diff --git a/Src/BlueDotBrigade.Weevil.Common/IRegionManager.cs b/Src/BlueDotBrigade.Weevil.Common/IRegionManager.cs
index 72129523..fd42d615 100644
--- a/Src/BlueDotBrigade.Weevil.Common/IRegionManager.cs
+++ b/Src/BlueDotBrigade.Weevil.Common/IRegionManager.cs
@@ -15,5 +15,11 @@ public interface IRegionManager
 		void MarkEnd(int lineNumber);
 
 		void MarkStart(int lineNumber);
+
+		bool StartsWith(int lineNumber);
+
+		bool EndsWith(int lineNumber);
+
+		public bool Contains(int lineNumber);
 	}
 }
\ No newline at end of file
diff --git a/Src/BlueDotBrigade.Weevil.Core/RegionManager.cs b/Src/BlueDotBrigade.Weevil.Core/RegionManager.cs
index ae755a5c..ba2e3169 100644
--- a/Src/BlueDotBrigade.Weevil.Core/RegionManager.cs
+++ b/Src/BlueDotBrigade.Weevil.Core/RegionManager.cs
@@ -103,6 +103,21 @@ public void MarkEnd(int lineNumber)
 			}
 		}
 
+		public bool StartsWith(int lineNumber)
+		{
+			return _regions.Any(r => r.Minimum.LineNumber == lineNumber);
+		}
+
+		public bool EndsWith(int lineNumber)
+		{
+			return _regions.Any(r => r.Maximum.LineNumber == lineNumber);
+		}
+
+		public bool Contains(int lineNumber)
+		{
+			return _regions.Any(r => r.Contains(lineNumber));
+		}
+
 		public void Clear()
 		{
 			_regions.Clear();
diff --git a/Src/BlueDotBrigade.Weevil.Gui/Converters/RegionConverter.cs b/Src/BlueDotBrigade.Weevil.Gui/Converters/RegionConverter.cs
new file mode 100644
index 00000000..bd743629
--- /dev/null
+++ b/Src/BlueDotBrigade.Weevil.Gui/Converters/RegionConverter.cs
@@ -0,0 +1,73 @@
+namespace BlueDotBrigade.Weevil.Gui.Converters
+{
+	using System;
+	using System.Collections.Generic;
+	using System.Globalization;
+	using System.Linq;
+	using System.Text;
+	using System.Threading.Tasks;
+	using BlueDotBrigade.Weevil.Data;
+	using System.Windows.Data;
+	using System.Windows;
+	using BlueDotBrigade.Weevil.Gui.Filter;
+
+	using System;
+	using System.Globalization;
+	using System.Windows;
+	using System.Windows.Data;
+
+	using System;
+	using System.Globalization;
+	using System.Windows.Data;
+
+	public class RegionStringConverter : IMultiValueConverter
+	{
+		/// <summary>
+		/// Expects:
+		///   values[0]: The current IRecord (the item in the ListView)
+		///   values[1]: The parent FilterViewModel (the DataContext of the UserControl/Window)
+		/// Returns a string indicating the record's region status:
+		///   - "Start of Region"
+		///   - "In Region"
+		///   - "End of Region"
+		///   - string.Empty (when the record isn't in any region)
+		/// </summary>
+		public object Convert(object[] values, Type targetType, object parameter, CultureInfo culture)
+		{
+			if (values?.Length < 2)
+				return string.Empty;
+
+			var record = values[0] as IRecord;
+			var viewModel = values[1] as FilterViewModel;
+
+			if (record == null || viewModel == null)
+				return string.Empty;
+
+			// You can define your own logic:
+			// e.g., if region is a single continuous block, you might define:
+			//  - starts with a region if ...
+			//  - ends with a region if ...
+			//  - or "in region" otherwise
+			if (viewModel.RegionStartsWith(record))
+			{
+				return "Start of Region";
+			}
+			else if (viewModel.RegionEndsWith(record))
+			{
+				return "End of Region";
+			}
+			else if (viewModel.RegionContains(record))
+			{
+				return "In Region";
+			}
+
+			return string.Empty;
+		}
+
+		public object[] ConvertBack(object value, Type[] targetTypes, object parameter, CultureInfo culture)
+		{
+			throw new NotImplementedException();
+		}
+	}
+
+}
\ No newline at end of file
diff --git a/Src/BlueDotBrigade.Weevil.Gui/Filter/FilterView.xaml b/Src/BlueDotBrigade.Weevil.Gui/Filter/FilterView.xaml
index 21639307..bbc1b317 100644
--- a/Src/BlueDotBrigade.Weevil.Gui/Filter/FilterView.xaml
+++ b/Src/BlueDotBrigade.Weevil.Gui/Filter/FilterView.xaml
@@ -20,6 +20,7 @@
         <converters:FilterMultiValueConverter x:Key="FiltersMultiValueConverter" />
         <converters:ContentConverter x:Key="ContentConverter" />
         <converters:CheckBoxValidationErrorConverter x:Key="CheckBoxValidationErrorConverter" />
+        <converters:RegionStringConverter x:Key="RegionStringConverter" />
         <Style x:Key="CommandMenuItemStyle"
                TargetType="{x:Type MenuItem}">
             <Setter Property="Header"
@@ -257,9 +258,6 @@
                         <Separator/>
                         <MenuItem Header="Paste Comments" Command="{Binding ClipboardPasteCommand}" InputGestureText="Ctrl+V" />
                         <MenuItem Header="Overwrite Comments" Command="{Binding ClipboardPasteOverwriteCommand}" InputGestureText="Ctrl+Shift+V" />
-                        <Separator/>
-                        <MenuItem Header="Add Region" Command="{Binding AddRegionCommand}" InputGestureText="Ctrl+B" />
-                        <MenuItem Header="Remove All Regions" Command="{Binding RemoveAllRegionsCommand}" />
                     </MenuItem>
                     <Separator/>
                     <MenuItem Header="Filtering...">
@@ -306,6 +304,9 @@
                     <MenuItem Header="Show Dashboard" Command="{Binding ShowDashboardCommand}" InputGestureText="Ctrl+D" />
                     <MenuItem Header="Show Graph" Command="{Binding GraphDataCommand}" InputGestureText="Ctrl+Shift+G" />
                     <MenuItem Header="Analyze...">
+                        <MenuItem Header="Add Region" Command="{Binding AddRegionCommand}" InputGestureText="Ctrl+B" />
+                        <MenuItem Header="Remove All Regions" Command="{Binding RemoveAllRegionsCommand}" />
+                        <Separator/>
                         <MenuItem Header="Detect Data" Command="{Binding DetectDataCommand}" InputGestureText="F8"  />
                         <MenuItem Header="Detect Data Transitions" Command="{Binding DetectDataTransitionsCommand}" InputGestureText="F9" />
                         <MenuItem Header="Detect Rising Edges" Command="{Binding DataTransitionsRisingEdgeCommand}" />
@@ -432,8 +433,19 @@
                         <GridViewColumnHeader Content="Content" Padding="{StaticResource ColumnHeaderPadding}"/>
                         <GridViewColumn.CellTemplate>
                             <DataTemplate DataType="data:IRecord">
-                                <TextBlock TextWrapping="WrapWithOverflow" HorizontalAlignment="Right"
-                                    Text="{Binding Mode=OneWay, Converter={StaticResource ContentConverter}}">
+                                <TextBlock>
+                                    <TextBlock TextWrapping="WrapWithOverflow" HorizontalAlignment="Right"
+                                        Text="{Binding Mode=OneWay, Converter={StaticResource ContentConverter}}"/>
+                                    <TextBlock Margin="0,5,0,0" FontWeight="Bold" Foreground="Red">
+                                        <TextBlock.Text>
+                                            <MultiBinding Converter="{StaticResource RegionStringConverter}">
+                                                <!-- 1) The current item (record) -->
+                                                <Binding Path="." />
+                                                <!-- 2) The parent ViewModel (the UserControl.DataContext) -->
+                                                <Binding Path="DataContext" RelativeSource="{RelativeSource AncestorType=UserControl}" />
+                                            </MultiBinding>
+                                        </TextBlock.Text>
+                                    </TextBlock>
                                 </TextBlock>
                             </DataTemplate>
                         </GridViewColumn.CellTemplate>
diff --git a/Src/BlueDotBrigade.Weevil.Gui/Filter/FilterViewModel.cs b/Src/BlueDotBrigade.Weevil.Gui/Filter/FilterViewModel.cs
index 82d58c16..dfe351dc 100644
--- a/Src/BlueDotBrigade.Weevil.Gui/Filter/FilterViewModel.cs
+++ b/Src/BlueDotBrigade.Weevil.Gui/Filter/FilterViewModel.cs
@@ -1475,5 +1475,20 @@ private Dictionary<string, object> GetFilterConfiguration()
 
 			return configuration;
 		}
+
+		public bool RegionStartsWith(IRecord record)
+		{
+			return _engine.Regions.StartsWith(record.LineNumber);
+		}
+
+		public bool RegionEndsWith(IRecord record)
+		{
+			return _engine.Regions.EndsWith(record.LineNumber);
+		}
+
+		public bool RegionContains(IRecord record)
+		{
+			return _engine.Regions.Contains(record.LineNumber);
+		}
 	}
 }