Roof falls in longwall headgate can occur when weak roof and high horizontal stress are present. To prevent roof falls in the headgate under high horizontal stress, it is important to understand the ground response to high horizontal stress in the longwall headgate and the requirements for supplemental roof support. In this study, a longwall headgate under high horizontal stress was instrumented to monitor stress change in the pillars, deformations in the roof, and load in the cable bolts. The conditions in the headgate were monitored for about six months as the longwall face passed by the instrumented site. The roof behavior in the headgate near the face was carefully observed during longwall retreat. Numerical modeling was performed to correlate the modeling results with underground observation and instrumentation data and to quantify the effect of high horizontal stress on roof stability in the long-wall headgate. This paper discusses roof support requirements in the longwall headgate under high horizontal stress in regard to the pattern of supplemental cable bolts and the critical locations where additional supplemental support is necessary.