Quantitative clinical monitoring of musculoskeletal conditions and inflammatory joint diseases is challenging. Traditional measures to assess rheumatoid arthritis (RA), such as joint assessment, laboratory, imaging, and patient self-report measures, have limitations and provide only a reflection of the underlying inflammatory process. A gold standard to define disease activity in RA does not exist and various indices of disease activity must be used. Standard quantitative monitoring with a treatment goal has been shown to be beneficial to patient outcomes in randomized clinical trials. Quantitative monitoring has also contributed to improved long-term outcomes for RA in clinical care. Challenges of the measures need to be recognized and hurdles identified that prevent quantitative monitoring in every-day clinical care concerning disease activity and beyond. These aspects are discussed in this article.