diff --git a/src/Files.App/Constants.cs b/src/Files.App/Constants.cs
index f99cb68fd284..6c542a4e3d12 100644
--- a/src/Files.App/Constants.cs
+++ b/src/Files.App/Constants.cs
@@ -236,6 +236,7 @@ public static class GitHub
 			public const string BugReportUrl = @"https://github.com/files-community/Files/issues/new?labels=bug&template=bug_report.yml";
 			public const string PrivacyPolicyUrl = @"https://github.com/files-community/Files/blob/main/.github/PRIVACY.md";
 			public const string SupportUsUrl = @"https://github.com/sponsors/yaira2";
+			public const string ReinstallationNoticeDocsUrl = @"https://files.community/docs/install#:~:text=Steps%20required%20for%20the%20%E2%80%9Cclassic%20installer%E2%80%9D%20version%20after%203/21/2024";
 		}
 
 		public static class DocsPath
diff --git a/src/Files.App/Dialogs/ReinstallPromptDialog.xaml b/src/Files.App/Dialogs/ReinstallPromptDialog.xaml
new file mode 100644
index 000000000000..5f32273511ed
--- /dev/null
+++ b/src/Files.App/Dialogs/ReinstallPromptDialog.xaml
@@ -0,0 +1,20 @@
+<!--  Copyright (c) 2023 Files Community. Licensed under the MIT License. See the LICENSE.  -->
+<ContentDialog
+	x:Class="Files.App.Dialogs.ReinstallPromptDialog"
+	xmlns="http://schemas.microsoft.com/winfx/2006/xaml/presentation"
+	xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml"
+	xmlns:d="http://schemas.microsoft.com/expression/blend/2008"
+	xmlns:mc="http://schemas.openxmlformats.org/markup-compatibility/2006"
+	Title="Re-installation is required"
+	PrimaryButtonClick="ContentDialog_PrimaryButtonClick"
+	PrimaryButtonStyle="{StaticResource AccentButtonStyle}"
+	PrimaryButtonText="More info"
+	SecondaryButtonText="OK"
+	Style="{StaticResource DefaultContentDialogStyle}"
+	mc:Ignorable="d">
+
+	<StackPanel Width="360" Spacing="12">
+		<TextBlock Text="Starting 3/21/2024, a reinstallation of Files is required in order to continue receiving automatic updates." />
+		<TextBlock Text="Please see our documentation for additional help and resources regarding this message." />
+	</StackPanel>
+</ContentDialog>
diff --git a/src/Files.App/Dialogs/ReinstallPromptDialog.xaml.cs b/src/Files.App/Dialogs/ReinstallPromptDialog.xaml.cs
new file mode 100644
index 000000000000..a0692c08e7c8
--- /dev/null
+++ b/src/Files.App/Dialogs/ReinstallPromptDialog.xaml.cs
@@ -0,0 +1,24 @@
+// Copyright (c) 2023 Files Community
+// Licensed under the MIT License. See the LICENSE.
+
+using Microsoft.UI.Xaml.Controls;
+using Windows.System;
+
+namespace Files.App.Dialogs
+{
+	/// <summary>
+	/// Displays a dialog temporarily informing the user of the importance of reinstalling the app.
+	/// </summary>
+	public sealed partial class ReinstallPromptDialog : ContentDialog
+	{
+		public ReinstallPromptDialog()
+		{
+			this.InitializeComponent();
+		}
+
+		private async void ContentDialog_PrimaryButtonClick(ContentDialog sender, ContentDialogButtonClickEventArgs args)
+		{
+			await Launcher.LaunchUriAsync(new Uri(Constants.GitHub.ReinstallationNoticeDocsUrl));
+		}
+	}
+}
diff --git a/src/Files.App/UserControls/AddressToolbar.xaml b/src/Files.App/UserControls/AddressToolbar.xaml
index ae5f6861a303..f00ffb2bcb92 100644
--- a/src/Files.App/UserControls/AddressToolbar.xaml
+++ b/src/Files.App/UserControls/AddressToolbar.xaml
@@ -27,6 +27,23 @@
 			<converters:NullToTrueConverter x:Key="NullToFalseConverter" Inverse="True" />
 			<converters1:BoolNegationConverter x:Key="BoolNegationConverter" />
 
+			<ResourceDictionary.ThemeDictionaries>
+				<ResourceDictionary x:Key="Light">
+					<LinearGradientBrush x:Key="WarningGradientBrush" StartPoint="0,0" EndPoint="1,1">
+						<GradientStop Offset="0" Color="#FFA500" />
+						<GradientStop Offset="0.5" Color="#FF8C00" />
+						<GradientStop Offset="1" Color="#FF4500" />
+					</LinearGradientBrush>
+				</ResourceDictionary>
+				<ResourceDictionary x:Key="Dark">
+					<LinearGradientBrush x:Key="WarningGradientBrush" StartPoint="0,0" EndPoint="1,1">
+						<GradientStop Offset="0" Color="#ffd153" />
+						<GradientStop Offset="0.5" Color="#f9ae41" />
+						<GradientStop Offset="1" Color="#f69e38" />
+					</LinearGradientBrush>
+				</ResourceDictionary>
+			</ResourceDictionary.ThemeDictionaries>
+
 			<ResourceDictionary.MergedDictionaries>
 				<ResourceDictionary>
 					<SolidColorBrush x:Key="ButtonBorderBrushDisabled" Color="Transparent" />
@@ -508,6 +525,24 @@
 						Glyph="&#xF133;" />
 				</Button>
 
+				<!--  (TEMP) Re-install Prompt (Limited Time Only)  -->
+				<Button
+					x:Name="ReInstallPromptButton"
+					Width="36"
+					Height="32"
+					Padding="0"
+					x:Load="{x:Bind ViewModel.ShowReinstallationPrompt, Mode=OneWay}"
+					Click="ReInstallPromptButton_Click"
+					Style="{StaticResource AddressToolbarButtonStyle}">
+					<Grid>
+						<Viewbox Width="16">
+							<Image Source="ms-appx:///Assets/AppTiles/Dev/Logo.ico" />
+						</Viewbox>
+						<FontIcon Foreground="{ThemeResource WarningGradientBrush}" Glyph="&#xea82;" />
+						<FontIcon Foreground="Black" Glyph="&#xea84;" />
+					</Grid>
+				</Button>
+
 				<!--  Show The Files App Settings Dialog  -->
 				<Button
 					x:Name="SettingsButton"
diff --git a/src/Files.App/UserControls/AddressToolbar.xaml.cs b/src/Files.App/UserControls/AddressToolbar.xaml.cs
index a7a229b965db..c48baebd0139 100644
--- a/src/Files.App/UserControls/AddressToolbar.xaml.cs
+++ b/src/Files.App/UserControls/AddressToolbar.xaml.cs
@@ -1,6 +1,7 @@
 // Copyright (c) 2023 Files Community
 // Licensed under the MIT License. See the LICENSE.
 
+using Files.App.Dialogs;
 using Microsoft.UI.Input;
 using Microsoft.UI.Xaml;
 using Microsoft.UI.Xaml.Controls;
@@ -135,5 +136,13 @@ private void OngoingTasksActions_ProgressBannerPosted(object? _, StatusCenterIte
 				userSettingsService.AppSettingsService.ShowStatusCenterTeachingTip = false;
 			}
 		}
+
+		private async void ReInstallPromptButton_Click(object sender, RoutedEventArgs e)
+		{
+			ReinstallPromptDialog dialog = new();
+			dialog.XamlRoot = MainWindow.Instance.Content.XamlRoot;
+
+			await dialog.ShowAsync();
+		}
 	}
 }
diff --git a/src/Files.App/ViewModels/UserControls/ToolbarViewModel.cs b/src/Files.App/ViewModels/UserControls/ToolbarViewModel.cs
index 660442482c87..6c86e1a2e451 100644
--- a/src/Files.App/ViewModels/UserControls/ToolbarViewModel.cs
+++ b/src/Files.App/ViewModels/UserControls/ToolbarViewModel.cs
@@ -201,6 +201,13 @@ public Style LayoutOpacityIcon
 
 		private PointerRoutedEventArgs? pointerRoutedEventArgs;
 
+		private bool _ShowReinstallationPrompt;
+		public bool ShowReinstallationPrompt
+		{
+			get => _ShowReinstallationPrompt;
+			set => SetProperty(ref _ShowReinstallationPrompt, value);
+		}
+
 		public ToolbarViewModel()
 		{
 			RefreshClickCommand = new RelayCommand<RoutedEventArgs>(e => RefreshRequested?.Invoke(this, EventArgs.Empty));
@@ -212,6 +219,9 @@ public ToolbarViewModel()
 			SearchBox.Escaped += SearchRegion_Escaped;
 			UserSettingsService.OnSettingChangedEvent += UserSettingsService_OnSettingChangedEvent;
 			UpdateService.PropertyChanged += UpdateService_OnPropertyChanged;
+
+			if (DateTime.Today >= new DateTime(2024, 3, 21))
+				ShowReinstallationPrompt = true;
 		}
 
 		private async void UpdateService_OnPropertyChanged(object? sender, PropertyChangedEventArgs e)