Following education in Dublin, Richard Cripwell was commissioned into the Corps of Royal Engineers in August 1982. Following routine regimental and staff appointments, including operations in Northern Ireland, the Middle East and the Balkans, he commanded 26th Engineer Regiment, supporting 12th Mechanized Brigade and commanded the Intelligence, Surveillance and Reconnaissance Task Force in Kosovo, responsible for conducting operations relating to Persons Indicted for War Crimes in the Former Yugoslavia.
His training appointments have been on the Fighting in Built-Up Areas Training Team at the School of Infantry, the Mozambique Training Team (based in Zimbabwe) and as a company commander at the Royal Military Academy Sandhurst. On the staff he has served in the Defence Intelligence Staff, in HQ Kosovo Force (Rear), as Military Assistant to the Deputy Chief of Defence Staff (Equipment Capability) and as the Assistant Director for Information Operations in the Ministry of Defence.
As a Brigadier he served in Baghdad as the Director Energy Operations in Multi-National Forces – Iraq, as Commander Engineers in the Allied Rapid Reaction Corps, as the Assistant Chief of Staff for Intelligence at the Permanent Joint Headquarters in Northwood and in Kabul, where he was Director of the Strategic Transition and Assessment Group in HQ ISAF.
Promoted to Major General, he was dual-hatted as the Commander British Forces in Cyprus and Administrator (Governor) of the Sovereign Base Areas, one the United Kingdom's fourteen Overseas Territories. He then served as the British Defence Attaché in Washington and Head of the British Defence Staff in the United States.
His most recent appointment was as Deputy Commander Operation "Resolute Support", Afghanistan.