Inspired in part by the recent holding in Bland v. Roberts that the use of the “Like” feature in Facebook is not covered by the Free Speech Clause, this article makes a brief foray into the approach that courts have taken in the recent past towards questions of First Amendment coverage in the context of emerging technologies. Specifically, this article will take a closer look at how courts have dealt with the issue of functionality in the context of First Amendment coverage of computer source code. The analysis of this and other recent experiences, when put in a larger context, reflects a continuing dissatisfaction on the part of both courts and legislatures with the current Supreme Court doctrine on First Amendment coverage. From this discussion, we can also derive some meaningful normative insights regarding the interplay between emerging technologies and First Amendment coverage doctrine. Finally, this article hopes to serve as a stepping stone in a more profound and long term pursuit of a comprehensive theory of constitutional individual rights coverage issues that might serve us well as the future brings unexpected changes in our society.