Abstract The 48-h intensity forecasts for Hurricane Pamela (2021) from numerical weather prediction models, statistical–dynamical aids, and forecasters were a major forecast bust with Pamela making landfall as a minor rather than major hurricane. From the satellite presentation, Pamela exhibited a symmetric pattern referred to as central cold cover (CCC) in the subjective Dvorak intensity technique. Per the technique, the CCC pattern is accompanied by arrested development in intensity despite the seemingly favorable convective signature. To understand forecast uncertainty during occurrences, central cold cover frequency from 2011 to 2021 is documented. From these cases, composites of longwave infrared brightness temperatures from geostationary satellites for CCC cases are presented, and the surrounding tropical cyclone large-scale environment is quantified and compared with other tropical cyclones at similar latitudes and intensities. These composites show that central cold cover has a consistent presentation, but varies in the preceding hours for storms that eventually intensify or weaken. And, the synoptic-scale environment surrounding the tropical cyclone thermodynamically supports the vigorous deep convection associated with CCC. Finally, intensity forecast errors from numerical weather prediction models and statistical–dynamical aids are examined in comparison to similar tropical cyclones. This work shows that guidance struggles during CCC cases with intensity errors from these models being in the lowest percentiles of performance, particularly for 24- and 36-h forecasts. Significance Statement The appearance of symmetric cold clouds near the center of developing tropical cyclones is most often associated with future intensification. This simple relationship is widely used by statistical tropical cyclone intensity forecast models. Here, we reexamine and confirm that one subjectively determined nighttime cold cyclone cloud pattern termed the “central cold cover” pattern in Vern Dvorak’s seminal technique for estimating tropical cyclone intensity from infrared satellite images is indeed related to slow or arrested development, and represents a failure mode for these simple forecast models.