Tip-enhanced Raman spectroscopy (TERS), which utilizes the strong localized optical field generated at the apex of a metallic tip when illuminated, has been shown to successfully probe the vibrational spectrum of today’s and tomorrow’s state-of-the-art silicon and next-generation semiconductor devices, such as quantum dots. Collecting and analyzing the vibrational spectrum not only aids in material identification but also provides insight into strain distributions in semiconductors. Here, the potential of TERS for nanoscale characterization of strain in silicon devices is reviewed. Emphasis will be placed on the key challenges of obtaining spectroscopic images of strain in actual strained silicon devices.