12 October, 1943:   A massive raid with 107 aircraft of the 345th and 38th Bomb Groups attacked airfields at Vunakanau and Rapopo in the Rabaul area. Following other squadrons of the 345th, Capt. Michael Hochella led the 500th into the target. He was able to claim hits on six Bettys and set a Helen on fire. For 15 minutes the B-25s dodged Japanese Zekes. S/Sgt John A. Murphy, turret gunner on TONDELAYO, got hits on one fighter sending it down S/Sgt Michael R. Korczynski, turret gunner on BUGGER OFF, got another fighter, then minutes later another. Pvt. Jonas R. Weimer, manning the turret on SATURDAY NITE, also scored well by knocking down three Zekes.

16 October, 1943:  As part of the overall 345th Group effort, the 500th attacked the Wewak area again, during which several enemy fighters were strafed as they tried to take off Somewhere between Wewak and nearby Boram airfields, enemy machine gun fire swept through Capt. Hochella's "C" Flight. One bullet hit BOOM BOOM's electrical junction box, bounced off the armor plate and tapped Hochella lightly on the back.

On Hocholla's left wing, Lt. Donald L, Stookey was in trouble. Enemy flak had damaged his right engine, which began smoking and, as a result, his aircraft was having trouble keeping up. The 500th aircraft hugged the water as they exited the target area. During the exit, Sgt. Jack Hallack on HAWG MOUTH got one enemy fighter and S/Sgt. Charles C. Brown on SNAFU claimed two more. On Lt. Van Ausdell's BEDROOMCOMMANDO, T/Sgt. Claude C. Russel, accounted for one, while S/Sgt. Robert G. Gerhardt claimed one, and Sgt. Samuel Keller, Jr., another.

Unable to keep up with his flight, Lt. Stookey kept losing altitude and was eventually forced to ditch his B-25. He made a good water landing and his crew was seen boarding the life raft, but were later captured by the Japanese to face an uncertain fate. Details of what happened to the crew for the next few weeks are unknown. It was later learned that Stookey and his copilot, Lt. Herschel D. Evans, eventually wound up at the POW camp at Rabaul and are believed to have been executed. Stookey's three enlisted crewmembers,  S/Sgt. Max Gerstein, S/Sgt. Thomas H. Laird, and S/Sgt. Ernest S. Roberts are believed to have been taken to Wewak POW camp thier eventual fate is unknown.

18 October, 1943:  The  500th, together with other squadrons of the 345th and 38th Bomb Groups, attacked Rabaul unescorted. Leading the 500th, Lt. Max Mortensen's flight attacked a 5,000 ton freighter, while Capt. Lyle Anacker and his flight attacked the 6,187 ton cargo/passenger ship JOHORE MARU. Meanwhile Lt. Thane Hecox dropped his two 1,000 pounders in front of a subchaser, the four-second delay fuses provided just enough time for the warship to pass over the bombs as they exploded, ripping the vessel apart. It sank immediately.

Because the Japanese apparently had prior warning of our attack there were many airborne enemy fighters to greet us. As the strafers, exited their assigned target areas, the 500th was the most vulnerable. During the exit Mortensen's turret gunner, S/Sgt Mike F. Fresty, was credited with shooting down one Japanese fighter. The flight was under heavy attack.  Meanwhile TONDELAYO, piloted by Lt. Ralph G. Wallace, had lost the right engine from enemy fire during the original bomb run and was having-trouble keeping up. Noticing this, Capt Lyle Annexure, piloting SNAFU, took a position on Wallace's left wing while Lt. Harlan A. Peterson eased SORRY SATCHEL in on the right wing. Peterson's turret gunner, S/Sgt Mike Korczynski fought off several enemy attacks and was credited with two downed Zekes. As a result of the intense enemy air assault, both SORRYSATCHEL and SNAFU eventually made good water landings. However, the only surviving crewmembers were SNAFU's Lt. Jerome A. Migliacci and turret gunner Sgt. Robert T. Henderson, who were later rescued by Australian coast watchers.

Meanwhile, TONDELAYO's engineer gunner, S/SGT Weldon Isler, and radio gunner, T/Sgt Burton E. Eaton, were passing 50 caliber ammo belts to turret gunner, S/Sgt John A, Murphy, to replenish his supply. Murphy was able to down five enemy planes which made him an ace. TONDELAYO, with one prop feathered, made history on 18 October, 1943 by fighting a vicious 75-minute running gun battle with more than 50 Japanese fighters and still being able to land safely at Kiriwina. This heroic mission earned the 345th Bomb Group the coveted Distinguished Unit Citation. TONDELAYO'S individual ordeal eventually turned out to be the 345th Group's most famous flight, earning its crewmembers the Silver Star for what was considered the finest example of bravery, tenacity and endurance by any aircrew of the Group.

24 October, 1943:  The 345th Group and the 38th Bomb Group teamed up for a strike on Rabaul airfields. The 501st went in first followed by the 500th led by Capt. Michael Hochella, The exit route after the strike was over land toward the New Britain coast. The return flight was routine for all except the 500th. LIL de ICER, piloted by Lt. Alfred J. Naigle, developed smoke pouring from it's the left engine, which eventually quit. Within minutes Naigle was forced to ditch his B-25. The ditching was successful in a bay of calm water, allowing its entire crew to escape and board rafts. They were eventually rescued by a Navy PBY and returned to their base at Dobodura, New Guinea.

10 October, 1944:  The ground echelon of the 500th prepared to strike camp and board Liberty ships headed for the Philippines. Two days later the ground echelon was on its way to Lae, New Guinea where the troops were transferred to the MORRISON R. WAITE, which was poorly equipped for passengers.

20-30 October, 1944:  The ground echelon of the 345th Group was on board the MORRISON R. WAITE headed for San Pedro Bay on the east side of Leyte Island, which they reached on the 29th. They had to ride out a typhoon before going ashore.

23 October, 1944:   In a raid on shipping in the Halmaheras area, Lt. Frederick W. Dick, the 500th Operations Officer, attacked a large coastal freighter, missing with the first bomb but hitting with the second. His wingman, Lt, Dean H. Rasmussen, dropped his two bombs claiming a direct hit.