diff --git a/app/config/config.cpp b/app/config/config.cpp
index 27080faa3..7b9eaae02 100644
--- a/app/config/config.cpp
+++ b/app/config/config.cpp
@@ -81,6 +81,7 @@ void Config::SetDefaults()
   config_map_["SetNameWithMarker"] = false;
   config_map_["RectifiedWaveforms"] = false;
   config_map_["DropWithoutSequenceBehavior"] = TimelineWidget::kDWSAsk;
+  config_map_["Loop"] = false;
 
   config_map_["DiskCachePath"] = QStandardPaths::writableLocation(QStandardPaths::AppLocalDataLocation);
   config_map_["DiskCacheSize"] = 20.0;
diff --git a/app/panel/timebased/timebased.cpp b/app/panel/timebased/timebased.cpp
index e35628800..2b3363654 100644
--- a/app/panel/timebased/timebased.cpp
+++ b/app/panel/timebased/timebased.cpp
@@ -88,6 +88,11 @@ void TimeBasedPanel::PlayPause()
   emit PlayPauseRequested();
 }
 
+void TimeBasedPanel::PlayInToOut()
+{
+  emit PlayInToOutRequested();
+}
+
 void TimeBasedPanel::ShuttleLeft()
 {
   emit ShuttleLeftRequested();
diff --git a/app/panel/timebased/timebased.h b/app/panel/timebased/timebased.h
index a47a4ea18..9c68567b3 100644
--- a/app/panel/timebased/timebased.h
+++ b/app/panel/timebased/timebased.h
@@ -60,6 +60,8 @@ public:
 
   virtual void PlayPause() override;
 
+  virtual void PlayInToOut() override;
+
   virtual void ShuttleLeft() override;
 
   virtual void ShuttleStop() override;
@@ -96,6 +98,8 @@ signals:
 
   void PlayPauseRequested();
 
+  void PlayInToOutRequested();
+
   void ShuttleLeftRequested();
 
   void ShuttleStopRequested();
diff --git a/app/panel/viewer/viewerbase.cpp b/app/panel/viewer/viewerbase.cpp
index 85597a659..1cd35960f 100644
--- a/app/panel/viewer/viewerbase.cpp
+++ b/app/panel/viewer/viewerbase.cpp
@@ -32,6 +32,11 @@ void ViewerPanelBase::PlayPause()
   static_cast<ViewerWidget*>(GetTimeBasedWidget())->TogglePlayPause();
 }
 
+void ViewerPanelBase::PlayInToOut()
+{
+  static_cast<ViewerWidget*>(GetTimeBasedWidget())->Play(true);
+}
+
 void ViewerPanelBase::ShuttleLeft()
 {
   static_cast<ViewerWidget*>(GetTimeBasedWidget())->ShuttleLeft();
@@ -50,6 +55,7 @@ void ViewerPanelBase::ShuttleRight()
 void ViewerPanelBase::ConnectTimeBasedPanel(TimeBasedPanel *panel)
 {
   connect(panel, &TimeBasedPanel::PlayPauseRequested, this, &ViewerPanelBase::PlayPause);
+  connect(panel, &TimeBasedPanel::PlayInToOutRequested, this, &ViewerPanelBase::PlayInToOut);
   connect(panel, &TimeBasedPanel::ShuttleLeftRequested, this, &ViewerPanelBase::ShuttleLeft);
   connect(panel, &TimeBasedPanel::ShuttleStopRequested, this, &ViewerPanelBase::ShuttleStop);
   connect(panel, &TimeBasedPanel::ShuttleRightRequested, this, &ViewerPanelBase::ShuttleRight);
@@ -58,6 +64,7 @@ void ViewerPanelBase::ConnectTimeBasedPanel(TimeBasedPanel *panel)
 void ViewerPanelBase::DisconnectTimeBasedPanel(TimeBasedPanel *panel)
 {
   disconnect(panel, &TimeBasedPanel::PlayPauseRequested, this, &ViewerPanelBase::PlayPause);
+  disconnect(panel, &TimeBasedPanel::PlayInToOutRequested, this, &ViewerPanelBase::PlayInToOut);
   disconnect(panel, &TimeBasedPanel::ShuttleLeftRequested, this, &ViewerPanelBase::ShuttleLeft);
   disconnect(panel, &TimeBasedPanel::ShuttleStopRequested, this, &ViewerPanelBase::ShuttleStop);
   disconnect(panel, &TimeBasedPanel::ShuttleRightRequested, this, &ViewerPanelBase::ShuttleRight);
diff --git a/app/panel/viewer/viewerbase.h b/app/panel/viewer/viewerbase.h
index d9906a9f8..dd593b066 100644
--- a/app/panel/viewer/viewerbase.h
+++ b/app/panel/viewer/viewerbase.h
@@ -35,6 +35,8 @@ public:
 
   virtual void PlayPause() override;
 
+  virtual void PlayInToOut() override;
+
   virtual void ShuttleLeft() override;
 
   virtual void ShuttleStop() override;
diff --git a/app/widget/panel/panel.h b/app/widget/panel/panel.h
index 1eaa76367..2b666dfa7 100644
--- a/app/widget/panel/panel.h
+++ b/app/widget/panel/panel.h
@@ -91,6 +91,8 @@ public:
    */
   virtual void PlayPause(){}
 
+  virtual void PlayInToOut(){}
+
   virtual void NextFrame(){}
 
   virtual void GoToEnd(){}
diff --git a/app/widget/viewer/viewer.cpp b/app/widget/viewer/viewer.cpp
index 00b4b9486..1db2435cc 100644
--- a/app/widget/viewer/viewer.cpp
+++ b/app/widget/viewer/viewer.cpp
@@ -84,7 +84,7 @@ ViewerWidget::ViewerWidget(QWidget *parent) :
   controls_ = new PlaybackControls();
   controls_->SetTimecodeEnabled(true);
   controls_->setSizePolicy(QSizePolicy::Expanding, QSizePolicy::Maximum);
-  connect(controls_, &PlaybackControls::PlayClicked, this, &ViewerWidget::Play);
+  connect(controls_, &PlaybackControls::PlayClicked, this, static_cast<void(ViewerWidget::*)()>(&ViewerWidget::Play));
   connect(controls_, &PlaybackControls::PauseClicked, this, &ViewerWidget::Pause);
   connect(controls_, &PlaybackControls::PrevFrameClicked, this, &ViewerWidget::PrevFrame);
   connect(controls_, &PlaybackControls::NextFrameClicked, this, &ViewerWidget::NextFrame);
@@ -332,7 +332,7 @@ void ViewerWidget::UpdateTextureFromNode(const rational& time)
   }
 }
 
-void ViewerWidget::PlayInternal(int speed)
+void ViewerWidget::PlayInternal(int speed, bool in_to_out_only)
 {
   Q_ASSERT(speed != 0);
 
@@ -342,6 +342,7 @@ void ViewerWidget::PlayInternal(int speed)
   }
 
   playback_speed_ = speed;
+  play_in_to_out_only_ = in_to_out_only;
 
   QIODevice* audio_src = audio_renderer_->GetAudioPullDevice();
   if (audio_src != nullptr && audio_src->open(QIODevice::ReadOnly)) {
@@ -649,9 +650,21 @@ void ViewerWidget::ShowContextMenu(const QPoint &pos)
   menu.exec(static_cast<QWidget*>(sender())->mapToGlobal(pos));
 }
 
+void ViewerWidget::Play(bool in_to_out_only)
+{
+  if (in_to_out_only
+      && GetConnectedTimelinePoints()
+      && GetConnectedTimelinePoints()->workarea()->enabled()) {
+    // Jump to in point
+    SetTimeAndSignal(Timecode::time_to_timestamp(GetConnectedTimelinePoints()->workarea()->in(), timebase()));
+  }
+
+  PlayInternal(1, in_to_out_only);
+}
+
 void ViewerWidget::Play()
 {
-  PlayInternal(1);
+  Play(false);
 }
 
 void ViewerWidget::Pause()
@@ -683,7 +696,7 @@ void ViewerWidget::ShuttleLeft()
     current_speed--;
   }
 
-  PlayInternal(current_speed);
+  PlayInternal(current_speed, false);
 }
 
 void ViewerWidget::ShuttleStop()
@@ -705,7 +718,7 @@ void ViewerWidget::ShuttleRight()
     current_speed++;
   }
 
-  PlayInternal(current_speed);
+  PlayInternal(current_speed, false);
 }
 
 void ViewerWidget::SetOCIOParameters(const QString &display, const QString &view, const QString &look)
@@ -773,12 +786,64 @@ void ViewerWidget::PlaybackTimerUpdate()
 
   int64_t current_time = start_timestamp_ + frames_since_start * playback_speed_;
 
-  if (current_time < 0) {
-    SetTimeAndSignal(0);
+  int64_t min_time, max_time;
+
+  {
+    if ((play_in_to_out_only_ || Config::Current()["Loop"].toBool())
+        && GetConnectedTimelinePoints()
+        && GetConnectedTimelinePoints()->workarea()->enabled()) {
+
+      // If "play in to out" is enabled or we're looping AND we have a workarea, only play the workarea
+      min_time = Timecode::time_to_timestamp(GetConnectedTimelinePoints()->workarea()->in(), timebase());
+      max_time = Timecode::time_to_timestamp(GetConnectedTimelinePoints()->workarea()->out(), timebase());
+
+    } else {
+
+      // Otherwise set the bounds to the range of the sequence
+      min_time = 0;
+      max_time = Timecode::time_to_timestamp(GetConnectedNode()->Length(), timebase());
+
+    }
+  }
+
+  if ((playback_speed_ < 0 && current_time <= min_time)
+      || (playback_speed_ > 0 && current_time >= max_time)) {
+
+    // Determine which timestamp we tripped
+    int64_t tripped_time;
+
+    if (current_time <= min_time) {
+      tripped_time = min_time;
+    } else {
+      tripped_time = max_time;
+    }
+
+    if (Config::Current()["Loop"].toBool()) {
+
+      // If we're looping, jump to the other side of the workarea and continue
+      int64_t opposing_time = (tripped_time == min_time) ? max_time : min_time;
+
+      // Cache the current speed
+      int current_speed = playback_speed_;
+
+      // Jump to the other side and keep playing at the same speed
+      SetTimeAndSignal(opposing_time);
+      PlayInternal(current_speed, play_in_to_out_only_);
+
+    } else {
+
+      // Pause at the boundary
+      SetTimeAndSignal(tripped_time);
+
+    }
+
   } else {
+
+    // Sets time, wrapping in this bool ensures we don't pause from setting the time
     time_changed_from_timer_ = true;
     SetTimeAndSignal(current_time);
     time_changed_from_timer_ = false;
+
   }
 }
 
diff --git a/app/widget/viewer/viewer.h b/app/widget/viewer/viewer.h
index 892c5b5f0..1396f9a9c 100644
--- a/app/widget/viewer/viewer.h
+++ b/app/widget/viewer/viewer.h
@@ -83,6 +83,8 @@ public:
   VideoRenderBackend* video_renderer() const;
 
 public slots:
+  void Play(bool in_to_out_only);
+
   void Play();
 
   void Pause();
@@ -152,7 +154,7 @@ private:
 
   void UpdateTextureFromNode(const rational &time);
 
-  void PlayInternal(int speed);
+  void PlayInternal(int speed, bool in_to_out_only);
 
   void PushScrubbedAudio();
 
@@ -186,6 +188,8 @@ private:
 
   bool time_changed_from_timer_;
 
+  bool play_in_to_out_only_;
+
   AudioWaveformView* waveform_view_;
 
   QList<ViewerWindow*> windows_;
diff --git a/app/window/mainwindow/mainmenu.cpp b/app/window/mainwindow/mainmenu.cpp
index 133c8ea09..e75c8ce76 100644
--- a/app/window/mainwindow/mainmenu.cpp
+++ b/app/window/mainwindow/mainmenu.cpp
@@ -24,6 +24,7 @@
 #include <QStyleFactory>
 
 #include "common/timecodefunctions.h"
+#include "config/config.h"
 #include "core.h"
 #include "dialog/actionsearch/actionsearch.h"
 #include "panel/panelmanager.h"
@@ -152,7 +153,7 @@ MainMenu::MainMenu(MainWindow *parent) :
   //
   // PLAYBACK MENU
   //
-  playback_menu_ = new Menu(this);
+  playback_menu_ = new Menu(this, this, &MainMenu::PlaybackMenuAboutToShow);
   playback_gotostart_item_ = playback_menu_->AddItem("gotostart", this, &MainMenu::GoToStartTriggered, "Home");
   playback_prevframe_item_ = playback_menu_->AddItem("prevframe", this, &MainMenu::PrevFrameTriggered, "Left");
   playback_playpause_item_ = playback_menu_->AddItem("playpause", this, &MainMenu::PlayPauseTriggered, "Space");
@@ -179,7 +180,7 @@ MainMenu::MainMenu(MainWindow *parent) :
   playback_menu_->addSeparator();
 
   playback_loop_item_ = playback_menu_->AddItem("loop", this, &MainMenu::LoopTriggered);
-  //Menu::SetBooleanAction(playback_loop_item_, &olive::config.loop);
+  playback_loop_item_->setCheckable(true);
 
   //
   // WINDOW MENU
@@ -359,6 +360,11 @@ void MainMenu::ToolsMenuAboutToShow()
   tools_snapping_item_->setChecked(Core::instance()->snapping());
 }
 
+void MainMenu::PlaybackMenuAboutToShow()
+{
+  playback_loop_item_->setChecked(Config::Current()["Loop"].toBool());
+}
+
 void MainMenu::WindowMenuAboutToShow()
 {
   // QMainWindow generates a perfectly usable menu for this purpose, we just need to copy it to the window menu
@@ -450,12 +456,12 @@ void MainMenu::PlayPauseTriggered()
 
 void MainMenu::PlayInToOutTriggered()
 {
-  qDebug() << "FIXME: Stub";
+  PanelManager::instance()->CurrentlyFocused()->PlayInToOut();
 }
 
-void MainMenu::LoopTriggered()
+void MainMenu::LoopTriggered(bool enabled)
 {
-  qDebug() << "FIXME: Stub";
+  Config::Current()["Loop"] = enabled;
 }
 
 void MainMenu::NextFrameTriggered()
diff --git a/app/window/mainwindow/mainmenu.h b/app/window/mainwindow/mainmenu.h
index e866db597..142320986 100644
--- a/app/window/mainwindow/mainmenu.h
+++ b/app/window/mainwindow/mainmenu.h
@@ -84,6 +84,11 @@ private slots:
    */
   void ToolsMenuAboutToShow();
 
+  /**
+   * @brief PlaybackMenuAboutToShow
+   */
+  void PlaybackMenuAboutToShow();
+
   /**
    * @brief Slot triggered just before the Window menu shows
    */
@@ -133,7 +138,7 @@ private slots:
 
   void PlayInToOutTriggered();
 
-  void LoopTriggered();
+  void LoopTriggered(bool enabled);
 
   void NextFrameTriggered();
   void GoToEndTriggered();