smime.pod 14 KB

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  1. =pod
  2. =head1 NAME
  3. smime - S/MIME utility
  4. =head1 SYNOPSIS
  5. B<openssl> B<smime>
  6. [B<-encrypt>]
  7. [B<-decrypt>]
  8. [B<-sign>]
  9. [B<-resign>]
  10. [B<-verify>]
  11. [B<-pk7out>]
  12. [B<-[cipher]>]
  13. [B<-in file>]
  14. [B<-no_alt_chains>]
  15. [B<-certfile file>]
  16. [B<-signer file>]
  17. [B<-recip file>]
  18. [B<-inform SMIME|PEM|DER>]
  19. [B<-passin arg>]
  20. [B<-inkey file>]
  21. [B<-out file>]
  22. [B<-outform SMIME|PEM|DER>]
  23. [B<-content file>]
  24. [B<-to addr>]
  25. [B<-from ad>]
  26. [B<-subject s>]
  27. [B<-text>]
  28. [B<-indef>]
  29. [B<-noindef>]
  30. [B<-stream>]
  31. [B<-rand file(s)>]
  32. [B<-md digest>]
  33. [cert.pem]...
  34. =head1 DESCRIPTION
  35. The B<smime> command handles S/MIME mail. It can encrypt, decrypt, sign and
  36. verify S/MIME messages.
  37. =head1 COMMAND OPTIONS
  38. There are six operation options that set the type of operation to be performed.
  39. The meaning of the other options varies according to the operation type.
  40. =over 4
  41. =item B<-encrypt>
  42. encrypt mail for the given recipient certificates. Input file is the message
  43. to be encrypted. The output file is the encrypted mail in MIME format.
  44. =item B<-decrypt>
  45. decrypt mail using the supplied certificate and private key. Expects an
  46. encrypted mail message in MIME format for the input file. The decrypted mail
  47. is written to the output file.
  48. =item B<-sign>
  49. sign mail using the supplied certificate and private key. Input file is
  50. the message to be signed. The signed message in MIME format is written
  51. to the output file.
  52. =item B<-verify>
  53. verify signed mail. Expects a signed mail message on input and outputs
  54. the signed data. Both clear text and opaque signing is supported.
  55. =item B<-pk7out>
  56. takes an input message and writes out a PEM encoded PKCS#7 structure.
  57. =item B<-resign>
  58. resign a message: take an existing message and one or more new signers.
  59. =item B<-in filename>
  60. the input message to be encrypted or signed or the MIME message to
  61. be decrypted or verified.
  62. =item B<-inform SMIME|PEM|DER>
  63. this specifies the input format for the PKCS#7 structure. The default
  64. is B<SMIME> which reads an S/MIME format message. B<PEM> and B<DER>
  65. format change this to expect PEM and DER format PKCS#7 structures
  66. instead. This currently only affects the input format of the PKCS#7
  67. structure, if no PKCS#7 structure is being input (for example with
  68. B<-encrypt> or B<-sign>) this option has no effect.
  69. =item B<-out filename>
  70. the message text that has been decrypted or verified or the output MIME
  71. format message that has been signed or verified.
  72. =item B<-outform SMIME|PEM|DER>
  73. this specifies the output format for the PKCS#7 structure. The default
  74. is B<SMIME> which write an S/MIME format message. B<PEM> and B<DER>
  75. format change this to write PEM and DER format PKCS#7 structures
  76. instead. This currently only affects the output format of the PKCS#7
  77. structure, if no PKCS#7 structure is being output (for example with
  78. B<-verify> or B<-decrypt>) this option has no effect.
  79. =item B<-stream -indef -noindef>
  80. the B<-stream> and B<-indef> options are equivalent and enable streaming I/O
  81. for encoding operations. This permits single pass processing of data without
  82. the need to hold the entire contents in memory, potentially supporting very
  83. large files. Streaming is automatically set for S/MIME signing with detached
  84. data if the output format is B<SMIME> it is currently off by default for all
  85. other operations.
  86. =item B<-noindef>
  87. disable streaming I/O where it would produce and indefinite length constructed
  88. encoding. This option currently has no effect. In future streaming will be
  89. enabled by default on all relevant operations and this option will disable it.
  90. =item B<-content filename>
  91. This specifies a file containing the detached content, this is only
  92. useful with the B<-verify> command. This is only usable if the PKCS#7
  93. structure is using the detached signature form where the content is
  94. not included. This option will override any content if the input format
  95. is S/MIME and it uses the multipart/signed MIME content type.
  96. =item B<-text>
  97. this option adds plain text (text/plain) MIME headers to the supplied
  98. message if encrypting or signing. If decrypting or verifying it strips
  99. off text headers: if the decrypted or verified message is not of MIME
  100. type text/plain then an error occurs.
  101. =item B<-CAfile file>
  102. a file containing trusted CA certificates, only used with B<-verify>.
  103. =item B<-CApath dir>
  104. a directory containing trusted CA certificates, only used with
  105. B<-verify>. This directory must be a standard certificate directory: that
  106. is a hash of each subject name (using B<x509 -hash>) should be linked
  107. to each certificate.
  108. =item B<-md digest>
  109. digest algorithm to use when signing or resigning. If not present then the
  110. default digest algorithm for the signing key will be used (usually SHA1).
  111. =item B<-[cipher]>
  112. the encryption algorithm to use. For example DES (56 bits) - B<-des>,
  113. triple DES (168 bits) - B<-des3>,
  114. EVP_get_cipherbyname() function) can also be used preceded by a dash, for
  115. example B<-aes_128_cbc>. See L<B<enc>|enc(1)> for list of ciphers
  116. supported by your version of OpenSSL.
  117. If not specified triple DES is used. Only used with B<-encrypt>.
  118. =item B<-nointern>
  119. when verifying a message normally certificates (if any) included in
  120. the message are searched for the signing certificate. With this option
  121. only the certificates specified in the B<-certfile> option are used.
  122. The supplied certificates can still be used as untrusted CAs however.
  123. =item B<-noverify>
  124. do not verify the signers certificate of a signed message.
  125. =item B<-nochain>
  126. do not do chain verification of signers certificates: that is don't
  127. use the certificates in the signed message as untrusted CAs.
  128. =item B<-nosigs>
  129. don't try to verify the signatures on the message.
  130. =item B<-nocerts>
  131. when signing a message the signer's certificate is normally included
  132. with this option it is excluded. This will reduce the size of the
  133. signed message but the verifier must have a copy of the signers certificate
  134. available locally (passed using the B<-certfile> option for example).
  135. =item B<-noattr>
  136. normally when a message is signed a set of attributes are included which
  137. include the signing time and supported symmetric algorithms. With this
  138. option they are not included.
  139. =item B<-binary>
  140. normally the input message is converted to "canonical" format which is
  141. effectively using CR and LF as end of line: as required by the S/MIME
  142. specification. When this option is present no translation occurs. This
  143. is useful when handling binary data which may not be in MIME format.
  144. =item B<-nodetach>
  145. when signing a message use opaque signing: this form is more resistant
  146. to translation by mail relays but it cannot be read by mail agents that
  147. do not support S/MIME. Without this option cleartext signing with
  148. the MIME type multipart/signed is used.
  149. =item B<-certfile file>
  150. allows additional certificates to be specified. When signing these will
  151. be included with the message. When verifying these will be searched for
  152. the signers certificates. The certificates should be in PEM format.
  153. =item B<-signer file>
  154. a signing certificate when signing or resigning a message, this option can be
  155. used multiple times if more than one signer is required. If a message is being
  156. verified then the signers certificates will be written to this file if the
  157. verification was successful.
  158. =item B<-recip file>
  159. the recipients certificate when decrypting a message. This certificate
  160. must match one of the recipients of the message or an error occurs.
  161. =item B<-inkey file>
  162. the private key to use when signing or decrypting. This must match the
  163. corresponding certificate. If this option is not specified then the
  164. private key must be included in the certificate file specified with
  165. the B<-recip> or B<-signer> file. When signing this option can be used
  166. multiple times to specify successive keys.
  167. =item B<-passin arg>
  168. the private key password source. For more information about the format of B<arg>
  169. see the B<PASS PHRASE ARGUMENTS> section in L<openssl(1)|openssl(1)>.
  170. =item B<-rand file(s)>
  171. a file or files containing random data used to seed the random number
  172. generator, or an EGD socket (see L<RAND_egd(3)|RAND_egd(3)>).
  173. Multiple files can be specified separated by a OS-dependent character.
  174. The separator is B<;> for MS-Windows, B<,> for OpenVMS, and B<:> for
  175. all others.
  176. =item B<cert.pem...>
  177. one or more certificates of message recipients: used when encrypting
  178. a message.
  179. =item B<-to, -from, -subject>
  180. the relevant mail headers. These are included outside the signed
  181. portion of a message so they may be included manually. If signing
  182. then many S/MIME mail clients check the signers certificate's email
  183. address matches that specified in the From: address.
  184. =item B<-purpose, -ignore_critical, -issuer_checks, -crl_check, -crl_check_all, -policy_check, -extended_crl, -x509_strict, -policy -check_ss_sig -no_alt_chains>
  185. Set various options of certificate chain verification. See
  186. L<B<verify>|verify(1)> manual page for details.
  187. =back
  188. =head1 NOTES
  189. The MIME message must be sent without any blank lines between the
  190. headers and the output. Some mail programs will automatically add
  191. a blank line. Piping the mail directly to sendmail is one way to
  192. achieve the correct format.
  193. The supplied message to be signed or encrypted must include the
  194. necessary MIME headers or many S/MIME clients wont display it
  195. properly (if at all). You can use the B<-text> option to automatically
  196. add plain text headers.
  197. A "signed and encrypted" message is one where a signed message is
  198. then encrypted. This can be produced by encrypting an already signed
  199. message: see the examples section.
  200. This version of the program only allows one signer per message but it
  201. will verify multiple signers on received messages. Some S/MIME clients
  202. choke if a message contains multiple signers. It is possible to sign
  203. messages "in parallel" by signing an already signed message.
  204. The options B<-encrypt> and B<-decrypt> reflect common usage in S/MIME
  205. clients. Strictly speaking these process PKCS#7 enveloped data: PKCS#7
  206. encrypted data is used for other purposes.
  207. The B<-resign> option uses an existing message digest when adding a new
  208. signer. This means that attributes must be present in at least one existing
  209. signer using the same message digest or this operation will fail.
  210. The B<-stream> and B<-indef> options enable experimental streaming I/O support.
  211. As a result the encoding is BER using indefinite length constructed encoding
  212. and no longer DER. Streaming is supported for the B<-encrypt> operation and the
  213. B<-sign> operation if the content is not detached.
  214. Streaming is always used for the B<-sign> operation with detached data but
  215. since the content is no longer part of the PKCS#7 structure the encoding
  216. remains DER.
  217. =head1 EXIT CODES
  218. =over 4
  219. =item Z<>0
  220. the operation was completely successfully.
  221. =item Z<>1
  222. an error occurred parsing the command options.
  223. =item Z<>2
  224. one of the input files could not be read.
  225. =item Z<>3
  226. an error occurred creating the PKCS#7 file or when reading the MIME
  227. message.
  228. =item Z<>4
  229. an error occurred decrypting or verifying the message.
  230. =item Z<>5
  231. the message was verified correctly but an error occurred writing out
  232. the signers certificates.
  233. =back
  234. =head1 EXAMPLES
  235. Create a cleartext signed message:
  236. openssl smime -sign -in message.txt -text -out mail.msg \
  237. -signer mycert.pem
  238. Create an opaque signed message:
  239. openssl smime -sign -in message.txt -text -out mail.msg -nodetach \
  240. -signer mycert.pem
  241. Create a signed message, include some additional certificates and
  242. read the private key from another file:
  243. openssl smime -sign -in in.txt -text -out mail.msg \
  244. -signer mycert.pem -inkey mykey.pem -certfile mycerts.pem
  245. Create a signed message with two signers:
  246. openssl smime -sign -in message.txt -text -out mail.msg \
  247. -signer mycert.pem -signer othercert.pem
  248. Send a signed message under Unix directly to sendmail, including headers:
  249. openssl smime -sign -in in.txt -text -signer mycert.pem \
  250. -from steve@openssl.org -to someone@somewhere \
  251. -subject "Signed message" | sendmail someone@somewhere
  252. Verify a message and extract the signer's certificate if successful:
  253. openssl smime -verify -in mail.msg -signer user.pem -out signedtext.txt
  254. Send encrypted mail using triple DES:
  255. openssl smime -encrypt -in in.txt -from steve@openssl.org \
  256. -to someone@somewhere -subject "Encrypted message" \
  257. -des3 user.pem -out mail.msg
  258. Sign and encrypt mail:
  259. openssl smime -sign -in ml.txt -signer my.pem -text \
  260. | openssl smime -encrypt -out mail.msg \
  261. -from steve@openssl.org -to someone@somewhere \
  262. -subject "Signed and Encrypted message" -des3 user.pem
  263. Note: the encryption command does not include the B<-text> option because the
  264. message being encrypted already has MIME headers.
  265. Decrypt mail:
  266. openssl smime -decrypt -in mail.msg -recip mycert.pem -inkey key.pem
  267. The output from Netscape form signing is a PKCS#7 structure with the
  268. detached signature format. You can use this program to verify the
  269. signature by line wrapping the base64 encoded structure and surrounding
  270. it with:
  271. -----BEGIN PKCS7-----
  272. -----END PKCS7-----
  273. and using the command:
  274. openssl smime -verify -inform PEM -in signature.pem -content content.txt
  275. Alternatively you can base64 decode the signature and use:
  276. openssl smime -verify -inform DER -in signature.der -content content.txt
  277. Create an encrypted message using 128 bit Camellia:
  278. openssl smime -encrypt -in plain.txt -camellia128 -out mail.msg cert.pem
  279. Add a signer to an existing message:
  280. openssl smime -resign -in mail.msg -signer newsign.pem -out mail2.msg
  281. =head1 BUGS
  282. The MIME parser isn't very clever: it seems to handle most messages that I've
  283. thrown at it but it may choke on others.
  284. The code currently will only write out the signer's certificate to a file: if
  285. the signer has a separate encryption certificate this must be manually
  286. extracted. There should be some heuristic that determines the correct
  287. encryption certificate.
  288. Ideally a database should be maintained of a certificates for each email
  289. address.
  290. The code doesn't currently take note of the permitted symmetric encryption
  291. algorithms as supplied in the SMIMECapabilities signed attribute. This means the
  292. user has to manually include the correct encryption algorithm. It should store
  293. the list of permitted ciphers in a database and only use those.
  294. No revocation checking is done on the signer's certificate.
  295. The current code can only handle S/MIME v2 messages, the more complex S/MIME v3
  296. structures may cause parsing errors.
  297. =head1 HISTORY
  298. The use of multiple B<-signer> options and the B<-resign> command were first
  299. added in OpenSSL 1.0.0
  300. The -no_alt_chains options was first added to OpenSSL 1.0.2b.
  301. =cut