The credibility and reliability of health IT systems as a means of achieving changes towards safer and cost-effective care have been questioned for over two decades due to the lack of methodologically strong evidence. As national level adoption and implementation of health IT are becoming widespread across the EU and globally, but are also being offset by adverse reports, the demands for evidence become more pronounced and the stakes higher. The adaptation of HTA (health technology assessment) methodology as a means to address gaps in health IT evidence production has been proposed repeatedly and tested in the field of telemedicine services. HTA has in many ways run a course parallel to that of health IT, while in certain respects attaining more clear achievements. This contribution investigates aspects of a bilaterally beneficial relation between the two disciplines using three lines of exploration: the methodological goodness-of-fit between health IT evaluation and HTA; the solutions each has proposed to the problem of producing high quality evidence in reduced amount of time; and the way each has addressed the strengthened role and position of patients. The analysis demonstrates areas of convergence between health IT and HTA. It also highlights topics which would need to be jointly addressed in the process, such as innovative and high quality data collection and analysis, inclusion of patient reported outcomes and patient safety, and transferability and generalizability of findings. In closing, it takes a glimpse of the challenges emerging as a result of the progress at the cross-roads of medicine, science and technology.