v0.1.2: Config Checkpoints dialog, descriptions, daily auto-snapshot, docs (#3)

* Documentation: install/upgrade/uninstall guides + recipes incl. Zerto Adds a docs/ folder under the repo root with full operator documentation aimed at sysadmins (not webhook developers). The Zerto pre/post script recipe is the canonical "why does this exist" walkthrough; the GitHub HMAC, AD password reset, and UI-on-desktop recipes round out common patterns. Pages: - README.md (index) - concepts.md (5-minute "what is a webhook" explainer) - installation.md (interactive + silent install) - upgrading.md (single-click upgrade flow + edge cases) - uninstalling.md (clean removal + wiping ProgramData) - runas-modes.md (Service / InteractiveUser / SpecificUser decision flow) - service-account-and-ad.md (gMSA setup, delegated rights) - network-and-security.md (bind addresses, allowlists, HTTPS, secret storage) - troubleshooting.md (symptom -> first check, common errors) - recipes/zerto-pre-post-scripts.md (canonical use case) - recipes/github-style-hmac.md (GitHub / Stripe-shaped webhooks) - recipes/ad-password-reset.md (gMSA-backed self-service reset) - recipes/ui-on-desktop.md (InteractiveUser pattern) Top-level README.md restructured to point at docs/ as the source of truth, dropping the duplicated installation snippets. Installer ships docs/ alongside the binaries so they're available offline at C:\Program Files\WebhookServer\docs\. GUI Help menu gains a "Documentation" item that opens the docs site in a browser. Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com> * Config Checkpoints dialog + daily auto-checkpoint; drop installer GUI launch Three fixes: 1. Config Checkpoints submenu replaced with a proper dialog. Lists checkpoints with timestamp/size/filename, has a "Take Checkpoint Now" button, and a "Roll Back" button that becomes enabled when a row is selected. The previous click-a-menu-entry-immediate-restore flow was too easy to fire by accident. 2. New CheckpointScheduler BackgroundService creates a checkpoint at midnight every day. Combined with the existing auto-on-save snapshots, this guarantees a daily rollback point even if the config wasn't edited that day. A new "create-checkpoint" admin op plus AdminPipeServer.CreateCheckpoint helper does the actual file copy; both manual (via the dialog) and the scheduler use it. 3. Installer: drop the post-install "Launch Webhook Server" wizard step. It tried to launch the GUI un-elevated, which fails because the GUI's manifest is requireAdministrator. The Start Menu shortcut handles elevation correctly, so the user can launch from there. Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com> * Docs: replace AD-reset recipe with realistic Zerto failover walkthrough The AD password reset endpoint was a poor fit for what people actually need this server for. Replaced with a realistic Zerto post-failover example that's much closer to the project's purpose: - Update DNS A records for failed-over hostnames - Wait for the VM to come up at the DR site - PowerShell-remote into the VM and check / start critical services - Notify Teams with the result The flagship pattern is now: Zerto post-script (curl, fire-and-forget) calls an Async webhook endpoint -> 202 in milliseconds -> Zerto's failover sequence is never blocked. The server runs the actual work in the background, with full output captured in the daily log. A ready-to-use Zerto-side script ships at scripts/examples/zerto-post-failover.ps1 - pure curl.exe (no PowerShell modules), reads the bearer token from a file the ZVM service account can read. The installer now bundles scripts/examples/ alongside docs/ so the example is also available locally at C:\Program Files\WebhookServer\scripts\examples\. Removed: docs/recipes/ad-password-reset.md. Updated: docs/README.md, README.md, the recipe content itself. Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com> * Restore installer GUI launch (via shellexec) + checkpoint descriptions Two follow-ups to the previous Config Checkpoints commit: 1. Bring back the post-install "Launch Webhook Server" checkbox in the installer. The previous attempt failed because Inno Setup's postinstall flag launches via CreateProcess after Setup exits, bypassing the GUI's requireAdministrator manifest. Adding the shellexec flag switches to ShellExecute, which DOES honor the manifest and triggers a clean UAC prompt - so the post-install GUI launch works as expected. 2. Each checkpoint now carries a description, stored in a sidecar .meta.json file next to the snapshot. Defaults: - Auto-on-save: "Before save" - Midnight scheduler: "Nightly auto-checkpoint" - Manual: opens a small dialog so the user can type a meaningful description (defaults to "Manual checkpoint" if blank) The dialog and pruning both clean up sidecars alongside snapshots. The Config Checkpoints grid grows a Description column between When and Size. Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com> * v0.1.2: bump checkpoint retention 30 -> 90 Each checkpoint is a few KB of JSON plus a tiny sidecar; even at 90 entries on a config with hundreds of endpoints the on-disk footprint is negligible (worst case ~20 MB). With daily auto-checkpoints plus on-save snapshots, 30 entries could fill in a couple weeks of moderate use; 90 gives a comfortable ~3-month window. Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com> --------- Co-authored-by: Claude Opus 4.7 (1M context) <noreply@anthropic.com>
2026-05-08 10:49:09 -04:00
parent 7d94535d5d
commit f00ee0cf3a
30 changed files with 1871 additions and 146 deletions
@@ -26,6 +26,7 @@ public static class AdminOps
    public const string ListBackups = "list-backups";
    public const string RestoreBackup = "restore-backup";
    public const string ImportConfig = "import-config";
+    public const string CreateCheckpoint = "create-checkpoint";
 }

 public sealed class BackupEntry
@@ -33,6 +34,7 @@ public sealed class BackupEntry
    public string FileName { get; set; } = "";
    public DateTimeOffset SavedAt { get; set; }
    public long SizeBytes { get; set; }
+    public string? Description { get; set; }
 }

 public sealed class RestoreBackupArgs
@@ -40,6 +42,11 @@ public sealed class RestoreBackupArgs
    public string FileName { get; set; } = "";
 }

+public sealed class CreateCheckpointArgs
+{
+    public string? Description { get; set; }
+}
+
 public sealed class AdminRequest
 {
    [JsonPropertyName("op")] public string Op { get; set; } = "";
@@ -48,8 +48,15 @@ public sealed class ConfigStore
                Directory.CreateDirectory(backupsDir);
                var stamp = DateTime.UtcNow.ToString("yyyyMMdd-HHmmss");
                var backupPath = System.IO.Path.Combine(backupsDir, $"config-{stamp}.json");
-                File.Copy(Path, backupPath, overwrite: false);
-                PruneBackups(backupsDir, retain: 30);
+                if (!File.Exists(backupPath))
+                {
+                    File.Copy(Path, backupPath, overwrite: false);
+                    var sidecar = new { description = "Before save", reason = "before-save" };
+                    File.WriteAllText(
+                        System.IO.Path.ChangeExtension(backupPath, ".meta.json"),
+                        JsonSerializer.Serialize(sidecar, ConfigJson.Compact));
+                }
+                PruneBackups(backupsDir, retain: 90);
            }
            catch
            {
@@ -71,11 +78,18 @@ public sealed class ConfigStore
    private static void PruneBackups(string backupsDir, int retain)
    {
        var stale = new DirectoryInfo(backupsDir).GetFiles("config-*.json")
+            .Where(f => !f.Name.EndsWith(".meta.json", StringComparison.OrdinalIgnoreCase))
            .OrderByDescending(f => f.Name)
            .Skip(retain);
        foreach (var f in stale)
        {
-            try { f.Delete(); } catch { }
+            try
+            {
+                f.Delete();
+                var sidecar = System.IO.Path.ChangeExtension(f.FullName, ".meta.json");
+                if (File.Exists(sidecar)) File.Delete(sidecar);
+            }
+            catch { }
        }
    }

@@ -29,25 +29,7 @@
                <Separator/>
                <MenuItem Header="_Import config…" Command="{Binding ImportConfigCommand}"/>
                <MenuItem Header="_Export config…" Command="{Binding ExportConfigCommand}"/>
-                <MenuItem Header="Config _Checkpoints"
-                          ItemsSource="{Binding Backups}"
-                          ToolTip="Snapshots taken automatically before each save. Click one to restore."
-                          SubmenuOpened="OnBackupsSubmenuOpened">
-                    <MenuItem.ItemContainerStyle>
-                        <Style TargetType="MenuItem">
-                            <Setter Property="Header">
-                                <Setter.Value>
-                                    <MultiBinding StringFormat="{}{0:yyyy-MM-dd HH:mm:ss}  ({1:n0} bytes)">
-                                        <Binding Path="SavedAt"/>
-                                        <Binding Path="SizeBytes"/>
-                                    </MultiBinding>
-                                </Setter.Value>
-                            </Setter>
-                            <Setter Property="Command" Value="{Binding DataContext.RestoreBackupCommand, RelativeSource={RelativeSource AncestorType=Window}}"/>
-                            <Setter Property="CommandParameter" Value="{Binding}"/>
-                        </Style>
-                    </MenuItem.ItemContainerStyle>
-                </MenuItem>
+                <MenuItem Header="Config _Checkpoints…" Command="{Binding ShowConfigCheckpointsCommand}"/>
                <Separator/>
                <MenuItem Header="E_xit" Command="{Binding ExitCommand}"/>
            </MenuItem>
@@ -57,6 +39,8 @@
                <MenuItem Header="_Restart service" Command="{Binding RestartServiceCommand}"/>
            </MenuItem>
            <MenuItem Header="_Help">
+                <MenuItem Header="_Documentation…" Command="{Binding OpenDocumentationCommand}"/>
+                <Separator/>
                <MenuItem Header="_About Webhook Server…" Command="{Binding ShowAboutCommand}"/>
            </MenuItem>
        </Menu>
@@ -53,9 +53,4 @@ public partial class MainWindow : Window
            vm.EditEndpointCommand.Execute(null);
    }

-    private async void OnBackupsSubmenuOpened(object sender, RoutedEventArgs e)
-    {
-        if (DataContext is MainViewModel vm)
-            await vm.RefreshBackupsCommand.ExecuteAsync(null);
-    }
 }
@@ -100,4 +100,7 @@ public sealed class AdminPipeClient

    public Task<AdminResponse> ImportConfigAsync(ServerConfig config, CancellationToken ct = default) =>
        InvokeAsync(AdminOps.ImportConfig, config, ct);
+
+    public Task<BackupEntry?> CreateCheckpointAsync(string? description, CancellationToken ct = default) =>
+        InvokeAsync<BackupEntry>(AdminOps.CreateCheckpoint, new CreateCheckpointArgs { Description = description }, ct);
 }
@@ -0,0 +1,105 @@
+using System.Collections.ObjectModel;
+using System.Runtime.Versioning;
+using CommunityToolkit.Mvvm.ComponentModel;
+using CommunityToolkit.Mvvm.Input;
+using WebhookServer.Core.Ipc;
+using WebhookServer.Gui.Services;
+
+namespace WebhookServer.Gui.ViewModels;
+
+[SupportedOSPlatform("windows")]
+public sealed partial class ConfigCheckpointsViewModel : ObservableObject
+{
+    private readonly AdminPipeClient _client;
+
+    public ObservableCollection<BackupEntry> Checkpoints { get; } = new();
+
+    [ObservableProperty] private BackupEntry? _selected;
+    [ObservableProperty] private string _statusMessage = "";
+
+    public ConfigCheckpointsViewModel(AdminPipeClient client)
+    {
+        _client = client;
+    }
+
+    [RelayCommand]
+    public async Task RefreshAsync()
+    {
+        try
+        {
+            var list = await _client.ListBackupsAsync().ConfigureAwait(false);
+            Application.Current.Dispatcher.Invoke(() =>
+            {
+                Checkpoints.Clear();
+                foreach (var b in list) Checkpoints.Add(b);
+                StatusMessage = list.Count == 0
+                    ? "No checkpoints yet. Save the config or click Take Checkpoint Now."
+                    : $"{list.Count} checkpoint{(list.Count == 1 ? "" : "s")}.";
+            });
+        }
+        catch (Exception ex)
+        {
+            Application.Current.Dispatcher.Invoke(() => StatusMessage = $"Could not load: {ex.Message}");
+        }
+    }
+
+    [RelayCommand]
+    private async Task TakeCheckpointAsync()
+    {
+        // Prompt for an optional description on the UI thread.
+        string? description = null;
+        var prompted = Application.Current.Dispatcher.Invoke(() =>
+        {
+            var dlg = new Views.TakeCheckpointDialog { Owner = Application.Current.MainWindow };
+            if (dlg.ShowDialog() != true) return false;
+            description = string.IsNullOrWhiteSpace(dlg.Description) ? null : dlg.Description;
+            return true;
+        });
+        if (!prompted) return;
+
+        try
+        {
+            var entry = await _client.CreateCheckpointAsync(description).ConfigureAwait(false);
+            await RefreshAsync().ConfigureAwait(false);
+            if (entry is not null)
+            {
+                Application.Current.Dispatcher.Invoke(() =>
+                {
+                    Selected = Checkpoints.FirstOrDefault(c => c.FileName == entry.FileName);
+                    StatusMessage = $"Created {entry.FileName}";
+                });
+            }
+        }
+        catch (Exception ex)
+        {
+            Application.Current.Dispatcher.Invoke(() =>
+                MessageBox.Show(ex.Message, "Take checkpoint failed", MessageBoxButton.OK, MessageBoxImage.Error));
+        }
+    }
+
+    [RelayCommand]
+    private async Task RollbackAsync()
+    {
+        if (Selected is null) return;
+
+        var ok = MessageBox.Show(
+            $"Roll the configuration back to the checkpoint from {Selected.SavedAt.ToLocalTime():yyyy-MM-dd HH:mm:ss}?\n\nThe current configuration is automatically saved as a new checkpoint first, so you can roll forward again.",
+            "Confirm rollback",
+            MessageBoxButton.OKCancel,
+            MessageBoxImage.Warning);
+        if (ok != MessageBoxResult.OK) return;
+
+        try
+        {
+            await _client.RestoreBackupAsync(Selected.FileName).ConfigureAwait(false);
+            await RefreshAsync().ConfigureAwait(false);
+            Application.Current.Dispatcher.Invoke(() =>
+                StatusMessage = $"Rolled back to {Selected!.FileName}.");
+        }
+        catch (Exception ex)
+        {
+            Application.Current.Dispatcher.Invoke(() =>
+                MessageBox.Show(ex.Message, "Rollback failed", MessageBoxButton.OK, MessageBoxImage.Error));
+        }
+    }
+}
@@ -175,39 +175,18 @@ public sealed partial class MainViewModel : ObservableObject
        }
    }

-    [ObservableProperty] private System.Collections.ObjectModel.ObservableCollection<BackupEntry> _backups = new();
-
    [RelayCommand]
-    private async Task RefreshBackupsAsync()
+    private void ShowConfigCheckpoints()
    {
-        try
+        var dlg = new Views.ConfigCheckpointsDialog
        {
-            var list = await _client.ListBackupsAsync().ConfigureAwait(false);
-            Application.Current.Dispatcher.Invoke(() =>
-            {
-                Backups.Clear();
-                foreach (var b in list) Backups.Add(b);
-            });
-        }
-        catch { /* ignore - checkpoint listing isn't critical */ }
-    }
-
-    [RelayCommand]
-    private async Task RestoreBackupAsync(BackupEntry? entry)
-    {
-        if (entry is null) return;
-        var ok = MessageBox.Show(
-            $"Restore the configuration from the checkpoint taken at {entry.SavedAt:yyyy-MM-dd HH:mm}?\n\nThe current configuration is automatically saved as a new checkpoint first, so you can roll forward again.",
-            "Restore checkpoint",
-            MessageBoxButton.OKCancel,
-            MessageBoxImage.Question);
-        if (ok != MessageBoxResult.OK) return;
-        try
-        {
-            await _client.RestoreBackupAsync(entry.FileName).ConfigureAwait(false);
-            await RefreshAsync().ConfigureAwait(false);
-        }
-        catch (Exception ex) { ShowError("Restore failed", ex); }
+            Owner = Application.Current.MainWindow,
+            DataContext = new ConfigCheckpointsViewModel(_client),
+        };
+        dlg.ShowDialog();
+        // After the dialog closes, the live config may have changed via rollback,
+        // so refresh the main grid.
+        _ = RefreshAsync();
    }

    [RelayCommand]
@@ -290,6 +269,23 @@ public sealed partial class MainViewModel : ObservableObject
        dlg.ShowDialog();
    }

+    [RelayCommand]
+    private void OpenDocumentation()
+    {
+        try
+        {
+            System.Diagnostics.Process.Start(new System.Diagnostics.ProcessStartInfo
+            {
+                FileName = "https://github.com/recklessop/webhook-server/tree/main/docs",
+                UseShellExecute = true,
+            });
+        }
+        catch (Exception ex)
+        {
+            ShowError("Could not open documentation", ex);
+        }
+    }
+
    [RelayCommand]
    private void Exit()
    {
@@ -0,0 +1,53 @@
+<Window x:Class="WebhookServer.Gui.Views.ConfigCheckpointsDialog"
+        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"
+        xmlns:vm="clr-namespace:WebhookServer.Gui.ViewModels"
+        mc:Ignorable="d"
+        Title="Config Checkpoints"
+        Height="500" Width="640"
+        Icon="/webhook-server.ico"
+        WindowStartupLocation="CenterOwner"
+        d:DataContext="{d:DesignInstance Type=vm:ConfigCheckpointsViewModel}">
+    <DockPanel Margin="12">
+        <TextBlock DockPanel.Dock="Top" TextWrapping="Wrap" Margin="0,0,0,8" Foreground="#444">
+            A checkpoint is a snapshot of <Bold>config.json</Bold> taken before each save and once a day at midnight.
+            Pick one and click <Bold>Roll Back</Bold> to restore it. The current configuration is automatically saved
+            as a new checkpoint before any rollback, so you can always roll forward again.
+        </TextBlock>
+
+        <StackPanel DockPanel.Dock="Bottom" Orientation="Horizontal" HorizontalAlignment="Right" Margin="0,8,0,0">
+            <Button Content="Take Checkpoint Now" Command="{Binding TakeCheckpointCommand}" Margin="0,0,8,0" Padding="10,4"/>
+            <Button Content="Roll Back" Command="{Binding RollbackCommand}"
+                    IsEnabled="{Binding Selected, Converter={StaticResource NotNull}}"
+                    Margin="0,0,8,0" Padding="10,4"/>
+            <Button Content="Close" IsCancel="True" Click="OnClose" Padding="10,4"/>
+        </StackPanel>
+
+        <StackPanel DockPanel.Dock="Bottom" Orientation="Horizontal" Margin="0,4,0,0">
+            <Button Content="Refresh" Command="{Binding RefreshCommand}" Padding="8,2"/>
+            <TextBlock Text="{Binding StatusMessage}" Foreground="Gray" FontStyle="Italic" VerticalAlignment="Center" Margin="12,0,0,0"/>
+        </StackPanel>
+
+        <DataGrid ItemsSource="{Binding Checkpoints}"
+                  SelectedItem="{Binding Selected, Mode=TwoWay}"
+                  AutoGenerateColumns="False"
+                  CanUserAddRows="False"
+                  CanUserDeleteRows="False"
+                  IsReadOnly="True"
+                  HeadersVisibility="Column"
+                  GridLinesVisibility="Horizontal">
+            <DataGrid.Columns>
+                <DataGridTextColumn Header="When (local)" Width="170"
+                                    Binding="{Binding SavedAt, StringFormat='{}{0:yyyy-MM-dd HH:mm:ss}', ConverterCulture=en-US}"/>
+                <DataGridTextColumn Header="Description" Width="*"
+                                    Binding="{Binding Description}"/>
+                <DataGridTextColumn Header="Size" Width="100"
+                                    Binding="{Binding SizeBytes, StringFormat='{}{0:n0} bytes'}"/>
+                <DataGridTextColumn Header="File name" Width="200"
+                                    Binding="{Binding FileName}" FontFamily="Consolas"/>
+            </DataGrid.Columns>
+        </DataGrid>
+    </DockPanel>
+</Window>
@@ -0,0 +1,19 @@
+using System.Windows;
+using WebhookServer.Gui.ViewModels;
+
+namespace WebhookServer.Gui.Views;
+
+public partial class ConfigCheckpointsDialog : Window
+{
+    public ConfigCheckpointsDialog()
+    {
+        InitializeComponent();
+        Loaded += async (_, _) =>
+        {
+            if (DataContext is ConfigCheckpointsViewModel vm)
+                await vm.RefreshAsync();
+        };
+    }
+
+    private void OnClose(object sender, RoutedEventArgs e) => Close();
+}
@@ -0,0 +1,34 @@
+<Window x:Class="WebhookServer.Gui.Views.TakeCheckpointDialog"
+        xmlns="http://schemas.microsoft.com/winfx/2006/xaml/presentation"
+        xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml"
+        Title="Take checkpoint"
+        Height="180" Width="440"
+        ResizeMode="NoResize"
+        WindowStartupLocation="CenterOwner"
+        Icon="/webhook-server.ico"
+        ShowInTaskbar="False">
+    <Grid Margin="16">
+        <Grid.RowDefinitions>
+            <RowDefinition Height="Auto"/>
+            <RowDefinition Height="Auto"/>
+            <RowDefinition Height="Auto"/>
+            <RowDefinition Height="*"/>
+            <RowDefinition Height="Auto"/>
+        </Grid.RowDefinitions>
+
+        <TextBlock Grid.Row="0" TextWrapping="Wrap"
+                   Text="Description for this checkpoint (optional):"/>
+        <TextBox x:Name="DescriptionBox" Grid.Row="1" Margin="0,8,0,0" MaxLength="120">
+            <TextBox.InputBindings>
+                <KeyBinding Key="Enter" Command="{Binding OkCommand, ElementName=Self, FallbackValue={x:Null}}"/>
+            </TextBox.InputBindings>
+        </TextBox>
+        <TextBlock Grid.Row="2" Foreground="Gray" FontStyle="Italic" FontSize="11" Margin="0,4,0,0"
+                   Text="Examples: 'Before adding new endpoint', 'Pre-AD-policy-change'. Leave blank to use 'Manual checkpoint'."/>
+
+        <StackPanel Grid.Row="4" Orientation="Horizontal" HorizontalAlignment="Right" Margin="0,12,0,0">
+            <Button Content="OK" Width="80" IsDefault="True" Click="OnOk" Margin="0,0,8,0"/>
+            <Button Content="Cancel" Width="80" IsCancel="True" Click="OnCancel"/>
+        </StackPanel>
+    </Grid>
+</Window>
@@ -0,0 +1,27 @@
+using System.Windows;
+
+namespace WebhookServer.Gui.Views;
+
+public partial class TakeCheckpointDialog : Window
+{
+    public string Description { get; private set; } = "";
+
+    public TakeCheckpointDialog()
+    {
+        InitializeComponent();
+        Loaded += (_, _) => DescriptionBox.Focus();
+    }
+
+    private void OnOk(object sender, RoutedEventArgs e)
+    {
+        Description = DescriptionBox.Text?.Trim() ?? "";
+        DialogResult = true;
+        Close();
+    }
+
+    private void OnCancel(object sender, RoutedEventArgs e)
+    {
+        DialogResult = false;
+        Close();
+    }
+}
@@ -225,16 +225,65 @@ internal sealed class AdminPipeServer : BackgroundService
                return AdminResponse.Success(SafeSnapshotForWire(_state.Snapshot()));
            }

+            case AdminOps.CreateCheckpoint:
+            {
+                var args = DeserializeData<CreateCheckpointArgs>(request);
+                var description = args?.Description;
+                if (string.IsNullOrWhiteSpace(description)) description = "Manual checkpoint";
+                var entry = CreateCheckpoint("manual", description);
+                _logger.LogInformation("Manual checkpoint created: {File} ({Desc})", entry.FileName, description);
+                return AdminResponse.Success(entry);
+            }
+
            default:
                return AdminResponse.Failure($"unknown op '{request.Op}'");
        }
    }

+    /// <summary>
+    /// Snapshot the current config.json into the backups folder. Used by the
+    /// "Take checkpoint now" GUI action, the midnight scheduler, and the
+    /// auto-on-save hook in ConfigStore. Description is stored in a sidecar
+    /// .meta.json file next to the snapshot so it survives restarts and can
+    /// be rendered in the GUI.
+    /// </summary>
+    public static BackupEntry CreateCheckpoint(string reason, string description)
+    {
+        var configPath = ServicePaths.ConfigPath;
+        if (!File.Exists(configPath))
+            throw new FileNotFoundException("no config.json exists yet to snapshot");
+
+        var dir = Path.Combine(ServicePaths.DataRoot, "backups");
+        Directory.CreateDirectory(dir);
+
+        var stamp = DateTime.UtcNow.ToString("yyyyMMdd-HHmmss");
+        var dest = Path.Combine(dir, $"config-{stamp}.json");
+        if (File.Exists(dest))
+            dest = Path.Combine(dir, $"config-{stamp}-{reason}.json");
+
+        File.Copy(configPath, dest);
+
+        // Write the sidecar metadata.
+        var sidecarPath = Path.ChangeExtension(dest, ".meta.json");
+        var sidecar = new { description, reason };
+        File.WriteAllText(sidecarPath, JsonSerializer.Serialize(sidecar, ConfigJson.Compact));
+
+        var info = new FileInfo(dest);
+        return new BackupEntry
+        {
+            FileName = info.Name,
+            SavedAt = info.LastWriteTimeUtc,
+            SizeBytes = info.Length,
+            Description = description,
+        };
+    }
+
    private static List<BackupEntry> ListBackups()
    {
        var dir = Path.Combine(ServicePaths.DataRoot, "backups");
        if (!Directory.Exists(dir)) return new List<BackupEntry>();
        return new DirectoryInfo(dir).GetFiles("config-*.json")
+            .Where(f => !f.Name.EndsWith(".meta.json", StringComparison.OrdinalIgnoreCase))
            .OrderByDescending(f => f.Name)
            .Take(50)
            .Select(f => new BackupEntry
@@ -242,10 +291,23 @@ internal sealed class AdminPipeServer : BackgroundService
                FileName = f.Name,
                SavedAt = f.LastWriteTimeUtc,
                SizeBytes = f.Length,
+                Description = ReadSidecarDescription(f.FullName),
            })
            .ToList();
    }

+    private static string? ReadSidecarDescription(string snapshotPath)
+    {
+        try
+        {
+            var sidecarPath = Path.ChangeExtension(snapshotPath, ".meta.json");
+            if (!File.Exists(sidecarPath)) return null;
+            using var doc = JsonDocument.Parse(File.ReadAllText(sidecarPath));
+            return doc.RootElement.TryGetProperty("description", out var d) ? d.GetString() : null;
+        }
+        catch { return null; }
+    }
+
    private async Task<ServerConfig> RestoreBackupAsync(string fileName, CancellationToken ct)
    {
        // Refuse anything that tries to escape the backups directory.
@@ -0,0 +1,50 @@
+using System.Runtime.Versioning;
+using Microsoft.Extensions.Hosting;
+using Microsoft.Extensions.Logging;
+
+namespace WebhookServer.Service;
+
+/// <summary>
+/// Creates a daily config checkpoint at midnight (local time). Combined with
+/// the auto-on-save snapshots in ConfigStore.SaveAsync, this guarantees a
+/// rollback point for every day even if the user makes no changes.
+/// </summary>
+[SupportedOSPlatform("windows")]
+internal sealed class CheckpointScheduler : BackgroundService
+{
+    private readonly ILogger<CheckpointScheduler> _logger;
+
+    public CheckpointScheduler(ILogger<CheckpointScheduler> logger)
+    {
+        _logger = logger;
+    }
+
+    protected override async Task ExecuteAsync(CancellationToken stoppingToken)
+    {
+        _logger.LogInformation("Daily checkpoint scheduler running");
+
+        while (!stoppingToken.IsCancellationRequested)
+        {
+            var now = DateTime.Now;
+            var nextMidnight = now.Date.AddDays(1);
+            var delay = nextMidnight - now;
+
+            try { await Task.Delay(delay, stoppingToken).ConfigureAwait(false); }
+            catch (OperationCanceledException) { return; }
+
+            try
+            {
+                var entry = AdminPipeServer.CreateCheckpoint("daily", "Nightly auto-checkpoint");
+                _logger.LogInformation("Daily checkpoint created: {File}", entry.FileName);
+            }
+            catch (FileNotFoundException)
+            {
+                // No config.json yet (fresh install, GUI never opened) - skip silently.
+            }
+            catch (Exception ex)
+            {
+                _logger.LogWarning(ex, "Daily checkpoint creation failed");
+            }
+        }
+    }
+}
@@ -49,6 +49,7 @@ try
    builder.Services.AddSingleton<WebhookRouter>();
    builder.Services.AddHostedService<CallbackBackgroundService>();
    builder.Services.AddHostedService<AdminPipeServer>();
+    builder.Services.AddHostedService<CheckpointScheduler>();

    var app = builder.Build();