The aesthetic notion of the sublime has been traced in different fields in the growing spheres of technology, capitalism, and digitality. The variable character of the sublime is partly due to the fact that it is identified with specific objects or sources. It can emerge whenever there is an antithesis between the infinite extensions of reason and the limits of the representative faculty. Taking into account this variance, this article seeks to reexamine the relationship of the sublime to technology, especially in view of current digital capabilities. In doing so, I argue that the notion of the sublime involves its own peculiar traits for delimiting and even blurring the boundaries between the natural and the technical. This seems to be so because techniques and language may shift and sometimes contest the incommensurability of reason and representation that lies at the heart of the sublime. Moreover, this phenomenon is countered by an anti-sublime effect (Manovich) that is achieved through the extensive mapping and visualization abilities of digital media. In contrast to the sublime, the anti-sublime is not based on contemplation but on habitual behavior. By relating this characteristic of the anti-sublime to the work of Félix Ravaisson, it finally seems that the sublime has been significantly affected by digital culture and is likely to influence any further demarcations between the natural and the technical.