diff --git a/Userland/Applications/PixelPaint/BrushTool.cpp b/Userland/Applications/PixelPaint/BrushTool.cpp
index 5eb63bf338..7591506521 100644
--- a/Userland/Applications/PixelPaint/BrushTool.cpp
+++ b/Userland/Applications/PixelPaint/BrushTool.cpp
@@ -34,6 +34,14 @@ void BrushTool::on_mousedown(Layer* layer, MouseEvent& event)
     if (layer_event.button() != GUI::MouseButton::Left && layer_event.button() != GUI::MouseButton::Right)
         return;
 
+    if (layer_event.shift() && m_has_clicked) {
+        draw_line(layer->bitmap(), m_editor->color_for(layer_event), m_last_position, layer_event.position());
+        auto modified_rect = Gfx::IntRect::from_two_points(m_last_position, layer_event.position()).inflated(m_size * 2, m_size * 2);
+        layer->did_modify_bitmap(modified_rect);
+        m_last_position = layer_event.position();
+        return;
+    }
+
     const int first_draw_opacity = 10;
 
     for (int i = 0; i < first_draw_opacity; ++i)
@@ -41,6 +49,7 @@ void BrushTool::on_mousedown(Layer* layer, MouseEvent& event)
 
     layer->did_modify_bitmap(Gfx::IntRect::centered_on(layer_event.position(), Gfx::IntSize { m_size * 2, m_size * 2 }));
     m_last_position = layer_event.position();
+    m_has_clicked = true;
 }
 
 void BrushTool::on_mousemove(Layer* layer, MouseEvent& event)
diff --git a/Userland/Applications/PixelPaint/BrushTool.h b/Userland/Applications/PixelPaint/BrushTool.h
index 943988afff..0964d0d17e 100644
--- a/Userland/Applications/PixelPaint/BrushTool.h
+++ b/Userland/Applications/PixelPaint/BrushTool.h
@@ -26,6 +26,7 @@ private:
     int m_size { 20 };
     int m_hardness { 80 };
     bool m_was_drawing { false };
+    bool m_has_clicked { false };
     Gfx::IntPoint m_last_position;
 
     void draw_line(Gfx::Bitmap& bitmap, Gfx::Color const& color, Gfx::IntPoint const& start, Gfx::IntPoint const& end);