Didier Stevens

Starting with Microsoft Office 2003, digital signatures can be added to office documents (e.g. a spreadsheet). Macros can also be digitally signed. So if you’ve that special spreadsheet macro to execute, but your Excel configuration requires macros to be signed, this howto is what you’re looking for .

First step is to import our PKCS12 file.

First we’ll take a look ad signing the document (an Excel spreadsheet).

Adding a digital sigature is done with Tools / Options…

These actions added our digital signature:

Of course, when we change the spreadsheet, we have to sign it again:

The title bar warns us when we opened a signed spreadsheet:

The “unverified” word in the title is a reminder that we have to check the signature (via Tools / Options…) to make sure the spreadsheet wasn’t tampered with:

Now let’s sign a macro:

A default Office 2003 install requires macros to be signed:

After signing a Windows executable with our own certificate, let’s sign an XPI file.

There is a nice Firefox add-on we’ll use to achieve this: Key Manager. But the subordinate CA certificate we create is not suited to sign XPI files, because it doesn’t state explicitly that it can be used for code signing. We have to create another one with an extendedKeyUsage property for code signing.

First we need to create a config file with the extended key usage, eku.cnf:

[eku_codesigning]
extendedKeyUsage=codeSigning

Then we issue the next OpenSSL commands to create a new certificate and PKCS12 file:

openssl x509 -req -days 730 -in ia.csr -CA ca.crt -CAkey ca.key -set_serial 02 -out ia2.crt -extfile eku.cnf -extensions eku_codesigning

openssl pkcs12 -export -out ia2.p12 -inkey ia.key -in ia2.crt -chain -CAfile ca.crt

Now we use the Key Manager add-on to import the PKCS12 file (this can also be done with the Firefox options manager):

After importing the certificates and keys, we need to enable the root CA certificate for code signing:

Now this is done, we’re ready to sign an XPI file. As an example, I’m taking my WhoAmI Firefox add-on:

When installing this signed Firefox add-on, we get to see the identity of the signer:

For an unsigned add-on, it says “Author not verified”:

If we don’t trust the root CA for code signing (or the root CA certificate is missing), we can’t install the add-on!

So it doesn’t make sense to sign a Firefox add-on with your own self-signed certificate if you plan to make it public (e.g. publish it on the Mozilla add-on site). Users will not be able to install your add-on if they don’t have imported and approved your root CA certificate.

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.

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.