We report on the electrical and structural properties of boron-doped diamond tips commonly used for in-situ electromechanical testing during nanoindentation. The boron dopant environment, as evidenced by cathodoluminescence (CL) microscopy, revealed significantly different boron states within each tip. Characteristic emission bands of both electrically activated and nonelectrically activated boron centers were identified in all boron-doped tips. Surface CL mapping also revealed vastly different surface properties, confirming a high amount of nonelectrically activated boron clusters at the tip surface. Raman microspectroscopy analysis showed that structural characteristics at the atomic scale for boron-doped tips also differ significantly when compared to an undoped diamond tip. Furthermore, the active boron concentration, as inferred via the Raman analysis, varied greatly from tip-to-tip. It was found that tips (or tip areas) with low overall boron concentration have a higher number of electrically inactive boron, and thus non-Ohmic contacts were made when these tips contacted metallic substrates. Conversely, tips that have higher boron concentrations and a higher number of electrically active boron centers display Ohmic-like contacts. Our results demonstrate the necessity to understand and fully characterize the boron environments, boron concentrations, and atomic structure of the tips prior to performing in situ electromechanical experiments, particularly if quantitative electrical data are required.