Small businesses face a unique and challenging dilemma in today’s business landscape. On the one hand, they are typically and rightfully considered the more powerful party in their contractual relations with consumers, thus prompting a need to protect consumers against unfair contractual terms. On the other hand, when engaging with larger businesses, small businesses typically find themselves in the position of the weaker, more vulnerable party, possibly in need of greater protection themselves from unfair terms. This Article addresses the inherent dilemma faced by small businesses and argues that the prevailing perception of businesses as sophisticated and experienced, based exclusively on their categorization as “business parties” unjustly disregards the economic and market realities they encounter.