Penn, 37, played in an FA Trophy final for Kiddy, won eight caps for England C and spent seven seasons in the EFL with Burton, Cheltenham and York.
As manager of the Harriers, he also enjoyed a run to FA Cup fourth round last season, coming within 60 seconds of scalping the mighty West Ham.
Yet all of that will pale into insignificance if Kidder-minster can overcome Brackley Town in today’s National League North promotion final to end a long-standing play-off hoodoo and return to the top flight for the first time in seven years.
“This would be my biggest achievement in the game, on and off the field,” said the former Gateshead midfielder, who took charge in 2020.
“We’re not there yet. We’re one game away and we’ve got to give it everything. But yeah – if this happens, it would top anything I’ve done before.”
Penn’s caution is understandable after the heartbreak of last May, when Kiddy were bundled out at the Eliminator stage by Boston United.
It was the club’s fourth play-off defeat in as many attempts, none of them yielding a final and all coming within the last decade.
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