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Be honest on your applications and upfront about the circumstances and result of the arrest.
I concur. Be absolutely up-front and do not down-play or soft-pedal the original charges. Expunged means nothing because that is just the disposition. The background investigation turns up the arrest and that is where the story begins as far as the DoD Central Adjudication Facility (DoDCAF) is concerned. I saw this burn people 20 years ago who were told by judges, their JPO, and everyone else that their records were sealed or expunged.
One particular case stands out in my memory because the recruit enlisted with a Type-1 program (no criminal involvement other than minor traffic violations) and shipped to boot camp just before the 1996 government shut-down. He was happily in third phase at recruit training when the backlog of background investigations was cleared and his record check showed an undisclosed arrest for possession of marijuana. Later in the day after I got the news at the recruiting station I got a call from the recruit's father who tells me, "It's my fault because I told my son not to disclose the arrest. The case was sealed as a juvenile record based on a plea of nolo contendre and the judge said the case was sealed."
The father then tells me that he's a retired USAF LtCol who had commanded a recruiting unit in the Air Force and he asked some friends in local law enforcement to run background checks which showed no arrests. I told him that his son was an adult who lied to me at pre-ship screening and that why he lied was not really relevant to the question of whether he would be discharged for fraudulent enlistment. I read to him on the phone the screening questions where it explicitly states that recruits must disclose all police involvement where they were arrested or detained regardless of initial or pleaded charges, sealed records, expungement, or not guilty pleas.
The recruit did stay and graduate because up to that point he was doing well enough that he was a platoon guide and his DI went to bat for him and the CG issued him a waiver after the fact. He did however lose his Type-1 program and got another MOS assignment that was probably far less desirable than the Comm-Data OccField guarantee with which he had shipped to boot camp.
There was also a recruiting scandal in 1989 when Recruiting Station Pittsburgh was found to have had lots of recruits enlisted with forged high school diplomas that were submitted with the knowledge (and probably assistance) of some recruiters. This went on for several years and when it was discovered and the guilty in uniform were prosecuted the Corps tracked down the Marines that had made it through boot camp but had no high school diploma and they discharged them for not having a high school diploma. This took about a year from the time the scandal broke till the court martials were over and they tracked down the non-grad Marines.
One of those Marines was a Sergeant in the platoon of a friend of mine who realized what was about to happen when the story broke. He immediately enrolled in community college and took classes in the evening until he got the 15 semester credit hours of college level course work that is treated as equivalent to a high school diploma. When NCIS finally verified that he was one of the non-grads that had enlisted and informed his command he was allowed to remain because he had gotten the Tier 1 equivalency.
Lies will catch up to you eventually so document it all now and spend the effort to get the necessary waiver.