diff --git a/src/openrct2/paint/Supports.cpp b/src/openrct2/paint/Supports.cpp
index 1da900e662..dda5aa9ea4 100644
--- a/src/openrct2/paint/Supports.cpp
+++ b/src/openrct2/paint/Supports.cpp
@@ -353,19 +353,19 @@ static constexpr UnkSupportsDescriptor Byte97B23C[] = {
     {{{0,  0,  0}, {1,  1,  8}},  0, 1},
     {{{0,  0,  0}, {1,  1,  8}},  0, 1},
     {{{0,  0,  0}, {1,  1,  8}},  0, 1},
+    {{{0,  0,  0}, {1,  1,  8}},  0, 1}, // ?
     {{{0,  0,  0}, {1,  1,  8}},  0, 1},
     {{{0,  0,  0}, {1,  1,  8}},  0, 1},
     {{{0,  0,  0}, {1,  1,  8}},  0, 1},
+    {{{0,  0,  0}, {1,  1,  8}},  0, 1}, // ?
     {{{0,  0,  0}, {1,  1,  8}},  0, 1},
     {{{0,  0,  0}, {1,  1,  8}},  0, 1},
     {{{0,  0,  0}, {1,  1,  8}},  0, 1},
+    {{{0,  0,  0}, {1,  1,  8}},  0, 1}, // ?
     {{{0,  0,  0}, {1,  1,  8}},  0, 1},
     {{{0,  0,  0}, {1,  1,  8}},  0, 1},
     {{{0,  0,  0}, {1,  1,  8}},  0, 1},
-    {{{0,  0,  0}, {1,  1,  8}},  0, 1},
-    {{{0,  0,  0}, {1,  1,  8}},  0, 1},
-    {{{0,  0,  0}, {1,  1,  8}},  0, 1},
-    {{{2,  2,  1}, {28, 28, 2}},  0, 1},
+    {{{2,  2,  1}, {28, 28, 2}},  0, 1}, // Large scenery (all directions)
     {{{0,  0,  0}, {1,  1,  8}},  0, 1}, // Flat to steep large 1
     {{{0,  0,  0}, {1,  1,  8}},  0, 1},
     {{{0,  0,  0}, {1,  1,  8}},  0, 1},
@@ -680,16 +680,32 @@ bool WoodenASupportsPaintSetup(
     return hasSupports;
 }
 
+static int32_t GetSpecialOffsetForTransitionType(WoodenSupportTransitionType transitionType, Direction direction)
+{
+    if (transitionType == WoodenSupportTransitionType::None)
+        return 0;
+
+    // "Special" values are an offset into tables like Byte97B23C, plus 1.
+    // Save for WoodenSupportTransitionType::LargeScenery, there are four entries (one per direction) for every
+    // transition type. While these tables will have to be refactored in due course, we can only do so once all
+    // drawing functions use WoodenSupportTransitionType instead of passing the "special" value directly.
+    int32_t specialOffset = 0;
+    if (transitionType < WoodenSupportTransitionType::Scenery)
+        specialOffset = (EnumValue(transitionType) * NumOrthogonalDirections) + direction;
+    else if (transitionType == WoodenSupportTransitionType::Scenery)
+        specialOffset = (EnumValue(transitionType) * NumOrthogonalDirections);
+    else
+        specialOffset = (EnumValue(transitionType) * NumOrthogonalDirections) + direction - 3;
+
+    return specialOffset + 1;
+}
+
 bool WoodenASupportsPaintSetup(
     PaintSession& session, WoodenSupportType supportType, WoodenSupportSubType subType, int32_t height, ImageId imageTemplate,
     WoodenSupportTransitionType transitionType, Direction direction)
 {
     int32_t oldSupportType = (EnumValue(supportType) * 6) + EnumValue(subType);
-    int32_t special = 0;
-    if (transitionType != WoodenSupportTransitionType::None)
-    {
-        special = (EnumValue(transitionType) * NumOrthogonalDirections) + direction + 1;
-    }
+    int32_t special = GetSpecialOffsetForTransitionType(transitionType, direction);
 
     return WoodenASupportsPaintSetup(session, oldSupportType, special, height, imageTemplate);
 }
@@ -829,11 +845,7 @@ bool WoodenBSupportsPaintSetup(
     WoodenSupportTransitionType transitionType, Direction direction)
 {
     int32_t oldSupportType = (EnumValue(supportType) * 6) + EnumValue(subType);
-    int32_t special = 0;
-    if (transitionType != WoodenSupportTransitionType::None)
-    {
-        special = (EnumValue(transitionType) * NumOrthogonalDirections) + direction + 1;
-    }
+    int32_t special = GetSpecialOffsetForTransitionType(transitionType, direction);
 
     return WoodenBSupportsPaintSetup(session, oldSupportType, special, height, imageTemplate);
 }
diff --git a/src/openrct2/paint/Supports.h b/src/openrct2/paint/Supports.h
index 54ee612f1c..f5e78570e1 100644
--- a/src/openrct2/paint/Supports.h
+++ b/src/openrct2/paint/Supports.h
@@ -42,6 +42,7 @@ enum class WoodenSupportTransitionType : uint8_t
     Up25DegToUp60Deg = 3,
     Up60DegToUp25Deg = 4,
     Up60Deg = 5,
+    Scenery = 12,
 };
 
 // There are 13 types of metal supports. A graphic showing all of them is available here:
diff --git a/src/openrct2/paint/tile_element/Paint.LargeScenery.cpp b/src/openrct2/paint/tile_element/Paint.LargeScenery.cpp
index 2f50f0cc51..3c661d216f 100644
--- a/src/openrct2/paint/tile_element/Paint.LargeScenery.cpp
+++ b/src/openrct2/paint/tile_element/Paint.LargeScenery.cpp
@@ -61,15 +61,16 @@ static void PaintLargeScenerySupports(
     if (tile.flags & LARGE_SCENERY_TILE_FLAG_NO_SUPPORTS)
         return;
 
-    auto special = 0;
+    auto transitionType = WoodenSupportTransitionType::None;
     auto supportHeight = height;
     if (supportHeight & 0xF)
     {
         supportHeight &= ~0xF;
-        special = 49;
+        transitionType = WoodenSupportTransitionType::Scenery;
     }
 
-    WoodenBSupportsPaintSetup(session, (direction & 1), special, supportHeight, imageTemplate);
+    WoodenBSupportsPaintSetupRotated(
+        session, WoodenSupportType::Truss, WoodenSupportSubType::NeSw, direction, supportHeight, imageTemplate, transitionType);
 
     int32_t clearanceHeight = Ceil2(tileElement.GetClearanceZ() + 15, 16);
     if (tile.flags & LARGE_SCENERY_TILE_FLAG_ALLOW_SUPPORTS_ABOVE)
diff --git a/src/openrct2/paint/tile_element/Paint.SmallScenery.cpp b/src/openrct2/paint/tile_element/Paint.SmallScenery.cpp
index 5654eb2679..6d22f0a07b 100644
--- a/src/openrct2/paint/tile_element/Paint.SmallScenery.cpp
+++ b/src/openrct2/paint/tile_element/Paint.SmallScenery.cpp
@@ -42,12 +42,12 @@ static void PaintSmallScenerySupports(
     if (sceneryEntry.HasFlag(SMALL_SCENERY_FLAG_NO_SUPPORTS))
         return;
 
-    auto special = 0;
+    auto transitionType = WoodenSupportTransitionType::None;
     auto supportHeight = height;
     if (supportHeight & 0xF)
     {
         supportHeight &= ~0xF;
-        special = 49;
+        transitionType = WoodenSupportTransitionType::Scenery;
     }
 
     auto supportImageTemplate = ImageId().WithRemap(0);
@@ -60,8 +60,9 @@ static void PaintSmallScenerySupports(
         supportImageTemplate = imageTemplate;
     }
 
-    auto supportType = (direction & 1) ? 1 : 0;
-    WoodenBSupportsPaintSetup(session, supportType, special, supportHeight, supportImageTemplate);
+    WoodenBSupportsPaintSetupRotated(
+        session, WoodenSupportType::Truss, WoodenSupportSubType::NeSw, direction, supportHeight, supportImageTemplate,
+        transitionType);
 }
 
 static void SetSupportHeights(