Didier Stevens

Signtool.exe is the default Windows development tool to add a digital signature (Authenticode) to Windows executables (PE files). This howto shows you how to use signtool. You’ll need to create your own certificate and key (or buy one) to sign code.

To obtain signtool, download the platform SDK or the .NET SDK.

I use signtool in my makefile with command line options to automatically sign compiled code, but in this howto, I’ll show the interactive use.

First we will install the certificate with key we’ll use to sign code. Double-click the file and let the wizard do its work with the default option:

Because the wizard will also install the root CA certificate found in the PKCS12 file, it will ask you if you trust it.

It is not necessary to install this root CA certificate for code signing purposes, but if you don’t, signtool will not include the root CA certificate in the certificate chain. And you also need to install this root CA certificate if you want to automatically trust all certificates issued by this root CA (or its subordinate CAs).

Now start signtool from a command-line like this: signtool signwizard.

For the purposes of this howto, we’ll sign notepad.exe. When you sign an executable that is already signed, the existing signature is overwritten. Actually, notepad is not signed by Microsoft with an embedded signature, but using a security catalog.

We’ll use the default options presented by the wizard (except for the timestamp):

Select the certificate with key we installed: use Select from Store…

By default, the signature doesn’t include a timestamp signed by an external authority (a counter-signature). It’s easy to add one, for example using Verisign’s timestamp service: http://timestamp.verisign.com/scripts/timstamp.dll (of course, using this option requires Internet access).

Finally, click finish for the wizard to do its work:

From now on, notepad.exe’s properties displays a Digital Signatures tab:

This certificate is OK because we installed the root CA certificate in our certificate store. But if you check this signature on another machine or with another account (which doesn’t trust our root CA), we’ll get a warning that although the signature is valid, we don’t trust the root CA:

If you didn’t make a backup of notepad.exe and want to remove the signature, use my digital signature tool disitool.

Update: if you don’t have access to a machine with OpenSSL, I created a website to generate certs using the procedure described here. Read through the procedure, and then use the website listed at the end. And if you don’t want your private key generated on a server you don’t own, download my tool I created for Windows that doesn’t require installation: CreateCertGUI.

I also made a video showing the full procedure.

Ever wanted to make your own public key certificate for digital signatures? There are many recipes and tools on the net, like this one. My howto uses OpenSSL, and gives you a cert with a nice chain to your root CA.

First we generate a 4096-bit long RSA key for our root CA and store it in file ca.key:

openssl genrsa -out ca.key 4096

Generating RSA private key, 4096 bit long modulus
...................................................................................++
........................................................................++
e is 65537 (0x10001)

If you want to password-protect this key, add option -des3.

Next, we create our self-signed root CA certificate ca.crt; you’ll need to provide an identity for your root CA:

openssl req -new -x509 -days 1826 -key ca.key -out ca.crt

You are about to be asked to enter information that will be incorporated
into your certificate request.
What you are about to enter is what is called a Distinguished Name or a DN.
There are quite a few fields but you can leave some blank
For some fields there will be a default value,
If you enter '.', the field will be left blank.
-----
Country Name (2 letter code) [GB]:BE
State or Province Name (full name) [Berkshire]:Brussels
Locality Name (eg, city) [Newbury]:Brussels
Organization Name (eg, company) [My Company Ltd]:https://DidierStevens.com
Organizational Unit Name (eg, section) []:
Common Name (eg, your name or your server's hostname) []:Didier Stevens (https://DidierStevens.com)
Email Address []:didier stevens Google mail

The -x509 option is used for a self-signed certificate. 1826 days gives us a cert valid for 5 years.

Next step: create our subordinate CA that will be used for the actual signing. First, generate the key:

openssl genrsa -out ia.key 4096

Generating RSA private key, 4096 bit long modulus
.....++
.............................................................................++
e is 65537 (0x10001)

Then, request a certificate for this subordinate CA:

openssl req -new -key ia.key -out ia.csr

You are about to be asked to enter information that will be incorporated
into your certificate request.
What you are about to enter is what is called a Distinguished Name or a DN.
There are quite a few fields but you can leave some blank
For some fields there will be a default value,
If you enter '.', the field will be left blank.
-----
Country Name (2 letter code) [GB]:BE
State or Province Name (full name) [Berkshire]:Brussels
Locality Name (eg, city) [Newbury]:Brussels
Organization Name (eg, company) [My Company Ltd]:https://DidierStevens.com
Organizational Unit Name (eg, section) []:Didier Stevens Code Signing (https://DidierStevens.com)
Common Name (eg, your name or your server's hostname) []:
Email Address []:didier stevens Google mail

Please enter the following 'extra' attributes
to be sent with your certificate request
A challenge password []:
An optional company name []:

Next step: process the request for the subordinate CA certificate and get it signed by the root CA.

openssl x509 -req -days 730 -in ia.csr -CA ca.crt -CAkey ca.key -set_serial 01 -out ia.crt

Signature ok
subject=/C=BE/ST=Brussels/L=Brussels/O=https://DidierStevens.com/OU=Didier Stevens Code Signing (https://DidierStevens.com)/emailAddress=didier stevens Google mail
Getting CA Private Key

The cert will be valid for 2 years (730 days) and I decided to choose my own serial number 01 for this cert (-set_serial 01). For the root CA, I let OpenSSL generate a random serial number.

That’s all there is to it! Of course, there are many options I didn’t use. Consult the OpenSSL documentation for more info. For example, I didn’t restrict my subordinate CA key usage to digital signatures. It can be used for anything, even making another subordinate CA. When you buy a code signing certificate, the CA company will limit its use to code signing.

To use this subordinate CA key for Authenticode signatures with Microsoft’s signtool, you’ll have to package the keys and certs in a PKCS12 file:

openssl pkcs12 -export -out ia.p12 -inkey ia.key -in ia.crt -chain -CAfile ca.crt

Enter Export Password:
Verifying - Enter Export Password:

To sign executables in Windows with the signtool: install file ia.p12 in your certificate store (e.g. double click it), and then use signtool /wizard to sign your PE file.

I’ve used this process to generate certs for my own code signing, and for my Authenticode Challenge.

Update: don’t have OpenSSL? Use my website https://toolbokz.com/gencert.psp