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- .\" ========================================================================
- .\"
- .IX Title "SMIME 1"
- .TH SMIME 1 "2022-03-15" "1.1.1n" "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"
- openssl\-smime, smime \- S/MIME utility
- .SH "SYNOPSIS"
- .IX Header "SYNOPSIS"
- \&\fBopenssl\fR \fBsmime\fR
- [\fB\-help\fR]
- [\fB\-encrypt\fR]
- [\fB\-decrypt\fR]
- [\fB\-sign\fR]
- [\fB\-resign\fR]
- [\fB\-verify\fR]
- [\fB\-pk7out\fR]
- [\fB\-binary\fR]
- [\fB\-crlfeol\fR]
- [\fB\-\f(BIcipher\fB\fR]
- [\fB\-in file\fR]
- [\fB\-CAfile file\fR]
- [\fB\-CApath dir\fR]
- [\fB\-no\-CAfile\fR]
- [\fB\-no\-CApath\fR]
- [\fB\-attime timestamp\fR]
- [\fB\-check_ss_sig\fR]
- [\fB\-crl_check\fR]
- [\fB\-crl_check_all\fR]
- [\fB\-explicit_policy\fR]
- [\fB\-extended_crl\fR]
- [\fB\-ignore_critical\fR]
- [\fB\-inhibit_any\fR]
- [\fB\-inhibit_map\fR]
- [\fB\-partial_chain\fR]
- [\fB\-policy arg\fR]
- [\fB\-policy_check\fR]
- [\fB\-policy_print\fR]
- [\fB\-purpose purpose\fR]
- [\fB\-suiteB_128\fR]
- [\fB\-suiteB_128_only\fR]
- [\fB\-suiteB_192\fR]
- [\fB\-trusted_first\fR]
- [\fB\-no_alt_chains\fR]
- [\fB\-use_deltas\fR]
- [\fB\-auth_level num\fR]
- [\fB\-verify_depth num\fR]
- [\fB\-verify_email email\fR]
- [\fB\-verify_hostname hostname\fR]
- [\fB\-verify_ip ip\fR]
- [\fB\-verify_name name\fR]
- [\fB\-x509_strict\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_or_id\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\-indef\fR]
- [\fB\-noindef\fR]
- [\fB\-stream\fR]
- [\fB\-rand file...\fR]
- [\fB\-writerand file\fR]
- [\fB\-md digest\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 "OPTIONS"
- .IX Header "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.
- .IP "\fB\-help\fR" 4
- .IX Item "-help"
- Print out a usage message.
- .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.
- .Sp
- 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.
- .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\-resign\fR" 4
- .IX Item "-resign"
- Resign a message: take an existing message and one or more new signers.
- .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\-stream \-indef \-noindef\fR" 4
- .IX Item "-stream -indef -noindef"
- The \fB\-stream\fR and \fB\-indef\fR 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 \fB\s-1SMIME\s0\fR it is currently off by default for all
- other operations.
- .IP "\fB\-noindef\fR" 4
- .IX Item "-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.
- .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\-no\-CAfile\fR" 4
- .IX Item "-no-CAfile"
- Do not load the trusted \s-1CA\s0 certificates from the default file location.
- .IP "\fB\-no\-CApath\fR" 4
- .IX Item "-no-CApath"
- Do not load the trusted \s-1CA\s0 certificates from the default directory location.
- .IP "\fB\-md digest\fR" 4
- .IX Item "-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 \s-1SHA1\s0).
- .IP "\fB\-\f(BIcipher\fB\fR" 4
- .IX Item "-cipher"
- The encryption algorithm to use. For example \s-1DES\s0 (56 bits) \- \fB\-des\fR,
- triple \s-1DES\s0 (168 bits) \- \fB\-des3\fR,
- \&\fBEVP_get_cipherbyname()\fR function) can also be used preceded by a dash, for
- example \fB\-aes\-128\-cbc\fR. See \fBenc\fR for list of ciphers
- supported by your version of OpenSSL.
- .Sp
- 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\-crlfeol\fR" 4
- .IX Item "-crlfeol"
- Normally the output file uses a single \fB\s-1LF\s0\fR as end of line. When this
- option is present \fB\s-1CRLF\s0\fR is used instead.
- .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"
- 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.
- .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_or_id\fR" 4
- .IX Item "-inkey file_or_id"
- 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. When signing this option can be used
- multiple times to specify successive keys.
- If no engine is used, the argument is taken as a file; if an engine is
- specified, the argument is given to the engine as a key identifier.
- .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 \*(L"Pass Phrase Options\*(R" in \fBopenssl\fR\|(1).
- .IP "\fB\-rand file...\fR" 4
- .IX Item "-rand file..."
- A file or files containing random data used to seed the random number
- generator.
- Multiple files can be specified separated by an OS-dependent character.
- The separator is \fB;\fR for MS-Windows, \fB,\fR for OpenVMS, and \fB:\fR for
- all others.
- .IP "[\fB\-writerand file\fR]" 4
- .IX Item "[-writerand file]"
- Writes random data to the specified \fIfile\fR upon exit.
- This can be used with a subsequent \fB\-rand\fR flag.
- .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.
- .IP "\fB\-attime\fR, \fB\-check_ss_sig\fR, \fB\-crl_check\fR, \fB\-crl_check_all\fR, \fB\-explicit_policy\fR, \fB\-extended_crl\fR, \fB\-ignore_critical\fR, \fB\-inhibit_any\fR, \fB\-inhibit_map\fR, \fB\-no_alt_chains\fR, \fB\-partial_chain\fR, \fB\-policy\fR, \fB\-policy_check\fR, \fB\-policy_print\fR, \fB\-purpose\fR, \fB\-suiteB_128\fR, \fB\-suiteB_128_only\fR, \fB\-suiteB_192\fR, \fB\-trusted_first\fR, \fB\-use_deltas\fR, \fB\-auth_level\fR, \fB\-verify_depth\fR, \fB\-verify_email\fR, \fB\-verify_hostname\fR, \fB\-verify_ip\fR, \fB\-verify_name\fR, \fB\-x509_strict\fR" 4
- .IX Item "-attime, -check_ss_sig, -crl_check, -crl_check_all, -explicit_policy, -extended_crl, -ignore_critical, -inhibit_any, -inhibit_map, -no_alt_chains, -partial_chain, -policy, -policy_check, -policy_print, -purpose, -suiteB_128, -suiteB_128_only, -suiteB_192, -trusted_first, -use_deltas, -auth_level, -verify_depth, -verify_email, -verify_hostname, -verify_ip, -verify_name, -x509_strict"
- Set various options of certificate chain verification. See
- \&\fBverify\fR\|(1) manual page for details.
- .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 won't 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.
- .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 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 option was added in OpenSSL 1.1.0.
- .SH "COPYRIGHT"
- .IX Header "COPYRIGHT"
- Copyright 2000\-2021 The OpenSSL Project Authors. All Rights Reserved.
- .PP
- Licensed under the OpenSSL license (the \*(L"License\*(R"). You may not use
- this file except in compliance with the License. You can obtain a copy
- in the file \s-1LICENSE\s0 in the source distribution or at
- <https://www.openssl.org/source/license.html>.
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