diff --git a/src/Files.App.Storage/Legacy/RecycleBinWatcher.cs b/src/Files.App.Storage/Legacy/RecycleBinWatcher.cs
index c312fe8e5570..853c7b40e5dd 100644
--- a/src/Files.App.Storage/Legacy/RecycleBinWatcher.cs
+++ b/src/Files.App.Storage/Legacy/RecycleBinWatcher.cs
@@ -39,36 +39,46 @@ public void StartWatcher()
 		{
 			// NOTE: SHChangeNotifyRegister only works if recycle bin is open in File Explorer.
 
+			foreach (var drive in SystemIO.DriveInfo.GetDrives())
+				StartWatcher(drive.Name);
+		}
+
+		/// <summary>
+		/// Starts watching the Recycle Bin on the given drive if it isn't watched already.
+		/// Re-arms monitoring after a failed eject and when a drive appears after startup.
+		/// </summary>
+		public void StartWatcher(string driveRoot)
+		{
 			// Listen changes only on the Recycle Bin that the current logon user has
 			var sid = WindowsIdentity.GetCurrent().User?.ToString() ?? string.Empty;
 			if (string.IsNullOrEmpty(sid))
 				return;
 
-			foreach (var drive in SystemIO.DriveInfo.GetDrives())
+			// NOTE: Suppressed NullReferenceException caused by EnableRaisingEvents in #15808
+			SafetyExtensions.IgnoreExceptions(() =>
 			{
-				var recyclePath = SystemIO.Path.Combine(drive.Name, "$RECYCLE.BIN", sid);
+				var recyclePath = SystemIO.Path.Combine(driveRoot, "$RECYCLE.BIN", sid);
 
-				if (drive.DriveType is SystemIO.DriveType.Network ||
+				if (new SystemIO.DriveInfo(driveRoot).DriveType is SystemIO.DriveType.Network ||
 					!SystemIO.Directory.Exists(recyclePath))
-					continue;
+					return;
+
+				if (_watchers.Any(x => string.Equals(x.Path, recyclePath, StringComparison.OrdinalIgnoreCase)))
+					return;
 
-				// NOTE: Suppressed NullReferenceException caused by EnableRaisingEvents in #15808
-				SafetyExtensions.IgnoreExceptions(() =>
+				SystemIO.FileSystemWatcher watcher = new()
 				{
-					SystemIO.FileSystemWatcher watcher = new()
-					{
-						Path = recyclePath,
-						Filter = "*.*",
-						NotifyFilter = SystemIO.NotifyFilters.LastWrite | SystemIO.NotifyFilters.FileName | SystemIO.NotifyFilters.DirectoryName
-					};
-
-					watcher.Created += Watcher_Changed;
-					watcher.Deleted += Watcher_Changed;
-					watcher.EnableRaisingEvents = true;
-
-					_watchers.Add(watcher);
-				});
-			}
+					Path = recyclePath,
+					Filter = "*.*",
+					NotifyFilter = SystemIO.NotifyFilters.LastWrite | SystemIO.NotifyFilters.FileName | SystemIO.NotifyFilters.DirectoryName
+				};
+
+				watcher.Created += Watcher_Changed;
+				watcher.Deleted += Watcher_Changed;
+				watcher.EnableRaisingEvents = true;
+
+				_watchers.Add(watcher);
+			});
 		}
 
 		/// <inheritdoc/>
@@ -78,6 +88,21 @@ public void StopWatcher()
 				watcher.Dispose();
 		}
 
+		/// <summary>
+		/// Stops watching the Recycle Bin on the given drive so the watcher's handle can't block ejection.
+		/// </summary>
+		public void StopWatcher(string driveRoot)
+		{
+			for (int i = _watchers.Count - 1; i >= 0; i--)
+			{
+				if (_watchers[i].Path.StartsWith(driveRoot, StringComparison.OrdinalIgnoreCase))
+				{
+					_watchers[i].Dispose();
+					_watchers.RemoveAt(i);
+				}
+			}
+		}
+
 		private void Watcher_Changed(object sender, SystemIO.FileSystemEventArgs e)
 		{
 			// Don't listen changes on files starting with '$I'
diff --git a/src/Files.App/Data/Models/DrivesViewModel.cs b/src/Files.App/Data/Models/DrivesViewModel.cs
index 9cf463c636d7..d84dfdad9030 100644
--- a/src/Files.App/Data/Models/DrivesViewModel.cs
+++ b/src/Files.App/Data/Models/DrivesViewModel.cs
@@ -93,6 +93,10 @@ private void Watcher_DeviceAdded(object? sender, IFolder e)
 				Drives.Add(e);
 			}
 
+			// Watch the Recycle Bin on drives that appear after startup (including reinserted ones)
+			if (!string.IsNullOrEmpty(e.Id))
+				Ioc.Default.GetRequiredService<IStorageTrashBinService>().Watcher.StartWatcher(e.Id.EndsWith('\\') ? e.Id : e.Id + '\\');
+
 			Watcher_EnumerationCompleted(null, EventArgs.Empty);
 		}
 
diff --git a/src/Files.App/Utils/Storage/Helpers/DriveHelpers.cs b/src/Files.App/Utils/Storage/Helpers/DriveHelpers.cs
index e1d4c36e040f..b296644851b6 100644
--- a/src/Files.App/Utils/Storage/Helpers/DriveHelpers.cs
+++ b/src/Files.App/Utils/Storage/Helpers/DriveHelpers.cs
@@ -15,7 +15,52 @@ public static class DriveHelpers
 	{
 		public static async void EjectDeviceAsync(string path)
 		{
+			var driveRoot = path.EndsWith('\\') ? path : path + '\\';
+
+			ReleaseDriveHandles(driveRoot);
+
+			// Give the released handles a moment to close before the shell issues the removal query
+			await Task.Delay(300);
+
 			await ContextMenu.InvokeVerb("eject", path);
+
+			// If the volume is still mounted the eject was vetoed; re-arm the Recycle Bin watcher
+			await Task.Delay(2000);
+			if (SystemIO.Directory.Exists(driveRoot))
+				Ioc.Default.GetRequiredService<IStorageTrashBinService>().Watcher.StartWatcher(driveRoot);
+		}
+
+		/// <summary>
+		/// Releases the handles Files itself holds on the drive (directory change watchers, sidebar
+		/// subtree watchers, the Recycle Bin watcher) so they can't veto the device removal.
+		/// </summary>
+		private static void ReleaseDriveHandles(string driveRoot)
+		{
+			// Navigate every pane showing the drive to Home and close its directory watcher
+			var multitaskingContext = Ioc.Default.GetRequiredService<IMultitaskingContext>();
+			foreach (var tab in multitaskingContext.Control?.GetAllTabInstances() ?? [])
+			{
+				if (tab is not ShellPanesPage panesPage)
+					continue;
+
+				foreach (var pane in panesPage.GetPanes())
+				{
+					var panePath = pane.ShellViewModel?.CurrentFolder?.ItemPath;
+					if (panePath is not null && (panePath + '\\').StartsWith(driveRoot, StringComparison.OrdinalIgnoreCase))
+					{
+						pane.ShellViewModel?.CloseWatcher();
+						pane.NavigateHome();
+					}
+				}
+			}
+
+			// Stop sidebar subtree watchers rooted on the drive
+			var drivesViewModel = Ioc.Default.GetRequiredService<DrivesViewModel>();
+			if (drivesViewModel.Drives.Cast<DriveItem>().FirstOrDefault(x => string.Equals(x.Path?.TrimEnd('\\'), driveRoot.TrimEnd('\\'), StringComparison.OrdinalIgnoreCase)) is { } driveItem)
+				driveItem.StopWatchingSubfoldersAndDescendants();
+
+			// Drop the Recycle Bin watcher for this drive
+			Ioc.Default.GetRequiredService<IStorageTrashBinService>().Watcher.StopWatcher(driveRoot);
 		}
 
 		public static async Task<bool> CheckEmptyDrive(string? drivePath)