We report detailed measurements of the optical properties of tapered photonic crystal fibers (PCFs). We observe a striking long-wavelength loss as the fiber diameter is reduced, despite the minimal airhole collapse along the taper. We associate this loss with a transition of the fundamental core mode as the fiber dimensions contract: At wavelengths shorter than this transition wavelength, the core mode is strongly confined in the fiber microstructure, whereas at longer wavelengths the mode expands beyond the microstructure and couples out to higher-order modes. These experimental results are discussed in the context of the so-called fundamental mode cutoff described by Kuhlmey et al. [Opt. Express 10, 1285 (2002)], which apply to PCFs with a finite microstructure.