In the High Plains region of Texas it is not unusual for cotton (Gossypium hirsutum L.) to suffer pre-bloom fruit loss from insect injury or abiotic factors. The objective of this study was to investigate cotton’s ability to compensate pre-bloom square loss and determine the impact this loss had on yield and fiber quality. Experiments were conducted in Lubbock, TX in 2009, 2010, and 2011 evaluating the impact of 0 to 100% pre-bloom square removal on cotton yield and fiber quality. During 2009 and 2010, cotton was able to either compensate up to 100% pre-bloom fruit loss, or suffered environmentally induced square loss resulting in limited boll carrying capacity that equalized yields and boll density across square removal treatments. If compensation was the reason for the lack of differences among treatments, the plants appear to compensate by producing more secondary or tertiary position fruit, as well as retaining additional mid- to upper-canopy fruit. However, evidence suggested that fiber quality may decline in some compensated bolls due to maturity issues. When environmental conditions were harsh, as in 2011, the cotton plant did not appear to be able to compensate fully for yield due to some pre-bloom fruit loss. This was most evident when an early-season termination event, such as a freeze, was simulated. Where cotton was allowed to mature fully, overcompensation was evident in 2011, with the greatest yields occurring at approximately 27% pre-bloom square removal. As with previous years, fiber quality in 2011 might be impacted adversely from compensated fruit.