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1=pod
2
3=head1 NAME
4
5smime - S/MIME utility
6
7=head1 SYNOPSIS
8
9B<openssl> B<smime>
10[B<-encrypt>]
11[B<-decrypt>]
12[B<-sign>]
13[B<-verify>]
14[B<-pk7out>]
3fc9635e 15[B<-des>]
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16[B<-des3>]
17[B<-rc2-40>]
18[B<-rc2-64>]
19[B<-rc2-128>]
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20[B<-aes128>]
21[B<-aes192>]
22[B<-aes256>]
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23[B<-camellia128>]
24[B<-camellia192>]
25[B<-camellia256>]
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26[B<-in file>]
27[B<-certfile file>]
28[B<-signer file>]
29[B<-recip file>]
fd13f0ee 30[B<-inform SMIME|PEM|DER>]
84b65340 31[B<-passin arg>]
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32[B<-inkey file>]
33[B<-out file>]
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34[B<-outform SMIME|PEM|DER>]
35[B<-content file>]
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36[B<-to addr>]
37[B<-from ad>]
38[B<-subject s>]
39[B<-text>]
d13e4eb0 40[B<-rand file(s)>]
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41[cert.pem]...
42
43=head1 DESCRIPTION
44
45The B<smime> command handles S/MIME mail. It can encrypt, decrypt, sign and
46verify S/MIME messages.
47
48=head1 COMMAND OPTIONS
49
50There are five operation options that set the type of operation to be performed.
51The meaning of the other options varies according to the operation type.
52
53=over 4
54
55=item B<-encrypt>
56
57encrypt mail for the given recipient certificates. Input file is the message
58to be encrypted. The output file is the encrypted mail in MIME format.
59
60=item B<-decrypt>
61
62decrypt mail using the supplied certificate and private key. Expects an
63encrypted mail message in MIME format for the input file. The decrypted mail
64is written to the output file.
65
66=item B<-sign>
67
68sign mail using the supplied certificate and private key. Input file is
69the message to be signed. The signed message in MIME format is written
70to the output file.
71
72=item B<-verify>
73
74verify signed mail. Expects a signed mail message on input and outputs
75the signed data. Both clear text and opaque signing is supported.
76
77=item B<-pk7out>
78
79takes an input message and writes out a PEM encoded PKCS#7 structure.
80
81=item B<-in filename>
82
83the input message to be encrypted or signed or the MIME message to
84be decrypted or verified.
85
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86=item B<-inform SMIME|PEM|DER>
87
88this specifies the input format for the PKCS#7 structure. The default
89is B<SMIME> which reads an S/MIME format message. B<PEM> and B<DER>
90format change this to expect PEM and DER format PKCS#7 structures
91instead. This currently only affects the input format of the PKCS#7
92structure, if no PKCS#7 structure is being input (for example with
93B<-encrypt> or B<-sign>) this option has no effect.
94
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95=item B<-out filename>
96
97the message text that has been decrypted or verified or the output MIME
98format message that has been signed or verified.
99
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100=item B<-outform SMIME|PEM|DER>
101
102this specifies the output format for the PKCS#7 structure. The default
103is B<SMIME> which write an S/MIME format message. B<PEM> and B<DER>
104format change this to write PEM and DER format PKCS#7 structures
105instead. This currently only affects the output format of the PKCS#7
106structure, if no PKCS#7 structure is being output (for example with
107B<-verify> or B<-decrypt>) this option has no effect.
108
109=item B<-content filename>
110
111This specifies a file containing the detached content, this is only
112useful with the B<-verify> command. This is only usable if the PKCS#7
113structure is using the detached signature form where the content is
114not included. This option will override any content if the input format
115is S/MIME and it uses the multipart/signed MIME content type.
116
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117=item B<-text>
118
119this option adds plain text (text/plain) MIME headers to the supplied
120message if encrypting or signing. If decrypting or verifying it strips
121off text headers: if the decrypted or verified message is not of MIME
122type text/plain then an error occurs.
123
124=item B<-CAfile file>
125
126a file containing trusted CA certificates, only used with B<-verify>.
127
128=item B<-CApath dir>
129
130a directory containing trusted CA certificates, only used with
131B<-verify>. This directory must be a standard certificate directory: that
132is a hash of each subject name (using B<x509 -hash>) should be linked
133to each certificate.
134
f3dea9a5 135=item B<-des -des3 -rc2-40 -rc2-64 -rc2-128 -aes128 -aes192 -aes256 -camellia128 -camellia192 -camellia256>
e3775a33 136
8bb0c852 137the encryption algorithm to use. DES (56 bits), triple DES (168 bits),
f3dea9a5 13840, 64 or 128 bit RC2, 128, 192 or 256 bit AES, or 128, 192 or 256 bit Camellia respectively. If not
8bb0c852 139specified 40 bit RC2 is used. Only used with B<-encrypt>.
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140
141=item B<-nointern>
142
143when verifying a message normally certificates (if any) included in
144the message are searched for the signing certificate. With this option
145only the certificates specified in the B<-certfile> option are used.
146The supplied certificates can still be used as untrusted CAs however.
147
148=item B<-noverify>
149
150do not verify the signers certificate of a signed message.
151
152=item B<-nochain>
153
19d2bb57 154do not do chain verification of signers certificates: that is don't
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155use the certificates in the signed message as untrusted CAs.
156
157=item B<-nosigs>
158
159don't try to verify the signatures on the message.
160
161=item B<-nocerts>
162
163when signing a message the signer's certificate is normally included
164with this option it is excluded. This will reduce the size of the
165signed message but the verifier must have a copy of the signers certificate
166available locally (passed using the B<-certfile> option for example).
167
168=item B<-noattr>
169
170normally when a message is signed a set of attributes are included which
171include the signing time and supported symmetric algorithms. With this
172option they are not included.
173
174=item B<-binary>
175
176normally the input message is converted to "canonical" format which is
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177effectively using CR and LF as end of line: as required by the S/MIME
178specification. When this option is present no translation occurs. This
179is useful when handling binary data which may not be in MIME format.
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180
181=item B<-nodetach>
182
183when signing a message use opaque signing: this form is more resistant
184to translation by mail relays but it cannot be read by mail agents that
185do not support S/MIME. Without this option cleartext signing with
186the MIME type multipart/signed is used.
187
188=item B<-certfile file>
189
190allows additional certificates to be specified. When signing these will
191be included with the message. When verifying these will be searched for
192the signers certificates. The certificates should be in PEM format.
193
194=item B<-signer file>
195
196the signers certificate when signing a message. If a message is
197being verified then the signers certificates will be written to this
198file if the verification was successful.
199
200=item B<-recip file>
201
202the recipients certificate when decrypting a message. This certificate
203must match one of the recipients of the message or an error occurs.
204
205=item B<-inkey file>
206
207the private key to use when signing or decrypting. This must match the
208corresponding certificate. If this option is not specified then the
209private key must be included in the certificate file specified with
210the B<-recip> or B<-signer> file.
211
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212=item B<-passin arg>
213
214the private key password source. For more information about the format of B<arg>
215see the B<PASS PHRASE ARGUMENTS> section in L<openssl(1)|openssl(1)>.
216
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217=item B<-rand file(s)>
218
219a file or files containing random data used to seed the random number
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220generator, or an EGD socket (see L<RAND_egd(3)|RAND_egd(3)>).
221Multiple files can be specified separated by a OS-dependent character.
b87ef946 222The separator is B<;> for MS-Windows, B<,> for OpenVMS, and B<:> for
a4cfd178 223all others.
d13e4eb0 224
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225=item B<cert.pem...>
226
227one or more certificates of message recipients: used when encrypting
228a message.
229
230=item B<-to, -from, -subject>
231
232the relevant mail headers. These are included outside the signed
233portion of a message so they may be included manually. If signing
234then many S/MIME mail clients check the signers certificate's email
235address matches that specified in the From: address.
236
237=back
238
239=head1 NOTES
240
241The MIME message must be sent without any blank lines between the
242headers and the output. Some mail programs will automatically add
243a blank line. Piping the mail directly to sendmail is one way to
244achieve the correct format.
245
3fc9635e 246The supplied message to be signed or encrypted must include the
fd13f0ee 247necessary MIME headers or many S/MIME clients wont display it
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248properly (if at all). You can use the B<-text> option to automatically
249add plain text headers.
250
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251A "signed and encrypted" message is one where a signed message is
252then encrypted. This can be produced by encrypting an already signed
3fc9635e 253message: see the examples section.
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254
255This version of the program only allows one signer per message but it
256will verify multiple signers on received messages. Some S/MIME clients
19d2bb57 257choke if a message contains multiple signers. It is possible to sign
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258messages "in parallel" by signing an already signed message.
259
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260The options B<-encrypt> and B<-decrypt> reflect common usage in S/MIME
261clients. Strictly speaking these process PKCS#7 enveloped data: PKCS#7
262encrypted data is used for other purposes.
263
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264=head1 EXIT CODES
265
266=over 4
267
268=item 0
269
3fc9635e 270the operation was completely successfully.
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271
272=item 1
273
274an error occurred parsing the command options.
275
276=item 2
277
278one of the input files could not be read.
279
280=item 3
281
282an error occurred creating the PKCS#7 file or when reading the MIME
283message.
284
285=item 4
286
287an error occurred decrypting or verifying the message.
288
289=item 5
290
19d2bb57 291the message was verified correctly but an error occurred writing out
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292the signers certificates.
293
294=back
295
296=head1 EXAMPLES
297
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298Create a cleartext signed message:
299
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300 openssl smime -sign -in message.txt -text -out mail.msg \
301 -signer mycert.pem
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302
303Create and opaque signed message
304
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305 openssl smime -sign -in message.txt -text -out mail.msg -nodetach \
306 -signer mycert.pem
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307
308Create a signed message, include some additional certificates and
309read the private key from another file:
310
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311 openssl smime -sign -in in.txt -text -out mail.msg \
312 -signer mycert.pem -inkey mykey.pem -certfile mycerts.pem
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313
314Send a signed message under Unix directly to sendmail, including headers:
315
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316 openssl smime -sign -in in.txt -text -signer mycert.pem \
317 -from steve@openssl.org -to someone@somewhere \
318 -subject "Signed message" | sendmail someone@somewhere
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319
320Verify a message and extract the signer's certificate if successful:
321
322 openssl smime -verify -in mail.msg -signer user.pem -out signedtext.txt
323
324Send encrypted mail using triple DES:
325
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326 openssl smime -encrypt -in in.txt -from steve@openssl.org \
327 -to someone@somewhere -subject "Encrypted message" \
328 -des3 user.pem -out mail.msg
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329
330Sign and encrypt mail:
331
1675f6eb 332 openssl smime -sign -in ml.txt -signer my.pem -text \
dbba890c 333 | openssl smime -encrypt -out mail.msg \
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334 -from steve@openssl.org -to someone@somewhere \
335 -subject "Signed and Encrypted message" -des3 user.pem
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336
337Note: the encryption command does not include the B<-text> option because the message
338being encrypted already has MIME headers.
339
340Decrypt mail:
341
342 openssl smime -decrypt -in mail.msg -recip mycert.pem -inkey key.pem
343
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344The output from Netscape form signing is a PKCS#7 structure with the
345detached signature format. You can use this program to verify the
346signature by line wrapping the base64 encoded structure and surrounding
347it with:
348
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349 -----BEGIN PKCS7-----
350 -----END PKCS7-----
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351
352and using the command,
353
354 openssl smime -verify -inform PEM -in signature.pem -content content.txt
355
356alternatively you can base64 decode the signature and use
357
358 openssl smime -verify -inform DER -in signature.der -content content.txt
359
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360Create an encrypted message using 128 bit Camellia:
361
362 openssl smime -encrypt -in plain.txt -camellia128 -out mail.msg cert.pem
363
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364=head1 BUGS
365
366The MIME parser isn't very clever: it seems to handle most messages that I've thrown
367at it but it may choke on others.
368
369The code currently will only write out the signer's certificate to a file: if the
370signer has a separate encryption certificate this must be manually extracted. There
371should be some heuristic that determines the correct encryption certificate.
372
373Ideally a database should be maintained of a certificates for each email address.
374
375The code doesn't currently take note of the permitted symmetric encryption
376algorithms as supplied in the SMIMECapabilities signed attribute. this means the
377user has to manually include the correct encryption algorithm. It should store
378the list of permitted ciphers in a database and only use those.
379
380No revocation checking is done on the signer's certificate.
381
382The current code can only handle S/MIME v2 messages, the more complex S/MIME v3
383structures may cause parsing errors.
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384
385=cut