Sign Authenticode files with osslsigncode using OpenSSL PKCS11 engine

osslsigncode is a command-line tool used to code sign, timestamp, and verify signatures executable files. osslsigncode leverages the OpenSSL library for performing code signing operations. osslsigncode can be compiled on most platforms where OpenSSL and cURL exist.

Follow these instructions to sign directly using osslsigncode and securely reference your private key stored in DigiCert® KeyLocker. Alternatively, integrate osslsigncode with Signing Manager Controller (SMCTL) for simplified signing.

Astuce

DigiCert® KeyLocker only supports osslsigncode signing on Linux.
To sign on Windows or macOS, use Jsign.
To avoid errors when signing large files, use osslsigncode instead of Jsign.
If you encounter unclear errors, it may be useful to sign via SMCTL and if errors persist, refer to SMCTL logs.

Prerequisites

A note for Ubuntu users

If you run Ubuntu version 24.04 or above, you may receive the following error when attempting a signature:

bad engine id
Failed to set 'dynamic' engine
Failed to read key or certificates
4019CC0F7E7F0000:error:1300006D:engine routines:dynamic_load:init failed:../crypto/engine/eng_dyn.c:514:
Failed

This error is caused by an incompatibility with the PKCS11 engine packaged with the OS and osslsigncode.

To troubleshoot:

Download and compile the latest version of LibP11 from GitHub.
Review the Unix Build instructions for compiling from GitHub.
- Running the final make install command replaces the previously installed version of the libengine-pkcs11-openssl package.

Sign with osslsigncode

The downloaded certificate is referred to as cert.pem in the scenarios below.

Note

Use a full chain certificate instead of a keypair certificate. This action ensures the intermediate certificate is bundled with the signature, preventing chain validation failures during verification.

To download the full chain certificate, use the smctl command with the full chain flag enabled.

To sign and timestamp:

osslsigncode sign -pkcs11engine /usr/lib/x86_64-linux-gnu/engines-1.1/libpkcs11.so -pkcs11module /root/smpkcs11.so -certs <path to keypair certificate> -key 'pkcs11:object=<keypair alias>;type=private' -in <file to be signed> -out <output signed file> -h sha256 -t http://timestamp.digicert.com

Command sample:

osslsigncode sign -pkcs11engine /usr/lib/x86_64-linux-gnu/engines-1.1/libpkcs11.so -pkcs11module /root/smpkcs11.so -certs cert.pem -key 'pkcs11:object=keypair;type=private' -in test.msi -out test-signed.msi -h sha256 -t http://timestamp.digicert.com

Command output:

root@dcd6f73b44b0:~# osslsigncode sign     -pkcs11engine /usr/lib/x86_64-linux-gnu/engines-1.1/libpkcs11.so     -pkcs11module /root/smpkcs11.so     -certs cert.pem     -key 'pkcs11:object=keypair;type=private'     -in test.msi -out test-signed.msi -h sha256 -t http://timestamp.digicert.com
Succeeded

Verify signature with osslsigncode

To verify signature:

osslsigncode verify -in <signed file>