diff --git a/app/src/processing/app/Editor.java b/app/src/processing/app/Editor.java
index 774d20f74ec..09f716f51be 100644
--- a/app/src/processing/app/Editor.java
+++ b/app/src/processing/app/Editor.java
@@ -539,6 +539,9 @@ public void actionPerformed(ActionEvent e) {
     item.addActionListener(new ActionListener() {
         public void actionPerformed(ActionEvent e) {
           handleExport(false);
+          // Hide the serial monitor window. It will reopen at the appropriate time
+          // if "auto show" is enabled
+          serialMonitor.setVisible(false);
         }
       });
     fileMenu.add(item);
@@ -662,10 +665,25 @@ protected JMenu buildToolsMenu() {
     item = newJMenuItemShift(_("Serial Monitor"), 'M');
     item.addActionListener(new ActionListener() {
         public void actionPerformed(ActionEvent e) {
-          handleSerial();
+          handleSerial(true);
         }
       });
     menu.add(item);
+
+    // Create the "Auto Show Serial Monitor" menu item (a checkbox). Read the prefs
+    // to see if it should be enabled.
+    final boolean autoShowSerialMonitor = Preferences.getBoolean("serial.auto_show_monitor_window");
+    item = new JCheckBoxMenuItem("Auto Show Serial Monitor", autoShowSerialMonitor);
+    item.addActionListener(new ActionListener() {
+     public void actionPerformed(ActionEvent e) {
+       // Make sure the choice in Preferences matches the checkbox state
+       JCheckBoxMenuItem checkboxMenuItem = (JCheckBoxMenuItem)e.getSource();
+       Preferences.setBoolean("serial.auto_show_monitor_window", checkboxMenuItem.isSelected());
+       // The pref needs to be saved so that other parts of the app will stay in sync
+       Preferences.save();
+     }
+    });
+    menu.add(item);
     
     addTools(menu, Base.getToolsFolder());
     File sketchbookTools = new File(Base.getSketchbookFolder(), "tools");
@@ -941,7 +959,6 @@ protected void selectSerialPort(String name) {
     //System.out.println(item.getLabel());
     Preferences.set("serial.port", name);
     serialMonitor.closeSerialPort();
-    serialMonitor.setVisible(false);
     serialMonitor = new SerialMonitor(Preferences.get("serial.port"));
     //System.out.println("set to " + get("serial.port"));
   }
@@ -1893,6 +1910,10 @@ public void handleRun(final boolean verbose) {
   class DefaultRunHandler implements Runnable {
     public void run() {
       try {
+        // Ensure the serial monitor window is closed until after we successfully 
+        // upload a sketch
+        serialMonitor.setVisible(false);
+
         sketch.prepare();
         sketch.build(false);
         statusNotice(_("Done compiling."));
@@ -2370,16 +2391,21 @@ synchronized public void handleExport(final boolean usingProgrammer) {
   // DAM: in Arduino, this is upload
   class DefaultExportHandler implements Runnable {
     public void run() {
+    
+      // Hide the serial monitor window until we are certain the sketch
+      // uploaded successfully
+      serialMonitor.setVisible(false);
 
+      boolean uploadSuccessful = false;
       try {
         serialMonitor.closeSerialPort();
-        serialMonitor.setVisible(false);
-            
+
         uploading = true;
           
         boolean success = sketch.exportApplet(false);
         if (success) {
           statusNotice(_("Done uploading."));
+          uploadSuccessful = true;
         } else {
           // error message will already be visible
         }
@@ -2398,6 +2424,17 @@ public void run() {
       }
       status.unprogress();
       uploading = false;
+
+      // If auto show is enabled make sure the serial monitor is hooked up and visible
+      if (uploadSuccessful) {
+        if (Preferences.getBoolean("serial.auto_show_monitor_window")) {
+          handleSerial(true);
+        }
+      }
+      else {
+        serialMonitor.setVisible(false);
+      }
+
       //toolbar.clear();
       toolbar.deactivate(EditorToolbar.EXPORT);
     }
@@ -2409,7 +2446,6 @@ public void run() {
 
       try {
         serialMonitor.closeSerialPort();
-        serialMonitor.setVisible(false);
             
         uploading = true;
           
@@ -2474,12 +2510,14 @@ protected boolean handleExportCheckModified() {
   }
 
 
-  public void handleSerial() {
+  public void handleSerial(boolean makeVisible) {
     if (uploading) return;
     
     try {
       serialMonitor.openSerialPort();
-      serialMonitor.setVisible(true);
+      if (makeVisible) {
+        serialMonitor.setVisible(true);
+      }
     } catch (SerialException e) {
       statusError(e);
     }
diff --git a/app/src/processing/app/EditorToolbar.java b/app/src/processing/app/EditorToolbar.java
index e7b8d3752d8..750b5743758 100644
--- a/app/src/processing/app/EditorToolbar.java
+++ b/app/src/processing/app/EditorToolbar.java
@@ -350,7 +350,7 @@ public void mousePressed(MouseEvent e) {
       break;
 
     case SERIAL:
-      editor.handleSerial();
+      editor.handleSerial(true);
       break;
     }
   }
diff --git a/build/shared/lib/preferences.txt b/build/shared/lib/preferences.txt
index 67246f860e7..720d9fe06a6 100755
--- a/build/shared/lib/preferences.txt
+++ b/build/shared/lib/preferences.txt
@@ -255,6 +255,7 @@ serial.databits=8
 serial.stopbits=1
 serial.parity=N
 serial.debug_rate=9600
+serial.auto_show_monitor_window=false
 
 # I18 Preferences