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SMIME(1)                            OpenSSL                           SMIME(1)



NAME
       smime - S/MIME utility

SYNOPSIS
       openssl smime [-encrypt] [-decrypt] [-sign] [-resign] [-verify] [-pk7out]
       [-[cipher]] [-in file] [-CAfile file] [-CApath dir] [-trusted_first] [-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.

       -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.

       -trusted_first
           Use certificates in CA file or CA directory over certificates provided in the
           message when building the trust chain to verify a certificate.  This is mainly
           useful in environments with Bridge CA or Cross-Certified CAs.

       -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 40 bit RC2 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
           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 AT 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 AT 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 AT 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



1.0.1e                            2017-03-22                          SMIME(1)

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