The Near-Field Scanning Microwave Microscope (NSMM) can quantitatively image materials properties at length scales far shorter than the free space wavelength (λ). Here we report a study of the effect of tip-geometry on the NSMM signals. This particular NSMM utilizes scanning tunneling microscopy (STM) for distance-following control. We systematically examined many commercially available STM tips, and find them to have a conical structure on the macroscopic scale, with an embedded sphere (of radius r sphere ) at the apex of the tip. The r sphere values used in the study ranged from 0.1 μm to 12.6 μm. Tips with larger r sphere show good signal contrast (as measured by the frequency shift (Δf) signal between tunneling height and 2 μm away from the sample) with NSMM. For example, the tips with r sphere = 8 μm give signal contrast of 1000 kHz compared to 85 kHz with a tip of r sphere = 0.55 μm. However, large r sphere tips distort the topographic features acquired through STM. A theoretical model is used to understand the tip-to-sample interaction. The model a email address: anlage@umd.edu 1 quantitatively explains the measured change in quality factor (Q) as a function of height over bulk Copper and Silicon samples.