=pod

=head1 NAME

openssl-smime,

smime - S/MIME utility

=head1 SYNOPSIS

B<openssl> B<smime>

[B<-help>]

[B<-encrypt>]

[B<-decrypt>]

[B<-sign>]

[B<-resign>]

[B<-verify>]

[B<-pk7out>]

[B<-binary>]

[B<-crlfeol>]

[B<-I<cipher>>]

[B<-in file>]

[B<-CAfile file>]

[B<-CApath dir>]

[B<-no-CAfile>]

[B<-no-CApath>]

[B<-attime timestamp>]

[B<-check_ss_sig>]

[B<-crl_check>]

[B<-crl_check_all>]

[B<-explicit_policy>]

[B<-extended_crl>]

[B<-ignore_critical>]

[B<-inhibit_any>]

[B<-inhibit_map>]

[B<-partial_chain>]

[B<-policy arg>]

[B<-policy_check>]

[B<-policy_print>]

[B<-purpose purpose>]

[B<-suiteB_128>]

[B<-suiteB_128_only>]

[B<-suiteB_192>]

[B<-trusted_first>]

[B<-no_alt_chains>]

[B<-use_deltas>]

[B<-auth_level num>]

[B<-verify_depth num>]

[B<-verify_email email>]

[B<-verify_hostname hostname>]

[B<-verify_ip ip>]

[B<-verify_name name>]

[B<-x509_strict>]

[B<-certfile file>]

[B<-signer file>]

[B<-recip  file>]

[B<-inform SMIME|PEM|DER>]

[B<-passin arg>]

[B<-inkey file_or_id>]

[B<-out file>]

[B<-outform SMIME|PEM|DER>]

[B<-content file>]

[B<-to addr>]

[B<-from ad>]

[B<-subject s>]

[B<-text>]

[B<-indef>]

[B<-noindef>]

[B<-stream>]

[B<-rand file...>]

[B<-writerand file>]

[B<-md digest>]

[cert.pem]...

=head1 DESCRIPTION

The B<smime> command handles S/MIME mail. It can encrypt, decrypt, sign and

verify S/MIME messages.

=head1 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.

=over 4

=item B<-help>

Print out a usage message.

=item B<-encrypt>

Encrypt mail for the given recipient certificates. Input file is the message

to be encrypted. The output file is the encrypted mail in MIME format.

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.

=item B<-decrypt>

Decrypt mail using the supplied certificate and private key. Expects an

encrypted mail message in MIME format for the input file. The decrypted mail

is written to the output file.

=item B<-sign>

Sign mail using the supplied certificate and private key. Input file is

the message to be signed. The signed message in MIME format is written

to the output file.

=item B<-verify>

Verify signed mail. Expects a signed mail message on input and outputs

the signed data. Both clear text and opaque signing is supported.

=item B<-pk7out>

Takes an input message and writes out a PEM encoded PKCS#7 structure.

=item B<-resign>

Resign a message: take an existing message and one or more new signers.

=item B<-in filename>

The input message to be encrypted or signed or the MIME message to

be decrypted or verified.

=item B<-inform SMIME|PEM|DER>

This specifies the input format for the PKCS#7 structure. The default

is B<SMIME> which reads an S/MIME format message. B<PEM> and B<DER>

format change this to expect PEM and DER format PKCS#7 structures

instead. This currently only affects the input format of the PKCS#7

structure, if no PKCS#7 structure is being input (for example with

B<-encrypt> or B<-sign>) this option has no effect.

=item B<-out filename>

The message text that has been decrypted or verified or the output MIME

format message that has been signed or verified.

=item B<-outform SMIME|PEM|DER>

This specifies the output format for the PKCS#7 structure. The default

is B<SMIME> which write an S/MIME format message. B<PEM> and B<DER>

format change this to write PEM and DER format PKCS#7 structures

instead. This currently only affects the output format of the PKCS#7

structure, if no PKCS#7 structure is being output (for example with

B<-verify> or B<-decrypt>) this option has no effect.

=item B<-stream -indef -noindef>

The B<-stream> and B<-indef> options are equivalent and enable streaming I/O

for encoding operations. This permits single pass processing of data without

the need to hold the entire contents in memory, potentially supporting very

large files. Streaming is automatically set for S/MIME signing with detached

data if the output format is B<SMIME> it is currently off by default for all

other operations.

=item B<-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.

=item B<-content filename>

This specifies a file containing the detached content, this is only

useful with the B<-verify> command. This is only usable if the PKCS#7

structure is using the detached signature form where the content is

not included. This option will override any content if the input format

is S/MIME and it uses the multipart/signed MIME content type.

=item B<-text>

This option adds plain text (text/plain) MIME headers to the supplied

message if encrypting or signing. If decrypting or verifying it strips

off text headers: if the decrypted or verified message is not of MIME

type text/plain then an error occurs.

=item B<-CAfile file>

A file containing trusted CA certificates, only used with B<-verify>.

=item B<-CApath dir>

A directory containing trusted CA certificates, only used with

B<-verify>. This directory must be a standard certificate directory: that

is a hash of each subject name (using B<x509 -hash>) should be linked

to each certificate.

=item B<-no-CAfile>

Do not load the trusted CA certificates from the default file location.

=item B<-no-CApath>

Do not load the trusted CA certificates from the default directory location.

=item B<-md digest>

Digest algorithm to use when signing or resigning. If not present then the

default digest algorithm for the signing key will be used (usually SHA1).

=item B<-I<cipher>>

The encryption algorithm to use. For example DES  (56 bits) - B<-des>,

triple DES (168 bits) - B<-des3>,

EVP_get_cipherbyname() function) can also be used preceded by a dash, for

example B<-aes-128-cbc>. See L<B<enc>|enc(1)> for list of ciphers

supported by your version of OpenSSL.

If not specified triple DES is used. Only used with B<-encrypt>.

=item B<-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 B<-certfile> option are used.

The supplied certificates can still be used as untrusted CAs however.

=item B<-noverify>

Do not verify the signers certificate of a signed message.

=item B<-nochain>

Do not do chain verification of signers certificates: that is don't

use the certificates in the signed message as untrusted CAs.

=item B<-nosigs>

Don't try to verify the signatures on the message.

=item B<-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 B<-certfile> option for example).

=item B<-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.

=item B<-binary>

Normally the input message is converted to "canonical" format which is

effectively using CR and LF as end of line: as required by the S/MIME

specification. When this option is present no translation occurs. This

is useful when handling binary data which may not be in MIME format.

=item B<-crlfeol>

Normally the output file uses a single B<LF> as end of line. When this

option is present B<CRLF> is used instead.

=item B<-nodetach>

When signing a message use opaque signing: this form is more resistant

to translation by mail relays but it cannot be read by mail agents that

do not support S/MIME.  Without this option cleartext signing with

the MIME type multipart/signed is used.

=item B<-certfile file>

Allows additional certificates to be specified. When signing these will

be included with the message. When verifying these will be searched for

the signers certificates. The certificates should be in PEM format.

=item B<-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.

=item B<-recip file>

The recipients certificate when decrypting a message. This certificate

must match one of the recipients of the message or an error occurs.

=item B<-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 B<-recip> or B<-signer> 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.

=item B<-passin arg>

The private key password source. For more information about the format of B<arg>

see the B<PASS PHRASE ARGUMENTS> section in L<openssl(1)>.

=item B<-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 B<;> for MS-Windows, B<,> for OpenVMS, and B<:> for

all others.

=item [B<-writerand file>]

Writes random data to the specified I<file> upon exit.

This can be used with a subsequent B<-rand> flag.

=item B<cert.pem...>

One or more certificates of message recipients: used when encrypting

a message.

=item B<-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.

=item B<-attime>, B<-check_ss_sig>, B<-crl_check>, B<-crl_check_all>,

B<-explicit_policy>, B<-extended_crl>, B<-ignore_critical>, B<-inhibit_any>,

B<-inhibit_map>, B<-no_alt_chains>, B<-partial_chain>, B<-policy>,

B<-policy_check>, B<-policy_print>, B<-purpose>, B<-suiteB_128>,

B<-suiteB_128_only>, B<-suiteB_192>, B<-trusted_first>, B<-use_deltas>,

B<-auth_level>, B<-verify_depth>, B<-verify_email>, B<-verify_hostname>,

B<-verify_ip>, B<-verify_name>, B<-x509_strict>

Set various options of certificate chain verification. See

L<verify(1)> manual page for details.

=back

=head1 NOTES

The MIME message must be sent without any blank lines between the

headers and the output. Some mail programs will automatically add

a blank line. Piping the mail directly to sendmail is one way to

achieve the correct format.

The supplied message to be signed or encrypted must include the

necessary MIME headers or many S/MIME clients won't display it

properly (if at all). You can use the B<-text> option to automatically

add plain text headers.

A "signed and encrypted" message is one where a signed message is

then encrypted. This can be produced by encrypting an already signed

message: see the examples section.

This version of the program only allows one signer per message but it

will verify multiple signers on received messages. Some S/MIME clients

choke if a message contains multiple signers. It is possible to sign

messages "in parallel" by signing an already signed message.

The options B<-encrypt> and B<-decrypt> reflect common usage in S/MIME

clients. Strictly speaking these process PKCS#7 enveloped data: PKCS#7

encrypted data is used for other purposes.

The B<-resign> option uses an existing message digest when adding a new

signer. This means that attributes must be present in at least one existing

signer using the same message digest or this operation will fail.

The B<-stream> and B<-indef> options enable streaming I/O support.

As a result the encoding is BER using indefinite length constructed encoding

and no longer DER. Streaming is supported for the B<-encrypt> operation and the

B<-sign> operation if the content is not detached.

Streaming is always used for the B<-sign> operation with detached data but

since the content is no longer part of the PKCS#7 structure the encoding

remains DER.

=head1 EXIT CODES

=over 4

=item Z<>0

The operation was completely successfully.

=item Z<>1

An error occurred parsing the command options.

=item Z<>2

One of the input files could not be read.

=item Z<>3

An error occurred creating the PKCS#7 file or when reading the MIME

message.

=item Z<>4

An error occurred decrypting or verifying the message.

=item Z<>5

The message was verified correctly but an error occurred writing out

the signers certificates.

=back

=head1 EXAMPLES

Create a cleartext signed message:

 openssl smime -sign -in message.txt -text -out mail.msg \

        -signer mycert.pem

Create an opaque signed message:

 openssl smime -sign -in message.txt -text -out mail.msg -nodetach \

        -signer mycert.pem

Create a signed message, include some additional certificates and

read the private key from another file:

 openssl smime -sign -in in.txt -text -out mail.msg \

        -signer mycert.pem -inkey mykey.pem -certfile mycerts.pem

Create a signed message with two signers:

 openssl smime -sign -in message.txt -text -out mail.msg \

        -signer mycert.pem -signer othercert.pem

Send a signed message under Unix directly to sendmail, including headers:

 openssl smime -sign -in in.txt -text -signer mycert.pem \

        -from steve@openssl.org -to someone@somewhere \

        -subject "Signed message" | sendmail someone@somewhere

Verify a message and extract the signer's certificate if successful:

 openssl smime -verify -in mail.msg -signer user.pem -out signedtext.txt

Send encrypted mail using triple DES:

 openssl smime -encrypt -in in.txt -from steve@openssl.org \

        -to someone@somewhere -subject "Encrypted message" \

        -des3 user.pem -out mail.msg

Sign and encrypt mail:

 openssl smime -sign -in ml.txt -signer my.pem -text \

        | openssl smime -encrypt -out mail.msg \

        -from steve@openssl.org -to someone@somewhere \

        -subject "Signed and Encrypted message" -des3 user.pem

Note: the encryption command does not include the B<-text> option because the

message being encrypted already has MIME headers.

Decrypt mail:

 openssl smime -decrypt -in mail.msg -recip mycert.pem -inkey key.pem

The output from Netscape form signing is a PKCS#7 structure with the

detached signature format. You can use this program to verify the

signature by line wrapping the base64 encoded structure and surrounding

it with:

 -----BEGIN PKCS7-----

 -----END PKCS7-----

and using the command:

 openssl smime -verify -inform PEM -in signature.pem -content content.txt

Alternatively you can base64 decode the signature and use:

 openssl smime -verify -inform DER -in signature.der -content content.txt

Create an encrypted message using 128 bit Camellia:

 openssl smime -encrypt -in plain.txt -camellia128 -out mail.msg cert.pem

Add a signer to an existing message:

 openssl smime -resign -in mail.msg -signer newsign.pem -out mail2.msg

=head1 BUGS

The MIME parser isn't very clever: it seems to handle most messages that I've

thrown at it but it may choke on others.

The code currently will only write out the signer's certificate to a file: if

the signer has a separate encryption certificate this must be manually

extracted. There should be some heuristic that determines the correct

encryption certificate.

Ideally a database should be maintained of a certificates for each email

address.

The code doesn't currently take note of the permitted symmetric encryption

algorithms as supplied in the SMIMECapabilities signed attribute. This means the

user has to manually include the correct encryption algorithm. It should store

the list of permitted ciphers in a database and only use those.

No revocation checking is done on the signer's certificate.

The current code can only handle S/MIME v2 messages, the more complex S/MIME v3

structures may cause parsing errors.

=head1 HISTORY

The use of multiple B<-signer> options and the B<-resign> command were first

added in OpenSSL 1.0.0

The -no_alt_chains option was added in OpenSSL 1.1.0.

=head1 COPYRIGHT

Copyright 2000-2017 The OpenSSL Project Authors. All Rights Reserved.

Licensed under the OpenSSL license (the "License").  You may not use

this file except in compliance with the License.  You can obtain a copy

in the file LICENSE in the source distribution or at

L<https://www.openssl.org/source/license.html>.

=cut