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Armstrong is relatively new to the art of punting. He was a defensive end and tight end during his high school days and also earlier in his collegiate career. After handling kickoff duties, he was given the task of being the punter at Harper College. In his first year of performing those chores, he led the National Junior College Athletics Association with a 43.74-yard average.
At Conant High School, Armstrong lettered as a defensive end and tight end. He also handled some kickoff chores. He was contemplating walking on at Purdue, but decided to enroll at Harper College after graduating from Conant High.
In 2003, he played defensive end, seeing a few snaps on offense, where he caught two passes for 28 yards for the national championship team. He sat out the 2004 season, returning to the gridiron at Harper College in 2005.
He earned NJCAA All-American and All-Iowa Community College Athletic Conference first-team honors that year. He handled all of the kicking duties, leading the junior college ranks with 43 punts for 1,881 yards (43.74 avg). He had 23 of his 48 kickoffs sail out of the end zone and scored 52 points on 7-of-12 field goals and 31-of-33 extra point attempts.
Armstrong finally got his wish when he enrolled at Purdue in time to compete in 2006 spring drills. Despite no formal training or coaching as a punter, he earned Academic All-Big Ten Conference and honorable mention All-Big Ten accolades from the league's coaches. He was a member of the Ray Guy Award Watch List.
That year, he did not have enough punts to qualify for the national title (would have ranked 22nd in the NCAA), but ranked second in the league with a 43.08-yard average on 50 punts. Armstrong had 16 of his attempts downed inside the 20-yard line, as 12 others were fair catches. The opposition returned 20 of his punts for a 7.9-yard average and one touchdown, as he also recorded a solo tackle.
Before his senior year, Armstrong enrolled a punting coach to help him with his craft. He punted 67 times for 2,724 yards (40.7 avg) with 14 of his attempts being ruled fair catches while 17 others were downed inside the 20-yard line. He recovered a fumble on the punt coverage unit, as 24 of his kicks were returned for 169 yards (7.0 avg). He also kicked off twice (both onside kicks).
In 27 games at Purdue, Armstrong punted 117 times for 4,878 yards (41.69 avg), as two of his attempts were blocked, nine were ruled touchbacks, 26 were good for fair catches and 33 others were downed inside the 20-yard line. He had 48 punts returned for 326 yards (6.79 avg) and one touchdown. He also recorded a solo tackle and recovered a fumble.
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