diff --git a/src/rail_cmd.cpp b/src/rail_cmd.cpp
index 3b93a5d32c..24e5c7b774 100644
--- a/src/rail_cmd.cpp
+++ b/src/rail_cmd.cpp
@@ -886,22 +886,32 @@ static CommandCost CmdRailTrackHelper(DoCommandFlag flags, TileIndex tile, TileI
 	if (ret.Failed()) return ret;
 
 	bool had_success = false;
+	bool under_tunnelbridge = false;
 	CommandCost last_error = CMD_ERROR;
 	for (;;) {
-		ret = remove ? Command<CMD_REMOVE_SINGLE_RAIL>::Do(flags, tile, TrackdirToTrack(trackdir)) : Command<CMD_BUILD_SINGLE_RAIL>::Do(flags, tile, railtype, TrackdirToTrack(trackdir), auto_remove_signals);
-
-		if (ret.Failed()) {
-			last_error = ret;
-			if (last_error.GetErrorMessage() != STR_ERROR_ALREADY_BUILT && !remove) {
-				if (fail_on_obstacle) return last_error;
-				if (had_success) break; // Keep going if we haven't constructed any rail yet, skipping the start of the drag
+		/* Don't try to place rail between tunnelbridge ends */
+		if (IsTileType(tile, MP_TUNNELBRIDGE)) {
+			under_tunnelbridge = !under_tunnelbridge;
+		} else if (!under_tunnelbridge) {
+			if (remove) {
+				ret = Command<CMD_REMOVE_SINGLE_RAIL>::Do(flags, tile, TrackdirToTrack(trackdir));
+			} else {
+				ret = Command<CMD_BUILD_SINGLE_RAIL>::Do(flags, tile, railtype, TrackdirToTrack(trackdir), auto_remove_signals);
 			}
 
-			/* Ownership errors are more important. */
-			if (last_error.GetErrorMessage() == STR_ERROR_OWNED_BY && remove) break;
-		} else {
-			had_success = true;
-			total_cost.AddCost(ret);
+			if (ret.Failed()) {
+				last_error = ret;
+				if (last_error.GetErrorMessage() != STR_ERROR_ALREADY_BUILT && !remove) {
+					if (fail_on_obstacle) return last_error;
+					if (had_success) break; // Keep going if we haven't constructed any rail yet, skipping the start of the drag
+				}
+
+				/* Ownership errors are more important. */
+				if (last_error.GetErrorMessage() == STR_ERROR_OWNED_BY && remove) break;
+			} else {
+				had_success = true;
+				total_cost.AddCost(ret);
+			}
 		}
 
 		if (tile == end_tile) break;
diff --git a/src/road_cmd.cpp b/src/road_cmd.cpp
index 1d814a65ee..c2501a1d12 100644
--- a/src/road_cmd.cpp
+++ b/src/road_cmd.cpp
@@ -1007,49 +1007,55 @@ CommandCost CmdBuildLongRoad(DoCommandFlag flags, TileIndex end_tile, TileIndex
 	bool had_bridge = false;
 	bool had_tunnel = false;
 	bool had_success = false;
+	bool under_tunnelbridge = false;
 
 	/* Start tile is the first tile clicked by the user. */
 	for (;;) {
-		RoadBits bits = AxisToRoadBits(axis);
-
-		/* Determine which road parts should be built. */
-		if (!is_ai && start_tile != end_tile) {
-			/* Only build the first and last roadbit if they can connect to something. */
-			if (tile == end_tile && !CanConnectToRoad(tile, rt, dir)) {
-				bits = DiagDirToRoadBits(ReverseDiagDir(dir));
-			} else if (tile == start_tile && !CanConnectToRoad(tile, rt, ReverseDiagDir(dir))) {
-				bits = DiagDirToRoadBits(dir);
+		/* Don't try to place road between tunnelbridge ends */
+		if (IsTileType(tile, MP_TUNNELBRIDGE)) {
+			under_tunnelbridge = !under_tunnelbridge;
+		} else if (!under_tunnelbridge) {
+			RoadBits bits = AxisToRoadBits(axis);
+
+			/* Determine which road parts should be built. */
+			if (!is_ai && start_tile != end_tile) {
+				/* Only build the first and last roadbit if they can connect to something. */
+				if (tile == end_tile && !CanConnectToRoad(tile, rt, dir)) {
+					bits = DiagDirToRoadBits(ReverseDiagDir(dir));
+				} else if (tile == start_tile && !CanConnectToRoad(tile, rt, ReverseDiagDir(dir))) {
+					bits = DiagDirToRoadBits(dir);
+				}
+			} else {
+				/* Road parts only have to be built at the start tile or at the end tile. */
+				if (tile == end_tile && !end_half) bits &= DiagDirToRoadBits(ReverseDiagDir(dir));
+				if (tile == start_tile && start_half) bits &= DiagDirToRoadBits(dir);
 			}
-		} else {
-			/* Road parts only have to be built at the start tile or at the end tile. */
-			if (tile == end_tile && !end_half) bits &= DiagDirToRoadBits(ReverseDiagDir(dir));
-			if (tile == start_tile && start_half) bits &= DiagDirToRoadBits(dir);
-		}
 
-		CommandCost ret = Command<CMD_BUILD_ROAD>::Do(flags, tile, bits, rt, drd, 0);
-		if (ret.Failed()) {
-			last_error = ret;
-			if (last_error.GetErrorMessage() != STR_ERROR_ALREADY_BUILT) {
-				if (is_ai) return last_error;
-				if (had_success) break; // Keep going if we haven't constructed any road yet, skipping the start of the drag
-			}
-		} else {
-			had_success = true;
-			/* Only pay for the upgrade on one side of the bridges and tunnels */
-			if (IsTileType(tile, MP_TUNNELBRIDGE)) {
-				if (IsBridge(tile)) {
-					if (!had_bridge || GetTunnelBridgeDirection(tile) == dir) {
-						cost.AddCost(ret);
-					}
-					had_bridge = true;
-				} else { // IsTunnel(tile)
-					if (!had_tunnel || GetTunnelBridgeDirection(tile) == dir) {
-						cost.AddCost(ret);
-					}
-					had_tunnel = true;
+			CommandCost ret = Command<CMD_BUILD_ROAD>::Do(flags, tile, bits, rt, drd, 0);
+			if (ret.Failed()) {
+				last_error = ret;
+				if (last_error.GetErrorMessage() != STR_ERROR_ALREADY_BUILT) {
+					if (is_ai) return last_error;
+					if (had_success) break; // Keep going if we haven't constructed any road yet, skipping the start of the drag
 				}
 			} else {
-				cost.AddCost(ret);
+				had_success = true;
+				/* Only pay for the upgrade on one side of the bridges and tunnels */
+				if (IsTileType(tile, MP_TUNNELBRIDGE)) {
+					if (IsBridge(tile)) {
+						if (!had_bridge || GetTunnelBridgeDirection(tile) == dir) {
+							cost.AddCost(ret);
+						}
+						had_bridge = true;
+					} else { // IsTunnel(tile)
+						if (!had_tunnel || GetTunnelBridgeDirection(tile) == dir) {
+							cost.AddCost(ret);
+						}
+						had_tunnel = true;
+					}
+				} else {
+					cost.AddCost(ret);
+				}
 			}
 		}