lh | 9ed821d | 2023-04-07 01:36:19 -0700 | [diff] [blame^] | 1 | =pod |
| 2 | |
| 3 | =head1 NAME |
| 4 | |
| 5 | openssl-smime, |
| 6 | smime - S/MIME utility |
| 7 | |
| 8 | =head1 SYNOPSIS |
| 9 | |
| 10 | B<openssl> B<smime> |
| 11 | [B<-help>] |
| 12 | [B<-encrypt>] |
| 13 | [B<-decrypt>] |
| 14 | [B<-sign>] |
| 15 | [B<-resign>] |
| 16 | [B<-verify>] |
| 17 | [B<-pk7out>] |
| 18 | [B<-binary>] |
| 19 | [B<-crlfeol>] |
| 20 | [B<-I<cipher>>] |
| 21 | [B<-in file>] |
| 22 | [B<-CAfile file>] |
| 23 | [B<-CApath dir>] |
| 24 | [B<-no-CAfile>] |
| 25 | [B<-no-CApath>] |
| 26 | [B<-attime timestamp>] |
| 27 | [B<-check_ss_sig>] |
| 28 | [B<-crl_check>] |
| 29 | [B<-crl_check_all>] |
| 30 | [B<-explicit_policy>] |
| 31 | [B<-extended_crl>] |
| 32 | [B<-ignore_critical>] |
| 33 | [B<-inhibit_any>] |
| 34 | [B<-inhibit_map>] |
| 35 | [B<-partial_chain>] |
| 36 | [B<-policy arg>] |
| 37 | [B<-policy_check>] |
| 38 | [B<-policy_print>] |
| 39 | [B<-purpose purpose>] |
| 40 | [B<-suiteB_128>] |
| 41 | [B<-suiteB_128_only>] |
| 42 | [B<-suiteB_192>] |
| 43 | [B<-trusted_first>] |
| 44 | [B<-no_alt_chains>] |
| 45 | [B<-use_deltas>] |
| 46 | [B<-auth_level num>] |
| 47 | [B<-verify_depth num>] |
| 48 | [B<-verify_email email>] |
| 49 | [B<-verify_hostname hostname>] |
| 50 | [B<-verify_ip ip>] |
| 51 | [B<-verify_name name>] |
| 52 | [B<-x509_strict>] |
| 53 | [B<-certfile file>] |
| 54 | [B<-signer file>] |
| 55 | [B<-recip file>] |
| 56 | [B<-inform SMIME|PEM|DER>] |
| 57 | [B<-passin arg>] |
| 58 | [B<-inkey file_or_id>] |
| 59 | [B<-out file>] |
| 60 | [B<-outform SMIME|PEM|DER>] |
| 61 | [B<-content file>] |
| 62 | [B<-to addr>] |
| 63 | [B<-from ad>] |
| 64 | [B<-subject s>] |
| 65 | [B<-text>] |
| 66 | [B<-indef>] |
| 67 | [B<-noindef>] |
| 68 | [B<-stream>] |
| 69 | [B<-rand file...>] |
| 70 | [B<-writerand file>] |
| 71 | [B<-md digest>] |
| 72 | [cert.pem]... |
| 73 | |
| 74 | =head1 DESCRIPTION |
| 75 | |
| 76 | The B<smime> command handles S/MIME mail. It can encrypt, decrypt, sign and |
| 77 | verify S/MIME messages. |
| 78 | |
| 79 | =head1 OPTIONS |
| 80 | |
| 81 | There are six operation options that set the type of operation to be performed. |
| 82 | The meaning of the other options varies according to the operation type. |
| 83 | |
| 84 | =over 4 |
| 85 | |
| 86 | =item B<-help> |
| 87 | |
| 88 | Print out a usage message. |
| 89 | |
| 90 | =item B<-encrypt> |
| 91 | |
| 92 | Encrypt mail for the given recipient certificates. Input file is the message |
| 93 | to be encrypted. The output file is the encrypted mail in MIME format. |
| 94 | |
| 95 | Note that no revocation check is done for the recipient cert, so if that |
| 96 | key has been compromised, others may be able to decrypt the text. |
| 97 | |
| 98 | =item B<-decrypt> |
| 99 | |
| 100 | Decrypt mail using the supplied certificate and private key. Expects an |
| 101 | encrypted mail message in MIME format for the input file. The decrypted mail |
| 102 | is written to the output file. |
| 103 | |
| 104 | =item B<-sign> |
| 105 | |
| 106 | Sign mail using the supplied certificate and private key. Input file is |
| 107 | the message to be signed. The signed message in MIME format is written |
| 108 | to the output file. |
| 109 | |
| 110 | =item B<-verify> |
| 111 | |
| 112 | Verify signed mail. Expects a signed mail message on input and outputs |
| 113 | the signed data. Both clear text and opaque signing is supported. |
| 114 | |
| 115 | =item B<-pk7out> |
| 116 | |
| 117 | Takes an input message and writes out a PEM encoded PKCS#7 structure. |
| 118 | |
| 119 | =item B<-resign> |
| 120 | |
| 121 | Resign a message: take an existing message and one or more new signers. |
| 122 | |
| 123 | =item B<-in filename> |
| 124 | |
| 125 | The input message to be encrypted or signed or the MIME message to |
| 126 | be decrypted or verified. |
| 127 | |
| 128 | =item B<-inform SMIME|PEM|DER> |
| 129 | |
| 130 | This specifies the input format for the PKCS#7 structure. The default |
| 131 | is B<SMIME> which reads an S/MIME format message. B<PEM> and B<DER> |
| 132 | format change this to expect PEM and DER format PKCS#7 structures |
| 133 | instead. This currently only affects the input format of the PKCS#7 |
| 134 | structure, if no PKCS#7 structure is being input (for example with |
| 135 | B<-encrypt> or B<-sign>) this option has no effect. |
| 136 | |
| 137 | =item B<-out filename> |
| 138 | |
| 139 | The message text that has been decrypted or verified or the output MIME |
| 140 | format message that has been signed or verified. |
| 141 | |
| 142 | =item B<-outform SMIME|PEM|DER> |
| 143 | |
| 144 | This specifies the output format for the PKCS#7 structure. The default |
| 145 | is B<SMIME> which write an S/MIME format message. B<PEM> and B<DER> |
| 146 | format change this to write PEM and DER format PKCS#7 structures |
| 147 | instead. This currently only affects the output format of the PKCS#7 |
| 148 | structure, if no PKCS#7 structure is being output (for example with |
| 149 | B<-verify> or B<-decrypt>) this option has no effect. |
| 150 | |
| 151 | =item B<-stream -indef -noindef> |
| 152 | |
| 153 | The B<-stream> and B<-indef> options are equivalent and enable streaming I/O |
| 154 | for encoding operations. This permits single pass processing of data without |
| 155 | the need to hold the entire contents in memory, potentially supporting very |
| 156 | large files. Streaming is automatically set for S/MIME signing with detached |
| 157 | data if the output format is B<SMIME> it is currently off by default for all |
| 158 | other operations. |
| 159 | |
| 160 | =item B<-noindef> |
| 161 | |
| 162 | Disable streaming I/O where it would produce and indefinite length constructed |
| 163 | encoding. This option currently has no effect. In future streaming will be |
| 164 | enabled by default on all relevant operations and this option will disable it. |
| 165 | |
| 166 | =item B<-content filename> |
| 167 | |
| 168 | This specifies a file containing the detached content, this is only |
| 169 | useful with the B<-verify> command. This is only usable if the PKCS#7 |
| 170 | structure is using the detached signature form where the content is |
| 171 | not included. This option will override any content if the input format |
| 172 | is S/MIME and it uses the multipart/signed MIME content type. |
| 173 | |
| 174 | =item B<-text> |
| 175 | |
| 176 | This option adds plain text (text/plain) MIME headers to the supplied |
| 177 | message if encrypting or signing. If decrypting or verifying it strips |
| 178 | off text headers: if the decrypted or verified message is not of MIME |
| 179 | type text/plain then an error occurs. |
| 180 | |
| 181 | =item B<-CAfile file> |
| 182 | |
| 183 | A file containing trusted CA certificates, only used with B<-verify>. |
| 184 | |
| 185 | =item B<-CApath dir> |
| 186 | |
| 187 | A directory containing trusted CA certificates, only used with |
| 188 | B<-verify>. This directory must be a standard certificate directory: that |
| 189 | is a hash of each subject name (using B<x509 -hash>) should be linked |
| 190 | to each certificate. |
| 191 | |
| 192 | =item B<-no-CAfile> |
| 193 | |
| 194 | Do not load the trusted CA certificates from the default file location. |
| 195 | |
| 196 | =item B<-no-CApath> |
| 197 | |
| 198 | Do not load the trusted CA certificates from the default directory location. |
| 199 | |
| 200 | =item B<-md digest> |
| 201 | |
| 202 | Digest algorithm to use when signing or resigning. If not present then the |
| 203 | default digest algorithm for the signing key will be used (usually SHA1). |
| 204 | |
| 205 | =item B<-I<cipher>> |
| 206 | |
| 207 | The encryption algorithm to use. For example DES (56 bits) - B<-des>, |
| 208 | triple DES (168 bits) - B<-des3>, |
| 209 | EVP_get_cipherbyname() function) can also be used preceded by a dash, for |
| 210 | example B<-aes-128-cbc>. See L<B<enc>|enc(1)> for list of ciphers |
| 211 | supported by your version of OpenSSL. |
| 212 | |
| 213 | If not specified triple DES is used. Only used with B<-encrypt>. |
| 214 | |
| 215 | =item B<-nointern> |
| 216 | |
| 217 | When verifying a message normally certificates (if any) included in |
| 218 | the message are searched for the signing certificate. With this option |
| 219 | only the certificates specified in the B<-certfile> option are used. |
| 220 | The supplied certificates can still be used as untrusted CAs however. |
| 221 | |
| 222 | =item B<-noverify> |
| 223 | |
| 224 | Do not verify the signers certificate of a signed message. |
| 225 | |
| 226 | =item B<-nochain> |
| 227 | |
| 228 | Do not do chain verification of signers certificates: that is don't |
| 229 | use the certificates in the signed message as untrusted CAs. |
| 230 | |
| 231 | =item B<-nosigs> |
| 232 | |
| 233 | Don't try to verify the signatures on the message. |
| 234 | |
| 235 | =item B<-nocerts> |
| 236 | |
| 237 | When signing a message the signer's certificate is normally included |
| 238 | with this option it is excluded. This will reduce the size of the |
| 239 | signed message but the verifier must have a copy of the signers certificate |
| 240 | available locally (passed using the B<-certfile> option for example). |
| 241 | |
| 242 | =item B<-noattr> |
| 243 | |
| 244 | Normally when a message is signed a set of attributes are included which |
| 245 | include the signing time and supported symmetric algorithms. With this |
| 246 | option they are not included. |
| 247 | |
| 248 | =item B<-binary> |
| 249 | |
| 250 | Normally the input message is converted to "canonical" format which is |
| 251 | effectively using CR and LF as end of line: as required by the S/MIME |
| 252 | specification. When this option is present no translation occurs. This |
| 253 | is useful when handling binary data which may not be in MIME format. |
| 254 | |
| 255 | =item B<-crlfeol> |
| 256 | |
| 257 | Normally the output file uses a single B<LF> as end of line. When this |
| 258 | option is present B<CRLF> is used instead. |
| 259 | |
| 260 | =item B<-nodetach> |
| 261 | |
| 262 | When signing a message use opaque signing: this form is more resistant |
| 263 | to translation by mail relays but it cannot be read by mail agents that |
| 264 | do not support S/MIME. Without this option cleartext signing with |
| 265 | the MIME type multipart/signed is used. |
| 266 | |
| 267 | =item B<-certfile file> |
| 268 | |
| 269 | Allows additional certificates to be specified. When signing these will |
| 270 | be included with the message. When verifying these will be searched for |
| 271 | the signers certificates. The certificates should be in PEM format. |
| 272 | |
| 273 | =item B<-signer file> |
| 274 | |
| 275 | A signing certificate when signing or resigning a message, this option can be |
| 276 | used multiple times if more than one signer is required. If a message is being |
| 277 | verified then the signers certificates will be written to this file if the |
| 278 | verification was successful. |
| 279 | |
| 280 | =item B<-recip file> |
| 281 | |
| 282 | The recipients certificate when decrypting a message. This certificate |
| 283 | must match one of the recipients of the message or an error occurs. |
| 284 | |
| 285 | =item B<-inkey file_or_id> |
| 286 | |
| 287 | The private key to use when signing or decrypting. This must match the |
| 288 | corresponding certificate. If this option is not specified then the |
| 289 | private key must be included in the certificate file specified with |
| 290 | the B<-recip> or B<-signer> file. When signing this option can be used |
| 291 | multiple times to specify successive keys. |
| 292 | If no engine is used, the argument is taken as a file; if an engine is |
| 293 | specified, the argument is given to the engine as a key identifier. |
| 294 | |
| 295 | =item B<-passin arg> |
| 296 | |
| 297 | The private key password source. For more information about the format of B<arg> |
| 298 | see L<openssl(1)/Pass Phrase Options>. |
| 299 | |
| 300 | =item B<-rand file...> |
| 301 | |
| 302 | A file or files containing random data used to seed the random number |
| 303 | generator. |
| 304 | Multiple files can be specified separated by an OS-dependent character. |
| 305 | The separator is B<;> for MS-Windows, B<,> for OpenVMS, and B<:> for |
| 306 | all others. |
| 307 | |
| 308 | =item [B<-writerand file>] |
| 309 | |
| 310 | Writes random data to the specified I<file> upon exit. |
| 311 | This can be used with a subsequent B<-rand> flag. |
| 312 | |
| 313 | =item B<cert.pem...> |
| 314 | |
| 315 | One or more certificates of message recipients: used when encrypting |
| 316 | a message. |
| 317 | |
| 318 | =item B<-to, -from, -subject> |
| 319 | |
| 320 | The relevant mail headers. These are included outside the signed |
| 321 | portion of a message so they may be included manually. If signing |
| 322 | then many S/MIME mail clients check the signers certificate's email |
| 323 | address matches that specified in the From: address. |
| 324 | |
| 325 | =item B<-attime>, B<-check_ss_sig>, B<-crl_check>, B<-crl_check_all>, |
| 326 | B<-explicit_policy>, B<-extended_crl>, B<-ignore_critical>, B<-inhibit_any>, |
| 327 | B<-inhibit_map>, B<-no_alt_chains>, B<-partial_chain>, B<-policy>, |
| 328 | B<-policy_check>, B<-policy_print>, B<-purpose>, B<-suiteB_128>, |
| 329 | B<-suiteB_128_only>, B<-suiteB_192>, B<-trusted_first>, B<-use_deltas>, |
| 330 | B<-auth_level>, B<-verify_depth>, B<-verify_email>, B<-verify_hostname>, |
| 331 | B<-verify_ip>, B<-verify_name>, B<-x509_strict> |
| 332 | |
| 333 | Set various options of certificate chain verification. See |
| 334 | L<verify(1)> manual page for details. |
| 335 | |
| 336 | =back |
| 337 | |
| 338 | =head1 NOTES |
| 339 | |
| 340 | The MIME message must be sent without any blank lines between the |
| 341 | headers and the output. Some mail programs will automatically add |
| 342 | a blank line. Piping the mail directly to sendmail is one way to |
| 343 | achieve the correct format. |
| 344 | |
| 345 | The supplied message to be signed or encrypted must include the |
| 346 | necessary MIME headers or many S/MIME clients won't display it |
| 347 | properly (if at all). You can use the B<-text> option to automatically |
| 348 | add plain text headers. |
| 349 | |
| 350 | A "signed and encrypted" message is one where a signed message is |
| 351 | then encrypted. This can be produced by encrypting an already signed |
| 352 | message: see the examples section. |
| 353 | |
| 354 | This version of the program only allows one signer per message but it |
| 355 | will verify multiple signers on received messages. Some S/MIME clients |
| 356 | choke if a message contains multiple signers. It is possible to sign |
| 357 | messages "in parallel" by signing an already signed message. |
| 358 | |
| 359 | The options B<-encrypt> and B<-decrypt> reflect common usage in S/MIME |
| 360 | clients. Strictly speaking these process PKCS#7 enveloped data: PKCS#7 |
| 361 | encrypted data is used for other purposes. |
| 362 | |
| 363 | The B<-resign> option uses an existing message digest when adding a new |
| 364 | signer. This means that attributes must be present in at least one existing |
| 365 | signer using the same message digest or this operation will fail. |
| 366 | |
| 367 | The B<-stream> and B<-indef> options enable streaming I/O support. |
| 368 | As a result the encoding is BER using indefinite length constructed encoding |
| 369 | and no longer DER. Streaming is supported for the B<-encrypt> operation and the |
| 370 | B<-sign> operation if the content is not detached. |
| 371 | |
| 372 | Streaming is always used for the B<-sign> operation with detached data but |
| 373 | since the content is no longer part of the PKCS#7 structure the encoding |
| 374 | remains DER. |
| 375 | |
| 376 | =head1 EXIT CODES |
| 377 | |
| 378 | =over 4 |
| 379 | |
| 380 | =item Z<>0 |
| 381 | |
| 382 | The operation was completely successfully. |
| 383 | |
| 384 | =item Z<>1 |
| 385 | |
| 386 | An error occurred parsing the command options. |
| 387 | |
| 388 | =item Z<>2 |
| 389 | |
| 390 | One of the input files could not be read. |
| 391 | |
| 392 | =item Z<>3 |
| 393 | |
| 394 | An error occurred creating the PKCS#7 file or when reading the MIME |
| 395 | message. |
| 396 | |
| 397 | =item Z<>4 |
| 398 | |
| 399 | An error occurred decrypting or verifying the message. |
| 400 | |
| 401 | =item Z<>5 |
| 402 | |
| 403 | The message was verified correctly but an error occurred writing out |
| 404 | the signers certificates. |
| 405 | |
| 406 | =back |
| 407 | |
| 408 | =head1 EXAMPLES |
| 409 | |
| 410 | Create a cleartext signed message: |
| 411 | |
| 412 | openssl smime -sign -in message.txt -text -out mail.msg \ |
| 413 | -signer mycert.pem |
| 414 | |
| 415 | Create an opaque signed message: |
| 416 | |
| 417 | openssl smime -sign -in message.txt -text -out mail.msg -nodetach \ |
| 418 | -signer mycert.pem |
| 419 | |
| 420 | Create a signed message, include some additional certificates and |
| 421 | read the private key from another file: |
| 422 | |
| 423 | openssl smime -sign -in in.txt -text -out mail.msg \ |
| 424 | -signer mycert.pem -inkey mykey.pem -certfile mycerts.pem |
| 425 | |
| 426 | Create a signed message with two signers: |
| 427 | |
| 428 | openssl smime -sign -in message.txt -text -out mail.msg \ |
| 429 | -signer mycert.pem -signer othercert.pem |
| 430 | |
| 431 | Send a signed message under Unix directly to sendmail, including headers: |
| 432 | |
| 433 | openssl smime -sign -in in.txt -text -signer mycert.pem \ |
| 434 | -from steve@openssl.org -to someone@somewhere \ |
| 435 | -subject "Signed message" | sendmail someone@somewhere |
| 436 | |
| 437 | Verify a message and extract the signer's certificate if successful: |
| 438 | |
| 439 | openssl smime -verify -in mail.msg -signer user.pem -out signedtext.txt |
| 440 | |
| 441 | Send encrypted mail using triple DES: |
| 442 | |
| 443 | openssl smime -encrypt -in in.txt -from steve@openssl.org \ |
| 444 | -to someone@somewhere -subject "Encrypted message" \ |
| 445 | -des3 user.pem -out mail.msg |
| 446 | |
| 447 | Sign and encrypt mail: |
| 448 | |
| 449 | openssl smime -sign -in ml.txt -signer my.pem -text \ |
| 450 | | openssl smime -encrypt -out mail.msg \ |
| 451 | -from steve@openssl.org -to someone@somewhere \ |
| 452 | -subject "Signed and Encrypted message" -des3 user.pem |
| 453 | |
| 454 | Note: the encryption command does not include the B<-text> option because the |
| 455 | message being encrypted already has MIME headers. |
| 456 | |
| 457 | Decrypt mail: |
| 458 | |
| 459 | openssl smime -decrypt -in mail.msg -recip mycert.pem -inkey key.pem |
| 460 | |
| 461 | The output from Netscape form signing is a PKCS#7 structure with the |
| 462 | detached signature format. You can use this program to verify the |
| 463 | signature by line wrapping the base64 encoded structure and surrounding |
| 464 | it with: |
| 465 | |
| 466 | -----BEGIN PKCS7----- |
| 467 | -----END PKCS7----- |
| 468 | |
| 469 | and using the command: |
| 470 | |
| 471 | openssl smime -verify -inform PEM -in signature.pem -content content.txt |
| 472 | |
| 473 | Alternatively you can base64 decode the signature and use: |
| 474 | |
| 475 | openssl smime -verify -inform DER -in signature.der -content content.txt |
| 476 | |
| 477 | Create an encrypted message using 128 bit Camellia: |
| 478 | |
| 479 | openssl smime -encrypt -in plain.txt -camellia128 -out mail.msg cert.pem |
| 480 | |
| 481 | Add a signer to an existing message: |
| 482 | |
| 483 | openssl smime -resign -in mail.msg -signer newsign.pem -out mail2.msg |
| 484 | |
| 485 | =head1 BUGS |
| 486 | |
| 487 | The MIME parser isn't very clever: it seems to handle most messages that I've |
| 488 | thrown at it but it may choke on others. |
| 489 | |
| 490 | The code currently will only write out the signer's certificate to a file: if |
| 491 | the signer has a separate encryption certificate this must be manually |
| 492 | extracted. There should be some heuristic that determines the correct |
| 493 | encryption certificate. |
| 494 | |
| 495 | Ideally a database should be maintained of a certificates for each email |
| 496 | address. |
| 497 | |
| 498 | The code doesn't currently take note of the permitted symmetric encryption |
| 499 | algorithms as supplied in the SMIMECapabilities signed attribute. This means the |
| 500 | user has to manually include the correct encryption algorithm. It should store |
| 501 | the list of permitted ciphers in a database and only use those. |
| 502 | |
| 503 | No revocation checking is done on the signer's certificate. |
| 504 | |
| 505 | The current code can only handle S/MIME v2 messages, the more complex S/MIME v3 |
| 506 | structures may cause parsing errors. |
| 507 | |
| 508 | =head1 HISTORY |
| 509 | |
| 510 | The use of multiple B<-signer> options and the B<-resign> command were first |
| 511 | added in OpenSSL 1.0.0 |
| 512 | |
| 513 | The -no_alt_chains option was added in OpenSSL 1.1.0. |
| 514 | |
| 515 | =head1 COPYRIGHT |
| 516 | |
| 517 | Copyright 2000-2021 The OpenSSL Project Authors. All Rights Reserved. |
| 518 | |
| 519 | Licensed under the OpenSSL license (the "License"). You may not use |
| 520 | this file except in compliance with the License. You can obtain a copy |
| 521 | in the file LICENSE in the source distribution or at |
| 522 | L<https://www.openssl.org/source/license.html>. |
| 523 | |
| 524 | =cut |