diff --git a/Userland/Applications/PixelPaint/Image.cpp b/Userland/Applications/PixelPaint/Image.cpp
index 7ce629a54a..7ca784a218 100644
--- a/Userland/Applications/PixelPaint/Image.cpp
+++ b/Userland/Applications/PixelPaint/Image.cpp
@@ -96,7 +96,7 @@ ErrorOr<NonnullRefPtr<Image>> Image::try_create_from_pixel_paint_json(JsonObject
             auto mask_base64_encoded = mask_object.as_string();
             auto mask_data = TRY(decode_base64(mask_base64_encoded));
             auto mask = TRY(try_decode_bitmap(mask_data));
-            layer->set_mask_bitmap(move(mask));
+            TRY(layer->try_set_bitmaps(layer->content_bitmap(), mask));
         }
 
         auto width = layer_object.get("width").to_i32();
@@ -485,10 +485,7 @@ void ImageUndoCommand::redo()
 void Image::flip(Gfx::Orientation orientation)
 {
     for (auto& layer : m_layers) {
-        auto flipped = layer.content_bitmap().flipped(orientation).release_value_but_fixme_should_propagate_errors();
-        layer.set_content_bitmap(*flipped);
-        layer.did_modify_bitmap(rect());
-        // FIXME: Respect mask
+        layer.flip(orientation);
     }
 
     did_change();
@@ -497,10 +494,7 @@ void Image::flip(Gfx::Orientation orientation)
 void Image::rotate(Gfx::RotationDirection direction)
 {
     for (auto& layer : m_layers) {
-        auto rotated = layer.content_bitmap().rotated(direction).release_value_but_fixme_should_propagate_errors();
-        layer.set_content_bitmap(*rotated);
-        layer.did_modify_bitmap(rect());
-        // FIXME: Respect mask
+        layer.rotate(direction);
     }
 
     m_size = { m_size.height(), m_size.width() };
@@ -510,10 +504,7 @@ void Image::rotate(Gfx::RotationDirection direction)
 void Image::crop(Gfx::IntRect const& cropped_rect)
 {
     for (auto& layer : m_layers) {
-        auto cropped = layer.content_bitmap().cropped(cropped_rect).release_value_but_fixme_should_propagate_errors();
-        layer.set_content_bitmap(*cropped);
-        layer.did_modify_bitmap(rect());
-        // FIXME: Respect mask
+        layer.crop(cropped_rect);
     }
 
     m_size = { cropped_rect.width(), cropped_rect.height() };
diff --git a/Userland/Applications/PixelPaint/Layer.cpp b/Userland/Applications/PixelPaint/Layer.cpp
index f3f5dc5e73..5298946c97 100644
--- a/Userland/Applications/PixelPaint/Layer.cpp
+++ b/Userland/Applications/PixelPaint/Layer.cpp
@@ -142,16 +142,42 @@ void Layer::erase_selection(Selection const& selection)
     did_modify_bitmap(translated_to_layer_space);
 }
 
-void Layer::set_content_bitmap(NonnullRefPtr<Gfx::Bitmap> bitmap)
+ErrorOr<void> Layer::try_set_bitmaps(NonnullRefPtr<Gfx::Bitmap> content, RefPtr<Gfx::Bitmap> mask)
 {
-    m_content_bitmap = move(bitmap);
+    if (mask && content->size() != mask->size())
+        return Error::from_string_literal("Layer content and mask must be same size"sv);
+
+    m_content_bitmap = move(content);
+    m_mask_bitmap = move(mask);
     update_cached_bitmap();
+    return {};
 }
 
-void Layer::set_mask_bitmap(NonnullRefPtr<Gfx::Bitmap> bitmap)
+void Layer::flip(Gfx::Orientation orientation)
 {
-    m_mask_bitmap = move(bitmap);
-    update_cached_bitmap();
+    m_content_bitmap = *m_content_bitmap->flipped(orientation).release_value_but_fixme_should_propagate_errors();
+    if (m_mask_bitmap)
+        m_mask_bitmap = *m_mask_bitmap->flipped(orientation).release_value_but_fixme_should_propagate_errors();
+
+    did_modify_bitmap();
+}
+
+void Layer::rotate(Gfx::RotationDirection direction)
+{
+    m_content_bitmap = *m_content_bitmap->rotated(direction).release_value_but_fixme_should_propagate_errors();
+    if (m_mask_bitmap)
+        m_mask_bitmap = *m_mask_bitmap->rotated(direction).release_value_but_fixme_should_propagate_errors();
+
+    did_modify_bitmap();
+}
+
+void Layer::crop(Gfx::IntRect const& rect)
+{
+    m_content_bitmap = *m_content_bitmap->cropped(rect).release_value_but_fixme_should_propagate_errors();
+    if (m_mask_bitmap)
+        m_mask_bitmap = *m_mask_bitmap->cropped(rect).release_value_but_fixme_should_propagate_errors();
+
+    did_modify_bitmap();
 }
 
 void Layer::update_cached_bitmap()
@@ -163,8 +189,9 @@ void Layer::update_cached_bitmap()
         return;
     }
 
-    if (m_content_bitmap.ptr() == m_cached_display_bitmap.ptr())
+    if (m_cached_display_bitmap.ptr() == m_content_bitmap.ptr() || m_cached_display_bitmap->size() != size()) {
         m_cached_display_bitmap = MUST(Gfx::Bitmap::try_create(Gfx::BitmapFormat::BGRA8888, size()));
+    }
 
     // FIXME: This can probably be done nicer
     m_cached_display_bitmap->fill(Color::Transparent);
diff --git a/Userland/Applications/PixelPaint/Layer.h b/Userland/Applications/PixelPaint/Layer.h
index b9197872c9..55a92d1ae0 100644
--- a/Userland/Applications/PixelPaint/Layer.h
+++ b/Userland/Applications/PixelPaint/Layer.h
@@ -53,8 +53,11 @@ public:
     String const& name() const { return m_name; }
     void set_name(String);
 
-    void set_content_bitmap(NonnullRefPtr<Gfx::Bitmap> bitmap);
-    void set_mask_bitmap(NonnullRefPtr<Gfx::Bitmap> bitmap);
+    void flip(Gfx::Orientation orientation);
+    void rotate(Gfx::RotationDirection direction);
+    void crop(Gfx::IntRect const& rect);
+
+    ErrorOr<void> try_set_bitmaps(NonnullRefPtr<Gfx::Bitmap> content, RefPtr<Gfx::Bitmap> mask);
 
     void did_modify_bitmap(Gfx::IntRect const& = {});