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 outputs the signed data. Both clear text and
opaque signing is supported.
- -pk7out
- takes an input message and writes out a
PEM encoded PKCS#7 structure.
- -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 example 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 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.
- -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
respectively. 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 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.
- -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 certificate 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 number generator, or an EGD socket (see (3)).
Multiple files can be specified separated by a OS-dependent
character. The separator is ; for MS-Windows, , for
OpenVMS, and : for all others.
- cert.pem...
- one or more certificates of message
recipients: used when encrypting 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 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 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 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 -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
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 -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
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.