Over the past few decades, boron and nucleic acid chemistries have attracted significant attention for their applications in biology, medicine, and analytical sciences. Our laboratory has maintained a long-standing interest in both fields. Leveraging the unique ability of boronic acids to interact with cis-diol functions in aqueous media, we have developed a wide range of applications—from molecular recognition and sensing to the design of reversible dynamic systems where the natural phosphodiester linkage is replaced with a boronate. The reversible formation of boronate esters occurs in a templated manner and has been shown to restore the activity of split DNA and RNA enzymes, as well as a split fluorescent light-up aptamer. This reversibility is a crucial feature for biological self-assembly. In this discussion, we will explore the fundamental concept of stimuli-responsive boronate formation applied to nucleic acids, highlighting its potential for future research and innovation.