The current study is a follow-up on the 2002 empirical study by Eshet-Alkalai and Amichai-Hamburger, which investigated digital literacy skills among different age groups. This study explores changes through time in digital literacy among the same participants 5 years later, and their performance is compared to new matched control groups. Results indicate an improvement over time among all age groups, but especially for the adults, in the tasks that require proficiency and technical control in using technology (e.g., photovisual and branching literacy skills). On the other hand, results indicate a drop in the skills that require creative and critical thinking (e.g., information and reproduction literacy skills), especially for the younger participants. Results show two major patterns of change over time: (a) closing the gap between younger and older participants in the tasks that emphasize proficiency and technical control and (b) widening the gap between younger and older participants in tasks that emphasize creativity and critical thinking. Based on the comparison with the matched control groups, we suggest that experience with technology, and not age, accounts for the observed lifelong changes in digital literacy skills.