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
10 /* S/MIME utility function */
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>
22 static int save_certs(char *signerfile, STACK_OF(X509) *signers);
23 static int smime_cb(int ok, X509_STORE_CTX *ctx);
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)
35 typedef enum OPTION_choice {
36 OPT_ERR = -1, OPT_EOF = 0, OPT_HELP,
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,
47 OPT_IN, OPT_INFORM, OPT_OUT,
48 OPT_OUTFORM, OPT_CONTENT
51 const OPTIONS smime_options[] = {
52 {OPT_HELP_STR, 1, '-', "Usage: %s [options] [cert...]\n"},
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 (PEM or ENGINE)"},
64 #ifndef OPENSSL_NO_ENGINE
65 {"engine", OPT_ENGINE, 's', "Use engine, possibly a hardware device"},
67 {"stream", OPT_STREAM, '-', "Enable CMS streaming" },
68 {"indef", OPT_INDEF, '-', "Same as -stream" },
69 {"noindef", OPT_NOINDEF, '-', "Disable CMS streaming"},
71 OPT_SECTION("Action"),
72 {"encrypt", OPT_ENCRYPT, '-', "Encrypt message"},
73 {"decrypt", OPT_DECRYPT, '-', "Decrypt encrypted message"},
74 {"sign", OPT_SIGN, '-', "Sign message"},
75 {"resign", OPT_RESIGN, '-', "Resign a signed message"},
76 {"verify", OPT_VERIFY, '-', "Verify signed message"},
78 OPT_SECTION("Signing/Encryption"),
79 {"passin", OPT_PASSIN, 's', "Input file pass phrase source"},
80 {"md", OPT_MD, 's', "Digest algorithm to use when signing or resigning"},
81 {"", OPT_CIPHER, '-', "Any supported cipher"},
82 {"pk7out", OPT_PK7OUT, '-', "Output PKCS#7 structure"},
83 {"nointern", OPT_NOINTERN, '-',
84 "Don't search certificates in message for signer"},
85 {"nodetach", OPT_NODETACH, '-', "Use opaque signing"},
86 {"noattr", OPT_NOATTR, '-', "Don't include any signed attributes"},
87 {"binary", OPT_BINARY, '-', "Don't translate message to text"},
88 {"signer", OPT_SIGNER, 's', "Signer certificate file"},
89 {"content", OPT_CONTENT, '<',
90 "Supply or override content for detached signature"},
91 {"nocerts", OPT_NOCERTS, '-',
92 "Don't include signers certificate when signing"},
94 OPT_SECTION("Verification/Decryption"),
95 {"nosigs", OPT_NOSIGS, '-', "Don't verify message signature"},
96 {"noverify", OPT_NOVERIFY, '-', "Don't verify signers certificate"},
98 {"certfile", OPT_CERTFILE, '<', "Other certificates file"},
99 {"recip", OPT_RECIP, '<', "Recipient certificate file for decryption"},
101 OPT_SECTION("Email"),
102 {"to", OPT_TO, 's', "To address"},
103 {"from", OPT_FROM, 's', "From address"},
104 {"subject", OPT_SUBJECT, 's', "Subject"},
105 {"text", OPT_TEXT, '-', "Include or delete text MIME headers"},
106 {"nosmimecap", OPT_NOSMIMECAP, '-', "Omit the SMIMECapabilities attribute"},
108 OPT_SECTION("Certificate chain"),
109 {"CApath", OPT_CAPATH, '/', "Trusted certificates directory"},
110 {"CAfile", OPT_CAFILE, '<', "Trusted certificates file"},
111 {"CAstore", OPT_CASTORE, ':', "Trusted certificates store URI"},
112 {"no-CAfile", OPT_NOCAFILE, '-',
113 "Do not load the default certificates file"},
114 {"no-CApath", OPT_NOCAPATH, '-',
115 "Do not load certificates from the default certificates directory"},
116 {"no-CAstore", OPT_NOCASTORE, '-',
117 "Do not load certificates from the default certificates store"},
118 {"nochain", OPT_NOCHAIN, '-',
119 "set PKCS7_NOCHAIN so certificates contained in the message are not used as untrusted CAs" },
120 {"crlfeol", OPT_CRLFEOL, '-', "Use CRLF as EOL termination instead of CR only"},
127 {"cert", 0, 0, "Recipient certs, used when encrypting"},
131 int smime_main(int argc, char **argv)
133 BIO *in = NULL, *out = NULL, *indata = NULL;
134 EVP_PKEY *key = NULL;
136 STACK_OF(OPENSSL_STRING) *sksigners = NULL, *skkeys = NULL;
137 STACK_OF(X509) *encerts = NULL, *other = NULL;
138 X509 *cert = NULL, *recip = NULL, *signer = NULL;
139 X509_STORE *store = NULL;
140 X509_VERIFY_PARAM *vpm = NULL;
141 const EVP_CIPHER *cipher = NULL;
142 const EVP_MD *sign_md = NULL;
143 const char *CAfile = NULL, *CApath = NULL, *CAstore = NULL, *prog = NULL;
144 char *certfile = NULL, *keyfile = NULL, *contfile = NULL;
145 char *infile = NULL, *outfile = NULL, *signerfile = NULL, *recipfile = NULL;
146 char *passinarg = NULL, *passin = NULL, *to = NULL, *from = NULL, *subject = NULL;
148 int noCApath = 0, noCAfile = 0, noCAstore = 0;
149 int flags = PKCS7_DETACHED, operation = 0, ret = 0, indef = 0;
150 int informat = FORMAT_SMIME, outformat = FORMAT_SMIME, keyform =
152 int vpmtouched = 0, rv = 0;
154 const char *mime_eol = "\n";
156 if ((vpm = X509_VERIFY_PARAM_new()) == NULL)
159 prog = opt_init(argc, argv, smime_options);
160 while ((o = opt_next()) != OPT_EOF) {
165 BIO_printf(bio_err, "%s: Use -help for summary.\n", prog);
168 opt_help(smime_options);
172 if (!opt_format(opt_arg(), OPT_FMT_PDS, &informat))
179 if (!opt_format(opt_arg(), OPT_FMT_PDS, &outformat))
186 operation = SMIME_ENCRYPT;
189 operation = SMIME_DECRYPT;
192 operation = SMIME_SIGN;
195 operation = SMIME_RESIGN;
198 operation = SMIME_VERIFY;
201 operation = SMIME_PK7OUT;
207 flags |= PKCS7_NOINTERN;
210 flags |= PKCS7_NOVERIFY;
213 flags |= PKCS7_NOCHAIN;
216 flags |= PKCS7_NOCERTS;
219 flags |= PKCS7_NOATTR;
222 flags &= ~PKCS7_DETACHED;
225 flags |= PKCS7_NOSMIMECAP;
228 flags |= PKCS7_BINARY;
231 flags |= PKCS7_NOSIGS;
241 flags |= PKCS7_CRLFEOL;
249 if (!opt_provider(o))
253 e = setup_engine(opt_arg(), 0);
256 passinarg = opt_arg();
268 /* If previous -signer argument add signer to list */
269 if (signerfile != NULL) {
270 if (sksigners == NULL
271 && (sksigners = sk_OPENSSL_STRING_new_null()) == NULL)
273 sk_OPENSSL_STRING_push(sksigners, signerfile);
275 keyfile = signerfile;
277 && (skkeys = sk_OPENSSL_STRING_new_null()) == NULL)
279 sk_OPENSSL_STRING_push(skkeys, keyfile);
282 signerfile = opt_arg();
285 recipfile = opt_arg();
288 if (!opt_md(opt_arg(), &sign_md))
292 if (!opt_cipher(opt_unknown(), &cipher))
296 /* If previous -inkey argument add signer to list */
297 if (keyfile != NULL) {
298 if (signerfile == NULL) {
300 "%s: Must have -signer before -inkey\n", prog);
303 if (sksigners == NULL
304 && (sksigners = sk_OPENSSL_STRING_new_null()) == NULL)
306 sk_OPENSSL_STRING_push(sksigners, signerfile);
309 && (skkeys = sk_OPENSSL_STRING_new_null()) == NULL)
311 sk_OPENSSL_STRING_push(skkeys, keyfile);
316 if (!opt_format(opt_arg(), OPT_FMT_ANY, &keyform))
320 certfile = opt_arg();
341 contfile = opt_arg();
344 if (!opt_verify(o, vpm))
350 argc = opt_num_rest();
353 if (!(operation & SMIME_SIGNERS) && (skkeys != NULL || sksigners != NULL)) {
354 BIO_puts(bio_err, "Multiple signers or keys not allowed\n");
358 if (operation & SMIME_SIGNERS) {
359 /* Check to see if any final signer needs to be appended */
360 if (keyfile && !signerfile) {
361 BIO_puts(bio_err, "Illegal -inkey without -signer\n");
364 if (signerfile != NULL) {
365 if (sksigners == NULL
366 && (sksigners = sk_OPENSSL_STRING_new_null()) == NULL)
368 sk_OPENSSL_STRING_push(sksigners, signerfile);
369 if (!skkeys && (skkeys = sk_OPENSSL_STRING_new_null()) == NULL)
372 keyfile = signerfile;
373 sk_OPENSSL_STRING_push(skkeys, keyfile);
375 if (sksigners == NULL) {
376 BIO_printf(bio_err, "No signer certificate specified\n");
381 } else if (operation == SMIME_DECRYPT) {
382 if (recipfile == NULL && keyfile == NULL) {
384 "No recipient certificate or key specified\n");
387 } else if (operation == SMIME_ENCRYPT) {
389 BIO_printf(bio_err, "No recipient(s) certificate(s) specified\n");
392 } else if (!operation) {
396 if (!app_passwd(passinarg, NULL, &passin, NULL)) {
397 BIO_printf(bio_err, "Error getting password\n");
403 if (!(operation & SMIME_SIGNERS))
404 flags &= ~PKCS7_DETACHED;
406 if (!(operation & SMIME_OP)) {
407 if (flags & PKCS7_BINARY)
408 outformat = FORMAT_BINARY;
411 if (!(operation & SMIME_IP)) {
412 if (flags & PKCS7_BINARY)
413 informat = FORMAT_BINARY;
416 if (operation == SMIME_ENCRYPT) {
417 if (cipher == NULL) {
418 #ifndef OPENSSL_NO_DES
419 cipher = EVP_des_ede3_cbc();
421 BIO_printf(bio_err, "No cipher selected\n");
425 encerts = sk_X509_new_null();
428 while (*argv != NULL) {
429 cert = load_cert(*argv, FORMAT_PEM,
430 "recipient certificate file");
433 sk_X509_push(encerts, cert);
439 if (certfile != NULL) {
440 if (!load_certs(certfile, &other, FORMAT_PEM, NULL,
441 "certificate file")) {
442 ERR_print_errors(bio_err);
447 if (recipfile != NULL && (operation == SMIME_DECRYPT)) {
448 if ((recip = load_cert(recipfile, FORMAT_PEM,
449 "recipient certificate file")) == NULL) {
450 ERR_print_errors(bio_err);
455 if (operation == SMIME_DECRYPT) {
458 } else if (operation == SMIME_SIGN) {
460 keyfile = signerfile;
465 if (keyfile != NULL) {
466 key = load_key(keyfile, keyform, 0, passin, e, "signing key file");
471 in = bio_open_default(infile, 'r', informat);
475 if (operation & SMIME_IP) {
476 if (informat == FORMAT_SMIME) {
477 p7 = SMIME_read_PKCS7(in, &indata);
478 } else if (informat == FORMAT_PEM) {
479 p7 = PEM_read_bio_PKCS7(in, NULL, NULL, NULL);
480 } else if (informat == FORMAT_ASN1) {
481 p7 = d2i_PKCS7_bio(in, NULL);
483 BIO_printf(bio_err, "Bad input format for PKCS#7 file\n");
488 BIO_printf(bio_err, "Error reading S/MIME message\n");
491 if (contfile != NULL) {
493 if ((indata = BIO_new_file(contfile, "rb")) == NULL) {
494 BIO_printf(bio_err, "Can't read content file %s\n", contfile);
500 out = bio_open_default(outfile, 'w', outformat);
504 if (operation == SMIME_VERIFY) {
505 if ((store = setup_verify(CAfile, noCAfile, CApath, noCApath,
506 CAstore, noCAstore)) == NULL)
508 X509_STORE_set_verify_cb(store, smime_cb);
510 X509_STORE_set1_param(store, vpm);
515 if (operation == SMIME_ENCRYPT) {
517 flags |= PKCS7_STREAM;
518 p7 = PKCS7_encrypt(encerts, in, cipher, flags);
519 } else if (operation & SMIME_SIGNERS) {
522 * If detached data content we only enable streaming if S/MIME output
525 if (operation == SMIME_SIGN) {
526 if (flags & PKCS7_DETACHED) {
527 if (outformat == FORMAT_SMIME)
528 flags |= PKCS7_STREAM;
530 flags |= PKCS7_STREAM;
532 flags |= PKCS7_PARTIAL;
533 p7 = PKCS7_sign(NULL, NULL, other, in, flags);
536 if (flags & PKCS7_NOCERTS) {
537 for (i = 0; i < sk_X509_num(other); i++) {
538 X509 *x = sk_X509_value(other, i);
539 PKCS7_add_certificate(p7, x);
543 flags |= PKCS7_REUSE_DIGEST;
545 for (i = 0; i < sk_OPENSSL_STRING_num(sksigners); i++) {
546 signerfile = sk_OPENSSL_STRING_value(sksigners, i);
547 keyfile = sk_OPENSSL_STRING_value(skkeys, i);
548 signer = load_cert(signerfile, FORMAT_PEM,
549 "signer certificate");
552 key = load_key(keyfile, keyform, 0, passin, e, "signing key file");
555 if (!PKCS7_sign_add_signer(p7, signer, key, sign_md, flags))
562 /* If not streaming or resigning finalize structure */
563 if ((operation == SMIME_SIGN) && !(flags & PKCS7_STREAM)) {
564 if (!PKCS7_final(p7, in, flags))
570 BIO_printf(bio_err, "Error creating PKCS#7 structure\n");
575 if (operation == SMIME_DECRYPT) {
576 if (!PKCS7_decrypt(p7, key, recip, out, flags)) {
577 BIO_printf(bio_err, "Error decrypting PKCS#7 structure\n");
580 } else if (operation == SMIME_VERIFY) {
581 STACK_OF(X509) *signers;
582 if (PKCS7_verify(p7, other, store, indata, out, flags))
583 BIO_printf(bio_err, "Verification successful\n");
585 BIO_printf(bio_err, "Verification failure\n");
588 signers = PKCS7_get0_signers(p7, other, flags);
589 if (!save_certs(signerfile, signers)) {
590 BIO_printf(bio_err, "Error writing signers to %s\n", signerfile);
594 sk_X509_free(signers);
595 } else if (operation == SMIME_PK7OUT) {
596 PEM_write_bio_PKCS7(out, p7);
599 BIO_printf(out, "To: %s%s", to, mime_eol);
601 BIO_printf(out, "From: %s%s", from, mime_eol);
603 BIO_printf(out, "Subject: %s%s", subject, mime_eol);
604 if (outformat == FORMAT_SMIME) {
605 if (operation == SMIME_RESIGN)
606 rv = SMIME_write_PKCS7(out, p7, indata, flags);
608 rv = SMIME_write_PKCS7(out, p7, in, flags);
609 } else if (outformat == FORMAT_PEM) {
610 rv = PEM_write_bio_PKCS7_stream(out, p7, in, flags);
611 } else if (outformat == FORMAT_ASN1) {
612 rv = i2d_PKCS7_bio_stream(out, p7, in, flags);
614 BIO_printf(bio_err, "Bad output format for PKCS#7 file\n");
618 BIO_printf(bio_err, "Error writing output\n");
626 ERR_print_errors(bio_err);
627 sk_X509_pop_free(encerts, X509_free);
628 sk_X509_pop_free(other, X509_free);
629 X509_VERIFY_PARAM_free(vpm);
630 sk_OPENSSL_STRING_free(sksigners);
631 sk_OPENSSL_STRING_free(skkeys);
632 X509_STORE_free(store);
642 OPENSSL_free(passin);
646 static int save_certs(char *signerfile, STACK_OF(X509) *signers)
651 if (signerfile == NULL)
653 tmp = BIO_new_file(signerfile, "w");
656 for (i = 0; i < sk_X509_num(signers); i++)
657 PEM_write_bio_X509(tmp, sk_X509_value(signers, i));
662 /* Minimal callback just to output policy info (if any) */
664 static int smime_cb(int ok, X509_STORE_CTX *ctx)
668 error = X509_STORE_CTX_get_error(ctx);
670 if ((error != X509_V_ERR_NO_EXPLICIT_POLICY)
671 && ((error != X509_V_OK) || (ok != 2)))