CERTTOOL(1)

NAME
certtool - create key pairs, certificates and certificate signing requests for use with Keychains

SYNOPSIS
certtool command [command-args] [options]

certtool c [options]

certtool r outFileName [options]

certtool v infileName [options]

certtool i inFileName [options]

certtool d inFileName [options]

certtool I inFileName [options]

certtool D inFileName [options]

certtool y [options]

CERTTOOL COMMAND SUMMARY
c Create keypair and Certificate

r Create CSR

v Verify CSR

i Import Certificate

d Display Certificate

I Import CRL

D Display CRL

I Import a CRL

y Display all certs and CRLs in keychain

CERTTOOL OPTION SUMMARY

c   Create the keychain, if one is needed.

d   Create a CSR in DER format; default is PEM

k=keychainName
    Specify the Keychain to use for the operation. If keychainName starts with a '/', an absolute path is assumed; otherwise, the specified filename is relative to the user's Library/Keychains directory.

p=passphrase
    Specify the keychain passphrase when creating

r=privateKeyFileName
    Optional private key, for Import Certificate only

f=[18f]
    Private Key Format = PKCS1/PKCS8/FIPS186; default is PKCS1 (openssl)

x=[aSsm]
    Extended Key Usage: a=Any; s=SSL Client; S=SSL Server; m=SMIME

a   Generate private key with default ACL

h   Print usage message

v   Execute in verbose mode.

DESCRIPTION
Certtool is a UNIX command-line program which is used to create key pairs, certificates, and certificate signing requests; to import externally generated certificates and Certificate Revocation Lists (CRLs) into a Keychain, and to display the contents of certificates and CRLs. Currently, the primary use of CertTool is to perform the certificate-related administration required to configure an SSL server based on Mac OS X's SecureTransport library.

EXAMPLES

Generating a Self-Signed Certificate

This command generates a key pair and a self-signed (root) certificate and places them in a keychain. The root cert is signed by the private key generated during this command. The cert generated by this command is totally untrustworthy and cannot be used in the "real world"; the primary use of this command is to facilitate early development of SSL server applications based on SecureTransport. In particular, "real world" SSL clients (e.g., web browsers) will complain to varying degrees when they attempt to connect to an SSL server which presents a cert which is generated by this command. Some broswers, after a fair amount of handholding, will allow you to conditionally "trust" this cert.
    # CertTool c [options]
The available options are:
    k=keyChainName
Where "keyChainName" is the name of the keychain into which keys and the cert will be added. If no keychain is specified, keys and certs are added to the default keychain. The specified keychain must exist unless you specify the 'c' option.
    c
Specifies that the designated keychain is to be created.
    x=[aSsm]
Specifies an optional Extended Key Usage extension. Values are 'a' for ExtendedKeyUseAny; 's' for SSL client (ClientAuth); 'S' for SSL server (ServerAuth); and 'm' for S/MIME (EmailProtection).

This an interactive command; you will be prompted for a number of different items which are used to generate the keypair and the cert. A sample session follows.
    # CertTool k=certkc
    Enter key and certificate label: testCert
    Please specify parameters for the key pair you will generate.
    	r RSA
    	d DSA
    	f FEE
    Select key algorithm by letter: r
    Valid key sizes for RSA are 512..2048; default is 512
    Enter key size in bits or CR for default: 512
    You have selected algorithm RSA, key size 512 bits.
    OK (y/anything)? y
    Enter cert/key usage (s=signing, b=signing AND encrypting): b
     ...Generating key pair...
Note: you will be prompted for the Keychain's passphrase by the Keychain system at this point if the specified keychain is not open and you have not specified the passphrase via the 'p' option.
    Please specify the algorithm with which your certificate will be signed.
    	5 RSA with MD5
    	s RSA with SHA1
    Select signature algorithm by letter: s
    You have selected algorithm RSA with SHA1.
    OK (y/anything)? y
You will now specify the various components of the certificate's Relative Distinguished Name (RDN). An RDN has a number of components, all of which are optional, but at least one of which must be present.

Note that if you are creating a certificate for use in an SSL/TLS server, the Common Name component of the RDN must match exactly the host name of the server. This must not be an IP address, but the actual domain name, e.g. www.apple.com. Entering a CR for a given RDN component results in no value for that component.
    Common Name       (e.g. www.apple.com) : 10.0.61.5
    Country           (e.g. US) :
    Organization      (e.g. Apple Computer, Inc.) : Apple
    Organization Unit (e.g. Apple Data Security) :
    State/Province    (e.g. California) : California
    Email Address     (e.g. johngalt@rand.com) :
    You have specified:
     Common Name	: 10.0.61.5
     Organization	: Apple
     State/Province : California
    Is this OK (y/anything)? y
    #
The "Common Name" portion of the RDN - in the above case, "10.0.61.5" - MUST match the host name of the machine you'll running sslServer on. (In this case the test machine doesn't have an actual hostname; it's DHCP'd behind a firewall which is why "10.0.61.5" was specified for Common Name.) This is part of SSL's certificate verification; it prevents an attack using DNS spoofing.

A brief note about cert/key usage: the normal configuration of SecureTransport is that the server cert specified in SSLSetCertificate() is capable of both signing and encryption. If this cert is only capable of signing, then you must create a second keychain ontaining a cert which is capable of encryption, and pass that to SSLSetEncryptionCertificate().

Generating a Certificate Signing Request (CSR)

A CSR is the standard means by which an administrator of a web server provides information to a Certificate Authority (CA) in order to obtain a valid certificate which is signed by the CA. This type of cert is used in the real world; certs signed by CAs such as Verisign or Thawte are recognized by all web browsers when performing SSL transactions.

The general procedure for obtaining a "real" cert is: Generate a key pair Generate a CSR Provide the CSR and some other information and/or documentation to the CA CA sends you a certificate which is signed by the CA. You import that certificate, obtained from the CA, into your keychain.

The items in that keychain can now be used in SecureTransport's SSLSetCertificate() call.

This command performs the first two steps in the above procedure. See the section below entitled "Importing a Certificate" for information on importing the resulting certificate into your keychain. The format of this command is
    # CertTool r outFileName [options]
The resulting CSR will be written to "outFileName". The available options are:
    k=keyChainName
Where "KeyChainName" is the name of the keychain into which keys and the cert will be added. If no keychain is specified, keys and certs are added to the default keychain. The specified keychain must exist unless you specify the 'c' option.
     d
The 'd' option tells CertTool to create the CSR in DER-encoded format. The default is PEM-encoded, which is what most CAs expect. PEM encoded data consists of printable ASCII text which can, for example, be pasted into an email message. DER-encoded data is nonprintable binary data.
     c
Specifies that the designated keychain is to be created.

This an interactive command; you will be prompted for a number of different items which are used to generate the keypair and the CSR. The prompts given, and the format of the data you must supply, are identical to the data shown in the sample session in Section 2.

Verifying a CSR

A CSR contains, among other things, the public key which was generated in as described above. The CSR is signed with the associated private key. Thus the integrity of a CSR can be verified by extracting its public key and verifying the signature of the CSR. This command performs this integrity check. The format of this command is
    # CertTool v inFileName [options]
The only available option is the 'd' flag, which as described above in the section entitled "Generating a Certificate Signing Request", indiciates that the CSR is in DER format rather than the default PEM format. A typical (successful) run of this command is like so:
    # CertTool v myCsr.pem
     ...CSR verified successfully.
A large number of things can go wrong if the verification fails; suffice it to say that if you see anything other than the above success message, you have a bad or corrupted CSR.

Importing a Certificate from a Certificate Authority

Once you have negotiated with your CA, and provided them with the CSR generated as described above as well as any other information, documentation, and payment they require, the CA will provide you with a certificate. Use this command to add that certificate to the keychain containing the keypair you generated previously.

The format of this command is
    # CertTool i inFileName [options]
The cert to import is obtained from "inFileName". The available options are:
    k=keyChainName
Where "keyChainName" is the name of the keychain to which the cert will be added. If no keychain is specified, the cert is added to the default keychain. The specified keychain typically contains the keypair you generated previously. (Note you can import a certificate into a keychain which does not contain keys you generated but there will be no linkage between the imported certificate and a private key if you do this.) If the keychain is not open when this command is executed, you will be prompted by the Keychain system for its passphrase.
    r=privateKeyFileName
Where "privateKeyFileName" is the name of the optional private key file to imported along with the certificate. This option is used to import cert/key pairs which are generated by other means, such as OpenSSL.
    f=privateKeyFormat
Where "privateKeyFormat" is the format of the private key specified with the 'r' option. The formats are: '1' for PKCS1 (OpenSSL format), '8' (PKCS8), and 'f' (FIPS186, BSAFE format). The default is OpenSSL format for both RSA and DSA keys.
     d
Specifies DER format as described above. The default is PEM format.
     c
Specifies that the designated keychain is to be created.

Displaying a Certificate

This displays the contents of an existing certificate, obtained from a file. The format of this command is
    # CertTool d inFileName [options]
The cert to display is obtained from "inFileName". The only available option is the 'd' flag, specifying DER format as described above. The default is PEM format. Actually, in the absence of this option, certtool will correctly determine the format of the certificate (PEM or DER).

Importing a CRL

This command is used to add a Certificate Revocation List (CRL) to a keychain. The format of this command is
    # CertTool I inFileName [options]
The CRL to import is obtained from "inFileName". The available options are:
    k=keyChainName
Where "KeyChainName" is the name of the keychain to which the CRL will be added. If no keychain is specified, the cert is added to the default keychain. If the keychain is not open when this command is executed, you will be prompted by the Keychain system for its passphrase.
     d
Specifies DER format as described above. The default is PEM format.
     c
Specifies that the designated keychain is to be created.

Displaying a CRL

This displays the contents of an existing Certificate Revocation List (CRL), obtained from a file. The format of this command is
    # CertTool D inFileName [options]
The cert to display is obtained from "inFileName". The only available option is the 'd' flag, specifying DER format as described above. The default is PEM format.

Displaying Certificates and CRLs in a keychain

This displays the contents of all certificates and CRLs in a keychain. The format of this command is
    # CertTool y [options]
The available options are:
    k=keyChainName
Where "KeyChainName" is the name of the keychain to display.
    v
Specifies verbose mode.

Certificate Authorities and CSRs

As mentioned above, the general procedure for obtaining a "real" cert is: Generate a key pair Generate a CSR Provide the CSR and some other information and/or documentation to the CA CA sends you a certificate which is signed by the CA. You import that certificate, obtained from the CA, into your keychain.

The items in that keychain can now be used in SecureTranspoert's SSLSetCertificate() call.

One CA with an excellent web-based interface for obtaining a cert is Verisign (http://www.verisign.com/products/site/index.html). You can get a free 14-day trial certificate using nothing but CertTool, Verisign's web site, and email. You need to provide some personal information; then you paste in the CSR generated as described in the section entitled "Generating a Certificate Signing Request" into a form on the web site. A few minutes later Verisign emails you a certificate, which you import into your keychain. The whole process takes less than 10 minutes. The free certificate obtained in this manner is signed by a temporary root cert which is not recognized by any browsers, but Verisign also provides a means of installing this temporary root cert into your browser, directly from their web site. Typically one would use the free, temporary cert to perform initial configuration of a server and to ring out the general SSL infrastructure. Once you feel comfortable with the operation of the server, then it's time to buy a "real" certificate which will allow your web server to be recognized by any browser.

Thawte has a similar, very friendly service at http://www.thawte.com/. Note that, for early web server development and/or testing, you can skip the entire procedure described above and just generate your own self-signed root cert as described above. No CA is involved; no CSR is generated; no cert needs to be imported - CertTool generates a cert for you and immediately adds it to your keychain. Bear in mind that this option requires tolerance of the various SSL clients you'll be testing with, none of whom recognize your root cert.

FILES
/System/Library/Keychains/X509Anchors System root certificate database

SEE ALSO
openssl(1)