Digital signatures are an important mechanism for ensuring data trustworthiness via source authenticity, integrity, and source nonrepudiation. However, their trustworthiness guarantee can be subverted in the real world by sophisticated attacks, which can obtain cryptographically legitimate digital signatures without actually compromising the private signing key. This problem cannot be adequately addressed by a purely cryptographic approach, by the revocation mechanism of Public Key Infrastructure (PKI) because it may take a long time to detect the compromise, or by using tamper-resistant hardware because the attacker does not need to compromise the hardware. This problem will become increasingly more important and evident because of stealthy malware (or Advanced Persistent Threats). In this paper, we propose a novel solution, dubbed Assured Digital Signing (ADS), to enhancing the data trustworthiness vouched by digital signatures. In order to minimize the modifications to the Trusted Computing Base (TCB), ADS simultaneously takes advantage of trusted computing and virtualization technologies. Specifically, ADS allows a signature verifier to examine not only a signature's cryptographic validity but also its system security validity that the private signing key and the signing function are secure, despite the powerful attack that the signing application program and the general-purpose Operating System (OS) kernel are malicious. The modular design of ADS makes it application-transparent (i.e., no need to modify the application source code in order to deploy it) and almost hypervisor-independent (i.e., it can be implemented with any Type I hypervisor). To demonstrate the feasibility of ADS, we report the implementation and analysis of an Xen-based ADS system.