We show experimentally, and explain theoretically, what velocity is needed to break an elongated droplet entering a microfluidic T-junction. Our experiments on short droplets confirm previous experimental and theoretical work that shows that the critical velocity for breakup scales with the inverse of the length of the droplet raised to the fifth power. For long elongated droplets that have a length about thrice the channel width, we reveal a drastically different scaling. Taking into account that a long droplet remains squeezed between the channel walls when it enters a T-junction, such that the gutters in the corners of the channel are the main route for the continuous phase to flow around the droplet, we developed a model that explains that the critical velocity for breakup is inversely proportional to the droplet length. This model for the transition between breaking and nonbreaking droplets is in excellent agreement with our experiments.