Among state bars, the Florida Bar has been a pioneer in regulating attorney advertising, especially with respect to new technology. The Bar’s efforts have been years in the making, but only until relatively recently did constitutional considerations percolate to the fore as the Bar faced litigation threats, and federal appellate courts issued opinions expounding on attorneys’ First Amendment rights to advertise. Now, with the release of a proposed new code of advertising rules that coincides with the release of the American Bar Association 20/20 Commission’s proposal to amend the attorney advertising and communication model rules, questions have arisen anew as to whether the Florida Bar has drafted rules that will prove relevant and effective in vindicating the public interest while simultaneously respecting attorneys’ constitutionally protected speech. Drawing from the Florida Bar’s experience, this Article suggests that bar associations and the attorneys subject to their jurisdiction fare better if constitutional principles play a prominent role early on in regulators’ efforts to respond to the public-policy challenges that accompany new innovations in society. Regardless of the ultimate constitutional validity of the Florida Bar’s proposed rules, the process that it took to achieve them is a process that other bars may want to learn from and avoid.