diff --git a/src/app/tools/controller.h b/src/app/tools/controller.h
index 0ec00bfed..dcd0f0ab1 100644
--- a/src/app/tools/controller.h
+++ b/src/app/tools/controller.h
@@ -8,6 +8,7 @@
 #define APP_TOOLS_CONTROLLER_H_INCLUDED
 #pragma once
 
+#include "app/tools/trace_policy.h"
 #include "gfx/point.h"
 
 #include <string>
@@ -28,6 +29,8 @@ namespace app {
       virtual bool isFreehand() { return false; }
       virtual bool isOnePoint() { return false; }
 
+      virtual void prepareController(ToolLoop* loop) { }
+
       // Called when the user starts drawing and each time a new button is
       // pressed. The controller could be sure that this method is called
       // at least one time. The point is a position relative to sprite
@@ -47,6 +50,13 @@ namespace app {
       // Last point used by this controller, useful to save the last
       // point of a freehand tool.
       virtual gfx::Point getLastPoint() const { return gfx::Point(0, 0); }
+
+      // Special trace policy that can change in the middle of the
+      // ToolLoop. This is for LineFreehandController which uses a
+      // TracePolicy::Last for TwoPoints controller (Line-like tool)
+      // and then a TracePolicy::Accumulate for freehand (Pencil tool).
+      virtual bool handleTracePolicy() const { return false; }
+      virtual TracePolicy getTracePolicy() const { return TracePolicy::Accumulate; }
     };
 
   } // namespace tools
diff --git a/src/app/tools/controllers.h b/src/app/tools/controllers.h
index b2b2a28db..5518da79f 100644
--- a/src/app/tools/controllers.h
+++ b/src/app/tools/controllers.h
@@ -99,6 +99,10 @@ private:
 // Controls clicks for tools like line
 class TwoPointsController : public MoveOriginCapability {
 public:
+  TwoPointsController(const bool enableModifiers)
+    : m_enableModifiers(enableModifiers) {
+  }
+
   void pressButton(Stroke& stroke, const Point& point) override {
     MoveOriginCapability::pressButton(stroke, point);
 
@@ -122,7 +126,8 @@ public:
 
     stroke[1] = point;
 
-    if (int(loop->getModifiers()) & int(ToolLoopModifiers::kSquareAspect)) {
+    if (m_enableModifiers &&
+        (int(loop->getModifiers()) & int(ToolLoopModifiers::kSquareAspect))) {
       int dx = stroke[1].x - m_first.x;
       int dy = stroke[1].y - m_first.y;
       int minsize = MIN(ABS(dx), ABS(dy));
@@ -167,7 +172,8 @@ public:
 
     stroke[0] = m_first;
 
-    if (int(loop->getModifiers()) & int(ToolLoopModifiers::kFromCenter)) {
+    if (m_enableModifiers &&
+        (int(loop->getModifiers()) & int(ToolLoopModifiers::kFromCenter))) {
       int rx = stroke[1].x - m_first.x;
       int ry = stroke[1].y - m_first.y;
       stroke[0].x = m_first.x - rx;
@@ -226,6 +232,7 @@ private:
   }
 
   Point m_first;
+  bool m_enableModifiers;
 };
 
 // Controls clicks for tools like polygon
@@ -379,5 +386,64 @@ private:
   int m_clickCounter;
 };
 
+// Controls the shift+click to draw a two-points line and then
+// freehand until the mouse is released.
+class LineFreehandController : public Controller {
+public:
+  LineFreehandController() : m_twoPoints(false) { }
+
+  bool isFreehand() override { return true; }
+
+  gfx::Point getLastPoint() const override { return m_last; }
+
+  void prepareController(ToolLoop* loop) override {
+    m_controller = nullptr;
+  }
+
+  void pressButton(Stroke& stroke, const Point& point) override {
+    m_last = point;
+
+    if (m_controller == nullptr)
+      m_controller = &m_twoPoints;
+    else if (m_controller == &m_twoPoints) {
+      m_controller = &m_freehand;
+      return;                   // Don't send first pressButton() click to the freehand controller
+    }
+
+    m_controller->pressButton(stroke, point);
+  }
+
+  bool releaseButton(Stroke& stroke, const Point& point) override {
+    return false;
+  }
+
+  void movement(ToolLoop* loop, Stroke& stroke, const Point& point) override {
+    m_last = point;
+    m_controller->movement(loop, stroke, point);
+  }
+
+  void getStrokeToInterwine(const Stroke& input, Stroke& output) override {
+    m_controller->getStrokeToInterwine(input, output);
+  }
+
+  void getStatusBarText(const Stroke& stroke, std::string& text) override {
+    m_controller->getStatusBarText(stroke, text);
+  }
+
+  bool handleTracePolicy() const override {
+    return (m_controller == &m_twoPoints);
+  }
+
+  TracePolicy getTracePolicy() const override {
+    return TracePolicy::Last;
+  }
+
+private:
+  Point m_last;
+  TwoPointsController m_twoPoints;
+  FreehandController m_freehand;
+  Controller* m_controller;
+};
+
 } // namespace tools
 } // namespace app
diff --git a/src/app/tools/tool_box.cpp b/src/app/tools/tool_box.cpp
index b45a6c92e..c4b32e47a 100644
--- a/src/app/tools/tool_box.cpp
+++ b/src/app/tools/tool_box.cpp
@@ -69,6 +69,13 @@ const char* WellKnownInks::MoveSlice = "move_slice";
 const char* WellKnownInks::Blur = "blur";
 const char* WellKnownInks::Jumble = "jumble";
 
+const char* WellKnownControllers::Freehand = "freehand";
+const char* WellKnownControllers::PointByPoint = "point_by_point";
+const char* WellKnownControllers::OnePoints = "one_point";
+const char* WellKnownControllers::TwoPoints = "two_points";
+const char* WellKnownControllers::FourPoints = "four_points";
+const char* WellKnownControllers::LineFreehand = "line_freehand";
+
 const char* WellKnownIntertwiners::None = "none";
 const char* WellKnownIntertwiners::FirstPoint = "first_point";
 const char* WellKnownIntertwiners::AsLines = "as_lines";
@@ -105,11 +112,12 @@ ToolBox::ToolBox()
   m_inks[WellKnownInks::Blur]            = new BlurInk();
   m_inks[WellKnownInks::Jumble]          = new JumbleInk();
 
-  m_controllers["freehand"]              = new FreehandController();
-  m_controllers["point_by_point"]        = new PointByPointController();
-  m_controllers["one_point"]             = new OnePointController();
-  m_controllers["two_points"]            = new TwoPointsController();
-  m_controllers["four_points"]           = new FourPointsController();
+  m_controllers[WellKnownControllers::Freehand] = new FreehandController();
+  m_controllers[WellKnownControllers::PointByPoint] = new PointByPointController();
+  m_controllers[WellKnownControllers::OnePoints] = new OnePointController();
+  m_controllers[WellKnownControllers::TwoPoints] = new TwoPointsController(true);
+  m_controllers[WellKnownControllers::FourPoints] = new FourPointsController();
+  m_controllers[WellKnownControllers::LineFreehand] = new LineFreehandController();
 
   m_pointshapers[WellKnownPointShapes::None] = new NonePointShape();
   m_pointshapers[WellKnownPointShapes::Pixel] = new PixelPointShape();
@@ -161,6 +169,11 @@ Ink* ToolBox::getInkById(const std::string& id)
   return m_inks[id];
 }
 
+Controller* ToolBox::getControllerById(const std::string& id)
+{
+  return m_controllers[id];
+}
+
 Intertwine* ToolBox::getIntertwinerById(const std::string& id)
 {
   return m_intertwiners[id];
diff --git a/src/app/tools/tool_box.h b/src/app/tools/tool_box.h
index 22d983bef..f40f687d2 100644
--- a/src/app/tools/tool_box.h
+++ b/src/app/tools/tool_box.h
@@ -52,6 +52,15 @@ namespace app {
       extern const char* Jumble;
     };
 
+    namespace WellKnownControllers {
+      extern const char* Freehand;
+      extern const char* PointByPoint;
+      extern const char* OnePoints;
+      extern const char* TwoPoints;
+      extern const char* FourPoints;
+      extern const char* LineFreehand;
+    };
+
     namespace WellKnownIntertwiners {
       extern const char* None;
       extern const char* FirstPoint;
@@ -92,6 +101,7 @@ namespace app {
 
       Tool* getToolById(const std::string& id);
       Ink* getInkById(const std::string& id);
+      Controller* getControllerById(const std::string& id);
       Intertwine* getIntertwinerById(const std::string& id);
       PointShape* getPointShapeById(const std::string& id);
       int getGroupsCount() const { return m_groups.size(); }
diff --git a/src/app/tools/tool_loop_manager.cpp b/src/app/tools/tool_loop_manager.cpp
index 42739d5a0..f7d69ee0d 100644
--- a/src/app/tools/tool_loop_manager.cpp
+++ b/src/app/tools/tool_loop_manager.cpp
@@ -54,6 +54,7 @@ void ToolLoopManager::prepareLoop(const Pointer& pointer)
 
   // Prepare the ink
   m_toolLoop->getInk()->prepareInk(m_toolLoop);
+  m_toolLoop->getController()->prepareController(m_toolLoop);
   m_toolLoop->getIntertwine()->prepareIntertwine();
   m_toolLoop->getPointShape()->preparePointShape(m_toolLoop);
 }
diff --git a/src/app/ui/editor/drawing_state.cpp b/src/app/ui/editor/drawing_state.cpp
index 2ac65f43b..e23db05bf 100644
--- a/src/app/ui/editor/drawing_state.cpp
+++ b/src/app/ui/editor/drawing_state.cpp
@@ -39,10 +39,13 @@ namespace app {
 
 using namespace ui;
 
-DrawingState::DrawingState(tools::ToolLoop* toolLoop)
-  : m_toolLoop(toolLoop)
+DrawingState::DrawingState(tools::ToolLoop* toolLoop,
+                           const DrawingType type)
+  : m_type(type)
+  , m_toolLoop(toolLoop)
   , m_toolLoopManager(new tools::ToolLoopManager(toolLoop))
   , m_mouseMoveReceived(false)
+  , m_mousePressedReceived(false)
 {
 }
 
@@ -51,7 +54,8 @@ DrawingState::~DrawingState()
   destroyLoop(nullptr);
 }
 
-void DrawingState::initToolLoop(Editor* editor, MouseMessage* msg)
+void DrawingState::initToolLoop(Editor* editor,
+                                const tools::Pointer& pointer)
 {
   // Prepare preview image (the destination image will be our preview
   // in the tool-loop time, so we can see what we are drawing)
@@ -65,35 +69,18 @@ void DrawingState::initToolLoop(Editor* editor, MouseMessage* msg)
      static_cast<LayerImage*>(m_toolLoop->getLayer())->blendMode():
      BlendMode::NEG_BW));
 
-  tools::Pointer pointer;
-  bool movement = false;
-
-  if (m_toolLoop->getController()->isFreehand() &&
-      m_toolLoop->getInk()->isPaint() &&
-      (editor->getCustomizationDelegate()
-         ->getPressedKeyAction(KeyContext::FreehandTool) & KeyAction::StraightLineFromLastPoint) == KeyAction::StraightLineFromLastPoint &&
-      editor->document()->lastDrawingPoint() != app::Document::NoLastDrawingPoint()) {
-    pointer = tools::Pointer(editor->document()->lastDrawingPoint(),
-                             button_from_msg(msg));
-    movement = true;
-  }
-  else {
-    pointer = pointer_from_msg(editor, msg);
-  }
-
   m_toolLoopManager->prepareLoop(pointer);
   m_toolLoopManager->pressButton(pointer);
 
-  // This first movement is done when the user pressed Shift+click in
-  // a freehand tool to draw a straight line.
-  if (movement) {
-    pointer = pointer_from_msg(editor, msg);
-    m_toolLoopManager->movement(pointer);
-  }
-
   editor->captureMouse();
 }
 
+void DrawingState::sendMovementToToolLoop(const tools::Pointer& pointer)
+{
+  ASSERT(m_toolLoopManager);
+  m_toolLoopManager->movement(pointer);
+}
+
 void DrawingState::notifyToolLoopModifiersChange(Editor* editor)
 {
   if (!m_toolLoopManager->isCanceled())
@@ -105,6 +92,8 @@ bool DrawingState::onMouseDown(Editor* editor, MouseMessage* msg)
   // Drawing loop
   ASSERT(m_toolLoopManager != NULL);
 
+  m_mousePressedReceived = true;
+
   // Notify the mouse button down to the tool loop manager.
   m_toolLoopManager->pressButton(pointer_from_msg(editor, msg));
 
@@ -195,8 +184,15 @@ bool DrawingState::onKeyDown(Editor* editor, KeyMessage* msg)
 
 bool DrawingState::onKeyUp(Editor* editor, KeyMessage* msg)
 {
-  if (msg->scancode() == ui::kKeyEsc)
+  // Cancel loop pressing Esc key...
+  if (msg->scancode() == ui::kKeyEsc ||
+      // Cancel "Shift on freehand" line preview when the Shift key is
+      // released and the user didn't press the mouse button..
+      (m_type == DrawingType::LineFreehand &&
+       !m_mousePressedReceived &&
+       !editor->startStraightLineWithFreehandTool())) {
     m_toolLoop->cancel();
+  }
 
   // The user might have canceled the tool loop pressing the 'Esc' key.
   destroyLoopIfCanceled(editor);
diff --git a/src/app/ui/editor/drawing_state.h b/src/app/ui/editor/drawing_state.h
index 20759e9f1..37bb55363 100644
--- a/src/app/ui/editor/drawing_state.h
+++ b/src/app/ui/editor/drawing_state.h
@@ -1,5 +1,5 @@
 // Aseprite
-// Copyright (C) 2001-2016  David Capello
+// Copyright (C) 2001-2017  David Capello
 //
 // This program is distributed under the terms of
 // the End-User License Agreement for Aseprite.
@@ -12,13 +12,15 @@
 
 namespace app {
   namespace tools {
+    class Pointer;
     class ToolLoop;
     class ToolLoopManager;
   }
 
   class DrawingState : public StandbyState {
   public:
-    DrawingState(tools::ToolLoop* loop);
+    DrawingState(tools::ToolLoop* loop,
+                 const DrawingType type);
     virtual ~DrawingState();
     virtual bool onMouseDown(Editor* editor, ui::MouseMessage* msg) override;
     virtual bool onMouseUp(Editor* editor, ui::MouseMessage* msg) override;
@@ -33,13 +35,21 @@ namespace app {
     // already drawing (viewing the real trace).
     virtual bool requireBrushPreview() override { return false; }
 
-    void initToolLoop(Editor* editor, ui::MouseMessage* msg);
+    void initToolLoop(Editor* editor,
+                      const tools::Pointer& pointer);
+
+    // Used to send a movement() to the ToolLoopManager when
+    // Shift+brush tool is used to paint a line.
+    void sendMovementToToolLoop(const tools::Pointer& pointer);
+
     void notifyToolLoopModifiersChange(Editor* editor);
 
   private:
     void destroyLoopIfCanceled(Editor* editor);
     void destroyLoop(Editor* editor);
 
+    DrawingType m_type;
+
     // The tool-loop.
     tools::ToolLoop* m_toolLoop;
 
@@ -55,6 +65,12 @@ namespace app {
     // DrawingState. It's used to restore the last drawing position in
     // case this stroke is canceled.
     gfx::Point m_lastPoint;
+
+    // Used to know if the button was pressed after the DrawingState
+    // was initialized. In this way we can cancel the ToolLoop if the
+    // Shift press is used to draw a line, but then released without a
+    // mouse click.
+    bool m_mousePressedReceived;
   };
 
 } // namespace app
diff --git a/src/app/ui/editor/editor.cpp b/src/app/ui/editor/editor.cpp
index c0ca4908e..fe01cc439 100644
--- a/src/app/ui/editor/editor.cpp
+++ b/src/app/ui/editor/editor.cpp
@@ -24,6 +24,7 @@
 #include "app/modules/palettes.h"
 #include "app/pref/preferences.h"
 #include "app/tools/active_tool.h"
+#include "app/tools/controller.h"
 #include "app/tools/ink.h"
 #include "app/tools/tool.h"
 #include "app/tools/tool_box.h"
@@ -59,6 +60,7 @@
 
 #include <cmath>
 #include <cstdio>
+#include <limits>
 
 namespace app {
 
@@ -1512,6 +1514,18 @@ app::Color Editor::getColorByPosition(const gfx::Point& mousePos)
     return app::Color::fromMask();
 }
 
+bool Editor::startStraightLineWithFreehandTool()
+{
+  tools::Tool* tool = App::instance()->activeToolManager()->selectedTool();
+  return
+    (tool &&
+     tool->getController(0)->isFreehand() &&
+     tool->getInk(0)->isPaint() &&
+     (getCustomizationDelegate()
+      ->getPressedKeyAction(KeyContext::FreehandTool) & KeyAction::StraightLineFromLastPoint) == KeyAction::StraightLineFromLastPoint &&
+     document()->lastDrawingPoint() != app::Document::NoLastDrawingPoint());
+}
+
 //////////////////////////////////////////////////////////////////////
 // Message handler for the editor
 
diff --git a/src/app/ui/editor/editor.h b/src/app/ui/editor/editor.h
index a8480937d..392b7555b 100644
--- a/src/app/ui/editor/editor.h
+++ b/src/app/ui/editor/editor.h
@@ -254,6 +254,10 @@ namespace app {
     void setTagFocusBand(int value) { m_tagFocusBand = value; }
     int tagFocusBand() const { return m_tagFocusBand; }
 
+    // Returns true if the Shift key to draw straight lines with a
+    // freehand tool is pressed.
+    bool startStraightLineWithFreehandTool();
+
   protected:
     bool onProcessMessage(ui::Message* msg) override;
     void onSizeHint(ui::SizeHintEvent& ev) override;
diff --git a/src/app/ui/editor/standby_state.cpp b/src/app/ui/editor/standby_state.cpp
index 97a2dcf77..3618e230a 100644
--- a/src/app/ui/editor/standby_state.cpp
+++ b/src/app/ui/editor/standby_state.cpp
@@ -28,6 +28,7 @@
 #include "app/ui/editor/drawing_state.h"
 #include "app/ui/editor/editor.h"
 #include "app/ui/editor/editor_customization_delegate.h"
+#include "app/ui/editor/glue.h"
 #include "app/ui/editor/handle_type.h"
 #include "app/ui/editor/moving_cel_state.h"
 #include "app/ui/editor/moving_pixels_state.h"
@@ -320,20 +321,9 @@ bool StandbyState::onMouseDown(Editor* editor, MouseMessage* msg)
     if (layerEdges)
       layerEdgesOption(false);
 
-    // We need to clear and redraw the brush boundaries after the
-    // first mouse pressed/point shape if drawn. This is to avoid
-    // graphical glitches (invalid areas in the ToolLoop's src/dst
-    // images).
-    HideBrushPreview hide(editor->brushPreview());
-
-    tools::ToolLoop* toolLoop = create_tool_loop(editor, context);
-    if (toolLoop) {
-      EditorStatePtr newState(new DrawingState(toolLoop));
-      editor->setState(newState);
-
-      static_cast<DrawingState*>(newState.get())
-        ->initToolLoop(editor, msg);
-    }
+    startDrawingState(editor,
+                      DrawingType::Regular,
+                      pointer_from_msg(editor, msg));
 
     // Restore layer edges
     if (layerEdges)
@@ -497,6 +487,22 @@ bool StandbyState::onSetCursor(Editor* editor, const gfx::Point& mouseScreenPos)
 
 bool StandbyState::onKeyDown(Editor* editor, KeyMessage* msg)
 {
+  // Start line preview with shift key
+  if (editor->startStraightLineWithFreehandTool()) {
+    DrawingState* drawingState =
+      startDrawingState(editor,
+                        DrawingType::LineFreehand,
+                        tools::Pointer(
+                          editor->document()->lastDrawingPoint(),
+                          tools::Pointer::Left));
+    if (drawingState) {
+      drawingState->sendMovementToToolLoop(
+        tools::Pointer(
+          editor->screenToEditor(ui::get_mouse_position()),
+          tools::Pointer::Left));
+      return true;
+    }
+  }
   return false;
 }
 
@@ -586,6 +592,35 @@ bool StandbyState::onUpdateStatusBar(Editor* editor)
   return true;
 }
 
+DrawingState* StandbyState::startDrawingState(Editor* editor,
+                                              const DrawingType drawingType,
+                                              const tools::Pointer& pointer)
+{
+  // We need to clear and redraw the brush boundaries after the
+  // first mouse pressed/point shape if drawn. This is to avoid
+  // graphical glitches (invalid areas in the ToolLoop's src/dst
+  // images).
+  HideBrushPreview hide(editor->brushPreview());
+
+  tools::ToolLoop* toolLoop = create_tool_loop(
+    editor,
+    UIContext::instance(),
+    (drawingType == DrawingType::LineFreehand));
+  if (!toolLoop)
+    return nullptr;
+
+  EditorStatePtr newState(
+    new DrawingState(toolLoop,
+                     drawingType));
+  editor->setState(newState);
+
+  static_cast<DrawingState*>(newState.get())
+    ->initToolLoop(editor,
+                   pointer);
+
+  return static_cast<DrawingState*>(newState.get());
+}
+
 Transformation StandbyState::getTransformation(Editor* editor)
 {
   Transformation t = editor->document()->getTransformation();
diff --git a/src/app/ui/editor/standby_state.h b/src/app/ui/editor/standby_state.h
index 2b4d131d2..27309e3df 100644
--- a/src/app/ui/editor/standby_state.h
+++ b/src/app/ui/editor/standby_state.h
@@ -17,12 +17,16 @@
 namespace app {
   namespace tools {
     class Ink;
+    class Pointer;
   }
 
+  class DrawingState;
   class TransformHandles;
 
   class StandbyState : public StateWithWheelBehavior {
   public:
+    enum class DrawingType { Regular, LineFreehand };
+
     StandbyState();
     virtual ~StandbyState();
     virtual void onEnterState(Editor* editor) override;
@@ -76,6 +80,9 @@ namespace app {
     };
 
   private:
+    DrawingState* startDrawingState(Editor* editor,
+                                    const DrawingType drawingType,
+                                    const tools::Pointer& pointer);
     void transformSelection(Editor* editor, ui::MouseMessage* msg, HandleType handle);
     void onPivotChange(Editor* editor);
     gfx::Rect resizeCelBounds(Editor* editor) const;
diff --git a/src/app/ui/editor/tool_loop_impl.cpp b/src/app/ui/editor/tool_loop_impl.cpp
index d66f40486..e203c828c 100644
--- a/src/app/ui/editor/tool_loop_impl.cpp
+++ b/src/app/ui/editor/tool_loop_impl.cpp
@@ -97,6 +97,7 @@ public:
                Layer* layer,
                tools::Tool* tool,
                tools::Ink* ink,
+               tools::Controller* controller,
                Document* document,
                tools::ToolLoop::Button button,
                const app::Color& fgColor,
@@ -116,7 +117,7 @@ public:
     , m_contiguous(m_toolPref.contiguous())
     , m_button(button)
     , m_ink(ink->clone())
-    , m_controller(m_tool->getController(m_button))
+    , m_controller(controller)
     , m_pointShape(m_tool->getPointShape(m_button))
     , m_intertwine(m_tool->getIntertwine(m_button))
     , m_tracePolicy(m_tool->getTracePolicy(m_button))
@@ -243,7 +244,12 @@ public:
   tools::Controller* getController() override { return m_controller; }
   tools::PointShape* getPointShape() override { return m_pointShape; }
   tools::Intertwine* getIntertwine() override { return m_intertwine; }
-  tools::TracePolicy getTracePolicy() override { return m_tracePolicy; }
+  tools::TracePolicy getTracePolicy() override {
+    if (m_controller->handleTracePolicy())
+      return m_controller->getTracePolicy();
+    else
+      return m_tracePolicy;
+  }
   tools::Symmetry* getSymmetry() override { return m_symmetry.get(); }
   doc::Remap* getShadingRemap() override { return m_shadingRemap; }
 
@@ -293,6 +299,7 @@ class ToolLoopImpl : public ToolLoopBase {
   Transaction m_transaction;
   ExpandCelCanvas* m_expandCelCanvas;
   Image* m_floodfillSrcImage;
+  bool m_saveLastPoint;
 
 public:
   ToolLoopImpl(Editor* editor,
@@ -300,12 +307,21 @@ public:
                Context* context,
                tools::Tool* tool,
                tools::Ink* ink,
+               tools::Controller* controller,
                Document* document,
                tools::ToolLoop::Button button,
                const app::Color& fgColor,
-               const app::Color& bgColor)
-    : ToolLoopBase(editor, layer, tool, ink, document,
-                   button, fgColor, bgColor)
+               const app::Color& bgColor,
+               const bool saveLastPoint)
+    : ToolLoopBase(editor,
+                   layer,
+                   tool,
+                   ink,
+                   controller,
+                   document,
+                   button,
+                   fgColor,
+                   bgColor)
     , m_context(context)
     , m_canceled(false)
     , m_transaction(m_context,
@@ -318,6 +334,7 @@ public:
                                             ModifyDocument))
     , m_expandCelCanvas(nullptr)
     , m_floodfillSrcImage(nullptr)
+    , m_saveLastPoint(saveLastPoint)
   {
     ASSERT(m_context->activeDocument() == m_editor->document());
 
@@ -414,15 +431,16 @@ public:
     bool redraw = false;
 
     if (!m_canceled) {
+      // Freehand changes the last point
+      if (m_saveLastPoint) {
+        m_transaction.execute(
+          new cmd::SetLastPoint(
+            m_document,
+            getController()->getLastPoint()));
+      }
+
       // Paint ink
       if (getInk()->isPaint()) {
-        // Freehand changes the last point
-        if (getController()->isFreehand())
-          m_transaction.execute(
-            new cmd::SetLastPoint(
-              m_document,
-              getController()->getLastPoint()));
-
         try {
           ContextReader reader(m_context, 500);
           ContextWriter writer(reader, 500);
@@ -512,12 +530,15 @@ public:
 
 };
 
-tools::ToolLoop* create_tool_loop(Editor* editor, Context* context)
+tools::ToolLoop* create_tool_loop(
+  Editor* editor,
+  Context* context,
+  const bool convertLineToFreehand)
 {
-  tools::Tool* current_tool = editor->getCurrentEditorTool();
-  tools::Ink* current_ink = editor->getCurrentEditorInk();
-  if (!current_tool || !current_ink)
-    return NULL;
+  tools::Tool* tool = editor->getCurrentEditorTool();
+  tools::Ink* ink = editor->getCurrentEditorInk();
+  if (!tool || !ink)
+    return nullptr;
 
   Layer* layer;
 
@@ -530,8 +551,8 @@ tools::ToolLoop* create_tool_loop(Editor* editor, Context* context)
   // Anyway this cannot be used in 'magic wand' tool (isSelection +
   // isFloodFill) because we need the original layer source
   // image/pixels to stop the flood-fill algorithm.
-  if (current_ink->isSelection() &&
-      !current_tool->getPointShape(editor->isSecondaryButton() ? 1: 0)->isFloodFill()) {
+  if (ink->isSelection() &&
+      !tool->getPointShape(editor->isSecondaryButton() ? 1: 0)->isFloodFill()) {
     layer = nullptr;
   }
   else {
@@ -578,13 +599,30 @@ tools::ToolLoop* create_tool_loop(Editor* editor, Context* context)
 
   // Create the new tool loop
   try {
+    tools::ToolLoop::Button button =
+      (!editor->isSecondaryButton() ? tools::ToolLoop::Left:
+                                      tools::ToolLoop::Right);
+
+    tools::Controller* controller =
+      (convertLineToFreehand ?
+       App::instance()->toolBox()->getControllerById(
+         tools::WellKnownControllers::LineFreehand):
+       tool->getController(button));
+
+    const bool saveLastPoint =
+      (ink->isPaint() &&
+       (controller->isFreehand() ||
+        convertLineToFreehand));
+
     return new ToolLoopImpl(
       editor, layer, context,
-      current_tool,
-      current_ink,
+      tool,
+      ink,
+      controller,
       editor->document(),
-      !editor->isSecondaryButton() ? tools::ToolLoop::Left: tools::ToolLoop::Right,
-      fg, bg);
+      button,
+      fg, bg,
+      saveLastPoint);
   }
   catch (const std::exception& ex) {
     Alert::show(PACKAGE
@@ -612,8 +650,15 @@ public:
     const app::Color& bgColor,
     Image* image,
     const gfx::Point& celOrigin)
-    : ToolLoopBase(editor, editor->layer(), tool, ink, document,
-                   tools::ToolLoop::Left, fgColor, bgColor)
+    : ToolLoopBase(editor,
+                   editor->layer(),
+                   tool,
+                   ink,
+                   tool->getController(tools::ToolLoop::Left),
+                   document,
+                   tools::ToolLoop::Left,
+                   fgColor,
+                   bgColor)
     , m_image(image)
   {
     m_celOrigin = celOrigin;
@@ -661,9 +706,9 @@ tools::ToolLoop* create_tool_loop_preview(
   Editor* editor, Image* image,
   const gfx::Point& celOrigin)
 {
-  tools::Tool* current_tool = editor->getCurrentEditorTool();
-  tools::Ink* current_ink = editor->getCurrentEditorInk();
-  if (!current_tool || !current_ink)
+  tools::Tool* tool = editor->getCurrentEditorTool();
+  tools::Ink* ink = editor->getCurrentEditorInk();
+  if (!tool || !ink)
     return NULL;
 
   Layer* layer = editor->layer();
@@ -685,8 +730,8 @@ tools::ToolLoop* create_tool_loop_preview(
   try {
     return new PreviewToolLoopImpl(
       editor,
-      current_tool,
-      current_ink,
+      tool,
+      ink,
       editor->document(),
       fg, bg, image, celOrigin);
   }
diff --git a/src/app/ui/editor/tool_loop_impl.h b/src/app/ui/editor/tool_loop_impl.h
index e195afca5..b25b621e0 100644
--- a/src/app/ui/editor/tool_loop_impl.h
+++ b/src/app/ui/editor/tool_loop_impl.h
@@ -1,5 +1,5 @@
 // Aseprite
-// Copyright (C) 2001-2015  David Capello
+// Copyright (C) 2001-2017  David Capello
 //
 // This program is distributed under the terms of
 // the End-User License Agreement for Aseprite.
@@ -24,10 +24,13 @@ namespace app {
   }
 
   tools::ToolLoop* create_tool_loop(
-    Editor* editor, Context* context);
+    Editor* editor,
+    Context* context,
+    const bool convertLineToFreehand);
 
   tools::ToolLoop* create_tool_loop_preview(
-    Editor* editor, doc::Image* image,
+    Editor* editor,
+    doc::Image* image,
     const gfx::Point& celOrigin);
 
 } // namespace app