Authenticode in 2016

Last month, I noticed that my eToken USB code-signing key only supports SHA1 and not SHA256. I began hunting for a replacement that can sign using the stronger hash. Fortunately, I didn’t have to look far—the Yubico YubiKey 4 is $40 and supports SHA256, RSA 4096, and ECC p384. Beyond supporting stronger algorithms, it seems to integrate better with Windows – I don’t need to install third-party software to use it after loading my certificate with the YubiKey PIV Manager.

To take advantage of SHA256, I needed to update my scripts to use signtool.exe instead of the older signcode.exe, which only supports SHA1.

My script is simply:

signtool sign /d "Brotli [De]compressor" /du "" /n "Eric Lawrence" /t /fd SHA1 brotli.exe
signtool sign /as /d "Brotli [De]compressor" /du "" /n "Eric Lawrence" /tr /td SHA256 /fd SHA256 brotli.exe

Notably, we sign the file twice:

Windows File Properties show two signatures

First, sign using a SHA1 digest (older Windows versions don’t support SHA256). Then add an additional signature (the /as argument) using the stronger SHA256 file digest (the /fd argument).

For the stronger signature, use /tr to specify the timestamp URL (SHA256 signatures should use RFC3161 timestamps) and request that the timestamping server use a SHA256 digest (the /td argument).

Both signtool invocations will prompt for your PIN to access the private key stored on the token:

Windows PIN prompt

I was somewhat annoyed that the YubiKey only supports an 8 character PIN/password; I later learned that I can use the same 10 character password my old token uses—the final two characters are silently ignored.

After you’ve signed the file, you should use Windows Explorer to verify that each of the signatures and timestamps is valid:

Signature OK

Timestamp Signature OK

Interestingly, most public CAs will use SHA256 for the timestamp’s digest but not for the signature itself; you can see this if you look closely at the timestamp signature (“RSA”):

Just RSA

This is likely due to a limitation in OpenSSL, and isn’t seen in Microsoft’s signatures (“sha256RSA”):


A Few Caveats

Authenticode in 2016

4 thoughts on “Authenticode in 2016

  1. Alex says:

    Bare with me here Eric. So you are using a Yubikey to sign your SSL certificates instead of say openssl(1) ? If yes, what is the advantage of that ? If no – I don’t get it.



Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s