Col Cummings received his commission through Officer Candidate Course (OCC) in April 2001.
Following his training at The Basic School and the Infantry Officer Course, 2ndLt Cummings reported to Company K, 3d Battalion, 2nd Marines for duty. He deployed in 2003 with Task Force Tawara during Operation IRAQI FREEDOM (OIF) as a rifle platoon commander. In 2004, he deployed with Task Force 3/2 to Djibouti, Africa as part of 4th MEB Anti-Terrorism Battalion during Operation ENDURING FREEDOM as a security force commander with Kilo Company.
In 2005, he deployed with 3/2 during OIF as the weapons platoon commander and Fire Support Team (FiST) Leader with Kilo Company. In 2006, Capt Cummings transferred to MCBH Headquarters Battalion and served as operations officer until reassigned to 3d Marine Regiment. In 2008, he deployed with Embedded Training Team (ETT) 5-3, 3d Marine Regiment to the Korengal Valley with an Afghanistan National Army infantry company during Operation ENDURING FREEDOM as an embedded combat advisor and team leader.
In 2009, he transferred to the Selected Marine Corps Reserve (SMCR) and became a municipal police officer. Remaining affiliated with the Marine Corps Reserve, Maj Cummings pursued his law enforcement career and attended graduate school receiving a Masters in Business Administration.
In 2016, Maj Cummings mobilized and deployed with Special Purpose Marine Air Ground Task Force (SPMAGTF) – Southern Command to Central America as an infantry advisor, assistant operations officer and Humanitarian Assistance Survey Team (HAST) officer in charge for the Hurricane Matthew response in Haiti.
In 2017, Maj Cummings served as company commander of Anti-Tank Company, 25th Marine Regiment in Broken Arrow, OK. Prior to assuming command of 1st Battalion, 25th Marines in 2018, LtCol Cummings served as Future Operations Officer for 25th Marine Regiment.
In 2019, LtCol Cummings mobilized and deployed with 1st Battalion, 25th Marines under 7th Marine Regiment as Forward Deployed Battalion – West (Unit Deployment Program 20.1) as the battalion commander. He was then selected for TLS and reported to Marine Corps War College in 2020.
In 2021, LtCol Cummings graduated from the Marine Corps War College in Quantico, VA receiving a Masters in Strategic Studies. He then accepted follow-on orders for a tour with Marine Corps Forces Pacific – Fleet Marine Forces Pacific. Assigned to the G35, he served as the deputy director for Future Operations, GFM, and Exercises in the Operations Directorate.
In 2022, LtCol Cummings returned to a drilling reservist status and transferred to Marine Corps Warfighting Lab where he was a project officer with III MEF CDT within the Experimentation Division.
In 2023, Col Cummings became the commanding officer of Marine Corps Advisor Company Bravo (MCAC-B).
As a civilian, he served as a strategic planner with USINDOPACOM in the strategy branch of the Strategic Planning and Policy Directorate. In 2023, Col Cummings transferred civilian defense analyst companies and now works as an operational and strategic planner for COMPACFLT with TF504.
Col Cummings also instructs for Davis Defense Group as an adjunct professor for Command and Staff College Distance Education Program since 2022.
His military decorations include the Bronze Star Medal with combat distinguishing device, Meritorious Service Medal, Joint Service Commendation Medal, Navy Commendation Medal with combat distinguishing device and 2 gold stars in lieu of third award, Navy and Marine Corps Achievement Medal with combat distinguishing device, Army Achievement Medal, Combat Action Ribbon with gold star and Humanitarian Service Medal.