The new work builds on last summer's launch of the Harry campaign and aims to dispel the notion that Pimm's - traditionally seen as the quintessential summer drink - should only be drunk when the sun comes out.
Harry appears in two new 30-second spots "hurricane" and "crusties", each of which tells the humorous story of how he and his Pimm's hamper overcome the elements during a typical English summer downpour.
One film shows Harry bringing refreshment to some sodden farmworkers, while a second execution has him doing the same for a group of "crusty" tree protesters.
Harry is also set to feature in his own weekly column in the London Evening Standard's ES. He will also debut on radio this summer in a heavyweight promotional campaign to support the TV work.
Sam Walker at Mother said: "Once again, Harry shows true British pluck and grit as he refuses to let a piddly hurricane or a vertiginous tree-borne road protest get between him and the quintessential Pimm's moment."
The TV work was directed by Jim Jenkins through Hungry Man and airs in London and the south east and Meridian TV region. Media planning and buying is through Carat.