f4401cd869
alter des.h to be friendly with openssl/des.h (you can include both in the same file) make libkrb to depend on libdes. bump major. massage various portioin of heimdal to be friendly with openssl 0.9.7b.
478 lines
17 KiB
Groff
478 lines
17 KiB
Groff
.\" $NetBSD: openssl_smime.1,v 1.10 2003/07/24 14:16:53 itojun Exp $
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.\"
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.\" Automatically generated by Pod::Man version 1.02
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.\" Thu Jul 24 13:07:46 2003
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.\" ======================================================================
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.\"
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.IX Title "SMIME 1"
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.TH SMIME 1 "0.9.7b" "2002-11-10" "OpenSSL"
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.UC
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.SH "NAME"
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smime \- S/MIME utility
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.SH "LIBRARY"
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libcrypto, -lcrypto
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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\-verify\fR]
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[\fB\-pk7out\fR]
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[\fB\-des\fR]
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[\fB\-des3\fR]
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[\fB\-rc2\-40\fR]
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[\fB\-rc2\-64\fR]
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[\fB\-rc2\-128\fR]
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[\fB\-in file\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\-rand \f(BIfile\fB\|(s)\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 five 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\-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\-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\-des \-des3 \-rc2\-40 \-rc2\-64 \-rc2\-128\fR" 4
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.IX Item "-des -des3 -rc2-40 -rc2-64 -rc2-128"
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the encryption algorithm to use. \s-1DES\s0 (56 bits), triple \s-1DES\s0 (168 bits)
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or 40, 64 or 128 bit \s-1RC2\s0 respectively if not specified 40 bit \s-1RC2\s0 is
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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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the signers certificate when signing a message. If a message is
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being verified then the signers certificates will be written to this
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file if the 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.
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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\s0 \s-1PHRASE\s0 \s-1ARGUMENTS\s0\fR section in openssl(1).
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.Ip "\fB\-rand \f(BIfile\fB\|(s)\fR" 4
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.IX Item "-rand file"
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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 RAND_egd(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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.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
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encrypted data is used for other purposes.
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.SH "EXIT CODES"
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.IX Header "EXIT CODES"
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.Ip "0" 4
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the operation was completely successfully.
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.Ip "1" 4
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.IX Item "1"
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an error occurred parsing the command options.
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.Ip "2" 4
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.IX Item "2"
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one of the input files could not be read.
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.Ip "3" 4
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.IX Item "3"
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an error occurred creating the PKCS#7 file or when reading the \s-1MIME\s0
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message.
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.Ip "4" 4
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.IX Item "4"
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an error occurred decrypting or verifying the message.
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.Ip "5" 4
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.IX Item "5"
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the message was verified correctly but an error occurred writing out
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the signers certificates.
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.SH "EXAMPLES"
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.IX Header "EXAMPLES"
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Create a cleartext signed message:
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.PP
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.Vb 2
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\& openssl smime -sign -in message.txt -text -out mail.msg \e
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\& -signer mycert.pem
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.Ve
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Create and opaque signed message
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.PP
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.Vb 2
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\& openssl smime -sign -in message.txt -text -out mail.msg -nodetach \e
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\& -signer mycert.pem
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.Ve
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Create a signed message, include some additional certificates and
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read the private key from another file:
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.PP
|
|
.Vb 2
|
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\& openssl smime -sign -in in.txt -text -out mail.msg \e
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\& -signer mycert.pem -inkey mykey.pem -certfile mycerts.pem
|
|
.Ve
|
|
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
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|
\& -subject "Signed message" | sendmail someone@somewhere
|
|
.Ve
|
|
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
|
|
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
|
|
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
|
|
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
|
|
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
|
|
and using the command,
|
|
.PP
|
|
.Vb 1
|
|
\& openssl smime -verify -inform PEM -in signature.pem -content content.txt
|
|
.Ve
|
|
alternatively you can base64 decode the signature and use
|
|
.PP
|
|
.Vb 1
|
|
\& openssl smime -verify -inform DER -in signature.der -content content.txt
|
|
.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.
|