diff --git a/bundles/org.eclipse.ui.workbench/eclipseui/org/eclipse/ui/internal/Workbench.java b/bundles/org.eclipse.ui.workbench/eclipseui/org/eclipse/ui/internal/Workbench.java
index 5bc2f90cb1c..9a7aa487f35 100644
--- a/bundles/org.eclipse.ui.workbench/eclipseui/org/eclipse/ui/internal/Workbench.java
+++ b/bundles/org.eclipse.ui.workbench/eclipseui/org/eclipse/ui/internal/Workbench.java
@@ -773,6 +773,13 @@ public static Display createDisplay() {
 
 		setRescaleAtRuntimePropertyFromPreference();
 
+		if (DPIUtil.isMonitorSpecificScalingActive() && !DPIUtil.isSetupCompatibleToMonitorSpecificScaling()) {
+			System.setProperty(SWT_RESCALE_AT_RUNTIME_PROPERTY, Boolean.toString(false));
+			MessageDialog.openError(new Shell(Display.getDefault()),
+					WorkbenchMessages.RescaleAtRuntimeIncompatibilityTitle, NLS.bind(
+							WorkbenchMessages.RescaleAtRuntimeIncompatibilityDescription, DPIUtil.getAutoScaleValue()));
+		}
+
 		// create the display
 		Display newDisplay = Display.getCurrent();
 		if (newDisplay == null) {
diff --git a/bundles/org.eclipse.ui.workbench/eclipseui/org/eclipse/ui/internal/WorkbenchMessages.java b/bundles/org.eclipse.ui.workbench/eclipseui/org/eclipse/ui/internal/WorkbenchMessages.java
index 7f1f1435b4f..740d78a0db4 100644
--- a/bundles/org.eclipse.ui.workbench/eclipseui/org/eclipse/ui/internal/WorkbenchMessages.java
+++ b/bundles/org.eclipse.ui.workbench/eclipseui/org/eclipse/ui/internal/WorkbenchMessages.java
@@ -38,6 +38,12 @@ public class WorkbenchMessages extends NLS {
 
 	public static String RescaleAtRuntimeDescription;
 
+	public static String RescaleAtRuntimeDisabledDescription;
+
+	public static String RescaleAtRuntimeIncompatibilityTitle;
+
+	public static String RescaleAtRuntimeIncompatibilityDescription;
+
 	public static String RescaleAtRuntimeEnabled;
 
 	public static String RescaleAtRuntimeSettingChangeWarningTitle;
diff --git a/bundles/org.eclipse.ui.workbench/eclipseui/org/eclipse/ui/internal/dialogs/ViewsPreferencePage.java b/bundles/org.eclipse.ui.workbench/eclipseui/org/eclipse/ui/internal/dialogs/ViewsPreferencePage.java
index af350f44b9b..c034c136739 100644
--- a/bundles/org.eclipse.ui.workbench/eclipseui/org/eclipse/ui/internal/dialogs/ViewsPreferencePage.java
+++ b/bundles/org.eclipse.ui.workbench/eclipseui/org/eclipse/ui/internal/dialogs/ViewsPreferencePage.java
@@ -53,6 +53,7 @@
 import org.eclipse.jface.dialogs.MessageDialog;
 import org.eclipse.jface.fieldassist.ControlDecoration;
 import org.eclipse.jface.fieldassist.FieldDecorationRegistry;
+import org.eclipse.jface.layout.GridDataFactory;
 import org.eclipse.jface.preference.IPreferenceStore;
 import org.eclipse.jface.preference.PreferencePage;
 import org.eclipse.jface.viewers.ArrayContentProvider;
@@ -65,7 +66,9 @@
 import org.eclipse.swt.SWT;
 import org.eclipse.swt.events.SelectionEvent;
 import org.eclipse.swt.events.SelectionListener;
+import org.eclipse.swt.graphics.Font;
 import org.eclipse.swt.graphics.Image;
+import org.eclipse.swt.internal.DPIUtil;
 import org.eclipse.swt.layout.GridData;
 import org.eclipse.swt.layout.GridLayout;
 import org.eclipse.swt.widgets.Button;
@@ -222,7 +225,16 @@ private void createRescaleAtRuntimeCheckButton(Composite parent) {
 				.getBoolean(IWorkbenchPreferenceConstants.RESCALING_AT_RUNTIME, true);
 		rescaleAtRuntime = createCheckButton(parent, WorkbenchMessages.RescaleAtRuntimeEnabled,
 				initialStateRescaleAtRuntime);
-		rescaleAtRuntime.setToolTipText(WorkbenchMessages.RescaleAtRuntimeDescription);
+		if (!DPIUtil.isSetupCompatibleToMonitorSpecificScaling()) {
+			rescaleAtRuntime.setEnabled(false);
+			Font font = parent.getFont();
+			Composite note = createNoteComposite(font, parent, WorkbenchMessages.Preference_note,
+					WorkbenchMessages.RescaleAtRuntimeDisabledDescription);
+			note.setLayoutData(GridDataFactory.swtDefaults().span(2, 1).create());
+		} else {
+			rescaleAtRuntime.setEnabled(true);
+			rescaleAtRuntime.setToolTipText(WorkbenchMessages.RescaleAtRuntimeDescription);
+		}
 	}
 
 	private void createThemeIndependentComposits(Composite comp) {
diff --git a/bundles/org.eclipse.ui.workbench/eclipseui/org/eclipse/ui/internal/messages.properties b/bundles/org.eclipse.ui.workbench/eclipseui/org/eclipse/ui/internal/messages.properties
index aa3e02edf00..b6a65144981 100644
--- a/bundles/org.eclipse.ui.workbench/eclipseui/org/eclipse/ui/internal/messages.properties
+++ b/bundles/org.eclipse.ui.workbench/eclipseui/org/eclipse/ui/internal/messages.properties
@@ -504,7 +504,10 @@ RescaleAtRuntimeSettingChangeWarningTitle = DPI Setting Changed
 RescaleAtRuntimeSettingChangeWarningText = Restart for the DPI setting changes to take effect
 HiDpiSettingsGroupTitle = HiDPI settings
 RescaleAtRuntimeDescription = Activating this option will dynamically scale all windows according to the monitor they are currently in
+RescaleAtRuntimeDisabledDescription = Incompatible autoscale value was defined via system property or ini
 RescaleAtRuntimeEnabled = Use monitor-specific UI &scaling
+RescaleAtRuntimeIncompatibilityTitle = Scaling Configuration Error
+RescaleAtRuntimeIncompatibilityDescription = Monitor-specific scaling is currently active with the wrong autoscale value (''{0}''). This combination may lead to unexpected UI scaling behavior, For this reason the monitor-specific scaling has been disabled. Please review your auto-scaling configuration.
 # --- Workbench -----
 WorkbenchPreference_openMode=Open mode
 WorkbenchPreference_doubleClick=D&ouble click