diff --git a/Userland/Applications/PixelPaint/Tools/LineTool.cpp b/Userland/Applications/PixelPaint/Tools/LineTool.cpp
index e520c2c9b1..c365d15620 100644
--- a/Userland/Applications/PixelPaint/Tools/LineTool.cpp
+++ b/Userland/Applications/PixelPaint/Tools/LineTool.cpp
@@ -22,19 +22,6 @@
 
 namespace PixelPaint {
 
-static Gfx::IntPoint constrain_line_angle(Gfx::IntPoint start_pos, Gfx::IntPoint end_pos, float angle_increment)
-{
-    float current_angle = AK::atan2<float>(end_pos.y() - start_pos.y(), end_pos.x() - start_pos.x()) + float { M_PI * 2 };
-
-    float constrained_angle = ((int)((current_angle + angle_increment / 2) / angle_increment)) * angle_increment;
-
-    auto diff = end_pos - start_pos;
-    float line_length = AK::hypot<float>(diff.x(), diff.y());
-
-    return { start_pos.x() + (int)(AK::cos(constrained_angle) * line_length),
-        start_pos.y() + (int)(AK::sin(constrained_angle) * line_length) };
-}
-
 void LineTool::on_mousedown(Layer* layer, MouseEvent& event)
 {
     if (!layer)
@@ -95,12 +82,10 @@ void LineTool::on_mousemove(Layer* layer, MouseEvent& event)
     if (m_drawing_button == GUI::MouseButton::None)
         return;
 
-    if (layer_event.shift()) {
-        constexpr auto ANGLE_STEP = M_PI / 8;
-        m_line_end_position = constrain_line_angle(m_drag_start_position, layer_event.position(), ANGLE_STEP);
-    } else {
+    if (layer_event.shift())
+        m_line_end_position = constrain_line_angle(m_drag_start_position, layer_event.position());
+    else
         m_line_end_position = layer_event.position();
-    }
 
     if (layer_event.alt()) {
         m_line_start_position = m_drag_start_position + (m_drag_start_position - m_line_end_position);
diff --git a/Userland/Applications/PixelPaint/Tools/PolygonalSelectTool.cpp b/Userland/Applications/PixelPaint/Tools/PolygonalSelectTool.cpp
index e3664f26b3..218d54322e 100644
--- a/Userland/Applications/PixelPaint/Tools/PolygonalSelectTool.cpp
+++ b/Userland/Applications/PixelPaint/Tools/PolygonalSelectTool.cpp
@@ -92,6 +92,8 @@ void PolygonalSelectTool::on_mousedown(Layer*, MouseEvent& event)
     m_selecting = true;
 
     auto new_point = event.layer_event().position();
+    if (!m_polygon_points.is_empty() && event.layer_event().shift())
+        new_point = Tool::constrain_line_angle(m_polygon_points.last(), new_point);
 
     // This point matches the first point exactly. Consider this polygon finished.
     if (m_polygon_points.size() > 0 && new_point == m_polygon_points.at(0)) {
@@ -115,8 +117,14 @@ void PolygonalSelectTool::on_mousedown(Layer*, MouseEvent& event)
 
 void PolygonalSelectTool::on_mousemove(Layer*, MouseEvent& event)
 {
-    if (m_selecting)
+    if (!m_selecting)
+        return;
+
+    if (event.layer_event().shift())
+        m_last_selecting_cursor_position = Tool::constrain_line_angle(m_polygon_points.last(), event.layer_event().position());
+    else
         m_last_selecting_cursor_position = event.layer_event().position();
+
     m_editor->update();
 }
 
diff --git a/Userland/Applications/PixelPaint/Tools/Tool.cpp b/Userland/Applications/PixelPaint/Tools/Tool.cpp
index a0e3e601f4..9ac6fb6169 100644
--- a/Userland/Applications/PixelPaint/Tools/Tool.cpp
+++ b/Userland/Applications/PixelPaint/Tools/Tool.cpp
@@ -70,4 +70,17 @@ Gfx::IntPoint Tool::editor_stroke_position(Gfx::IntPoint pixel_coords, int strok
     return position.to_type<int>();
 }
 
+Gfx::IntPoint Tool::constrain_line_angle(Gfx::IntPoint start_pos, Gfx::IntPoint end_pos, float angle_increment)
+{
+    float current_angle = AK::atan2<float>(end_pos.y() - start_pos.y(), end_pos.x() - start_pos.x()) + float { M_PI * 2 };
+
+    float constrained_angle = ((int)((current_angle + angle_increment / 2) / angle_increment)) * angle_increment;
+
+    auto diff = end_pos - start_pos;
+    float line_length = AK::hypot<float>(diff.x(), diff.y());
+
+    return { start_pos.x() + (int)(AK::cos(constrained_angle) * line_length),
+        start_pos.y() + (int)(AK::sin(constrained_angle) * line_length) };
+}
+
 }
diff --git a/Userland/Applications/PixelPaint/Tools/Tool.h b/Userland/Applications/PixelPaint/Tools/Tool.h
index 7a9430794f..b48744f84c 100644
--- a/Userland/Applications/PixelPaint/Tools/Tool.h
+++ b/Userland/Applications/PixelPaint/Tools/Tool.h
@@ -95,6 +95,8 @@ protected:
     void set_primary_slider(GUI::ValueSlider* primary) { m_primary_slider = primary; }
     void set_secondary_slider(GUI::ValueSlider* secondary) { m_secondary_slider = secondary; }
 
+    static Gfx::IntPoint constrain_line_angle(Gfx::IntPoint start_pos, Gfx::IntPoint end_pos, float angle_increment = M_PI / 8);
+
     GUI::ValueSlider* m_primary_slider { nullptr };
     GUI::ValueSlider* m_secondary_slider { nullptr };
 };