diff --git a/ILSpy/Commands/SelectPdbContextMenuEntry.cs b/ILSpy/Commands/SelectPdbContextMenuEntry.cs
new file mode 100644
index 000000000..89a4125d7
--- /dev/null
+++ b/ILSpy/Commands/SelectPdbContextMenuEntry.cs
@@ -0,0 +1,107 @@
+// Copyright (c) 2026 AlphaSierraPapa for the SharpDevelop Team
+//
+// Permission is hereby granted, free of charge, to any person obtaining a copy of this
+// software and associated documentation files (the "Software"), to deal in the Software
+// without restriction, including without limitation the rights to use, copy, modify, merge,
+// publish, distribute, sublicense, and/or sell copies of the Software, and to permit persons
+// to whom the Software is furnished to do so, subject to the following conditions:
+//
+// The above copyright notice and this permission notice shall be included in all copies or
+// substantial portions of the Software.
+//
+// THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR IMPLIED,
+// INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY, FITNESS FOR A PARTICULAR
+// PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE AUTHORS OR COPYRIGHT HOLDERS BE LIABLE
+// FOR ANY CLAIM, DAMAGES OR OTHER LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR
+// OTHERWISE, ARISING FROM, OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER
+// DEALINGS IN THE SOFTWARE.
+
+using System.Composition;
+using System.IO;
+using System.Linq;
+using System.Threading.Tasks;
+
+using Avalonia.Controls.ApplicationLifetimes;
+using Avalonia.Platform.Storage;
+
+using ICSharpCode.Decompiler.CSharp.ProjectDecompiler;
+using ICSharpCode.ILSpy.Properties;
+
+using ILSpy.AssemblyTree;
+using ILSpy.TreeNodes;
+
+namespace ILSpy.Commands
+{
+	/// <summary>
+	/// Right-click an assembly → "Select PDB". File-picks a portable / Windows PDB and
+	/// associates it with the assembly's debug-info provider, then refreshes the
+	/// decompiled view so the new symbols feed back into the output.
+	/// </summary>
+	[ExportContextMenuEntry(Header = nameof(Resources.SelectPDB))]
+	[Shared]
+	public sealed class SelectPdbContextMenuEntry : IContextMenuEntry
+	{
+		readonly AssemblyTreeModel assemblyTreeModel;
+
+		[ImportingConstructor]
+		public SelectPdbContextMenuEntry(AssemblyTreeModel assemblyTreeModel)
+		{
+			this.assemblyTreeModel = assemblyTreeModel;
+		}
+
+		public bool IsEnabled(TextViewContext context) => true;
+
+		public bool IsVisible(TextViewContext context)
+			=> context.SelectedTreeNodes?.Length == 1
+				&& context.SelectedTreeNodes[0] is AssemblyTreeNode asm
+				&& asm.LoadedAssembly.IsLoadedAsValidAssembly;
+
+		public void Execute(TextViewContext context)
+		{
+			var assembly = (context.SelectedTreeNodes?.FirstOrDefault() as AssemblyTreeNode)?.LoadedAssembly;
+			if (assembly == null)
+				return;
+			_ = ExecuteAsync(assembly);
+		}
+
+		async Task ExecuteAsync(ICSharpCode.ILSpyX.LoadedAssembly assembly)
+		{
+			var owner = (global::Avalonia.Application.Current?.ApplicationLifetime
+				as IClassicDesktopStyleApplicationLifetime)?.MainWindow;
+			if (owner == null)
+				return;
+			var initialDir = Path.GetDirectoryName(assembly.FileName);
+			var suggested = WholeProjectDecompiler.CleanUpFileName(assembly.ShortName, ".pdb");
+			IStorageFolder? startLocation = null;
+			if (!string.IsNullOrEmpty(initialDir))
+			{
+				try
+				{ startLocation = await owner.StorageProvider.TryGetFolderFromPathAsync(initialDir); }
+				catch { /* picker accepts a null start location */ }
+			}
+			var files = await owner.StorageProvider.OpenFilePickerAsync(new FilePickerOpenOptions {
+				Title = Resources.SelectPDB,
+				FileTypeFilter = new[] {
+					new FilePickerFileType("Portable PDB / .pdb / All files") {
+						Patterns = new[] { "*.pdb", "*.*" },
+					},
+				},
+				SuggestedStartLocation = startLocation,
+				SuggestedFileName = suggested,
+			});
+			if (files.Count == 0)
+				return;
+			var path = files[0].TryGetLocalPath();
+			if (string.IsNullOrEmpty(path))
+				return;
+			await assembly.LoadDebugInfo(path);
+			// Refresh the tree node + re-decompile the current selection so the new debug
+			// symbols feed back into the output. Mirrors WPF's RefreshDecompiledView call.
+			if (assemblyTreeModel.SelectedItem is { } current)
+			{
+				assemblyTreeModel.SelectedItem = null;
+				assemblyTreeModel.SelectedItem = current;
+			}
+		}
+	}
+}