openssl-smime, smime - S/MIME utility
openssl smime [-help] [-encrypt] [-decrypt]
[-sign] [-resign] [-verify] [-pk7out]
[-binary] [-crlfeol] [-cipher]
[-in file] [-CAfile file] [-CApath dir]
[-no-CAfile] [-no-CApath] [-attime timestamp]
[-check_ss_sig] [-crl_check] [-crl_check_all]
[-explicit_policy] [-extended_crl] [-ignore_critical]
[-inhibit_any] [-inhibit_map] [-partial_chain]
[-policy arg] [-policy_check] [-policy_print]
[-purpose purpose] [-suiteB_128] [-suiteB_128_only]
[-suiteB_192] [-trusted_first] [-no_alt_chains]
[-use_deltas] [-auth_level num] [-verify_depth num]
[-verify_email email] [-verify_hostname hostname] [-verify_ip
ip] [-verify_name name] [-x509_strict] [-certfile
file] [-signer file] [-recip file] [-inform
SMIME|PEM|DER] [-passin arg] [-inkey file_or_id] [-out
file] [-outform SMIME|PEM|DER] [-content file] [-to
addr] [-from ad] [-subject s] [-text] [-indef]
[-noindef] [-stream] [-rand file...] [-writerand
file] [-md digest] [cert.pem]...
The smime command handles S/MIME mail. It can encrypt, decrypt, sign and
verify S/MIME messages.
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.
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.
- Print out a usage message.
- Encrypt mail for the given recipient certificates. Input file is the
message to be encrypted. The output file is the encrypted mail in MIME
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
- 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 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 signed mail. Expects a signed mail message on input and outputs the
signed data. Both clear text and opaque signing is supported.
- Takes an input message and writes out a PEM encoded PKCS#7 structure.
- Resign a message: take an existing message and one or more new
- -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.
- -stream -indef -noindef
- The -stream and -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 SMIME
it is currently off by default for all other operations.
- 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.
- -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.
- 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
- -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.
- Do not load the trusted CA certificates from the default file
- Do not load the trusted CA certificates from the default directory
- -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
- The encryption algorithm to use. For example DES (56 bits) - -des,
triple DES (168 bits) - -des3, EVP_get_cipherbyname()
function) can also be used preceded by a dash, for example
-aes-128-cbc. See enc for list of ciphers supported by your
version of OpenSSL.
If not specified triple DES is used. Only used with
- 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.
- Do not verify the signers certificate of a signed message.
- Do not do chain verification of signers certificates: that is don't use
the certificates in the signed message as untrusted CAs.
- Don't try to verify the signatures on the message.
- 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
- 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.
- 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
- Normally the output file uses a single LF as end of line. When this
option is present CRLF is used instead.
- 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
- 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.
- -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_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
-recip or -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.
- -passin arg
- The private key password source. For more information about the format of
arg see "Pass Phrase Options" in openssl(1).
- -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 ; for MS-Windows, , for OpenVMS,
and : for all others.
- [-writerand file]
- Writes random data to the specified file upon exit. This can be
used with a subsequent -rand flag.
- One or more certificates of message recipients: used when encrypting a
- -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.
-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
verify(1) manual page for details.
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 -text option to automatically add plain text
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.
The -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
The -stream and -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 -encrypt
operation and the -sign operation if the content is not detached.
Streaming is always used for the -sign operation with
detached data but since the content is no longer part of the PKCS#7
structure the encoding remains DER.
Create a cleartext signed message:
- The operation was completely successfully.
- An error occurred parsing the command options.
- One of the input files could not be read.
- An error occurred creating the PKCS#7 file or when reading the MIME
- An error occurred decrypting or verifying the message.
- The message was verified correctly but an error occurred writing out the
openssl smime -sign -in message.txt -text -out mail.msg \
Create an opaque signed message:
openssl smime -sign -in message.txt -text -out mail.msg -nodetach \
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
openssl smime -sign -in in.txt -text -signer mycert.pem \
-from firstname.lastname@example.org -to someone@somewhere \
-subject "Signed message" | sendmail someone@somewhere
Verify a message and extract the signer's certificate if
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 email@example.com \
-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 firstname.lastname@example.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.
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
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
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
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.
The use of multiple -signer options and the -resign command were
first added in OpenSSL 1.0.0
The -no_alt_chains option was added in OpenSSL 1.1.0.
Copyright 2000-2021 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