2 * Copyright 1999-2021 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
{
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
,
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 (ENGINE, other values ignored)"},
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"},
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"},
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"},
95 OPT_SECTION("Verification/Decryption"),
96 {"nosigs", OPT_NOSIGS
, '-', "Don't verify message signature"},
97 {"noverify", OPT_NOVERIFY
, '-', "Don't verify signers certificate"},
99 {"certfile", OPT_CERTFILE
, '<', "Other certificates file"},
100 {"recip", OPT_RECIP
, '<', "Recipient certificate file for decryption"},
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"},
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 CR only"},
128 {"cert", 0, 0, "Recipient certs, used when encrypting"},
132 int smime_main(int argc
, char **argv
)
135 BIO
*in
= NULL
, *out
= NULL
, *indata
= NULL
;
136 EVP_PKEY
*key
= 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
;
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
=
155 int vpmtouched
= 0, rv
= 0;
157 const char *mime_eol
= "\n";
158 OSSL_LIB_CTX
*libctx
= app_get0_libctx();
160 if ((vpm
= X509_VERIFY_PARAM_new()) == NULL
)
163 prog
= opt_init(argc
, argv
, smime_options
);
164 while ((o
= opt_next()) != OPT_EOF
) {
169 BIO_printf(bio_err
, "%s: Use -help for summary.\n", prog
);
172 opt_help(smime_options
);
176 if (!opt_format(opt_arg(), OPT_FMT_PDS
, &informat
))
183 if (!opt_format(opt_arg(), OPT_FMT_PDS
, &outformat
))
190 operation
= SMIME_ENCRYPT
;
193 operation
= SMIME_DECRYPT
;
196 operation
= SMIME_SIGN
;
199 operation
= SMIME_RESIGN
;
202 operation
= SMIME_VERIFY
;
205 operation
= SMIME_PK7OUT
;
211 flags
|= PKCS7_NOINTERN
;
214 flags
|= PKCS7_NOVERIFY
;
217 flags
|= PKCS7_NOCHAIN
;
220 flags
|= PKCS7_NOCERTS
;
223 flags
|= PKCS7_NOATTR
;
226 flags
&= ~PKCS7_DETACHED
;
229 flags
|= PKCS7_NOSMIMECAP
;
232 flags
|= PKCS7_BINARY
;
235 flags
|= PKCS7_NOSIGS
;
245 flags
|= PKCS7_CRLFEOL
;
253 if (!opt_provider(o
))
257 conf
= app_load_config_modules(opt_arg());
262 e
= setup_engine(opt_arg(), 0);
265 passinarg
= opt_arg();
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
)
282 sk_OPENSSL_STRING_push(sksigners
, signerfile
);
284 keyfile
= signerfile
;
286 && (skkeys
= sk_OPENSSL_STRING_new_null()) == NULL
)
288 sk_OPENSSL_STRING_push(skkeys
, keyfile
);
291 signerfile
= opt_arg();
294 recipfile
= opt_arg();
297 digestname
= opt_arg();
300 ciphername
= opt_unknown();
303 /* If previous -inkey argument add signer to list */
304 if (keyfile
!= NULL
) {
305 if (signerfile
== NULL
) {
307 "%s: Must have -signer before -inkey\n", prog
);
310 if (sksigners
== NULL
311 && (sksigners
= sk_OPENSSL_STRING_new_null()) == NULL
)
313 sk_OPENSSL_STRING_push(sksigners
, signerfile
);
316 && (skkeys
= sk_OPENSSL_STRING_new_null()) == NULL
)
318 sk_OPENSSL_STRING_push(skkeys
, keyfile
);
323 if (!opt_format(opt_arg(), OPT_FMT_ANY
, &keyform
))
327 certfile
= opt_arg();
348 contfile
= opt_arg();
351 if (!opt_verify(o
, vpm
))
358 /* Extra arguments are files with recipient keys. */
359 argc
= opt_num_rest();
362 if (!app_RAND_load())
365 if (digestname
!= NULL
) {
366 if (!opt_md(digestname
, &sign_md
))
369 if (!opt_cipher_any(ciphername
, &cipher
))
371 if (!(operation
& SMIME_SIGNERS
) && (skkeys
!= NULL
|| sksigners
!= NULL
)) {
372 BIO_puts(bio_err
, "Multiple signers or keys not allowed\n");
377 "No operation (-encrypt|-sign|...) specified\n");
381 if (operation
& SMIME_SIGNERS
) {
382 /* Check to see if any final signer needs to be appended */
383 if (keyfile
&& !signerfile
) {
384 BIO_puts(bio_err
, "Illegal -inkey without -signer\n");
387 if (signerfile
!= NULL
) {
388 if (sksigners
== NULL
389 && (sksigners
= sk_OPENSSL_STRING_new_null()) == NULL
)
391 sk_OPENSSL_STRING_push(sksigners
, signerfile
);
392 if (!skkeys
&& (skkeys
= sk_OPENSSL_STRING_new_null()) == NULL
)
395 keyfile
= signerfile
;
396 sk_OPENSSL_STRING_push(skkeys
, keyfile
);
398 if (sksigners
== NULL
) {
399 BIO_printf(bio_err
, "No signer certificate specified\n");
404 } else if (operation
== SMIME_DECRYPT
) {
405 if (recipfile
== NULL
&& keyfile
== NULL
) {
407 "No recipient certificate or key specified\n");
410 } else if (operation
== SMIME_ENCRYPT
) {
412 BIO_printf(bio_err
, "No recipient(s) certificate(s) specified\n");
417 if (!app_passwd(passinarg
, NULL
, &passin
, NULL
)) {
418 BIO_printf(bio_err
, "Error getting password\n");
424 if (!(operation
& SMIME_SIGNERS
))
425 flags
&= ~PKCS7_DETACHED
;
427 if (!(operation
& SMIME_OP
)) {
428 if (flags
& PKCS7_BINARY
)
429 outformat
= FORMAT_BINARY
;
432 if (!(operation
& SMIME_IP
)) {
433 if (flags
& PKCS7_BINARY
)
434 informat
= FORMAT_BINARY
;
437 if (operation
== SMIME_ENCRYPT
) {
438 if (cipher
== NULL
) {
439 #ifndef OPENSSL_NO_DES
440 cipher
= (EVP_CIPHER
*)EVP_des_ede3_cbc();
442 BIO_printf(bio_err
, "No cipher selected\n");
446 encerts
= sk_X509_new_null();
449 while (*argv
!= NULL
) {
450 cert
= load_cert(*argv
, FORMAT_UNDEF
,
451 "recipient certificate file");
454 sk_X509_push(encerts
, cert
);
460 if (certfile
!= NULL
) {
461 if (!load_certs(certfile
, 0, &other
, NULL
, "certificates")) {
462 ERR_print_errors(bio_err
);
467 if (recipfile
!= NULL
&& (operation
== SMIME_DECRYPT
)) {
468 if ((recip
= load_cert(recipfile
, FORMAT_UNDEF
,
469 "recipient certificate file")) == NULL
) {
470 ERR_print_errors(bio_err
);
475 if (operation
== SMIME_DECRYPT
) {
478 } else if (operation
== SMIME_SIGN
) {
480 keyfile
= signerfile
;
485 if (keyfile
!= NULL
) {
486 key
= load_key(keyfile
, keyform
, 0, passin
, e
, "signing key");
491 in
= bio_open_default(infile
, 'r', informat
);
495 if (operation
& SMIME_IP
) {
498 p7
= PKCS7_new_ex(libctx
, app_get0_propq());
500 BIO_printf(bio_err
, "Error allocating PKCS7 object\n");
503 if (informat
== FORMAT_SMIME
) {
504 p7_in
= SMIME_read_PKCS7_ex(in
, &indata
, &p7
);
505 } else if (informat
== FORMAT_PEM
) {
506 p7_in
= PEM_read_bio_PKCS7(in
, &p7
, NULL
, NULL
);
507 } else if (informat
== FORMAT_ASN1
) {
508 p7_in
= d2i_PKCS7_bio(in
, &p7
);
510 BIO_printf(bio_err
, "Bad input format for PKCS#7 file\n");
515 BIO_printf(bio_err
, "Error reading S/MIME message\n");
518 if (contfile
!= NULL
) {
520 if ((indata
= BIO_new_file(contfile
, "rb")) == NULL
) {
521 BIO_printf(bio_err
, "Can't read content file %s\n", contfile
);
527 out
= bio_open_default(outfile
, 'w', outformat
);
531 if (operation
== SMIME_VERIFY
) {
532 if ((store
= setup_verify(CAfile
, noCAfile
, CApath
, noCApath
,
533 CAstore
, noCAstore
)) == NULL
)
535 X509_STORE_set_verify_cb(store
, smime_cb
);
537 X509_STORE_set1_param(store
, vpm
);
542 if (operation
== SMIME_ENCRYPT
) {
544 flags
|= PKCS7_STREAM
;
545 p7
= PKCS7_encrypt_ex(encerts
, in
, cipher
, flags
, libctx
, app_get0_propq());
546 } else if (operation
& SMIME_SIGNERS
) {
549 * If detached data content we only enable streaming if S/MIME output
552 if (operation
== SMIME_SIGN
) {
553 if (flags
& PKCS7_DETACHED
) {
554 if (outformat
== FORMAT_SMIME
)
555 flags
|= PKCS7_STREAM
;
557 flags
|= PKCS7_STREAM
;
559 flags
|= PKCS7_PARTIAL
;
560 p7
= PKCS7_sign_ex(NULL
, NULL
, other
, in
, flags
, libctx
, app_get0_propq());
563 if (flags
& PKCS7_NOCERTS
) {
564 for (i
= 0; i
< sk_X509_num(other
); i
++) {
565 X509
*x
= sk_X509_value(other
, i
);
566 PKCS7_add_certificate(p7
, x
);
570 flags
|= PKCS7_REUSE_DIGEST
;
572 for (i
= 0; i
< sk_OPENSSL_STRING_num(sksigners
); i
++) {
573 signerfile
= sk_OPENSSL_STRING_value(sksigners
, i
);
574 keyfile
= sk_OPENSSL_STRING_value(skkeys
, i
);
575 signer
= load_cert(signerfile
, FORMAT_UNDEF
, "signer certificate");
578 key
= load_key(keyfile
, keyform
, 0, passin
, e
, "signing key");
582 if (!PKCS7_sign_add_signer(p7
, signer
, key
, sign_md
, flags
))
589 /* If not streaming or resigning finalize structure */
590 if ((operation
== SMIME_SIGN
) && !(flags
& PKCS7_STREAM
)) {
591 if (!PKCS7_final(p7
, in
, flags
))
597 BIO_printf(bio_err
, "Error creating PKCS#7 structure\n");
602 if (operation
== SMIME_DECRYPT
) {
603 if (!PKCS7_decrypt(p7
, key
, recip
, out
, flags
)) {
604 BIO_printf(bio_err
, "Error decrypting PKCS#7 structure\n");
607 } else if (operation
== SMIME_VERIFY
) {
608 STACK_OF(X509
) *signers
;
609 if (PKCS7_verify(p7
, other
, store
, indata
, out
, flags
))
610 BIO_printf(bio_err
, "Verification successful\n");
612 BIO_printf(bio_err
, "Verification failure\n");
615 signers
= PKCS7_get0_signers(p7
, other
, flags
);
616 if (!save_certs(signerfile
, signers
)) {
617 BIO_printf(bio_err
, "Error writing signers to %s\n", signerfile
);
621 sk_X509_free(signers
);
622 } else if (operation
== SMIME_PK7OUT
) {
623 PEM_write_bio_PKCS7(out
, p7
);
626 BIO_printf(out
, "To: %s%s", to
, mime_eol
);
628 BIO_printf(out
, "From: %s%s", from
, mime_eol
);
630 BIO_printf(out
, "Subject: %s%s", subject
, mime_eol
);
631 if (outformat
== FORMAT_SMIME
) {
632 if (operation
== SMIME_RESIGN
)
633 rv
= SMIME_write_PKCS7(out
, p7
, indata
, flags
);
635 rv
= SMIME_write_PKCS7(out
, p7
, in
, flags
);
636 } else if (outformat
== FORMAT_PEM
) {
637 rv
= PEM_write_bio_PKCS7_stream(out
, p7
, in
, flags
);
638 } else if (outformat
== FORMAT_ASN1
) {
639 rv
= i2d_PKCS7_bio_stream(out
, p7
, in
, flags
);
641 BIO_printf(bio_err
, "Bad output format for PKCS#7 file\n");
645 BIO_printf(bio_err
, "Error writing output\n");
653 ERR_print_errors(bio_err
);
654 sk_X509_pop_free(encerts
, X509_free
);
655 sk_X509_pop_free(other
, X509_free
);
656 X509_VERIFY_PARAM_free(vpm
);
657 sk_OPENSSL_STRING_free(sksigners
);
658 sk_OPENSSL_STRING_free(skkeys
);
659 X509_STORE_free(store
);
664 EVP_MD_free(sign_md
);
665 EVP_CIPHER_free(cipher
);
671 OPENSSL_free(passin
);
676 static int save_certs(char *signerfile
, STACK_OF(X509
) *signers
)
681 if (signerfile
== NULL
)
683 tmp
= BIO_new_file(signerfile
, "w");
686 for (i
= 0; i
< sk_X509_num(signers
); i
++)
687 PEM_write_bio_X509(tmp
, sk_X509_value(signers
, i
));
692 /* Minimal callback just to output policy info (if any) */
694 static int smime_cb(int ok
, X509_STORE_CTX
*ctx
)
698 error
= X509_STORE_CTX_get_error(ctx
);
700 if ((error
!= X509_V_ERR_NO_EXPLICIT_POLICY
)
701 && ((error
!= X509_V_OK
) || (ok
!= 2)))