At the Fairchild air show on 8 August 1993, Holland once again commanded the B-52 demonstration flight. As before, the demonstration profile included bank angles of greater than 45°, low-altitude passes, and another high pitch climbing maneuver, this time in excess of 80° nose high. The climb was so steep that fuel flowed out through the vent holes from the aircraft's wing tanks. The new wing commander, Brigadier General James M. Richards, and the new DO, Colonel William E. Pellerin, both witnessed the demonstration, but neither took any action

On 10 March 1994, Holland commanded a single-aircraft training mission to the Yakima Bombing Range, to provide an authorized photographer an opportunity to document the aircraft as it dropped training munitions. The minimum aircraft altitude permitted for that area was 500 feet (150 m) AGL; during the mission, Holland's aircraft was filmed crossing one ridgeline about 30 feet (10 m) above the ground. Fearing for their safety, the photography crew ceased filming and took cover as Holland's aircraft again passed low over the ground, this time estimated as clearing the ridgeline by only three feet (1 m). The co-pilot on Holland's aircraft testified that he grabbed the controls to prevent Holland from flying the aircraft into the ridge while the aircraft's other two aircrew members repeatedly screamed at Holland: "Climb! Climb!" Holland responded by laughing and calling one of the crew members "a pussy"

In preparation for the 1994 Fairchild air show, Holland was again selected as the command pilot for the B-52 demonstration flight. On 15 June 1994, Holland briefed the new wing commander, Colonel William Brooks, on the proposed flight plan. Holland's demonstration profile violated numerous regulations, including steep bank angles, low-altitude passes, and steep pitch attitudes. Brooks ordered Holland not to exceed 45° bank angle or 25° pitch attitude during the demonstration. During the first practice session, on 17 June, Holland repeatedly violated these orders. Brooks witnessed this, but took no action. Pellerin flew with Holland on that flight and reported to Brooks that, "the profile looks good to him; looks very safe, well within parameters." The next practice flight on 24 June ended with the fatal crash