NAME¶

SYNOPSIS¶

DESCRIPTION¶

OPTIONS¶

-help

Print out a usage message.

-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. The actual CMS type is <B>EnvelopedData<B>.

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.

-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.

-debug_decrypt

This option sets the CMS_DEBUG_DECRYPT flag. This option should be used with caution: see the notes section below.

-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.

-cmsout

Takes an input message and writes out a PEM encoded CMS structure.

-resign

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

-data_create

Create a CMS Data type.

-data_out

Data type and output the content.

-digest_create

Create a CMS DigestedData type.

-digest_verify

Verify a CMS DigestedData type and output the content.

-compress

Create a CMS CompressedData type. OpenSSL must be compiled with zlib support for this option to work, otherwise it will output an error.

-uncompress

Uncompress a CMS CompressedData type and output the content. OpenSSL must be compiled with zlib support for this option to work, otherwise it will output an error.

-EncryptedData_encrypt

Encrypt content using supplied symmetric key and algorithm using a CMS EncryptedData type and output the content.

-sign_receipt

Generate and output a signed receipt for the supplied message. The input message must contain a signed receipt request. Functionality is otherwise similar to the -sign operation.

-verify_receipt receipt

Verify a signed receipt in filename receipt. The input message must contain the original receipt request. Functionality is otherwise similar to the -verify operation.

-in filename

The input message to be encrypted or signed or the message to be decrypted or verified.

-inform SMIME|PEM|DER

This specifies the input format for the CMS structure. The default is SMIME which reads an S/MIME format message. PEM and DER format change this to expect PEM and DER format CMS structures instead. This currently only affects the input format of the CMS structure, if no CMS structure is being input (for example with -encrypt or -sign) this option has no effect.

-rctform SMIME|PEM|DER

Specify the format for a signed receipt for use with the -receipt_verify operation.

-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 CMS structure. The default is SMIME which writes an S/MIME format message. PEM and DER format change this to write PEM and DER format CMS structures instead. This currently only affects the output format of the CMS structure, if no CMS 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.

-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.

-content filename

This specifies a file containing the detached content, this is only useful with the -verify command. This is only usable if the CMS 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.

-noout

For the -cmsout operation do not output the parsed CMS structure. This is useful when combined with the -print option or if the syntax of the CMS structure is being checked.

-print

For the -cmsout operation print out all fields of the CMS structure. This is mainly useful for testing purposes.

-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.

-no-CAfile

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

-no-CApath

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

-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).

-cipher

The encryption algorithm to use. For example triple DES (168 bits) - -des3 or 256 bit AES - -aes256. Any standard algorithm name (as used by the EVP_get_cipherbyname() function) can also be used preceded by a dash, for example -aes-128-cbc. See enc(1) for a list of ciphers supported by your version of OpenSSL.

If not specified triple DES is used. Only used with -encrypt and -EncryptedData_create commands.

-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.

-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.

-nosmimecap

Exclude the list of supported algorithms from signed attributes, other options such as signing time and content type are still 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.

-crlfeol

Normally the output file uses a single LF as end of line. When this option is present CRLF is used instead.

-asciicrlf

When signing use ASCII CRLF format canonicalisation. This strips trailing whitespace from all lines, deletes trailing blank lines at EOF and sets the encapsulated content type. This option is normally used with detached content and an output signature format of DER. This option is not normally needed when verifying as it is enabled automatically if the encapsulated content format is detected.

-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.

-certsout file

Any certificates contained in the message are written to file.

-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

When decrypting a message this specifies the recipients certificate. The certificate must match one of the recipients of the message or an error occurs.

When encrypting a message this option may be used multiple times to specify each recipient. This form must be used if customised parameters are required (for example to specify RSA-OAEP).

Only certificates carrying RSA, Diffie-Hellman or EC keys are supported by this option.

-keyid

Use subject key identifier to identify certificates instead of issuer name and serial number. The supplied certificate must include a subject key identifier extension. Supported by -sign and -encrypt options.

-receipt_request_all, -receipt_request_first

For -sign option include a signed receipt request. Indicate requests should be provided by all recipient or first tier recipients (those mailed directly and not from a mailing list). Ignored it -receipt_request_from is included.

-receipt_request_from emailaddress

For -sign option include a signed receipt request. Add an explicit email address where receipts should be supplied.

-receipt_request_to emailaddress

Add an explicit email address where signed receipts should be sent to. This option must but supplied if a signed receipt it requested.

-receipt_request_print

For the -verify operation print out the contents of any signed receipt requests.

-secretkey key

Specify symmetric key to use. The key must be supplied in hex format and be consistent with the algorithm used. Supported by the -EncryptedData_encrypt -EncryptedData_decrypt, -encrypt and -decrypt options. When used with -encrypt or -decrypt the supplied key is used to wrap or unwrap the content encryption key using an AES key in the KEKRecipientInfo type.

-secretkeyid id

The key identifier for the supplied symmetric key for KEKRecipientInfo type. This option must be present if the -secretkey option is used with -encrypt. With -decrypt operations the id is used to locate the relevant key if it is not supplied then an attempt is used to decrypt any KEKRecipientInfo structures.

-econtent_type type

Set the encapsulated content type to type if not supplied the Data type is used. The type argument can be any valid OID name in either text or numerical format.

-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. When signing this option can be used multiple times to specify successive keys.

-keyopt name:opt

For signing and encryption this option can be used multiple times to set customised parameters for the preceding key or certificate. It can currently be used to set RSA-PSS for signing, RSA-OAEP for encryption or to modify default parameters for ECDH.

-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...

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.

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.

-attime, -check_ss_sig, -crl_check, -crl_check_all, -explicit_policy, -extended_crl, -ignore_critical, -inhibit_any, -inhibit_map, -no_alt_chains, -no_check_time, -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 certificate chain validation options. See the verify(1) manual page for details.

NOTES¶

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 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 CMS enveloped data: CMS 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 fail.

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 CMS structure the encoding remains DER.

If the -decrypt option is used without a recipient certificate then an attempt is made to locate the recipient by trying each potential recipient in turn using the supplied private key. To thwart the MMA attack (Bleichenbacher's attack on PKCS #1 v1.5 RSA padding) all recipients are tried whether they succeed or not and if no recipients match the message is "decrypted" using a random key which will typically output garbage. The -debug_decrypt option can be used to disable the MMA attack protection and return an error if no recipient can be found: this option should be used with caution. For a fuller description see CMS_decrypt(3)).

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 CMS 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.

COMPATIBILITY WITH PKCS#7 format.¶

The use of the -keyid option with -sign or -encrypt.

The -outform PEM option uses different headers.

The -compress option.

The -secretkey option when used with -encrypt.

The use of PSS with -sign.

The use of OAEP or non-RSA keys with -encrypt.

Additionally the -EncryptedData_create and -data_create type cannot be processed by the older smime command.

EXAMPLES¶

 openssl cms -sign -in message.txt -text -out mail.msg \
        -signer mycert.pem

Create an opaque signed message

 openssl cms -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 cms -sign -in in.txt -text -out mail.msg \
        -signer mycert.pem -inkey mykey.pem -certfile mycerts.pem

Create a signed message with two signers, use key identifier:

 openssl cms -sign -in message.txt -text -out mail.msg \
        -signer mycert.pem -signer othercert.pem -keyid

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

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

Send encrypted mail using triple DES:

 openssl cms -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 cms -sign -in ml.txt -signer my.pem -text \
        | openssl cms -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 cms -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 cms -verify -inform PEM -in signature.pem -content content.txt

alternatively you can base64 decode the signature and use

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

Create an encrypted message using 128 bit Camellia:

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

Add a signer to an existing message:

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

Sign mail using RSA-PSS:

 openssl cms -sign -in message.txt -text -out mail.msg \
        -signer mycert.pem -keyopt rsa_padding_mode:pss

Create encrypted mail using RSA-OAEP:

 openssl cms -encrypt -in plain.txt -out mail.msg \
        -recip cert.pem -keyopt rsa_padding_mode:oaep

Use SHA256 KDF with an ECDH certificate:

 openssl cms -encrypt -in plain.txt -out mail.msg \
        -recip ecdhcert.pem -keyopt ecdh_kdf_md:sha256

BUGS¶

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.

HISTORY¶

The keyopt option was added in OpenSSL 1.0.2.

Support for RSA-OAEP and RSA-PSS was added in OpenSSL 1.0.2.

The use of non-RSA keys with -encrypt and -decrypt was added in OpenSSL 1.0.2.

The -no_alt_chains option was added in OpenSSL 1.0.2b.

COPYRIGHT¶

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