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smime(1)

SMIME(1)                            OpenSSL                           SMIME(1)

NAME
       smime - S/MIME utility

SYNOPSIS
       openssl smime [-encrypt] [-decrypt] [-sign] [-resign] [-verify]
       [-pk7out] [-[cipher]] [-in file] [-no_alt_chains] [-certfile file]
       [-signer file] [-recip  file] [-inform SMIME|PEM|DER] [-passin arg]
       [-inkey file] [-out file] [-outform SMIME|PEM|DER] [-content file] [-to
       addr] [-from ad] [-subject s] [-text] [-indef] [-noindef] [-stream]
       [-rand file(s)] [-md digest] [cert.pem]...

DESCRIPTION
       The smime command handles S/MIME mail. It can encrypt, decrypt, sign
       and verify S/MIME messages.

COMMAND OPTIONS
       There are six operation options that set the type of operation to be
       performed.  The meaning of the other options varies according to the
       operation type.

       -encrypt
           encrypt  mail  for  the given recipient certificates. Input file is
           the message to be encrypted. The output file is the encrypted  mail
           in MIME format.

           Note that no revocation check is done for the recipient cert, so if
           that  key  has  been compromised, others may be able to decrypt the
           text.

       -decrypt
           decrypt mail  using  the  supplied  certificate  and  private  key.
           Expects  an  encrypted  mail  message  in MIME format for the input
           file. The decrypted mail is written to the output file.

       -sign
           sign mail using the supplied certificate  and  private  key.  Input
           file is the message to be signed. The signed message in MIME format
           is written to the output file.

       -verify
           verify  signed  mail.  Expects  a  signed mail message on input and
           outputs the signed data. Both clear  text  and  opaque  signing  is
           supported.

       -pk7out
           takes  an  input  message  and  writes  out  a  PEM  encoded PKCS#7
           structure.

       -resign
           resign a message: take an existing message  and  one  or  more  new
           signers.

       -in filename
           the  input message to be encrypted or signed or the MIME message to
           be decrypted or verified.

       -inform SMIME|PEM|DER
           this specifies the input  format  for  the  PKCS#7  structure.  The
           default  is SMIME which reads an S/MIME format message. PEM and DER
           format change this to expect PEM and DER format  PKCS#7  structures
           instead. This currently only affects the input format of the PKCS#7
           structure,  if no PKCS#7 structure is being input (for example with
           -encrypt or -sign) this option has no effect.

       -out filename
           the message text that has been decrypted or verified or the  output
           MIME format message that has been signed or verified.

       -outform SMIME|PEM|DER
           this  specifies  the  output  format  for the PKCS#7 structure. The
           default is SMIME which write an S/MIME format message. PEM and  DER
           format  change  this  to write PEM and DER format PKCS#7 structures
           instead. This currently only  affects  the  output  format  of  the
           PKCS#7  structure,  if  no  PKCS#7  structure  is being output (for
           example with -verify or -decrypt) this option has no effect.

       -stream -indef -noindef
           the -stream and -indef options are equivalent and enable  streaming
           I/O for encoding operations. This permits single pass processing of
           data  without  the  need  to  hold  the  entire contents in memory,
           potentially supporting very large files. Streaming is automatically
           set for S/MIME signing with detached data if the output  format  is
           SMIME it is currently off by default for all other operations.

       -noindef
           disable  streaming I/O where it would produce and indefinite length
           constructed encoding. This  option  currently  has  no  effect.  In
           future  streaming  will  be  enabled  by  default  on  all relevant
           operations and this option will disable it.

       -content filename
           This specifies a file containing the detached content, this is only
           useful with the -verify command. This is only usable if the  PKCS#7
           structure is using the detached signature form where the content is
           not  included.  This  option will override any content if the input
           format is S/MIME and it  uses  the  multipart/signed  MIME  content
           type.

       -text
           this  option  adds  plain  text  (text/plain)  MIME  headers to the
           supplied  message  if  encrypting  or  signing.  If  decrypting  or
           verifying  it strips off text headers: if the decrypted or verified
           message is not of MIME type text/plain then an error occurs.

       -CAfile file
           a file containing trusted CA certificates, only used with -verify.

       -CApath dir
           a directory containing trusted  CA  certificates,  only  used  with
           -verify.  This  directory must be a standard certificate directory:
           that is a hash of each subject name (using x509  -hash)  should  be
           linked to each certificate.

       -md digest
           digest  algorithm  to use when signing or resigning. If not present
           then the default digest algorithm for the signing key will be  used
           (usually SHA1).

       -[cipher]
           the encryption algorithm to use. For example DES  (56 bits) - -des,
           triple DES (168 bits) - -des3, EVP_get_cipherbyname() function) can
           also  be used preceded by a dash, for example -aes_128_cbc. See enc
           for list of ciphers supported by your version of OpenSSL.

           If not specified triple DES is used. Only used with -encrypt.

       -nointern
           when verifying a message normally certificates (if any) included in
           the message are searched for the  signing  certificate.  With  this
           option  only the certificates specified in the -certfile option are
           used.  The supplied certificates can still be used as untrusted CAs
           however.

       -noverify
           do not verify the signers certificate of a signed message.

       -nochain
           do not do chain verification of signers certificates: that is don't
           use the certificates in the signed message as untrusted CAs.

       -nosigs
           don't try to verify the signatures on the message.

       -nocerts
           when  signing  a  message  the  signer's  certificate  is  normally
           included with this option it is excluded. This will reduce the size
           of  the  signed  message  but  the verifier must have a copy of the
           signers certificate available locally (passed using  the  -certfile
           option for example).

       -noattr
           normally  when a message is signed a set of attributes are included
           which include the signing time and supported symmetric  algorithms.
           With this option they are not included.

       -binary
           normally the input message is converted to "canonical" format which
           is  effectively  using CR and LF as end of line: as required by the
           S/MIME specification. When this option is  present  no  translation
           occurs.  This  is useful when handling binary data which may not be
           in MIME format.

       -nodetach
           when signing a message  use  opaque  signing:  this  form  is  more
           resistant  to  translation  by mail relays but it cannot be read by
           mail agents that  do  not  support  S/MIME.   Without  this  option
           cleartext signing with the MIME type multipart/signed is used.

       -certfile file
           allows  additional certificates to be specified. When signing these
           will be included with the message. When  verifying  these  will  be
           searched  for  the signers certificates. The certificates should be
           in PEM format.

       -signer file
           a signing certificate when signing or  resigning  a  message,  this
           option  can  be  used  multiple  times  if  more than one signer is
           required.  If  a  message  is  being  verified  then  the   signers
           certificates  will  be written to this file if the verification was
           successful.

       -recip file
           the  recipients  certificate  when  decrypting  a   message.   This
           certificate  must  match one of the recipients of the message or an
           error occurs.

       -inkey file
           the private key to use when signing or decrypting. This must  match
           the corresponding certificate. If this option is not specified then
           the  private key must be included in the certificate file specified
           with the -recip or -signer file. When signing this  option  can  be
           used multiple times to specify successive keys.

       -passin arg
           the  private  key  password  source. For more information about the
           format of arg see the PASS PHRASE ARGUMENTS section in openssl(1).

       -rand file(s)
           a file or files containing random data  used  to  seed  the  random
           number  generator,  or  an  EGD socket (see RAND_egd(3)).  Multiple
           files can be specified separated by a OS-dependent character.   The
           separator is ; for MS-Windows, , for OpenVMS, and : for all others.

       cert.pem...
           one   or   more  certificates  of  message  recipients:  used  when
           encrypting a message.

       -to, -from, -subject
           the relevant mail headers. These are included  outside  the  signed
           portion  of  a message so they may be included manually. If signing
           then many S/MIME mail clients check the signers certificate's email
           address matches that specified in the From: address.

       -purpose, -ignore_critical, -issuer_checks, -crl_check, -crl_check_all,
       -policy_check, -extended_crl, -x509_strict, -policy -check_ss_sig
       -no_alt_chains
           Set various options of certificate chain verification.  See  verify
           manual page for details.

NOTES
       The  MIME  message  must  be  sent  without any blank lines between the
       headers and the output. Some mail programs  will  automatically  add  a
       blank  line. Piping the mail directly to sendmail is one way to achieve
       the correct format.

       The supplied message  to  be  signed  or  encrypted  must  include  the
       necessary  MIME headers or many S/MIME clients wont display it properly
       (if at all). You can use the -text option to  automatically  add  plain
       text headers.

       A  "signed and encrypted" message is one where a signed message is then
       encrypted. This  can  be  produced  by  encrypting  an  already  signed
       message: see the examples section.

       This  version  of the program only allows one signer per message but it
       will verify multiple signers on received messages. Some S/MIME  clients
       choke  if  a  message contains multiple signers. It is possible to sign
       messages "in parallel" by signing an already signed message.

       The options -encrypt  and  -decrypt  reflect  common  usage  in  S/MIME
       clients.  Strictly speaking these process PKCS#7 enveloped data: PKCS#7
       encrypted data is used for other purposes.

       The -resign option uses an existing message digest when  adding  a  new
       signer.  This  means  that  attributes  must be present in at least one
       existing signer using the same message digest or  this  operation  will
       fail.

       The  -stream  and  -indef  options  enable  experimental  streaming I/O
       support.  As a result the  encoding  is  BER  using  indefinite  length
       constructed  encoding and no longer DER. Streaming is supported for the
       -encrypt operation and the  -sign  operation  if  the  content  is  not
       detached.

       Streaming is always used for the -sign operation with detached data but
       since  the  content  is  no  longer  part  of  the PKCS#7 structure the
       encoding remains DER.

EXIT CODES
       0   the operation was completely successfully.

       1   an error occurred parsing the command options.

       2   one of the input files could not be read.

       3   an error occurred creating the PKCS#7 file or when reading the MIME
           message.

       4   an error occurred decrypting or verifying the message.

       5   the message was verified correctly but an  error  occurred  writing
           out the signers certificates.

EXAMPLES
       Create a cleartext signed message:

        openssl smime -sign -in message.txt -text -out mail.msg \
               -signer mycert.pem

       Create an opaque signed message:

        openssl smime -sign -in message.txt -text -out mail.msg -nodetach \
               -signer mycert.pem

       Create  a signed message, include some additional certificates and read
       the private key from another file:

        openssl smime -sign -in in.txt -text -out mail.msg \
               -signer mycert.pem -inkey mykey.pem -certfile mycerts.pem

       Create a signed message with two signers:

        openssl smime -sign -in message.txt -text -out mail.msg \
               -signer mycert.pem -signer othercert.pem

       Send a signed  message  under  Unix  directly  to  sendmail,  including
       headers:

        openssl smime -sign -in in.txt -text -signer mycert.pem \
               -from steve@openssl.org -to someone@somewhere \
               -subject "Signed message" | sendmail someone@somewhere

       Verify a message and extract the signer's certificate if successful:

        openssl smime -verify -in mail.msg -signer user.pem -out signedtext.txt

       Send encrypted mail using triple DES:

        openssl smime -encrypt -in in.txt -from steve@openssl.org \
               -to someone@somewhere -subject "Encrypted message" \
               -des3 user.pem -out mail.msg

       Sign and encrypt mail:

        openssl smime -sign -in ml.txt -signer my.pem -text \
               | openssl smime -encrypt -out mail.msg \
               -from steve@openssl.org -to someone@somewhere \
               -subject "Signed and Encrypted message" -des3 user.pem

       Note:  the encryption command does not include the -text option because
       the message being encrypted already has MIME headers.

       Decrypt mail:

        openssl smime -decrypt -in mail.msg -recip mycert.pem -inkey key.pem

       The output from Netscape form signing is a PKCS#7  structure  with  the
       detached  signature  format.  You  can  use  this program to verify the
       signature by line wrapping the base64 encoded structure and surrounding
       it with:

        -----BEGIN PKCS7-----
        -----END PKCS7-----

       and using the command:

        openssl smime -verify -inform PEM -in signature.pem -content content.txt

       Alternatively you can base64 decode the signature and use:

        openssl smime -verify -inform DER -in signature.der -content content.txt

       Create an encrypted message using 128 bit Camellia:

        openssl smime -encrypt -in plain.txt -camellia128 -out mail.msg cert.pem

       Add a signer to an existing message:

        openssl smime -resign -in mail.msg -signer newsign.pem -out mail2.msg

BUGS
       The MIME parser isn't very clever: it seems  to  handle  most  messages
       that I've thrown at it but it may choke on others.

       The  code  currently  will only write out the signer's certificate to a
       file: if the signer has a separate encryption certificate this must  be
       manually  extracted. There should be some heuristic that determines the
       correct encryption certificate.

       Ideally a database should be maintained  of  a  certificates  for  each
       email address.

       The  code  doesn't  currently  take  note  of  the  permitted symmetric
       encryption algorithms  as  supplied  in  the  SMIMECapabilities  signed
       attribute.  This  means  the  user  has to manually include the correct
       encryption algorithm. It should store the list of permitted ciphers  in
       a database and only use those.

       No revocation checking is done on the signer's certificate.

       The  current  code can only handle S/MIME v2 messages, the more complex
       S/MIME v3 structures may cause parsing errors.

HISTORY
       The use of multiple -signer options and the -resign command were  first
       added in OpenSSL 1.0.0

       The -no_alt_chains options was first added to OpenSSL 1.0.2b.

1.0.2l                            2017-05-25                          SMIME(1)
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