At 09.26 hours on 5 March 1943, U-255 fired a spread of three torpedoes at convoy RA-53 and heard two detonations. The Executive was sunk and Richard Bland was damaged, but five days later finished off by the same U-boat.

Lookouts on the Executive (Master James Walden) in station #52 (orginally in #51) spotted the first torpedo, which crossed the bow of the ship. But the second torpedo struck on the starboard side between the #4 hatch and the engine room. The explosion blew the hatch covers off the #4 hatch and demolished the booms, the engine, the dynamos and all the equipment in the immediate area. The #4 hold was rapidly flooded and the ship began to settle slowly by the stern. The eight officers, 30 men and 24 armed guards (the ship was armed with one 4in, two .50cal and two .30cal guns) abandoned ship without orders in three lifeboats and one raft. One armed guard, three officers and five crewmen died. Eleven survivors were picked up immediately by HMS St. Elstan (FY 240) (Lt R.M. Roberts, RNR) and 42 survivors by HMS Northern Pride (FY 105) (T/Lt A.L.F. Bell, RNR) and landed in Iceland five days later. The drifting ship was scuttled by gunfire from a destroyer about one hour after the attack.