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1=pod
2
3=head1 NAME
4
b6b66573 5openssl-smime - S/MIME utility
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6
7=head1 SYNOPSIS
8
9B<openssl> B<smime>
169394d4 10[B<-help>]
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11[B<-encrypt>]
12[B<-decrypt>]
13[B<-sign>]
d884c5ba 14[B<-resign>]
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15[B<-verify>]
16[B<-pk7out>]
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17[B<-binary>]
18[B<-crlfeol>]
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19[B<->I<cipher>]
20[B<-in> I<file>]
21[B<-CAfile> I<file>]
22[B<-CApath> I<dir>]
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23[B<-no-CAfile>]
24[B<-no-CApath>]
e8769719 25[B<-attime> I<timestamp>]
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26[B<-check_ss_sig>]
27[B<-crl_check>]
28[B<-crl_check_all>]
29[B<-explicit_policy>]
30[B<-extended_crl>]
31[B<-ignore_critical>]
32[B<-inhibit_any>]
33[B<-inhibit_map>]
e42d84be 34[B<-partial_chain>]
e8769719 35[B<-policy> I<arg>]
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36[B<-policy_check>]
37[B<-policy_print>]
e8769719 38[B<-purpose> I<purpose>]
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39[B<-suiteB_128>]
40[B<-suiteB_128_only>]
41[B<-suiteB_192>]
6d3d5793 42[B<-trusted_first>]
fa7b0111 43[B<-no_alt_chains>]
e42d84be 44[B<-use_deltas>]
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45[B<-auth_level> I<num>]
46[B<-verify_depth> I<num>]
47[B<-verify_email> I<email>]
48[B<-verify_hostname> I<hostname>]
49[B<-verify_ip> I<ip>]
50[B<-verify_name> I<name>]
e42d84be 51[B<-x509_strict>]
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52[B<-certfile> I<file>]
53[B<-signer> I<file>]
54[B<-recip> I< file>]
55[B<-inform> B<DER>|B<PEM>|B<SMIME>]
56[B<-passin> I<arg>]
57[B<-inkey> I<file_or_id>]
58[B<-out> I<file>]
59[B<-outform> B<DER>|B<PEM>|B<SMIME>]
60[B<-content> I<file>]
61[B<-to> I<addr>]
62[B<-from> I<ad>]
63[B<-subject> I<s>]
e3775a33 64[B<-text>]
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65[B<-indef>]
66[B<-noindef>]
67[B<-stream>]
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68[B<-rand> I<file...>]
69[B<-writerand> I<file>]
70[B<-md> I<digest>]
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71[cert.pem]...
72
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73=for comment ifdef engine
74
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75=head1 DESCRIPTION
76
77The B<smime> command handles S/MIME mail. It can encrypt, decrypt, sign and
78verify S/MIME messages.
79
3dfda1a6 80=head1 OPTIONS
e3775a33 81
76b46e77 82There are six operation options that set the type of operation to be performed.
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83The meaning of the other options varies according to the operation type.
84
85=over 4
86
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87=item B<-help>
88
89Print out a usage message.
90
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91=item B<-encrypt>
92
c4de074e 93Encrypt mail for the given recipient certificates. Input file is the message
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94to be encrypted. The output file is the encrypted mail in MIME format.
95
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96Note that no revocation check is done for the recipient cert, so if that
97key has been compromised, others may be able to decrypt the text.
98
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99=item B<-decrypt>
100
c4de074e 101Decrypt mail using the supplied certificate and private key. Expects an
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102encrypted mail message in MIME format for the input file. The decrypted mail
103is written to the output file.
104
105=item B<-sign>
106
c4de074e 107Sign mail using the supplied certificate and private key. Input file is
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108the message to be signed. The signed message in MIME format is written
109to the output file.
110
111=item B<-verify>
112
c4de074e 113Verify signed mail. Expects a signed mail message on input and outputs
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114the signed data. Both clear text and opaque signing is supported.
115
116=item B<-pk7out>
117
c4de074e 118Takes an input message and writes out a PEM encoded PKCS#7 structure.
e3775a33 119
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120=item B<-resign>
121
c4de074e 122Resign a message: take an existing message and one or more new signers.
d884c5ba 123
e8769719 124=item B<-in> I<filename>
e3775a33 125
c4de074e 126The input message to be encrypted or signed or the MIME message to
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127be decrypted or verified.
128
e8769719 129=item B<-inform> B<DER>|B<PEM>|B<SMIME>
fd13f0ee 130
c4de074e 131This specifies the input format for the PKCS#7 structure. The default
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132is B<SMIME> which reads an S/MIME format message. B<PEM> and B<DER>
133format change this to expect PEM and DER format PKCS#7 structures
134instead. This currently only affects the input format of the PKCS#7
135structure, if no PKCS#7 structure is being input (for example with
136B<-encrypt> or B<-sign>) this option has no effect.
137
e8769719 138=item B<-out> I<filename>
e3775a33 139
c4de074e 140The message text that has been decrypted or verified or the output MIME
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141format message that has been signed or verified.
142
e8769719 143=item B<-outform> B<DER>|B<PEM>|B<SMIME>
fd13f0ee 144
c4de074e 145This specifies the output format for the PKCS#7 structure. The default
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146is B<SMIME> which write an S/MIME format message. B<PEM> and B<DER>
147format change this to write PEM and DER format PKCS#7 structures
148instead. This currently only affects the output format of the PKCS#7
149structure, if no PKCS#7 structure is being output (for example with
150B<-verify> or B<-decrypt>) this option has no effect.
151
e8769719 152=item B<-stream>, B<-indef>, B<-noindef>
76b46e77 153
c4de074e 154The B<-stream> and B<-indef> options are equivalent and enable streaming I/O
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155for encoding operations. This permits single pass processing of data without
156the need to hold the entire contents in memory, potentially supporting very
157large files. Streaming is automatically set for S/MIME signing with detached
158data if the output format is B<SMIME> it is currently off by default for all
159other operations.
160
161=item B<-noindef>
162
c4de074e 163Disable streaming I/O where it would produce and indefinite length constructed
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164encoding. This option currently has no effect. In future streaming will be
165enabled by default on all relevant operations and this option will disable it.
166
e8769719 167=item B<-content> I<filename>
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168
169This specifies a file containing the detached content, this is only
170useful with the B<-verify> command. This is only usable if the PKCS#7
171structure is using the detached signature form where the content is
172not included. This option will override any content if the input format
173is S/MIME and it uses the multipart/signed MIME content type.
174
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175=item B<-text>
176
c4de074e 177This option adds plain text (text/plain) MIME headers to the supplied
e3775a33 178message if encrypting or signing. If decrypting or verifying it strips
1bc74519 179off text headers: if the decrypted or verified message is not of MIME
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180type text/plain then an error occurs.
181
e8769719 182=item B<-CAfile> I<file>
e3775a33 183
c4de074e 184A file containing trusted CA certificates, only used with B<-verify>.
e3775a33 185
e8769719 186=item B<-CApath> I<dir>
e3775a33 187
c4de074e 188A directory containing trusted CA certificates, only used with
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189B<-verify>. This directory must be a standard certificate directory: that
190is a hash of each subject name (using B<x509 -hash>) should be linked
191to each certificate.
192
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193=item B<-no-CAfile>
194
c4de074e 195Do not load the trusted CA certificates from the default file location.
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196
197=item B<-no-CApath>
198
c4de074e 199Do not load the trusted CA certificates from the default directory location.
40e2d76b 200
e8769719 201=item B<-md> I<digest>
d884c5ba 202
c4de074e 203Digest algorithm to use when signing or resigning. If not present then the
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204default digest algorithm for the signing key will be used (usually SHA1).
205
e8769719 206=item B<->I<cipher>
e3775a33 207
c4de074e 208The encryption algorithm to use. For example DES (56 bits) - B<-des>,
e5fa864f 209triple DES (168 bits) - B<-des3>,
1bc74519 210EVP_get_cipherbyname() function) can also be used preceded by a dash, for
9446daac 211example B<-aes-128-cbc>. See L<B<enc>|enc(1)> for list of ciphers
e5fa864f 212supported by your version of OpenSSL.
d884c5ba 213
6f719f06 214If not specified triple DES is used. Only used with B<-encrypt>.
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215
216=item B<-nointern>
217
c4de074e 218When verifying a message normally certificates (if any) included in
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219the message are searched for the signing certificate. With this option
220only the certificates specified in the B<-certfile> option are used.
221The supplied certificates can still be used as untrusted CAs however.
222
223=item B<-noverify>
224
c4de074e 225Do not verify the signers certificate of a signed message.
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226
227=item B<-nochain>
228
c4de074e 229Do not do chain verification of signers certificates: that is don't
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230use the certificates in the signed message as untrusted CAs.
231
232=item B<-nosigs>
233
c4de074e 234Don't try to verify the signatures on the message.
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235
236=item B<-nocerts>
237
c4de074e 238When signing a message the signer's certificate is normally included
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239with this option it is excluded. This will reduce the size of the
240signed message but the verifier must have a copy of the signers certificate
241available locally (passed using the B<-certfile> option for example).
242
243=item B<-noattr>
244
c4de074e 245Normally when a message is signed a set of attributes are included which
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246include the signing time and supported symmetric algorithms. With this
247option they are not included.
248
249=item B<-binary>
250
c4de074e 251Normally the input message is converted to "canonical" format which is
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252effectively using CR and LF as end of line: as required by the S/MIME
253specification. When this option is present no translation occurs. This
254is useful when handling binary data which may not be in MIME format.
e3775a33 255
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256=item B<-crlfeol>
257
c4de074e 258Normally the output file uses a single B<LF> as end of line. When this
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259option is present B<CRLF> is used instead.
260
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261=item B<-nodetach>
262
c4de074e 263When signing a message use opaque signing: this form is more resistant
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264to translation by mail relays but it cannot be read by mail agents that
265do not support S/MIME. Without this option cleartext signing with
266the MIME type multipart/signed is used.
267
e8769719 268=item B<-certfile> I<file>
e3775a33 269
c4de074e 270Allows additional certificates to be specified. When signing these will
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271be included with the message. When verifying these will be searched for
272the signers certificates. The certificates should be in PEM format.
273
e8769719 274=item B<-signer> I<file>
e3775a33 275
c4de074e 276A signing certificate when signing or resigning a message, this option can be
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277used multiple times if more than one signer is required. If a message is being
278verified then the signers certificates will be written to this file if the
279verification was successful.
e3775a33 280
e8769719 281=item B<-recip> I<file>
e3775a33 282
c4de074e 283The recipients certificate when decrypting a message. This certificate
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284must match one of the recipients of the message or an error occurs.
285
e8769719 286=item B<-inkey> I<file_or_id>
e3775a33 287
c4de074e 288The private key to use when signing or decrypting. This must match the
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289corresponding certificate. If this option is not specified then the
290private key must be included in the certificate file specified with
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291the B<-recip> or B<-signer> file. When signing this option can be used
292multiple times to specify successive keys.
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293If no engine is used, the argument is taken as a file; if an engine is
294specified, the argument is given to the engine as a key identifier.
e3775a33 295
e8769719 296=item B<-passin> I<arg>
84b65340 297
c4de074e 298The private key password source. For more information about the format of B<arg>
e8769719 299see L<openssl(1)/Pass phrase options>.
84b65340 300
e8769719 301=item B<-rand> I<file...>
d13e4eb0 302
c4de074e 303A file or files containing random data used to seed the random number
3ee1eac2 304generator.
35ed393e 305Multiple files can be specified separated by an OS-dependent character.
b87ef946 306The separator is B<;> for MS-Windows, B<,> for OpenVMS, and B<:> for
a4cfd178 307all others.
d13e4eb0 308
e8769719 309=item B<-writerand> I<file>
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310
311Writes random data to the specified I<file> upon exit.
312This can be used with a subsequent B<-rand> flag.
313
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314=item B<cert.pem...>
315
c4de074e 316One or more certificates of message recipients: used when encrypting
1bc74519 317a message.
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318
319=item B<-to, -from, -subject>
320
c4de074e 321The relevant mail headers. These are included outside the signed
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322portion of a message so they may be included manually. If signing
323then many S/MIME mail clients check the signers certificate's email
324address matches that specified in the From: address.
325
e42d84be 326=item B<-attime>, B<-check_ss_sig>, B<-crl_check>, B<-crl_check_all>,
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327B<-explicit_policy>, B<-extended_crl>, B<-ignore_critical>, B<-inhibit_any>,
328B<-inhibit_map>, B<-no_alt_chains>, B<-partial_chain>, B<-policy>,
e42d84be 329B<-policy_check>, B<-policy_print>, B<-purpose>, B<-suiteB_128>,
d33def66 330B<-suiteB_128_only>, B<-suiteB_192>, B<-trusted_first>, B<-use_deltas>,
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331B<-auth_level>, B<-verify_depth>, B<-verify_email>, B<-verify_hostname>,
332B<-verify_ip>, B<-verify_name>, B<-x509_strict>
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333
334Set various options of certificate chain verification. See
9b86974e 335L<verify(1)> manual page for details.
e5fa864f 336
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337=back
338
339=head1 NOTES
340
341The MIME message must be sent without any blank lines between the
342headers and the output. Some mail programs will automatically add
343a blank line. Piping the mail directly to sendmail is one way to
344achieve the correct format.
345
3fc9635e 346The supplied message to be signed or encrypted must include the
60250017 347necessary MIME headers or many S/MIME clients won't display it
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348properly (if at all). You can use the B<-text> option to automatically
349add plain text headers.
350
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351A "signed and encrypted" message is one where a signed message is
352then encrypted. This can be produced by encrypting an already signed
3fc9635e 353message: see the examples section.
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354
355This version of the program only allows one signer per message but it
356will verify multiple signers on received messages. Some S/MIME clients
19d2bb57 357choke if a message contains multiple signers. It is possible to sign
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358messages "in parallel" by signing an already signed message.
359
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360The options B<-encrypt> and B<-decrypt> reflect common usage in S/MIME
361clients. Strictly speaking these process PKCS#7 enveloped data: PKCS#7
362encrypted data is used for other purposes.
363
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364The B<-resign> option uses an existing message digest when adding a new
365signer. This means that attributes must be present in at least one existing
366signer using the same message digest or this operation will fail.
367
e4ef2e25 368The B<-stream> and B<-indef> options enable streaming I/O support.
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369As a result the encoding is BER using indefinite length constructed encoding
370and no longer DER. Streaming is supported for the B<-encrypt> operation and the
371B<-sign> operation if the content is not detached.
372
373Streaming is always used for the B<-sign> operation with detached data but
374since the content is no longer part of the PKCS#7 structure the encoding
375remains DER.
376
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377=head1 EXIT CODES
378
379=over 4
380
c8919dde 381=item Z<>0
e3775a33 382
c4de074e 383The operation was completely successfully.
e3775a33 384
c8919dde 385=item Z<>1
e3775a33 386
c4de074e 387An error occurred parsing the command options.
e3775a33 388
c8919dde 389=item Z<>2
e3775a33 390
c4de074e 391One of the input files could not be read.
e3775a33 392
c8919dde 393=item Z<>3
e3775a33 394
c4de074e 395An error occurred creating the PKCS#7 file or when reading the MIME
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396message.
397
c8919dde 398=item Z<>4
e3775a33 399
c4de074e 400An error occurred decrypting or verifying the message.
e3775a33 401
c8919dde 402=item Z<>5
e3775a33 403
c4de074e 404The message was verified correctly but an error occurred writing out
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405the signers certificates.
406
407=back
408
409=head1 EXAMPLES
410
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411Create a cleartext signed message:
412
1675f6eb 413 openssl smime -sign -in message.txt -text -out mail.msg \
1bc74519 414 -signer mycert.pem
3fc9635e 415
0d638dc1 416Create an opaque signed message:
3fc9635e 417
1675f6eb 418 openssl smime -sign -in message.txt -text -out mail.msg -nodetach \
1bc74519 419 -signer mycert.pem
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420
421Create a signed message, include some additional certificates and
422read the private key from another file:
423
1675f6eb 424 openssl smime -sign -in in.txt -text -out mail.msg \
1bc74519 425 -signer mycert.pem -inkey mykey.pem -certfile mycerts.pem
3fc9635e 426
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427Create a signed message with two signers:
428
429 openssl smime -sign -in message.txt -text -out mail.msg \
1bc74519 430 -signer mycert.pem -signer othercert.pem
d884c5ba 431
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432Send a signed message under Unix directly to sendmail, including headers:
433
1675f6eb 434 openssl smime -sign -in in.txt -text -signer mycert.pem \
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435 -from steve@openssl.org -to someone@somewhere \
436 -subject "Signed message" | sendmail someone@somewhere
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437
438Verify a message and extract the signer's certificate if successful:
439
440 openssl smime -verify -in mail.msg -signer user.pem -out signedtext.txt
441
442Send encrypted mail using triple DES:
443
1675f6eb 444 openssl smime -encrypt -in in.txt -from steve@openssl.org \
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445 -to someone@somewhere -subject "Encrypted message" \
446 -des3 user.pem -out mail.msg
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447
448Sign and encrypt mail:
449
1675f6eb 450 openssl smime -sign -in ml.txt -signer my.pem -text \
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451 | openssl smime -encrypt -out mail.msg \
452 -from steve@openssl.org -to someone@somewhere \
453 -subject "Signed and Encrypted message" -des3 user.pem
3fc9635e 454
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455Note: the encryption command does not include the B<-text> option because the
456message being encrypted already has MIME headers.
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457
458Decrypt mail:
459
460 openssl smime -decrypt -in mail.msg -recip mycert.pem -inkey key.pem
461
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462The output from Netscape form signing is a PKCS#7 structure with the
463detached signature format. You can use this program to verify the
464signature by line wrapping the base64 encoded structure and surrounding
465it with:
466
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467 -----BEGIN PKCS7-----
468 -----END PKCS7-----
fd13f0ee 469
1bc74519 470and using the command:
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471
472 openssl smime -verify -inform PEM -in signature.pem -content content.txt
473
0d638dc1 474Alternatively you can base64 decode the signature and use:
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475
476 openssl smime -verify -inform DER -in signature.der -content content.txt
477
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478Create an encrypted message using 128 bit Camellia:
479
480 openssl smime -encrypt -in plain.txt -camellia128 -out mail.msg cert.pem
481
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482Add a signer to an existing message:
483
484 openssl smime -resign -in mail.msg -signer newsign.pem -out mail2.msg
485
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486=head1 BUGS
487
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488The MIME parser isn't very clever: it seems to handle most messages that I've
489thrown at it but it may choke on others.
3fc9635e 490
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491The code currently will only write out the signer's certificate to a file: if
492the signer has a separate encryption certificate this must be manually
493extracted. There should be some heuristic that determines the correct
494encryption certificate.
3fc9635e 495
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496Ideally a database should be maintained of a certificates for each email
497address.
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498
499The code doesn't currently take note of the permitted symmetric encryption
7e0de9e8 500algorithms as supplied in the SMIMECapabilities signed attribute. This means the
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501user has to manually include the correct encryption algorithm. It should store
502the list of permitted ciphers in a database and only use those.
503
504No revocation checking is done on the signer's certificate.
505
506The current code can only handle S/MIME v2 messages, the more complex S/MIME v3
507structures may cause parsing errors.
e3775a33 508
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509=head1 HISTORY
510
511The use of multiple B<-signer> options and the B<-resign> command were first
fb552ac6 512added in OpenSSL 1.0.0
d884c5ba 513
fc5ecadd 514The -no_alt_chains option was added in OpenSSL 1.1.0.
d884c5ba 515
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516=head1 COPYRIGHT
517
b6b66573 518Copyright 2000-2019 The OpenSSL Project Authors. All Rights Reserved.
e2f92610 519
449040b4 520Licensed under the Apache License 2.0 (the "License"). You may not use
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521this file except in compliance with the License. You can obtain a copy
522in the file LICENSE in the source distribution or at
523L<https://www.openssl.org/source/license.html>.
524
525=cut