554 lines
20 KiB
Groff
554 lines
20 KiB
Groff
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.\" ========================================================================
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.\"
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.IX Title "SMIME 1"
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.TH SMIME 1 "2015-07-09" "1.0.1p" "OpenSSL"
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.\" For nroff, turn off justification. Always turn off hyphenation; it makes
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.\" way too many mistakes in technical documents.
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.if n .ad l
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.nh
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.SH "NAME"
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smime \- S/MIME utility
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.SH "SYNOPSIS"
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.IX Header "SYNOPSIS"
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\&\fBopenssl\fR \fBsmime\fR
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[\fB\-encrypt\fR]
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[\fB\-decrypt\fR]
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[\fB\-sign\fR]
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[\fB\-resign\fR]
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[\fB\-verify\fR]
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[\fB\-pk7out\fR]
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[\fB\-[cipher]\fR]
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[\fB\-in file\fR]
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[\fB\-no_alt_chains\fR]
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[\fB\-certfile file\fR]
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[\fB\-signer file\fR]
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[\fB\-recip file\fR]
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[\fB\-inform SMIME|PEM|DER\fR]
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[\fB\-passin arg\fR]
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[\fB\-inkey file\fR]
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[\fB\-out file\fR]
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[\fB\-outform SMIME|PEM|DER\fR]
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[\fB\-content file\fR]
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[\fB\-to addr\fR]
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[\fB\-from ad\fR]
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[\fB\-subject s\fR]
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[\fB\-text\fR]
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[\fB\-indef\fR]
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[\fB\-noindef\fR]
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[\fB\-stream\fR]
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[\fB\-rand file(s)\fR]
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[\fB\-md digest\fR]
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[cert.pem]...
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.SH "DESCRIPTION"
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.IX Header "DESCRIPTION"
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The \fBsmime\fR command handles S/MIME mail. It can encrypt, decrypt, sign and
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verify S/MIME messages.
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.SH "COMMAND OPTIONS"
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.IX Header "COMMAND OPTIONS"
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There are six operation options that set the type of operation to be performed.
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The meaning of the other options varies according to the operation type.
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.IP "\fB\-encrypt\fR" 4
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.IX Item "-encrypt"
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encrypt mail for the given recipient certificates. Input file is the message
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to be encrypted. The output file is the encrypted mail in \s-1MIME\s0 format.
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.IP "\fB\-decrypt\fR" 4
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.IX Item "-decrypt"
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decrypt mail using the supplied certificate and private key. Expects an
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encrypted mail message in \s-1MIME\s0 format for the input file. The decrypted mail
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is written to the output file.
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.IP "\fB\-sign\fR" 4
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.IX Item "-sign"
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sign mail using the supplied certificate and private key. Input file is
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the message to be signed. The signed message in \s-1MIME\s0 format is written
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to the output file.
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.IP "\fB\-verify\fR" 4
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.IX Item "-verify"
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verify signed mail. Expects a signed mail message on input and outputs
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the signed data. Both clear text and opaque signing is supported.
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.IP "\fB\-pk7out\fR" 4
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.IX Item "-pk7out"
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takes an input message and writes out a \s-1PEM\s0 encoded PKCS#7 structure.
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.IP "\fB\-resign\fR" 4
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.IX Item "-resign"
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resign a message: take an existing message and one or more new signers.
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.IP "\fB\-in filename\fR" 4
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.IX Item "-in filename"
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the input message to be encrypted or signed or the \s-1MIME\s0 message to
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be decrypted or verified.
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.IP "\fB\-inform SMIME|PEM|DER\fR" 4
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.IX Item "-inform SMIME|PEM|DER"
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this specifies the input format for the PKCS#7 structure. The default
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is \fB\s-1SMIME\s0\fR which reads an S/MIME format message. \fB\s-1PEM\s0\fR and \fB\s-1DER\s0\fR
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format change this to expect \s-1PEM\s0 and \s-1DER\s0 format PKCS#7 structures
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instead. This currently only affects the input format of the PKCS#7
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structure, if no PKCS#7 structure is being input (for example with
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\&\fB\-encrypt\fR or \fB\-sign\fR) this option has no effect.
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.IP "\fB\-out filename\fR" 4
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.IX Item "-out filename"
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the message text that has been decrypted or verified or the output \s-1MIME\s0
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format message that has been signed or verified.
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.IP "\fB\-outform SMIME|PEM|DER\fR" 4
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.IX Item "-outform SMIME|PEM|DER"
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this specifies the output format for the PKCS#7 structure. The default
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is \fB\s-1SMIME\s0\fR which write an S/MIME format message. \fB\s-1PEM\s0\fR and \fB\s-1DER\s0\fR
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format change this to write \s-1PEM\s0 and \s-1DER\s0 format PKCS#7 structures
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instead. This currently only affects the output format of the PKCS#7
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structure, if no PKCS#7 structure is being output (for example with
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\&\fB\-verify\fR or \fB\-decrypt\fR) this option has no effect.
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.IP "\fB\-stream \-indef \-noindef\fR" 4
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.IX Item "-stream -indef -noindef"
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the \fB\-stream\fR and \fB\-indef\fR options are equivalent and enable streaming I/O
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for encoding operations. This permits single pass processing of data without
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the need to hold the entire contents in memory, potentially supporting very
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large files. Streaming is automatically set for S/MIME signing with detached
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data if the output format is \fB\s-1SMIME\s0\fR it is currently off by default for all
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other operations.
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.IP "\fB\-noindef\fR" 4
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.IX Item "-noindef"
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disable streaming I/O where it would produce and indefinite length constructed
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encoding. This option currently has no effect. In future streaming will be
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enabled by default on all relevant operations and this option will disable it.
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.IP "\fB\-content filename\fR" 4
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.IX Item "-content filename"
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This specifies a file containing the detached content, this is only
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useful with the \fB\-verify\fR command. This is only usable if the PKCS#7
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structure is using the detached signature form where the content is
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not included. This option will override any content if the input format
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is S/MIME and it uses the multipart/signed \s-1MIME\s0 content type.
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.IP "\fB\-text\fR" 4
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.IX Item "-text"
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this option adds plain text (text/plain) \s-1MIME\s0 headers to the supplied
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message if encrypting or signing. If decrypting or verifying it strips
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off text headers: if the decrypted or verified message is not of \s-1MIME \s0
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type text/plain then an error occurs.
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.IP "\fB\-CAfile file\fR" 4
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.IX Item "-CAfile file"
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a file containing trusted \s-1CA\s0 certificates, only used with \fB\-verify\fR.
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.IP "\fB\-CApath dir\fR" 4
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.IX Item "-CApath dir"
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a directory containing trusted \s-1CA\s0 certificates, only used with
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\&\fB\-verify\fR. This directory must be a standard certificate directory: that
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is a hash of each subject name (using \fBx509 \-hash\fR) should be linked
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to each certificate.
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.IP "\fB\-md digest\fR" 4
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.IX Item "-md digest"
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digest algorithm to use when signing or resigning. If not present then the
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default digest algorithm for the signing key will be used (usually \s-1SHA1\s0).
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.IP "\fB\-[cipher]\fR" 4
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.IX Item "-[cipher]"
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the encryption algorithm to use. For example \s-1DES \s0(56 bits) \- \fB\-des\fR,
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triple \s-1DES \s0(168 bits) \- \fB\-des3\fR,
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\&\fIEVP_get_cipherbyname()\fR function) can also be used preceded by a dash, for
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example \fB\-aes_128_cbc\fR. See \fBenc\fR for list of ciphers
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supported by your version of OpenSSL.
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.Sp
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If not specified triple \s-1DES\s0 is used. Only used with \fB\-encrypt\fR.
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.IP "\fB\-nointern\fR" 4
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.IX Item "-nointern"
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when verifying a message normally certificates (if any) included in
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the message are searched for the signing certificate. With this option
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only the certificates specified in the \fB\-certfile\fR option are used.
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The supplied certificates can still be used as untrusted CAs however.
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.IP "\fB\-noverify\fR" 4
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.IX Item "-noverify"
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do not verify the signers certificate of a signed message.
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.IP "\fB\-nochain\fR" 4
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.IX Item "-nochain"
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do not do chain verification of signers certificates: that is don't
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use the certificates in the signed message as untrusted CAs.
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.IP "\fB\-nosigs\fR" 4
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.IX Item "-nosigs"
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don't try to verify the signatures on the message.
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.IP "\fB\-nocerts\fR" 4
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.IX Item "-nocerts"
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when signing a message the signer's certificate is normally included
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with this option it is excluded. This will reduce the size of the
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signed message but the verifier must have a copy of the signers certificate
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available locally (passed using the \fB\-certfile\fR option for example).
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.IP "\fB\-noattr\fR" 4
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.IX Item "-noattr"
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normally when a message is signed a set of attributes are included which
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include the signing time and supported symmetric algorithms. With this
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option they are not included.
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.IP "\fB\-binary\fR" 4
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.IX Item "-binary"
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normally the input message is converted to \*(L"canonical\*(R" format which is
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effectively using \s-1CR\s0 and \s-1LF\s0 as end of line: as required by the S/MIME
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specification. When this option is present no translation occurs. This
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is useful when handling binary data which may not be in \s-1MIME\s0 format.
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.IP "\fB\-nodetach\fR" 4
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.IX Item "-nodetach"
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when signing a message use opaque signing: this form is more resistant
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to translation by mail relays but it cannot be read by mail agents that
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do not support S/MIME. Without this option cleartext signing with
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the \s-1MIME\s0 type multipart/signed is used.
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.IP "\fB\-certfile file\fR" 4
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.IX Item "-certfile file"
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allows additional certificates to be specified. When signing these will
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be included with the message. When verifying these will be searched for
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the signers certificates. The certificates should be in \s-1PEM\s0 format.
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.IP "\fB\-signer file\fR" 4
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.IX Item "-signer file"
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a signing certificate when signing or resigning a message, this option can be
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used multiple times if more than one signer is required. If a message is being
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verified then the signers certificates will be written to this file if the
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verification was successful.
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.IP "\fB\-recip file\fR" 4
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.IX Item "-recip file"
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the recipients certificate when decrypting a message. This certificate
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must match one of the recipients of the message or an error occurs.
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.IP "\fB\-inkey file\fR" 4
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.IX Item "-inkey file"
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the private key to use when signing or decrypting. This must match the
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corresponding certificate. If this option is not specified then the
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private key must be included in the certificate file specified with
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the \fB\-recip\fR or \fB\-signer\fR file. When signing this option can be used
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multiple times to specify successive keys.
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.IP "\fB\-passin arg\fR" 4
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.IX Item "-passin arg"
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the private key password source. For more information about the format of \fBarg\fR
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see the \fB\s-1PASS PHRASE ARGUMENTS\s0\fR section in \fIopenssl\fR\|(1).
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.IP "\fB\-rand file(s)\fR" 4
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.IX Item "-rand file(s)"
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a file or files containing random data used to seed the random number
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generator, or an \s-1EGD\s0 socket (see \fIRAND_egd\fR\|(3)).
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Multiple files can be specified separated by a OS-dependent character.
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The separator is \fB;\fR for MS-Windows, \fB,\fR for OpenVMS, and \fB:\fR for
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all others.
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.IP "\fBcert.pem...\fR" 4
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.IX Item "cert.pem..."
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one or more certificates of message recipients: used when encrypting
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a message.
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.IP "\fB\-to, \-from, \-subject\fR" 4
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.IX Item "-to, -from, -subject"
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the relevant mail headers. These are included outside the signed
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portion of a message so they may be included manually. If signing
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then many S/MIME mail clients check the signers certificate's email
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address matches that specified in the From: address.
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.IP "\fB\-purpose, \-ignore_critical, \-issuer_checks, \-crl_check, \-crl_check_all, \-policy_check, \-extended_crl, \-x509_strict, \-policy \-check_ss_sig \-no_alt_chains\fR" 4
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.IX Item "-purpose, -ignore_critical, -issuer_checks, -crl_check, -crl_check_all, -policy_check, -extended_crl, -x509_strict, -policy -check_ss_sig -no_alt_chains"
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Set various options of certificate chain verification. See
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\&\fBverify\fR manual page for details.
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.SH "NOTES"
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.IX Header "NOTES"
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The \s-1MIME\s0 message must be sent without any blank lines between the
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headers and the output. Some mail programs will automatically add
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a blank line. Piping the mail directly to sendmail is one way to
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achieve the correct format.
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.PP
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The supplied message to be signed or encrypted must include the
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necessary \s-1MIME\s0 headers or many S/MIME clients wont display it
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properly (if at all). You can use the \fB\-text\fR option to automatically
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add plain text headers.
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.PP
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A \*(L"signed and encrypted\*(R" message is one where a signed message is
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then encrypted. This can be produced by encrypting an already signed
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message: see the examples section.
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.PP
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This version of the program only allows one signer per message but it
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will verify multiple signers on received messages. Some S/MIME clients
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choke if a message contains multiple signers. It is possible to sign
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messages \*(L"in parallel\*(R" by signing an already signed message.
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.PP
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The options \fB\-encrypt\fR and \fB\-decrypt\fR reflect common usage in S/MIME
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clients. Strictly speaking these process PKCS#7 enveloped data: PKCS#7
|
|
encrypted data is used for other purposes.
|
|
.PP
|
|
The \fB\-resign\fR 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.
|
|
.PP
|
|
The \fB\-stream\fR and \fB\-indef\fR options enable experimental streaming I/O support.
|
|
As a result the encoding is \s-1BER\s0 using indefinite length constructed encoding
|
|
and no longer \s-1DER.\s0 Streaming is supported for the \fB\-encrypt\fR operation and the
|
|
\&\fB\-sign\fR operation if the content is not detached.
|
|
.PP
|
|
Streaming is always used for the \fB\-sign\fR operation with detached data but
|
|
since the content is no longer part of the PKCS#7 structure the encoding
|
|
remains \s-1DER.\s0
|
|
.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 an 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
|
|
Create a signed message with two signers:
|
|
.PP
|
|
.Vb 2
|
|
\& openssl smime \-sign \-in message.txt \-text \-out mail.msg \e
|
|
\& \-signer mycert.pem \-signer othercert.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
|
|
.PP
|
|
Add a signer to an existing message:
|
|
.PP
|
|
.Vb 1
|
|
\& openssl smime \-resign \-in mail.msg \-signer newsign.pem \-out mail2.msg
|
|
.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.
|
|
.SH "HISTORY"
|
|
.IX Header "HISTORY"
|
|
The use of multiple \fB\-signer\fR options and the \fB\-resign\fR command were first
|
|
added in OpenSSL 1.0.0
|
|
.PP
|
|
The \-no_alt_chains options was first added to OpenSSL 1.0.1n and 1.0.2b.
|