diff --git a/include/TimeLineWidget.h b/include/TimeLineWidget.h
index c7ac0124c9e..38ebd2857cd 100644
--- a/include/TimeLineWidget.h
+++ b/include/TimeLineWidget.h
@@ -190,9 +190,14 @@ public slots:
 	void mousePressEvent( QMouseEvent * _me ) override;
 	void mouseMoveEvent( QMouseEvent * _me ) override;
 	void mouseReleaseEvent( QMouseEvent * _me ) override;
+	void contextMenuEvent( QContextMenuEvent * _cme ) override;
 
 
 private:
+	void chooseMouseAction(QMouseEvent* event);
+	TimePos getPositionFromX(const int x) const;
+	void setLoopPoint(bool end, int x, bool unquantized=false);
+
 	static QPixmap * s_posMarkerPixmap;
 
 	QColor m_inactiveLoopColor;
@@ -217,6 +222,7 @@ public slots:
 	int m_xOffset;
 	int m_posMarkerX;
 	float m_ppb;
+	float m_snapSize;
 	Song::PlayPos & m_pos;
 	const TimePos & m_begin;
 	const Song::PlayModes m_mode;
@@ -232,14 +238,16 @@ public slots:
 	enum actions
 	{
 		NoAction,
+		Thresholded,
 		MovePositionMarker,
 		MoveLoopBegin,
 		MoveLoopEnd,
+		MoveLoopClosest,
+		DragLoop,
 		SelectSongTCO,
+		ShowContextMenu
 	} m_action;
 
-	int m_moveXOff;
-
 
 signals:
 	void positionChanged( const TimePos & _t );
diff --git a/src/gui/TimeLineWidget.cpp b/src/gui/TimeLineWidget.cpp
index e7e7ca113e0..95934de97bc 100644
--- a/src/gui/TimeLineWidget.cpp
+++ b/src/gui/TimeLineWidget.cpp
@@ -30,6 +30,7 @@
 #include <QMouseEvent>
 #include <QPainter>
 #include <QToolBar>
+#include <QMenu>
 
 
 #include "TimeLineWidget.h"
@@ -62,13 +63,13 @@ TimeLineWidget::TimeLineWidget( const int xoff, const int yoff, const float ppb,
 	m_xOffset( xoff ),
 	m_posMarkerX( 0 ),
 	m_ppb( ppb ),
+	m_snapSize( 1.0 ),
 	m_pos( pos ),
 	m_begin( begin ),
 	m_mode( mode ),
 	m_savedPos( -1 ),
 	m_hint( NULL ),
-	m_action( NoAction ),
-	m_moveXOff( 0 )
+	m_action( NoAction )
 {
 	m_loopPos[0] = 0;
 	m_loopPos[1] = DefaultTicksPerBar;
@@ -93,6 +94,10 @@ TimeLineWidget::TimeLineWidget( const int xoff, const int yoff, const float ppb,
 	updateTimer->start( 1000 / 60 );  // 60 fps
 	connect( Engine::getSong(), SIGNAL( timeSignatureChanged( int,int ) ),
 					this, SLOT( update() ) );
+	
+	// Required to prevent modified right click from triggering the context menu
+	// Instead, manually trigger the context menu on unmodified right clicks
+	setContextMenuPolicy(Qt::PreventContextMenu);
 }
 
 
@@ -304,60 +309,52 @@ void TimeLineWidget::paintEvent( QPaintEvent * )
 
 
 
-void TimeLineWidget::mousePressEvent( QMouseEvent* event )
+void TimeLineWidget::contextMenuEvent(QContextMenuEvent*)
 {
-	if( event->x() < m_xOffset )
-	{
-		return;
-	}
-	if( event->button() == Qt::LeftButton  && !(event->modifiers() & Qt::ShiftModifier) )
-	{
-		m_action = MovePositionMarker;
-		if( event->x() - m_xOffset < s_posMarkerPixmap->width() )
-		{
-			m_moveXOff = event->x() - m_xOffset;
-		}
-		else
-		{
-			m_moveXOff = s_posMarkerPixmap->width() / 2;
-		}
-	}
-	else if( event->button() == Qt::LeftButton  && (event->modifiers() & Qt::ShiftModifier) )
-	{
-		m_action = SelectSongTCO;
-		m_initalXSelect = event->x();
-	}
-	else if( event->button() == Qt::RightButton )
-	{
-		m_moveXOff = s_posMarkerPixmap->width() / 2;
-		const TimePos t = m_begin + static_cast<int>( qMax( event->x() - m_xOffset - m_moveXOff, 0 ) * TimePos::ticksPerBar() / m_ppb );
-		const TimePos loopMid = ( m_loopPos[0] + m_loopPos[1] ) / 2;
+	QMenu contextMenu(tr("Timeline"), this);
+
+	// TODO: Shortcut hints should be read from a config
+
+	QAction setStartPoint(tr("Loop start (shift + left click)"), this);
+	connect(&setStartPoint, &QAction::triggered, this, [this](){
+		setLoopPoint(0, m_initalXSelect);
+	});
+	QAction setEndPoint(tr("Loop end (shift + right click)"), this);
+	connect(&setEndPoint, &QAction::triggered, this, [this](){
+		setLoopPoint(1, m_initalXSelect);
+	});
+	QAction selectLoopPoints(tr("Select between loop points"), this);
+	connect(&selectLoopPoints, &QAction::triggered, this, [this](){
+		emit regionSelectedFromPixels(
+			m_xOffset + m_loopPos[0] * m_ppb / TimePos::ticksPerBar(),
+			m_xOffset + m_loopPos[1] * m_ppb / TimePos::ticksPerBar()
+		);
+		emit selectionFinished();
+	});
+	contextMenu.addAction(&setStartPoint);
+	contextMenu.addAction(&setEndPoint);
+	contextMenu.addAction(&selectLoopPoints);
+	contextMenu.exec(QCursor::pos());
+}
 
-		if( t < loopMid )
-		{
-			m_action = MoveLoopBegin;
-		}
-		else if( t > loopMid )
-		{
-			m_action = MoveLoopEnd;
-		}
 
-		if( m_loopPos[0] > m_loopPos[1]  )
-		{
-			qSwap( m_loopPos[0], m_loopPos[1] );
-		}
 
-		m_loopPos[( m_action == MoveLoopBegin ) ? 0 : 1] = t;
-	}
 
-	if( m_action == MoveLoopBegin || m_action == MoveLoopEnd )
-	{
-		delete m_hint;
-		m_hint = TextFloat::displayMessage( tr( "Hint" ),
-					tr( "Press <%1> to disable magnetic loop points." ).arg(UI_CTRL_KEY),
-					embed::getIconPixmap( "hint" ), 0 );
-	}
-	mouseMoveEvent( event );
+void TimeLineWidget::mousePressEvent( QMouseEvent* event )
+{
+	auto button = event->button();
+	auto mods = event->modifiers();
+
+	if (event->x() < m_xOffset || m_action != NoAction) { return; }
+	// Handles moving playhead
+	else if (button == Qt::LeftButton && mods == Qt::NoModifier) { m_action = MovePositionMarker; }
+	// Wait for drag or release
+	else { m_action = Thresholded; }
+
+	// Set initial position for actions that need it
+	m_initalXSelect = event->x();
+
+	mouseMoveEvent(event);
 }
 
 
@@ -366,14 +363,35 @@ void TimeLineWidget::mousePressEvent( QMouseEvent* event )
 void TimeLineWidget::mouseMoveEvent( QMouseEvent* event )
 {
 	parentWidget()->update(); // essential for widgets that this timeline had taken their mouse move event from.
-	const TimePos t = m_begin + static_cast<int>( qMax( event->x() - m_xOffset - m_moveXOff, 0 ) * TimePos::ticksPerBar() / m_ppb );
+	const TimePos t = getPositionFromX(event->x());
+	// Fine adjust when both ctrl and shift are held, hide ctrl+shift hint
+	bool unquantized = event->modifiers() == (Qt::ControlModifier | Qt::ShiftModifier);
+	if (unquantized)
+	{
+		delete m_hint;
+		m_hint = nullptr;
+	}
 
-	switch( m_action )
+	// Change action when mouse exceeds drag threshold
+	static const int dragThreshold = 5;
+	if (m_action == Thresholded && abs(event->x() - m_initalXSelect) > dragThreshold)
+	{
+		chooseMouseAction(event);
+	}
+
+	// Translate MoveLoopClosest into left or right based on distance
+	if (m_action == MoveLoopClosest)
+	{
+		const TimePos loopMid = (m_loopPos[0] + m_loopPos[1]) / 2;
+		m_action = t < loopMid ? MoveLoopBegin : MoveLoopEnd;
+	}
+
+	switch (m_action)
 	{
 		case MovePositionMarker:
 			m_pos.setTicks(t.getTicks());
 			Engine::getSong()->setToTime(t, m_mode);
-			if (!( Engine::getSong()->isPlaying()))
+			if (!(Engine::getSong()->isPlaying()))
 			{
 				//Song::Mode_None is used when nothing is being played.
 				Engine::getSong()->setToTime(t, Song::Mode_None);
@@ -387,38 +405,20 @@ void TimeLineWidget::mouseMoveEvent( QMouseEvent* event )
 		case MoveLoopBegin:
 		case MoveLoopEnd:
 		{
-			const int i = m_action - MoveLoopBegin; // i == 0 || i == 1
-			if( event->modifiers() & Qt::ControlModifier )
-			{
-				// no ctrl-press-hint when having ctrl pressed
-				delete m_hint;
-				m_hint = NULL;
-				m_loopPos[i] = t;
-			}
-			else
-			{
-				m_loopPos[i] = t.quantize(1.0);
-			}
-			// Catch begin == end
-			if( m_loopPos[0] == m_loopPos[1] )
-			{
-				// Note, swap 1 and 0 below and the behavior "skips" the other
-				// marking instead of pushing it.
-				if( m_action == MoveLoopBegin ) 
-				{
-					m_loopPos[0] -= TimePos::ticksPerBar();
-				}
-				else
-				{
-					m_loopPos[1] += TimePos::ticksPerBar();
-				}
-			}
+			const int i = m_action == MoveLoopBegin ? 0 : 1;
+			setLoopPoint(i, event->x(), unquantized);
+			break;
+		}
+		case DragLoop:
+		{
+			if (unquantized) { m_loopPos[1] = t; }
+			else { m_loopPos[1] = t.quantize(m_snapSize); }
 			update();
 			break;
 		}
-	case SelectSongTCO:
-			emit regionSelectedFromPixels( m_initalXSelect , event->x() );
-		break;
+		case SelectSongTCO:
+			emit regionSelectedFromPixels(m_initalXSelect , event->x());
+			break;
 
 		default:
 			break;
@@ -432,6 +432,126 @@ void TimeLineWidget::mouseReleaseEvent( QMouseEvent* event )
 {
 	delete m_hint;
 	m_hint = NULL;
-	if ( m_action == SelectSongTCO ) { emit selectionFinished(); }
+
+	// Change action if mouse has not moved
+	if (m_action == Thresholded) { chooseMouseAction(event); }
+
+	mouseMoveEvent(event);
+
+	switch (m_action)
+	{
+		case SelectSongTCO:
+			emit selectionFinished();
+			break;
+
+		case ShowContextMenu:
+			contextMenuEvent(nullptr);
+			break;
+
+		default:
+			break;
+	}
+
+	// Required when m_action == DragLoop, not harmful otherwise
+	if (m_loopPos[0] > m_loopPos[1]) { qSwap(m_loopPos[0], m_loopPos[1]); }
+	m_action = NoAction;
+}
+
+
+
+
+void TimeLineWidget::chooseMouseAction(QMouseEvent* event)
+{
+	auto buttons = event->button() | event->buttons(); // include released button
+	auto mods = event->modifiers();
+	auto type = event->type();
+
+	// TODO: Read these from a config
+	auto leftCtrlAction = SelectSongTCO;
+	auto rightCtrlAction = NoAction;
+	auto leftShiftAction = MoveLoopBegin;
+	auto rightShiftAction = MoveLoopEnd;
+
+	// Unmodified LMB is reserved for playhead, unmodified RMB for context menu
+	// Shift or Ctrl modified press behavior is bound by the user
+	// Shift + Ctrl modifier is reserved for fine adjustment of Shift actions
+	// TODO: Let MMB be bound
+
 	m_action = NoAction;
+
+	// If mouse has moved past threshold
+	if (type == QEvent::MouseMove)
+	{
+		if (buttons & Qt::LeftButton)
+		{
+			if (mods & Qt::ShiftModifier) { m_action = leftShiftAction; }
+			else if (mods & Qt::ControlModifier) { m_action = leftCtrlAction; }
+		}
+		else if (buttons & Qt::RightButton)
+		{
+			if (mods & Qt::ShiftModifier) { m_action = rightShiftAction; }
+			else if (mods & Qt::ControlModifier) { m_action = rightCtrlAction; }
+		}
+	}
+	// If mouse has not moved
+	else if (type == QEvent::MouseButtonRelease)
+	{
+		if (buttons & Qt::LeftButton)
+		{
+			if (mods & Qt::ShiftModifier) { m_action = leftShiftAction; }
+		}
+		else if (buttons & Qt::RightButton)
+		{
+			if (mods & Qt::ShiftModifier) { m_action = rightShiftAction; }
+			else if (mods & Qt::ControlModifier) { m_action = rightCtrlAction; }
+			else { m_action = ShowContextMenu; }
+		}
+	}
+
+	// Notify the user if they can disable quantization
+	bool unquantizable = m_action == MoveLoopBegin || m_action == MoveLoopEnd
+						|| m_action == MoveLoopClosest || m_action == DragLoop;
+	bool unquantized = mods == (Qt::ControlModifier | Qt::ShiftModifier);
+	if (unquantizable && !unquantized && type == QEvent::MouseMove)
+	{
+		delete m_hint;
+		m_hint = TextFloat::displayMessage(tr("Hint"),
+			tr("Hold <%1> and <Shift> to disable quantization.").arg(UI_CTRL_KEY),
+			embed::getIconPixmap("hint"), 0);
+	}
+}
+
+
+
+
+TimePos TimeLineWidget::getPositionFromX(const int x) const
+{
+	return m_begin + std::max(x - m_xOffset - s_posMarkerPixmap->width() / 2, 0) * TimePos::ticksPerBar() / m_ppb;
+}
+
+
+
+
+void TimeLineWidget::setLoopPoint(bool end, int x, bool unquantized)
+{
+	// Move the specified loop point
+	int i = end ? 1 : 0;
+	TimePos pos = getPositionFromX(x);
+	m_loopPos[i] = unquantized ? pos : pos.quantize(m_snapSize);
+
+	// Length of quantization step
+	TimePos oneSnap = TimePos::ticksPerBar() * m_snapSize;
+	if (m_loopPos[1] == 0)
+	{
+		// End may not be at bar 0
+		m_loopPos[1] = oneSnap;
+	}
+	if (m_loopPos[0] >= m_loopPos[1])
+	{
+		// End moved before start - move start one step back
+		if (end) { m_loopPos[0] = std::max(0, m_loopPos[1] - oneSnap); }
+		// Start moved past end - move end one step forward
+		else { m_loopPos[1] = m_loopPos[0] + oneSnap; }
+	}
+	update();
 }