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SMIME(1) OpenSSL SMIME(1)
NAME
smime - S/MIME utility
SYNOPSIS
openssl smime [-encrypt] [-decrypt] [-sign] [-verify] [-pk7out] [-des]
[-des3] [-rc2-40] [-rc2-64] [-rc2-128] [-aes128] [-aes192] [-aes256]
[-in file] [-certfile file] [-signer file] [-recip file] [-inform
SMIME|PEM|DER] [-passin arg] [-inkey file] [-out file] [-outform
SMIME|PEM|DER] [-content file] [-to addr] [-from ad] [-subject s]
[-text] [-rand file(s)] [cert.pem]...
DESCRIPTION
The smime command handles S/MIME mail. It can encrypt, decrypt, sign
and verify S/MIME messages.
COMMAND OPTIONS
There are five operation options that set the type of operation to be
performed. The meaning of the other options varies according to the
operation type.
-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.
-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.
-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.
-verify
verify signed mail. Expects a signed mail message on input and out-
puts the signed data. Both clear text and opaque signing is sup-
ported.
-pk7out
takes an input message and writes out a PEM encoded PKCS#7 struc-
ture.
-in filename
the input message to be encrypted or signed or the MIME message to
be decrypted or verified.
-inform SMIME|PEM|DER
this specifies the input format for the PKCS#7 structure. The
default is SMIME which reads an S/MIME format message. PEM and 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
-encrypt or -sign) this option has no effect.
-out filename
the message text that has been decrypted or verified or the output
MIME format message that has been signed or verified.
-outform SMIME|PEM|DER
this specifies the output format for the PKCS#7 structure. The
default is SMIME which write an S/MIME format message. PEM and 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 exam-
ple with -verify or -decrypt) this option has no effect.
-content filename
This specifies a file containing the detached content, this is only
useful with the -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.
-text
this option adds plain text (text/plain) MIME headers to the sup-
plied 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.
-CAfile file
a file containing trusted CA certificates, only used with -verify.
-CApath dir
a directory containing trusted CA certificates, only used with
-verify. This directory must be a standard certificate directory:
that is a hash of each subject name (using x509 -hash) should be
linked to each certificate.
-des -des3 -rc2-40 -rc2-64 -rc2-128 -aes128 -aes192 -aes256
the encryption algorithm to use. DES (56 bits), triple DES (168
bits), 40, 64 or 128 bit RC2 or 128, 192 or 256 bit AES respec-
tively. If not specified 40 bit RC2 is used. Only used with
-encrypt.
-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 -certfile option are
used. The supplied certificates can still be used as untrusted CAs
however.
-noverify
do not verify the signers certificate of a signed message.
-nochain
do not do chain verification of signers certificates: that is don't
use the certificates in the signed message as untrusted CAs.
-nosigs
don't try to verify the signatures on the message.
-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 -certfile
option for example).
-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.
-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.
-nodetach
when signing a message use opaque signing: this form is more resis-
tant 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.
-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.
-signer file
the signers certificate when signing a message. If a message is
being verified then the signers certificates will be written to
this file if the verification was successful.
-recip file
the recipients certificate when decrypting a message. This certifi-
cate must match one of the recipients of the message or an error
occurs.
-inkey file
the private key to use when signing or decrypting. This must match
the corresponding certificate. If this option is not specified then
the private key must be included in the certificate file specified
with the -recip or -signer file.
-passin arg
the private key password source. For more information about the
format of arg see the PASS PHRASE ARGUMENTS section in openssl(1).
-rand file(s)
a file or files containing random data used to seed the random num-
ber generator, or an EGD socket (see RAND_egd(3)). Multiple files
can be specified separated by a OS-dependent character. The sepa-
rator is ; for MS-Windows, , for OpenVMS, and : for all others.
cert.pem...
one or more certificates of message recipients: used when encrypt-
ing a message.
-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.
NOTES
The MIME message must be sent without any blank lines between the head-
ers 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 neces-
sary MIME headers or many S/MIME clients wont display it properly (if
at all). You can use the -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 mes-
sage: 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 -encrypt and -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.
EXIT CODES
0 the operation was completely successfully.
1 an error occurred parsing the command options.
2 one of the input files could not be read.
3 an error occurred creating the PKCS#7 file or when reading the MIME
message.
4 an error occurred decrypting or verifying the message.
5 the message was verified correctly but an error occurred writing
out the signers certificates.
EXAMPLES
Create a cleartext signed message:
openssl smime -sign -in message.txt -text -out mail.msg \
-signer mycert.pem
Create and 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
Send a signed message under Unix directly to sendmail, including head-
ers:
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 -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 sig-
nature 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
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 encryp-
tion 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.
0.9.7d 2005-02-25 SMIME(1)
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