[3] As with so many construction businesses, war expanded the range of contracts: Henry Boot & Sons built the British Army camp at Catterick in Yorkshire; RAF Manston Aerodrome near Ramsgate; the Calshot Naval Air Station at Calshot in Hampshire; Tees Naval Base; a U.S. Army Rest Camp and hospital at Southampton and Chepstow Military Hospital.

[7] Charles was keenly interested in housing and, as soon as hostilities ended, he began what became a major housebuilding programme – both public and private.

[7] The outbreak of the Second World War led to the company quickly ceasing its housing construction work so that its resources could be concentrated on Britain's wartime requirements.

By the end of 1939, it had already commenced work for all three services; Boot's wartime projects included aerodromes, ordnance factories and hospital camps.

The emphasis of the group was changed: the traditional railway engineering business was sold in 1988 and private housing development gradually increased.

[4] During May 1990, Henry Boot announced that it had recorded pre-tax profits to £5.36 million, a 37 per cent rise over the year prior; its performance, which had included a number of successful property deals, was above that of most larger British construction companies at that time.

[23] During 1994, Jamie announced that the company would orientate itself more towards the building sector over that of civil engineering due to the poor margins being achieved within the latter market.

[4][26] Following the start of the Great Recession, Henry Book recorded a £20m loss as, even though its revenue from various construction activities remained steady, it had been hit heavily by the devaluation of its property portfolio.

[36] The Group is organised into the following divisions:[5] During the mid 1990s, the company had a payment dispute with a subcontractor, which led to a brick supplier for one of Henry Boot's Manchester-based project withdrawing and facing a winding-up order.

[39] In the late 1990s, the firm sued GEC Alsthom over a claims dispute related to work on the Connah's Quay Power Station in North Wales.

Estimated usage was predicted by Henry Boot Developments at 80,000 visitors per week, which turned out to be an overly optimistic forecast.

The tenant took Henry Boot Developments to court alleging fraudulent misrepresentation about the extent that motorway signage could be provided from the M20, about predicted visitor numbers, and about the scale of the facilities that could be offered.

The court rejected Food Co UK's claims because Henry Boot Developments had made statements based on reasonable grounds.