Surface contamination by microorganisms is of great concern in a wide range of applications, including, wound healing scaffolds, medical devices, food packaging, and membranes used for water purification. As both microbial resistance and infectious diseases remain, new approaches to delay the onset of biofilm formation with less evolutionary pressure on pathogens are needed. Our research explores the effect that “green” bioactive agents and materials properties have on bacteria. In this seminar, I will first highlight our use of antimicrobial compounds derived from edible plants to potentially help prevent biofilms with fewer unnecessary side effects. We demonstrate that flexible chitosan nanofiber coatings that release the cinnamon extract, cinnamaldehyde, exhibit time-dependent bacterial cytotoxicity against two Gram-negative bacteria, Escherichia coli and Pseudomonas aeruginosa. Then, our recent investigations into an even “greener” approach than cinnamon will be discussed. Systematically, we investigated poly(ethylene glycol) dimethacrylate and agar hydrogels as a function of Young’s moduli. Independent of hydrogel chemistry and incubation time, Escherichia coli attachment decreased on softer hydrogels. The overall goal of the talk will be to illustrate some of our recent findings and how synergistically, these results can guide the green engineering of multifunctional antibacterial and antifouling strategies.