The standard theory of radiation driven winds has provided a useful framework to understand stellar winds arising from massive stars (O stars, Wolf-Rayet stars, and luminous blue variables). However, with new diagnostics, and advances in spectral modeling, deficiencies in our understanding of stellar winds have been thrust to the forefront of our research efforts. Spectroscopic observations and analyses have shown the importance of inhomogeneities in stellar winds, and revealed that there are fundamental discrepancies between predicted and theoretical mass-loss rates. For late O stars, spectroscopic analyses derive mass-loss rates significantly lower than predicted. For all O stars, observed X-ray fluxes are difficult to reproduce using standard shock theory, while observed X-ray profiles indicate lower mass-loss rates, the potential importance of porosity effects, and an origin surprisingly close to the stellar photosphere. In O stars with weak winds, X-rays play a crucial role in determining the ionization balance, and must be taken into account.
