diff --git a/app/src/processing/app/AbstractMonitor.java b/app/src/processing/app/AbstractMonitor.java
index 1efbec7e2d6..4fb819a7346 100644
--- a/app/src/processing/app/AbstractMonitor.java
+++ b/app/src/processing/app/AbstractMonitor.java
@@ -1,6 +1,7 @@
 package processing.app;
 
 import cc.arduino.packages.BoardPort;
+import cc.arduino.packages.DiscoveryManager;
 import processing.app.legacy.PApplet;
 
 import javax.swing.*;
@@ -9,6 +10,7 @@
 import java.awt.event.ActionListener;
 import java.awt.event.WindowAdapter;
 import java.awt.event.WindowEvent;
+import java.util.List;
 
 @SuppressWarnings("serial")
 public abstract class AbstractMonitor extends JFrame implements ActionListener {
@@ -17,6 +19,7 @@ public abstract class AbstractMonitor extends JFrame implements ActionListener {
 
   private StringBuffer updateBuffer;
   private Timer updateTimer;
+  private Timer portExistsTimer;
 
   private BoardPort boardPort;
 
@@ -73,6 +76,26 @@ public void actionPerformed(ActionEvent event) {
     updateTimer = new Timer(33, this);  // redraw serial monitor at 30 Hz
     updateTimer.start();
 
+    ActionListener portExists = new ActionListener() {
+      @Override
+      public void actionPerformed(ActionEvent ae) {
+        try {
+          if (!Base.getDiscoveryManager().discovery().contains(boardPort)) {
+            if (!closed) {
+              suspend();
+            }
+          } else {
+            if (closed && (Editor.avoidMultipleOperations == false)) {
+              resume(boardPort);
+            }
+          }
+        } catch (Exception e) {}
+      }
+    };
+
+    portExistsTimer = new Timer(1000, portExists);  // check if the port is still there every second
+    portExistsTimer.start();
+
     closed = false;
   }
 
@@ -92,6 +115,11 @@ public void suspend() throws Exception {
     close();
   }
 
+  public void dispose() {
+    super.dispose();
+    portExistsTimer.stop();
+  }
+
   public void resume(BoardPort boardPort) throws Exception {
     setBoardPort(boardPort);
 
diff --git a/app/src/processing/app/Editor.java b/app/src/processing/app/Editor.java
index 49c092fd9d2..a8e5b7b7493 100644
--- a/app/src/processing/app/Editor.java
+++ b/app/src/processing/app/Editor.java
@@ -181,7 +181,7 @@ public boolean test(SketchController controller) {
 
   private int numTools = 0;
 
-  public boolean avoidMultipleOperations = false;
+  static public boolean avoidMultipleOperations = false;
 
   private final EditorToolbar toolbar;
   // these menus are shared so that they needn't be rebuilt for all windows
@@ -1015,22 +1015,20 @@ private void selectSerialPort(String name) {
     //System.out.println(item.getLabel());
 
     BaseNoGui.selectSerialPort(name);
-    if (serialMonitor != null) {
-      try {
+    try {
+      boolean reopenMonitor = ((serialMonitor != null && serialMonitor.isVisible()) ||
+                                serialPlotter != null && serialPlotter.isVisible());
+      if (serialMonitor != null) {
         serialMonitor.close();
-        serialMonitor.setVisible(false);
-      } catch (Exception e) {
-        // ignore
       }
-    }
-
-    if (serialPlotter != null) {
-      try {
+      if (serialPlotter != null) {
         serialPlotter.close();
-        serialPlotter.setVisible(false);
-      } catch (Exception e) {
-        // ignore
       }
+      if (reopenMonitor) {
+        handleSerial();
+      }
+    } catch (Exception e) {
+      // ignore
     }
 
     onBoardOrPortChange();
diff --git a/arduino-core/src/cc/arduino/packages/uploaders/SerialUploader.java b/arduino-core/src/cc/arduino/packages/uploaders/SerialUploader.java
index 8e65b3e598f..96ba383aceb 100644
--- a/arduino-core/src/cc/arduino/packages/uploaders/SerialUploader.java
+++ b/arduino-core/src/cc/arduino/packages/uploaders/SerialUploader.java
@@ -210,9 +210,9 @@ public boolean uploadUsingPreferences(File sourcePath, String buildPath, String
 
           // Reuse waitForUploadPort for this task, but this time we are simply waiting
           // for one port to reappear. If no port reappears before the timeout, actualUploadPort is selected
-          finalUploadPort = waitForUploadPort(actualUploadPort, Serial.list(), false);
+          finalUploadPort = waitForUploadPort(actualUploadPort, Serial.list(), false, 2000);
         }
-      } catch (InterruptedException ex) {
+      } catch (RunnerException ex) {
         // noop
       }
     }
@@ -229,13 +229,13 @@ public boolean uploadUsingPreferences(File sourcePath, String buildPath, String
   }
 
   private String waitForUploadPort(String uploadPort, List<String> before) throws InterruptedException, RunnerException {
-	  return waitForUploadPort(uploadPort, before, verbose);
+	  return waitForUploadPort(uploadPort, before, verbose, 10000);
   }
 
-  private String waitForUploadPort(String uploadPort, List<String> before, boolean verbose) throws InterruptedException, RunnerException {
+  private String waitForUploadPort(String uploadPort, List<String> before, boolean verbose, int timeout) throws InterruptedException, RunnerException {
     // Wait for a port to appear on the list
     int elapsed = 0;
-    while (elapsed < 10000) {
+    while (elapsed < timeout) {
       List<String> now = Serial.list();
       List<String> diff = new ArrayList<>(now);
       diff.removeAll(before);