--- a/src/vehicle.cpp
+++ b/src/vehicle.cpp
@@ -1848,11 +1848,18 @@
 		if (flags & DC_EXEC) {
 			w = GetVehicle(_new_vehicle_id);
 
-			if (v->cargo_type != w->cargo_type || v->cargo_subtype != w->cargo_subtype) {
-				// we can't pay for refitting because we can't estimate refitting costs for a vehicle before it's build
-				// if we pay for it anyway, the cost and the estimated cost will not be the same and we will have an assert
-				DoCommand(0, w->index, v->cargo_type | (v->cargo_subtype << 8), flags, GetCmdRefitVeh(v));
-			}
+			Vehicle *w2 = w;
+			Vehicle *v2 = v;
+			do {
+				if (v2->cargo_type != w2->cargo_type || v2->cargo_subtype != w2->cargo_subtype) {
+					/* We can't pay for refitting because we can't estimate refitting costs for a vehicle before it's build.
+					 * If we pay for it anyway, the cost and the estimated cost will not be the same and we will have an assert.
+					 * We need to check the whole chain if it is a train because some newgrf articulated engines can refit some units only (and not the front) */
+					DoCommand(0, w->index, v2->cargo_type | (v2->cargo_subtype << 8), flags, GetCmdRefitVeh(v));
+					break; // We learned that the engine in question needed a refit. No need to check anymore
+				}
+			} while (v->type == VEH_Train && (w2 = w2->next) != NULL && (v2 = v2->next) != NULL);
+
 			if (v->type == VEH_Train && HASBIT(v->u.rail.flags, VRF_REVERSE_DIRECTION)) {
 				SETBIT(w->u.rail.flags, VRF_REVERSE_DIRECTION);
 			}