The Pilgrims led 2-0 at half-time courtesy of Jake Wright's fourth minute header and Tom Platt's 34th minute effort.
However, United's evening quickly unravelled once Decarrey Sheriff had reduced the arrears in the 64th minute. Frankie Maguire equalised 10 minutes later and Lewis White won it for the Poppies with 12 minutes to play.
Manager Ian Culverhouse had made five changes ahead of kick-off, with Wright and Jordan Burrow forming an experienced frontline. It was WRIGHT who powered the Pilgrims into a fourth minute lead with a back post header from a Zak Mills right-wing cross.
United moved further in front 11 minutes before the break when the Pilgrims kept alive Scott Pollock's corner and PLATT stabbed the loose ball home from close-range.
Kettering's comeback started in earnest when SHERIFF guided the ball home after Maguire's burst into the penalty area.
Ten minutes later, MAGUIRE got himself on the scoresheet with a rising drive to beat a powerless Tiernan Brooks.
United's woes were compounded in the 78th minute when WHITE got himself on the end of George Forsyth's up-and-under delivery to complete Kettering's staggering comeback.
Kettering (3-5-2): Harrison Foulkes; Lewis White, Brad Gascoigne, George Forsyth; Ellis Myles, Frankie Maguire, Gary Stohrer, Rhys Sharpe, Josh Flanagan (Decarrey Sheriff 46); Tyrone Lewthwaite, Sam Bennett (Keaton Ward 73). Subs (not used): Ethan Hill, George Cooper, Harry Hogg (gk).
Boston (4-1-2-1-2): Tiernan Brooks; Zak Mills, Luke Shiels, Ben Pollock, Ethan Sephton; Tom Platt; Lirak Hasani, Will Atkinson (Luther Munakandafa 79); Scott Pollock (Tre Mitford 84); Jordan Burrow, Jake Wright (Zak Goodson 69). Subs (not used): Sam McLintock, Jo Cummings.
Referee: Liam Corbett.
Attendance: 985.
PIC: Russell Dossett.