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+.rm #[ #] #H #V #F C
+.\" ========================================================================
+.\"
+.IX Title "SMIME 1"
+.TH SMIME 1 "2014-06-05" "0.9.8za" "OpenSSL"
+.\" For nroff, turn off justification.  Always turn off hyphenation; it makes
+.\" way too many mistakes in technical documents.
+.if n .ad l
+.nh
+.SH "NAME"
+smime \- S/MIME utility
+.SH "SYNOPSIS"
+.IX Header "SYNOPSIS"
+\&\fBopenssl\fR \fBsmime\fR
+[\fB\-encrypt\fR]
+[\fB\-decrypt\fR]
+[\fB\-sign\fR]
+[\fB\-verify\fR]
+[\fB\-pk7out\fR]
+[\fB\-des\fR]
+[\fB\-des3\fR]
+[\fB\-rc2\-40\fR]
+[\fB\-rc2\-64\fR]
+[\fB\-rc2\-128\fR]
+[\fB\-aes128\fR]
+[\fB\-aes192\fR]
+[\fB\-aes256\fR]
+[\fB\-camellia128\fR]
+[\fB\-camellia192\fR]
+[\fB\-camellia256\fR]
+[\fB\-in file\fR]
+[\fB\-certfile file\fR]
+[\fB\-signer file\fR]
+[\fB\-recip  file\fR]
+[\fB\-inform SMIME|PEM|DER\fR]
+[\fB\-passin arg\fR]
+[\fB\-inkey file\fR]
+[\fB\-out file\fR]
+[\fB\-outform SMIME|PEM|DER\fR]
+[\fB\-content file\fR]
+[\fB\-to addr\fR]
+[\fB\-from ad\fR]
+[\fB\-subject s\fR]
+[\fB\-text\fR]
+[\fB\-rand file(s)\fR]
+[cert.pem]...
+.SH "DESCRIPTION"
+.IX Header "DESCRIPTION"
+The \fBsmime\fR command handles S/MIME mail. It can encrypt, decrypt, sign and
+verify S/MIME messages.
+.SH "COMMAND OPTIONS"
+.IX Header "COMMAND OPTIONS"
+There are five operation options that set the type of operation to be performed.
+The meaning of the other options varies according to the operation type.
+.IP "\fB\-encrypt\fR" 4
+.IX Item "-encrypt"
+encrypt mail for the given recipient certificates. Input file is the message
+to be encrypted. The output file is the encrypted mail in \s-1MIME\s0 format.
+.IP "\fB\-decrypt\fR" 4
+.IX Item "-decrypt"
+decrypt mail using the supplied certificate and private key. Expects an
+encrypted mail message in \s-1MIME\s0 format for the input file. The decrypted mail
+is written to the output file.
+.IP "\fB\-sign\fR" 4
+.IX Item "-sign"
+sign mail using the supplied certificate and private key. Input file is
+the message to be signed. The signed message in \s-1MIME\s0 format is written
+to the output file.
+.IP "\fB\-verify\fR" 4
+.IX Item "-verify"
+verify signed mail. Expects a signed mail message on input and outputs
+the signed data. Both clear text and opaque signing is supported.
+.IP "\fB\-pk7out\fR" 4
+.IX Item "-pk7out"
+takes an input message and writes out a \s-1PEM\s0 encoded PKCS#7 structure.
+.IP "\fB\-in filename\fR" 4
+.IX Item "-in filename"
+the input message to be encrypted or signed or the \s-1MIME\s0 message to
+be decrypted or verified.
+.IP "\fB\-inform SMIME|PEM|DER\fR" 4
+.IX Item "-inform SMIME|PEM|DER"
+this specifies the input format for the PKCS#7 structure. The default
+is \fB\s-1SMIME\s0\fR which reads an S/MIME format message. \fB\s-1PEM\s0\fR and \fB\s-1DER\s0\fR
+format change this to expect \s-1PEM\s0 and \s-1DER\s0 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
+\&\fB\-encrypt\fR or \fB\-sign\fR) this option has no effect.
+.IP "\fB\-out filename\fR" 4
+.IX Item "-out filename"
+the message text that has been decrypted or verified or the output \s-1MIME\s0
+format message that has been signed or verified.
+.IP "\fB\-outform SMIME|PEM|DER\fR" 4
+.IX Item "-outform SMIME|PEM|DER"
+this specifies the output format for the PKCS#7 structure. The default
+is \fB\s-1SMIME\s0\fR which write an S/MIME format message. \fB\s-1PEM\s0\fR and \fB\s-1DER\s0\fR
+format change this to write \s-1PEM\s0 and \s-1DER\s0 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
+\&\fB\-verify\fR or \fB\-decrypt\fR) this option has no effect.
+.IP "\fB\-content filename\fR" 4
+.IX Item "-content filename"
+This specifies a file containing the detached content, this is only
+useful with the \fB\-verify\fR 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 \s-1MIME\s0 content type.
+.IP "\fB\-text\fR" 4
+.IX Item "-text"
+this option adds plain text (text/plain) \s-1MIME\s0 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 \s-1MIME \s0
+type text/plain then an error occurs.
+.IP "\fB\-CAfile file\fR" 4
+.IX Item "-CAfile file"
+a file containing trusted \s-1CA\s0 certificates, only used with \fB\-verify\fR.
+.IP "\fB\-CApath dir\fR" 4
+.IX Item "-CApath dir"
+a directory containing trusted \s-1CA\s0 certificates, only used with
+\&\fB\-verify\fR. This directory must be a standard certificate directory: that
+is a hash of each subject name (using \fBx509 \-hash\fR) should be linked
+to each certificate.
+.IP "\fB\-des \-des3 \-rc2\-40 \-rc2\-64 \-rc2\-128 \-aes128 \-aes192 \-aes256 \-camellia128 \-camellia192 \-camellia256\fR" 4
+.IX Item "-des -des3 -rc2-40 -rc2-64 -rc2-128 -aes128 -aes192 -aes256 -camellia128 -camellia192 -camellia256"
+the encryption algorithm to use. \s-1DES \s0(56 bits), triple \s-1DES \s0(168 bits),
+40, 64 or 128 bit \s-1RC2, 128, 192\s0 or 256 bit \s-1AES,\s0 or 128, 192 or 256 bit Camellia respectively.
+If not specified triple \s-1DES\s0 is used. Only used with \fB\-encrypt\fR.
+.IP "\fB\-nointern\fR" 4
+.IX Item "-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 \fB\-certfile\fR option are used.
+The supplied certificates can still be used as untrusted CAs however.
+.IP "\fB\-noverify\fR" 4
+.IX Item "-noverify"
+do not verify the signers certificate of a signed message.
+.IP "\fB\-nochain\fR" 4
+.IX Item "-nochain"
+do not do chain verification of signers certificates: that is don't
+use the certificates in the signed message as untrusted CAs.
+.IP "\fB\-nosigs\fR" 4
+.IX Item "-nosigs"
+don't try to verify the signatures on the message.
+.IP "\fB\-nocerts\fR" 4
+.IX Item "-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 \fB\-certfile\fR option for example).
+.IP "\fB\-noattr\fR" 4
+.IX Item "-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.
+.IP "\fB\-binary\fR" 4
+.IX Item "-binary"
+normally the input message is converted to \*(L"canonical\*(R" format which is
+effectively using \s-1CR\s0 and \s-1LF\s0 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 \s-1MIME\s0 format.
+.IP "\fB\-nodetach\fR" 4
+.IX Item "-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 \s-1MIME\s0 type multipart/signed is used.
+.IP "\fB\-certfile file\fR" 4
+.IX Item "-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 \s-1PEM\s0 format.
+.IP "\fB\-signer file\fR" 4
+.IX Item "-signer file"
+the signers certificate when signing a message. If a message is
+being verified then the signers certificates will be written to this
+file if the verification was successful.
+.IP "\fB\-recip file\fR" 4
+.IX Item "-recip file"
+the recipients certificate when decrypting a message. This certificate
+must match one of the recipients of the message or an error occurs.
+.IP "\fB\-inkey file\fR" 4
+.IX Item "-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 \fB\-recip\fR or \fB\-signer\fR file.
+.IP "\fB\-passin arg\fR" 4
+.IX Item "-passin arg"
+the private key password source. For more information about the format of \fBarg\fR
+see the \fB\s-1PASS PHRASE ARGUMENTS\s0\fR section in \fIopenssl\fR\|(1).
+.IP "\fB\-rand file(s)\fR" 4
+.IX Item "-rand file(s)"
+a file or files containing random data used to seed the random number
+generator, or an \s-1EGD\s0 socket (see \fIRAND_egd\fR\|(3)).
+Multiple files can be specified separated by a OS-dependent character.
+The separator is \fB;\fR for MS-Windows, \fB,\fR for OpenVMS, and \fB:\fR for
+all others.
+.IP "\fBcert.pem...\fR" 4
+.IX Item "cert.pem..."
+one or more certificates of message recipients: used when encrypting
+a message.
+.IP "\fB\-to, \-from, \-subject\fR" 4
+.IX Item "-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.
+.SH "NOTES"
+.IX Header "NOTES"
+The \s-1MIME\s0 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.
+.PP
+The supplied message to be signed or encrypted must include the
+necessary \s-1MIME\s0 headers or many S/MIME clients wont display it
+properly (if at all). You can use the \fB\-text\fR option to automatically
+add plain text headers.
+.PP
+A \*(L"signed and encrypted\*(R" message is one where a signed message is
+then encrypted. This can be produced by encrypting an already signed
+message: see the examples section.
+.PP
+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 \*(L"in parallel\*(R" by signing an already signed message.
+.PP
+The options \fB\-encrypt\fR and \fB\-decrypt\fR reflect common usage in S/MIME
+clients. Strictly speaking these process PKCS#7 enveloped data: PKCS#7
+encrypted data is used for other purposes.
+.SH "EXIT CODES"
+.IX Header "EXIT CODES"
+.IP "0" 4
+the operation was completely successfully.
+.IP "1" 4
+.IX Item "1"
+an error occurred parsing the command options.
+.IP "2" 4
+.IX Item "2"
+one of the input files could not be read.
+.IP "3" 4
+.IX Item "3"
+an error occurred creating the PKCS#7 file or when reading the \s-1MIME\s0
+message.
+.IP "4" 4
+.IX Item "4"
+an error occurred decrypting or verifying the message.
+.IP "5" 4
+.IX Item "5"
+the message was verified correctly but an error occurred writing out
+the signers certificates.
+.SH "EXAMPLES"
+.IX Header "EXAMPLES"
+Create a cleartext signed message:
+.PP
+.Vb 2
+\& openssl smime \-sign \-in message.txt \-text \-out mail.msg \e
+\&        \-signer mycert.pem
+.Ve
+.PP
+Create and opaque signed message:
+.PP
+.Vb 2
+\& openssl smime \-sign \-in message.txt \-text \-out mail.msg \-nodetach \e
+\&        \-signer mycert.pem
+.Ve
+.PP
+Create a signed message, include some additional certificates and
+read the private key from another file:
+.PP
+.Vb 2
+\& openssl smime \-sign \-in in.txt \-text \-out mail.msg \e
+\&        \-signer mycert.pem \-inkey mykey.pem \-certfile mycerts.pem
+.Ve
+.PP
+Send a signed message under Unix directly to sendmail, including headers:
+.PP
+.Vb 3
+\& openssl smime \-sign \-in in.txt \-text \-signer mycert.pem \e
+\&        \-from steve@openssl.org \-to someone@somewhere \e
+\&        \-subject "Signed message" | sendmail someone@somewhere
+.Ve
+.PP
+Verify a message and extract the signer's certificate if successful:
+.PP
+.Vb 1
+\& openssl smime \-verify \-in mail.msg \-signer user.pem \-out signedtext.txt
+.Ve
+.PP
+Send encrypted mail using triple \s-1DES:\s0
+.PP
+.Vb 3
+\& openssl smime \-encrypt \-in in.txt \-from steve@openssl.org \e
+\&        \-to someone@somewhere \-subject "Encrypted message" \e
+\&        \-des3 user.pem \-out mail.msg
+.Ve
+.PP
+Sign and encrypt mail:
+.PP
+.Vb 4
+\& openssl smime \-sign \-in ml.txt \-signer my.pem \-text \e
+\&        | openssl smime \-encrypt \-out mail.msg \e
+\&        \-from steve@openssl.org \-to someone@somewhere \e
+\&        \-subject "Signed and Encrypted message" \-des3 user.pem
+.Ve
+.PP
+Note: the encryption command does not include the \fB\-text\fR option because the message
+being encrypted already has \s-1MIME\s0 headers.
+.PP
+Decrypt mail:
+.PP
+.Vb 1
+\& openssl smime \-decrypt \-in mail.msg \-recip mycert.pem \-inkey key.pem
+.Ve
+.PP
+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:
+.PP
+.Vb 2
+\& \-\-\-\-\-BEGIN PKCS7\-\-\-\-\-
+\& \-\-\-\-\-END PKCS7\-\-\-\-\-
+.Ve
+.PP
+and using the command:
+.PP
+.Vb 1
+\& openssl smime \-verify \-inform PEM \-in signature.pem \-content content.txt
+.Ve
+.PP
+Alternatively you can base64 decode the signature and use:
+.PP
+.Vb 1
+\& openssl smime \-verify \-inform DER \-in signature.der \-content content.txt
+.Ve
+.PP
+Create an encrypted message using 128 bit Camellia:
+.PP
+.Vb 1
+\& openssl smime \-encrypt \-in plain.txt \-camellia128 \-out mail.msg cert.pem
+.Ve
+.SH "BUGS"
+.IX Header "BUGS"
+The \s-1MIME\s0 parser isn't very clever: it seems to handle most messages that I've thrown
+at it but it may choke on others.
+.PP
+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.
+.PP
+Ideally a database should be maintained of a certificates for each email address.
+.PP
+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.
+.PP
+No revocation checking is done on the signer's certificate.
+.PP
+The current code can only handle S/MIME v2 messages, the more complex S/MIME v3
+structures may cause parsing errors.