diff --git a/include/editor.h b/include/editor.h
index 033c267a..510d942e 100644
--- a/include/editor.h
+++ b/include/editor.h
@@ -21,6 +21,7 @@
 #include "mappixmapitem.h"
 #include "settings.h"
 #include "movablerect.h"
+#include "cursortilerect.h"
 
 class DraggablePixmapItem;
 class MetatilesPixmapItem;
@@ -96,7 +97,7 @@ public:
     QList<QGraphicsPixmapItem*> borderItems;
     QList<QGraphicsLineItem*> gridLines;
     MovableRect *playerViewRect = nullptr;
-    MovableRect *cursorMapTileRect = nullptr;
+    CursorTileRect *cursorMapTileRect = nullptr;
 
     QGraphicsScene *scene_metatiles = nullptr;
     QGraphicsScene *scene_current_metatile_selection = nullptr;
@@ -149,6 +150,9 @@ private:
     QString getMovementPermissionText(uint16_t collision, uint16_t elevation);
 
 private slots:
+    void onMapStartPaint(QGraphicsSceneMouseEvent *event, MapPixmapItem *item);
+    void onMapEndPaint(QGraphicsSceneMouseEvent *event, MapPixmapItem *item);
+    void setSmartPathCursorMode(QGraphicsSceneMouseEvent *event);
     void mouseEvent_map(QGraphicsSceneMouseEvent *event, MapPixmapItem *item);
     void mouseEvent_collision(QGraphicsSceneMouseEvent *event, CollisionPixmapItem *item);
     void onConnectionMoved(MapConnection*);
diff --git a/include/ui/cursortilerect.h b/include/ui/cursortilerect.h
new file mode 100644
index 00000000..4edbcae4
--- /dev/null
+++ b/include/ui/cursortilerect.h
@@ -0,0 +1,77 @@
+#ifndef CURSORTILERECT_H
+#define CURSORTILERECT_H
+
+#include <QGraphicsItem>
+#include <QPainter>
+#include <QRgb>
+
+class CursorTileRect : public QGraphicsItem
+{
+public:
+    CursorTileRect(bool *enabled, QRgb color);
+    QRectF boundingRect() const override
+    {
+        int width = this->width;
+        int height = this->height;
+        if (this->singleTileMode) {
+            width = 16;
+            height = 16;
+        } else if (!this->rightClickSelectionAnchored && this->smartPathMode && this->selectionHeight == 3 && this->selectionWidth == 3) {
+            width = 32;
+            height = 32;
+        }
+        qreal penWidth = 4;
+        return QRectF(-penWidth,
+                      -penWidth,
+                      width + penWidth * 2,
+                      height + penWidth * 2);
+    }
+
+    void paint(QPainter *painter, const QStyleOptionGraphicsItem *option,
+               QWidget *widget) override
+    {
+        int width = this->width;
+        int height = this->height;
+        if (this->singleTileMode) {
+            width = 16;
+            height = 16;
+        } else if (this->smartPathInEffect()) {
+            width = 32;
+            height = 32;
+        }
+
+        painter->setPen(this->color);
+        painter->drawRect(-1, -1, width + 2, height + 2);
+        painter->setPen(QColor(0, 0, 0));
+        painter->drawRect(-2, -2, width + 4, height + 4);
+        painter->drawRect(0, 0, width, height);
+    }
+    void initAnchor(int coordX, int coordY);
+    void stopAnchor();
+    void initRightClickSelectionAnchor(int coordX, int coordY);
+    void stopRightClickSelectionAnchor();
+    void setSmartPathMode();
+    bool getSmartPathMode() { return this->smartPathMode; }
+    void setSingleTileMode();
+    void stopSingleTileMode();
+    void setNormalPathMode();
+    void updateLocation(int x, int y);
+    void updateSelectionSize(int width, int height);
+    bool *enabled;
+private:
+    int width;
+    int height;
+    bool anchored;
+    bool rightClickSelectionAnchored;
+    bool smartPathMode;
+    bool singleTileMode;
+    int anchorCoordX;
+    int anchorCoordY;
+    int selectionWidth;
+    int selectionHeight;
+    QRgb color;
+    bool smartPathInEffect();
+};
+
+
+#endif // CURSORTILERECT_H
diff --git a/include/ui/mappixmapitem.h b/include/ui/mappixmapitem.h
index 4ab66b21..e5723890 100644
--- a/include/ui/mappixmapitem.h
+++ b/include/ui/mappixmapitem.h
@@ -43,6 +43,8 @@ private:
     static QList<int> smartPathTable;
 
 signals:
+    void startPaint(QGraphicsSceneMouseEvent *, MapPixmapItem *);
+    void endPaint(QGraphicsSceneMouseEvent *, MapPixmapItem *);
     void mouseEvent(QGraphicsSceneMouseEvent *, MapPixmapItem *);
     void hoveredMapMetatileChanged(int x, int y);
     void hoveredMapMetatileCleared();
diff --git a/porymap.pro b/porymap.pro
index 1d22850a..fb81f994 100644
--- a/porymap.pro
+++ b/porymap.pro
@@ -32,6 +32,7 @@ SOURCES += src/core/block.cpp \
     src/ui/collisionpixmapitem.cpp \
     src/ui/connectionpixmapitem.cpp \
     src/ui/currentselectedmetatilespixmapitem.cpp \
+    src/ui/cursortilerect.cpp \
     src/ui/eventpropertiesframe.cpp \
     src/ui/filterchildrenproxymodel.cpp \
     src/ui/graphicsview.cpp \
@@ -79,6 +80,7 @@ HEADERS  += include/core/block.h \
     include/ui/collisionpixmapitem.h \
     include/ui/connectionpixmapitem.h \
     include/ui/currentselectedmetatilespixmapitem.h \
+    include/ui/cursortilerect.h \
     include/ui/eventpropertiesframe.h \
     include/ui/filterchildrenproxymodel.h \
     include/ui/graphicsview.h \
diff --git a/src/editor.cpp b/src/editor.cpp
index 1571d29a..72960f95 100644
--- a/src/editor.cpp
+++ b/src/editor.cpp
@@ -18,7 +18,7 @@ Editor::Editor(Ui::MainWindow* ui)
     this->selected_events = new QList<DraggablePixmapItem*>;
     this->settings = new Settings();
     this->playerViewRect = new MovableRect(&this->settings->playerViewRectEnabled, 30 * 8, 20 * 8, qRgb(255, 255, 255));
-    this->cursorMapTileRect = new MovableRect(&this->settings->cursorTileRectEnabled, 16, 16, qRgb(255, 255, 255));
+    this->cursorMapTileRect = new CursorTileRect(&this->settings->cursorTileRectEnabled, qRgb(255, 255, 255));
 }
 
 void Editor::saveProject() {
@@ -36,7 +36,7 @@ void Editor::save() {
 }
 
 void Editor::undo() {
-    if (current_view) {
+    if (current_view && map_item->paintingEnabled) {
         map->undo();
         map_item->draw();
         collision_item->draw();
@@ -44,7 +44,7 @@ void Editor::undo() {
 }
 
 void Editor::redo() {
-    if (current_view) {
+    if (current_view && map_item->paintingEnabled) {
         map->redo();
         map_item->draw();
         collision_item->draw();
@@ -75,6 +75,7 @@ void Editor::setEditingMap() {
     }
     setBorderItemsVisible(ui->checkBox_ToggleBorder->isChecked());
     setConnectionItemsVisible(false);
+    this->cursorMapTileRect->stopSingleTileMode();
 }
 
 void Editor::setEditingCollision() {
@@ -94,6 +95,7 @@ void Editor::setEditingCollision() {
     }
     setBorderItemsVisible(ui->checkBox_ToggleBorder->isChecked());
     setConnectionItemsVisible(false);
+    this->cursorMapTileRect->setSingleTileMode();
 }
 
 void Editor::setEditingObjects() {
@@ -111,6 +113,7 @@ void Editor::setEditingObjects() {
     }
     setBorderItemsVisible(ui->checkBox_ToggleBorder->isChecked());
     setConnectionItemsVisible(false);
+    this->cursorMapTileRect->setSingleTileMode();
 }
 
 void Editor::setEditingConnections() {
@@ -139,6 +142,7 @@ void Editor::setEditingConnections() {
     }
     setBorderItemsVisible(true, 0.4);
     setConnectionItemsVisible(true);
+    this->cursorMapTileRect->setSingleTileMode();
 }
 
 void Editor::setDiveEmergeControls() {
@@ -350,6 +354,8 @@ void Editor::onHoveredMetatileSelectionCleared() {
 }
 
 void Editor::onSelectedMetatilesChanged() {
+    QPoint size = this->metatile_selector_item->getSelectionDimensions();
+    this->cursorMapTileRect->updateSelectionSize(size.x(), size.y());
     this->redrawCurrentMetatilesSelection();
 }
 
@@ -441,7 +447,7 @@ bool Editor::setMap(QString map_name) {
     return true;
 }
 
-void Editor::mouseEvent_map(QGraphicsSceneMouseEvent *event, MapPixmapItem *item) {
+void Editor::onMapStartPaint(QGraphicsSceneMouseEvent *event, MapPixmapItem *item) {
     if (!item->paintingEnabled) {
         return;
     }
@@ -449,8 +455,36 @@ void Editor::mouseEvent_map(QGraphicsSceneMouseEvent *event, MapPixmapItem *item
     QPointF pos = event->pos();
     int x = static_cast<int>(pos.x()) / 16;
     int y = static_cast<int>(pos.y()) / 16;
-    this->playerViewRect->updateLocation(x, y);
-    this->cursorMapTileRect->updateLocation(x, y);
+    if (event->buttons() & Qt::RightButton && (map_edit_mode == "paint" || map_edit_mode == "fill")) {
+        this->cursorMapTileRect->initRightClickSelectionAnchor(x, y);
+    } else {
+        this->cursorMapTileRect->initAnchor(x, y);
+    }
+}
+
+void Editor::onMapEndPaint(QGraphicsSceneMouseEvent *event, MapPixmapItem *item) {
+    if (!item->paintingEnabled) {
+        return;
+    }
+    this->cursorMapTileRect->stopRightClickSelectionAnchor();
+    this->cursorMapTileRect->stopAnchor();
+}
+
+void Editor::setSmartPathCursorMode(QGraphicsSceneMouseEvent *event)
+{
+    bool smartPathsEnabled = event->modifiers() & Qt::ShiftModifier;
+    if (smartPathsEnabled || settings->smartPathsEnabled) {
+        this->cursorMapTileRect->setSmartPathMode();
+    } else {
+        this->cursorMapTileRect->setNormalPathMode();
+    }
+}
+
+void Editor::mouseEvent_map(QGraphicsSceneMouseEvent *event, MapPixmapItem *item) {
+    if (!item->paintingEnabled) {
+        return;
+    }
+
     if (map_edit_mode == "paint") {
         if (event->buttons() & Qt::RightButton) {
             item->updateMetatileSelection(event);
@@ -461,6 +495,7 @@ void Editor::mouseEvent_map(QGraphicsSceneMouseEvent *event, MapPixmapItem *item
                 item->floodFill(event);
             }
         } else {
+            this->setSmartPathCursorMode(event);
             item->paint(event);
         }
     } else if (map_edit_mode == "select") {
@@ -483,7 +518,14 @@ void Editor::mouseEvent_map(QGraphicsSceneMouseEvent *event, MapPixmapItem *item
     } else if (map_edit_mode == "shift") {
         item->shift(event);
     }
+
+    QPointF pos = event->pos();
+    int x = static_cast<int>(pos.x()) / 16;
+    int y = static_cast<int>(pos.y()) / 16;
+    this->playerViewRect->updateLocation(x, y);
+    this->cursorMapTileRect->updateLocation(x, y);
 }
+
 void Editor::mouseEvent_collision(QGraphicsSceneMouseEvent *event, CollisionPixmapItem *item) {
     if (!item->paintingEnabled) {
         return;
@@ -592,6 +634,10 @@ void Editor::displayMapMetatiles() {
     map_item = new MapPixmapItem(map, this->metatile_selector_item, this->settings);
     connect(map_item, SIGNAL(mouseEvent(QGraphicsSceneMouseEvent*,MapPixmapItem*)),
             this, SLOT(mouseEvent_map(QGraphicsSceneMouseEvent*,MapPixmapItem*)));
+    connect(map_item, SIGNAL(startPaint(QGraphicsSceneMouseEvent*,MapPixmapItem*)),
+            this, SLOT(onMapStartPaint(QGraphicsSceneMouseEvent*,MapPixmapItem*)));
+    connect(map_item, SIGNAL(endPaint(QGraphicsSceneMouseEvent*,MapPixmapItem*)),
+            this, SLOT(onMapEndPaint(QGraphicsSceneMouseEvent*,MapPixmapItem*)));
     connect(map_item, SIGNAL(hoveredMapMetatileChanged(int, int)),
             this, SLOT(onHoveredMapMetatileChanged(int, int)));
     connect(map_item, SIGNAL(hoveredMapMetatileCleared()),
diff --git a/src/mainwindow.cpp b/src/mainwindow.cpp
index 054f0e00..8759c319 100644
--- a/src/mainwindow.cpp
+++ b/src/mainwindow.cpp
@@ -1623,6 +1623,7 @@ void MainWindow::on_toolButton_Paint_clicked()
 {
     editor->map_edit_mode = "paint";
     editor->settings->mapCursor = QCursor(QPixmap(":/icons/pencil_cursor.ico"), 10, 10);
+    editor->cursorMapTileRect->stopSingleTileMode();
 
     ui->scrollArea->setHorizontalScrollBarPolicy(Qt::ScrollBarAsNeeded);
     ui->scrollArea->setVerticalScrollBarPolicy(Qt::ScrollBarAsNeeded);
@@ -1635,6 +1636,7 @@ void MainWindow::on_toolButton_Select_clicked()
 {
     editor->map_edit_mode = "select";
     editor->settings->mapCursor = QCursor(QPixmap(":/icons/cursor.ico"), 0, 0);
+    editor->cursorMapTileRect->setSingleTileMode();
 
     ui->scrollArea->setHorizontalScrollBarPolicy(Qt::ScrollBarAsNeeded);
     ui->scrollArea->setVerticalScrollBarPolicy(Qt::ScrollBarAsNeeded);
@@ -1647,6 +1649,7 @@ void MainWindow::on_toolButton_Fill_clicked()
 {
     editor->map_edit_mode = "fill";
     editor->settings->mapCursor = QCursor(QPixmap(":/icons/fill_color_cursor.ico"), 10, 10);
+    editor->cursorMapTileRect->setSingleTileMode();
 
     ui->scrollArea->setHorizontalScrollBarPolicy(Qt::ScrollBarAsNeeded);
     ui->scrollArea->setVerticalScrollBarPolicy(Qt::ScrollBarAsNeeded);
@@ -1659,6 +1662,7 @@ void MainWindow::on_toolButton_Dropper_clicked()
 {
     editor->map_edit_mode = "pick";
     editor->settings->mapCursor = QCursor(QPixmap(":/icons/pipette_cursor.ico"), 10, 10);
+    editor->cursorMapTileRect->setSingleTileMode();
 
     ui->scrollArea->setHorizontalScrollBarPolicy(Qt::ScrollBarAsNeeded);
     ui->scrollArea->setVerticalScrollBarPolicy(Qt::ScrollBarAsNeeded);
@@ -1671,6 +1675,7 @@ void MainWindow::on_toolButton_Move_clicked()
 {
     editor->map_edit_mode = "move";
     editor->settings->mapCursor = QCursor(QPixmap(":/icons/move.ico"), 7, 7);
+    editor->cursorMapTileRect->setSingleTileMode();
 
     ui->scrollArea->setHorizontalScrollBarPolicy(Qt::ScrollBarAlwaysOff);
     ui->scrollArea->setVerticalScrollBarPolicy(Qt::ScrollBarAlwaysOff);
@@ -1683,6 +1688,7 @@ void MainWindow::on_toolButton_Shift_clicked()
 {
     editor->map_edit_mode = "shift";
     editor->settings->mapCursor = QCursor(QPixmap(":/icons/shift_cursor.ico"), 10, 10);
+    editor->cursorMapTileRect->setSingleTileMode();
 
     ui->scrollArea->setHorizontalScrollBarPolicy(Qt::ScrollBarAsNeeded);
     ui->scrollArea->setVerticalScrollBarPolicy(Qt::ScrollBarAsNeeded);
@@ -1837,7 +1843,13 @@ void MainWindow::on_pushButton_clicked()
 
 void MainWindow::on_checkBox_smartPaths_stateChanged(int selected)
 {
-    editor->settings->smartPathsEnabled = selected == Qt::Checked;
+    bool enabled = selected == Qt::Checked;
+    editor->settings->smartPathsEnabled = enabled;
+    if (enabled) {
+        editor->cursorMapTileRect->setSmartPathMode();
+    } else {
+        editor->cursorMapTileRect->setNormalPathMode();
+    }
 }
 
 void MainWindow::on_checkBox_ToggleBorder_stateChanged(int selected)
diff --git a/src/ui/cursortilerect.cpp b/src/ui/cursortilerect.cpp
new file mode 100644
index 00000000..8881e7b6
--- /dev/null
+++ b/src/ui/cursortilerect.cpp
@@ -0,0 +1,100 @@
+#include "cursortilerect.h"
+#include "log.h"
+
+CursorTileRect::CursorTileRect(bool *enabled, QRgb color)
+{
+    this->enabled = enabled;
+    this->color = color;
+    this->width = 16;
+    this->height = 16;
+    this->smartPathMode = false;
+    this->singleTileMode = false;
+    this->anchored = false;
+    this->rightClickSelectionAnchored = false;
+    this->anchorCoordX = 0;
+    this->anchorCoordY = 0;
+    this->selectionWidth = 1;
+    this->selectionHeight = 1;
+}
+
+void CursorTileRect::initAnchor(int coordX, int coordY)
+{
+    this->anchorCoordX = coordX;
+    this->anchorCoordY = coordY;
+    this->anchored = true;
+}
+
+void CursorTileRect::stopAnchor()
+{
+    this->anchored = false;
+}
+
+void CursorTileRect::initRightClickSelectionAnchor(int coordX, int coordY)
+{
+    this->anchorCoordX = coordX;
+    this->anchorCoordY = coordY;
+    this->rightClickSelectionAnchored = true;
+}
+
+void CursorTileRect::stopRightClickSelectionAnchor()
+{
+    this->rightClickSelectionAnchored = false;
+}
+
+void CursorTileRect::updateSelectionSize(int width, int height)
+{
+    this->selectionWidth = width;
+    this->selectionHeight = height;
+    this->width = width * 16;
+    this->height = height * 16;
+    this->prepareGeometryChange();
+    this->update();
+}
+
+void CursorTileRect::setSmartPathMode()
+{
+    this->smartPathMode = true;
+}
+
+void CursorTileRect::setSingleTileMode()
+{
+    this->singleTileMode = true;
+}
+
+void CursorTileRect::stopSingleTileMode()
+{
+    this->singleTileMode = false;
+}
+
+void CursorTileRect::setNormalPathMode()
+{
+    this->smartPathMode = false;
+}
+
+bool CursorTileRect::smartPathInEffect()
+{
+    return !this->rightClickSelectionAnchored && this->smartPathMode && this->selectionHeight == 3 && this->selectionWidth == 3;
+}
+
+void CursorTileRect::updateLocation(int coordX, int coordY)
+{
+    if (!this->singleTileMode) {
+        if (this->rightClickSelectionAnchored) {
+            coordX = qMin(coordX, this->anchorCoordX);
+            coordY = qMin(coordY, this->anchorCoordY);
+        }
+        else if (this->anchored && !this->smartPathInEffect()) {
+            int xDiff = coordX - this->anchorCoordX;
+            int yDiff = coordY - this->anchorCoordY;
+            if (xDiff < 0 && xDiff % this->selectionWidth != 0) xDiff -= this->selectionWidth;
+            if (yDiff < 0 && yDiff % this->selectionHeight != 0) yDiff -= this->selectionHeight;
+
+            coordX = this->anchorCoordX + (xDiff / this->selectionWidth) * this->selectionWidth;
+            coordY = this->anchorCoordY + (yDiff / this->selectionHeight) * this->selectionHeight;
+        }
+    }
+
+    this->setX(coordX * 16);
+    this->setY(coordY * 16);
+    this->setVisible(*this->enabled);
+}
diff --git a/src/ui/mappixmapitem.cpp b/src/ui/mappixmapitem.cpp
index 0c7571bf..758b6802 100644
--- a/src/ui/mappixmapitem.cpp
+++ b/src/ui/mappixmapitem.cpp
@@ -515,6 +515,7 @@ void MapPixmapItem::mousePressEvent(QGraphicsSceneMouseEvent *event) {
     int y = static_cast<int>(pos.y()) / 16;
     this->paint_tile_initial_x = x;
     this->paint_tile_initial_y = y;
+    emit startPaint(event, this);
     emit mouseEvent(event, this);
 }
 void MapPixmapItem::mouseMoveEvent(QGraphicsSceneMouseEvent *event) {
@@ -524,5 +525,6 @@ void MapPixmapItem::mouseMoveEvent(QGraphicsSceneMouseEvent *event) {
     emit mouseEvent(event, this);
 }
 void MapPixmapItem::mouseReleaseEvent(QGraphicsSceneMouseEvent *event) {
+    emit endPaint(event, this);
     emit mouseEvent(event, this);
 }