From 0964439441298c5d483fe4592e000e8759654284 Mon Sep 17 00:00:00 2001
From: PointStar <chaim.marcus@gmail.com>
Date: Mon, 11 May 2026 15:47:36 +0300
Subject: [PATCH] =?UTF-8?q?feat(compose):=20Task=20#5=20=E2=80=94=20Compos?=
 =?UTF-8?q?e=20from=20Case=20+=20URL=20protocol=20+=20auto-file?=
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

UI:
- ComposeFromCaseDialog (RTL, search-then-pick a single Case via
  GlobalSearch + entityType=Case filter)
- ComposeFromCaseViewModel — debounced GlobalSearch, returns chosen
  EspoEntityRef

Host:
- ComposeService.ApplyCaseToMailAsync:
  * fetches Case + primary Contact
  * stamps UserProperties EspoCaseId, EspoCaseName, OutlookAddinGuid
  * pre-fills To/Subject and appends an RTL footer with a CRM deep link
- ItemSend hook (in AddInHost.HookItemSend): when the user sends a
  tagged compose, register guid → target with SentItemsWatcher
- SentItemsWatcher: rooted Items reference (prevents GC), 30s expiry
  sweep, 2-min default timeout per pending tag, MailMatched event
- AddInHost.OnSentMailMatched: extracts the sent MailItem, files via
  FilingService, stamps "Filed: {name}" category
- LaunchComposeFromCaseAsync (Inspector ribbon) and
  LaunchComposeFromCaseByIdAsync (URL protocol) entry points
- NamedPipeListener (\.\pipe\MarcusLaw.OutlookAddin) — listens for
  "COMPOSE <caseId>" lines, dispatches on WPF Dispatcher

Ribbon:
- InspectorRibbon.xml — "כתוב מתיק" button on Mail Compose ribbon, hidden
  for received/read mail via getVisible
- ExplorerRibbon class now serves both Explorer and Inspector ribbons
  (single IRibbonExtensibility, dispatches by ribbonID)

URL protocol:
- New OutlookAddinProtocolHandler console project (net48 WinExe):
  parses outlookaddin://compose?caseId=<id>, connects to named pipe,
  writes "COMPOSE <id>\n"
- tools/install-protocol.ps1 + uninstall-protocol.ps1 register the
  scheme under HKCU\Software\Classes\outlookaddin

Core/UI/Tests + protocol handler all build; 38 unit tests still green.

Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com>
---
 OutlookAddin.sln                              |   6 +
 .../Dialogs/ComposeFromCaseDialog.xaml        |  62 +++++
 .../Dialogs/ComposeFromCaseDialog.xaml.cs     |  36 +++
 .../ViewModels/ComposeFromCaseViewModel.cs    | 127 +++++++++++
 src/OutlookAddin/OutlookAddin.csproj          |  12 +
 src/OutlookAddin/Ribbon/ExplorerRibbon.cs     |  80 ++++++-
 src/OutlookAddin/Ribbon/InspectorRibbon.xml   |  19 ++
 src/OutlookAddin/Services/AddInHost.cs        | 215 ++++++++++++++++++
 src/OutlookAddin/Services/ComposeService.cs   | 162 +++++++++++++
 .../Services/NamedPipeListener.cs             |  87 +++++++
 src/OutlookAddin/Services/SentItemsWatcher.cs | 179 +++++++++++++++
 .../OutlookAddinProtocolHandler.csproj        |  17 ++
 src/OutlookAddinProtocolHandler/Program.cs    |  89 ++++++++
 tools/install-protocol.ps1                    |  41 ++++
 tools/uninstall-protocol.ps1                  |   3 +
 15 files changed, 1123 insertions(+), 12 deletions(-)
 create mode 100644 src/OutlookAddin.UI/Dialogs/ComposeFromCaseDialog.xaml
 create mode 100644 src/OutlookAddin.UI/Dialogs/ComposeFromCaseDialog.xaml.cs
 create mode 100644 src/OutlookAddin.UI/ViewModels/ComposeFromCaseViewModel.cs
 create mode 100644 src/OutlookAddin/Ribbon/InspectorRibbon.xml
 create mode 100644 src/OutlookAddin/Services/ComposeService.cs
 create mode 100644 src/OutlookAddin/Services/NamedPipeListener.cs
 create mode 100644 src/OutlookAddin/Services/SentItemsWatcher.cs
 create mode 100644 src/OutlookAddinProtocolHandler/OutlookAddinProtocolHandler.csproj
 create mode 100644 src/OutlookAddinProtocolHandler/Program.cs
 create mode 100644 tools/install-protocol.ps1
 create mode 100644 tools/uninstall-protocol.ps1

diff --git a/OutlookAddin.sln b/OutlookAddin.sln
index 6f7681d..8d7a47c 100644
--- a/OutlookAddin.sln
+++ b/OutlookAddin.sln
@@ -10,6 +10,8 @@ Project("{FAE04EC0-301F-11D3-BF4B-00C04F79EFBC}") = "OutlookAddin.Tests", "src\O
 EndProject
 Project("{FAE04EC0-301F-11D3-BF4B-00C04F79EFBC}") = "OutlookAddin", "src\OutlookAddin\OutlookAddin.csproj", "{7A8B6509-CB21-42BD-A42C-2735170AFFD2}"
 EndProject
+Project("{FAE04EC0-301F-11D3-BF4B-00C04F79EFBC}") = "OutlookAddinProtocolHandler", "src\OutlookAddinProtocolHandler\OutlookAddinProtocolHandler.csproj", "{A0000000-0000-0000-0000-000000000005}"
+EndProject
 Global
 	GlobalSection(SolutionConfigurationPlatforms) = preSolution
 		Debug|Any CPU = Debug|Any CPU
@@ -32,6 +34,10 @@ Global
 		{7A8B6509-CB21-42BD-A42C-2735170AFFD2}.Debug|Any CPU.Build.0 = Debug|Any CPU
 		{7A8B6509-CB21-42BD-A42C-2735170AFFD2}.Release|Any CPU.ActiveCfg = Release|Any CPU
 		{7A8B6509-CB21-42BD-A42C-2735170AFFD2}.Release|Any CPU.Build.0 = Release|Any CPU
+		{A0000000-0000-0000-0000-000000000005}.Debug|Any CPU.ActiveCfg = Debug|Any CPU
+		{A0000000-0000-0000-0000-000000000005}.Debug|Any CPU.Build.0 = Debug|Any CPU
+		{A0000000-0000-0000-0000-000000000005}.Release|Any CPU.ActiveCfg = Release|Any CPU
+		{A0000000-0000-0000-0000-000000000005}.Release|Any CPU.Build.0 = Release|Any CPU
 	EndGlobalSection
 	GlobalSection(SolutionProperties) = preSolution
 		HideSolutionNode = FALSE
diff --git a/src/OutlookAddin.UI/Dialogs/ComposeFromCaseDialog.xaml b/src/OutlookAddin.UI/Dialogs/ComposeFromCaseDialog.xaml
new file mode 100644
index 0000000..c551fb8
--- /dev/null
+++ b/src/OutlookAddin.UI/Dialogs/ComposeFromCaseDialog.xaml
@@ -0,0 +1,62 @@
+<Window x:Class="MarcusLaw.OutlookAddin.UI.Dialogs.ComposeFromCaseDialog"
+        xmlns="http://schemas.microsoft.com/winfx/2006/xaml/presentation"
+        xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml"
+        Title="כתוב מייל מתיק"
+        Height="450" Width="560"
+        MinHeight="320" MinWidth="500"
+        FlowDirection="RightToLeft"
+        WindowStartupLocation="CenterOwner"
+        ShowInTaskbar="False"
+        ResizeMode="CanResize">
+    <Grid Margin="12">
+        <Grid.RowDefinitions>
+            <RowDefinition Height="Auto" />
+            <RowDefinition Height="*" />
+            <RowDefinition Height="Auto" />
+            <RowDefinition Height="Auto" />
+        </Grid.RowDefinitions>
+
+        <DockPanel Grid.Row="0" Margin="0,0,0,8" LastChildFill="True">
+            <TextBlock DockPanel.Dock="Right" Text="חפש תיק:" VerticalAlignment="Center" Margin="0,0,8,0" />
+            <TextBox x:Name="SearchBox"
+                     Text="{Binding SearchText, UpdateSourceTrigger=PropertyChanged}"
+                     Padding="6,4"
+                     FontSize="14" />
+        </DockPanel>
+
+        <Border Grid.Row="1" BorderBrush="#CCC" BorderThickness="1" CornerRadius="3">
+            <ListBox ItemsSource="{Binding Cases}"
+                     SelectedItem="{Binding SelectedCase}"
+                     BorderThickness="0">
+                <ListBox.ItemTemplate>
+                    <DataTemplate>
+                        <StackPanel Margin="2,3">
+                            <TextBlock>
+                                <Run Text="[" /><Run Text="{Binding Number, Mode=OneWay}" /><Run Text="] " />
+                                <Run Text="{Binding Name, Mode=OneWay}" FontWeight="SemiBold" />
+                            </TextBlock>
+                            <TextBlock Text="{Binding Status}" Foreground="Gray" FontSize="10" />
+                        </StackPanel>
+                    </DataTemplate>
+                </ListBox.ItemTemplate>
+            </ListBox>
+        </Border>
+
+        <TextBlock Grid.Row="2" Text="{Binding StatusMessage}"
+                   Foreground="Gray" Margin="0,6,0,0" TextWrapping="Wrap" />
+
+        <StackPanel Grid.Row="3" Orientation="Horizontal" HorizontalAlignment="Left" Margin="0,8,0,0">
+            <Button Command="{Binding SubmitCommand}"
+                    IsDefault="True"
+                    Content="המשך"
+                    Padding="20,5"
+                    Margin="0,0,8,0"
+                    MinWidth="100" />
+            <Button Command="{Binding CancelCommand}"
+                    IsCancel="True"
+                    Content="ביטול"
+                    Padding="20,5"
+                    MinWidth="100" />
+        </StackPanel>
+    </Grid>
+</Window>
diff --git a/src/OutlookAddin.UI/Dialogs/ComposeFromCaseDialog.xaml.cs b/src/OutlookAddin.UI/Dialogs/ComposeFromCaseDialog.xaml.cs
new file mode 100644
index 0000000..22ed90a
--- /dev/null
+++ b/src/OutlookAddin.UI/Dialogs/ComposeFromCaseDialog.xaml.cs
@@ -0,0 +1,36 @@
+using System;
+using System.Windows;
+using MarcusLaw.OutlookAddin.UI.ViewModels;
+
+namespace MarcusLaw.OutlookAddin.UI.Dialogs
+{
+    public partial class ComposeFromCaseDialog : Window
+    {
+        private ComposeFromCaseViewModel? _viewModel;
+
+        public ComposeFromCaseDialog()
+        {
+            InitializeComponent();
+            Loaded += (_, __) => SearchBox.Focus();
+        }
+
+        public ComposeFromCaseDialog(ComposeFromCaseViewModel viewModel) : this()
+        {
+            AttachViewModel(viewModel);
+        }
+
+        public void AttachViewModel(ComposeFromCaseViewModel viewModel)
+        {
+            if (_viewModel != null) _viewModel.RequestClose -= OnRequestClose;
+            _viewModel = viewModel ?? throw new ArgumentNullException(nameof(viewModel));
+            DataContext = _viewModel;
+            _viewModel.RequestClose += OnRequestClose;
+        }
+
+        private void OnRequestClose(object? sender, EventArgs e)
+        {
+            DialogResult = _viewModel?.DialogResult;
+            Close();
+        }
+    }
+}
diff --git a/src/OutlookAddin.UI/ViewModels/ComposeFromCaseViewModel.cs b/src/OutlookAddin.UI/ViewModels/ComposeFromCaseViewModel.cs
new file mode 100644
index 0000000..6bdba63
--- /dev/null
+++ b/src/OutlookAddin.UI/ViewModels/ComposeFromCaseViewModel.cs
@@ -0,0 +1,127 @@
+using System;
+using System.Collections.ObjectModel;
+using System.Threading;
+using System.Threading.Tasks;
+using CommunityToolkit.Mvvm.ComponentModel;
+using CommunityToolkit.Mvvm.Input;
+using MarcusLaw.OutlookAddin.Core.Models;
+using MarcusLaw.OutlookAddin.Core.Services;
+using Serilog;
+
+namespace MarcusLaw.OutlookAddin.UI.ViewModels
+{
+    /// <summary>
+    /// Picks a single Case via the EspoCRM GlobalSearch API. Returns the
+    /// chosen <see cref="EspoEntityRef"/> so the host can fetch full details
+    /// (contacts, account, etc.) and populate the open MailItem.
+    /// </summary>
+    public sealed partial class ComposeFromCaseViewModel : ObservableObject
+    {
+        private readonly IEspoCrmClient _client;
+        private readonly ILogger _logger;
+        private CancellationTokenSource? _searchCts;
+
+        [ObservableProperty]
+        private string searchText = string.Empty;
+
+        [ObservableProperty]
+        private CaseEntity? selectedCase;
+
+        [ObservableProperty]
+        private string? statusMessage;
+
+        public ObservableCollection<CaseEntity> Cases { get; } = new ObservableCollection<CaseEntity>();
+
+        public EspoEntityRef? Result { get; private set; }
+
+        public bool? DialogResult { get; private set; }
+
+        public event EventHandler? RequestClose;
+
+        public ComposeFromCaseViewModel(IEspoCrmClient client, ILogger logger)
+        {
+            _client = client ?? throw new ArgumentNullException(nameof(client));
+            _logger = logger ?? throw new ArgumentNullException(nameof(logger));
+        }
+
+        partial void OnSearchTextChanged(string value)
+        {
+            _searchCts?.Cancel();
+            _searchCts = new CancellationTokenSource();
+            _ = SearchAsync(value, _searchCts.Token);
+        }
+
+        partial void OnSelectedCaseChanged(CaseEntity? value)
+        {
+            SubmitCommand.NotifyCanExecuteChanged();
+        }
+
+        private async Task SearchAsync(string query, CancellationToken ct)
+        {
+            try
+            {
+                await Task.Delay(250, ct).ConfigureAwait(true);
+
+                var trimmed = (query ?? string.Empty).Trim();
+                if (trimmed.Length < 2)
+                {
+                    Cases.Clear();
+                    StatusMessage = null;
+                    return;
+                }
+
+                var search = await _client.GlobalSearchAsync(trimmed, ct).ConfigureAwait(true);
+                ct.ThrowIfCancellationRequested();
+
+                Cases.Clear();
+                int kept = 0;
+                foreach (var hit in search.List)
+                {
+                    if (!string.Equals(hit.EntityType, "Case", StringComparison.OrdinalIgnoreCase)) continue;
+                    Cases.Add(new CaseEntity
+                    {
+                        Id = hit.Id,
+                        Name = hit.Name,
+                    });
+                    kept++;
+                }
+                StatusMessage = kept == 0
+                    ? "אין תוצאות מסוג תיק (Case)"
+                    : $"נמצאו {kept} תיקים";
+            }
+            catch (OperationCanceledException) { /* superseded */ }
+            catch (EspoCrmAuthorizationException)
+            {
+                StatusMessage = "מפתח ה-API נדחה — יש לעדכן בהגדרות";
+            }
+            catch (Exception ex)
+            {
+                _logger.Warning(ex, "ComposeFromCase search failed");
+                StatusMessage = "שגיאת חיפוש: " + ex.Message;
+            }
+        }
+
+        [RelayCommand(CanExecute = nameof(CanSubmit))]
+        private void Submit()
+        {
+            if (SelectedCase == null) return;
+            Result = new EspoEntityRef
+            {
+                Id = SelectedCase.Id,
+                Name = SelectedCase.Name,
+                EntityType = "Case"
+            };
+            DialogResult = true;
+            RequestClose?.Invoke(this, EventArgs.Empty);
+        }
+
+        private bool CanSubmit() => SelectedCase != null && !string.IsNullOrWhiteSpace(SelectedCase.Id);
+
+        [RelayCommand]
+        private void Cancel()
+        {
+            DialogResult = false;
+            RequestClose?.Invoke(this, EventArgs.Empty);
+        }
+    }
+}
diff --git a/src/OutlookAddin/OutlookAddin.csproj b/src/OutlookAddin/OutlookAddin.csproj
index 185f46d..9f7c993 100644
--- a/src/OutlookAddin/OutlookAddin.csproj
+++ b/src/OutlookAddin/OutlookAddin.csproj
@@ -232,18 +232,30 @@
     <EmbeddedResource Include="Ribbon\ExplorerRibbon.xml">
       <LogicalName>OutlookAddin.Ribbon.ExplorerRibbon.xml</LogicalName>
     </EmbeddedResource>
+    <EmbeddedResource Include="Ribbon\InspectorRibbon.xml">
+      <LogicalName>OutlookAddin.Ribbon.InspectorRibbon.xml</LogicalName>
+    </EmbeddedResource>
     <Compile Include="Services\AddInHost.cs">
       <SubType>Code</SubType>
     </Compile>
+    <Compile Include="Services\ComposeService.cs">
+      <SubType>Code</SubType>
+    </Compile>
     <Compile Include="Services\ExplorerSelectionHandler.cs">
       <SubType>Code</SubType>
     </Compile>
     <Compile Include="Services\MailItemExtractor.cs">
       <SubType>Code</SubType>
     </Compile>
+    <Compile Include="Services\NamedPipeListener.cs">
+      <SubType>Code</SubType>
+    </Compile>
     <Compile Include="Services\RetryQueueProcessor.cs">
       <SubType>Code</SubType>
     </Compile>
+    <Compile Include="Services\SentItemsWatcher.cs">
+      <SubType>Code</SubType>
+    </Compile>
     <Compile Include="Services\SidebarController.cs">
       <SubType>Code</SubType>
     </Compile>
diff --git a/src/OutlookAddin/Ribbon/ExplorerRibbon.cs b/src/OutlookAddin/Ribbon/ExplorerRibbon.cs
index f032e36..e841d31 100644
--- a/src/OutlookAddin/Ribbon/ExplorerRibbon.cs
+++ b/src/OutlookAddin/Ribbon/ExplorerRibbon.cs
@@ -7,36 +7,44 @@ using Outlook = Microsoft.Office.Interop.Outlook;
 
 namespace OutlookAddin.Ribbon
 {
+    /// <summary>
+    /// Single <see cref="IRibbonExtensibility"/> implementation that serves
+    /// both the Explorer ribbon (Inbox / list view) and the Inspector ribbon
+    /// (compose window) — VSTO calls <see cref="GetCustomUI"/> with a
+    /// ribbonID identifying which host is asking.
+    /// </summary>
     [ComVisible(true)]
     public class ExplorerRibbon : IRibbonExtensibility
     {
-        private const string ResourceName = "OutlookAddin.Ribbon.ExplorerRibbon.xml";
-        private const string ButtonId = "FileToEspoCrm";
+        private const string ExplorerResource = "OutlookAddin.Ribbon.ExplorerRibbon.xml";
+        private const string InspectorResource = "OutlookAddin.Ribbon.InspectorRibbon.xml";
+        private const string FileButtonId = "FileToEspoCrm";
 
-        private IRibbonUI? _ribbon;
+        private IRibbonUI? _explorerRibbon;
+        private IRibbonUI? _inspectorRibbon;
 
         public string GetCustomUI(string ribbonID)
         {
-            if (ribbonID != "Microsoft.Outlook.Explorer") return string.Empty;
-            using (var stream = Assembly.GetExecutingAssembly().GetManifestResourceStream(ResourceName))
+            switch (ribbonID)
             {
-                if (stream == null) return string.Empty;
-                using (var reader = new StreamReader(stream))
-                {
-                    return reader.ReadToEnd();
-                }
+                case "Microsoft.Outlook.Explorer":
+                    return LoadResource(ExplorerResource);
+                case "Microsoft.Outlook.Mail.Compose":
+                    return LoadResource(InspectorResource);
+                default:
+                    return string.Empty;
             }
         }
 
         public void OnRibbonLoad(IRibbonUI ribbon)
         {
-            _ribbon = ribbon;
+            _explorerRibbon = ribbon;
             try
             {
                 var explorer = Globals.ThisAddIn.Application.ActiveExplorer();
                 if (explorer != null)
                 {
-                    explorer.SelectionChange += () => _ribbon?.InvalidateControl(ButtonId);
+                    explorer.SelectionChange += () => _explorerRibbon?.InvalidateControl(FileButtonId);
                 }
             }
             catch
@@ -45,6 +53,11 @@ namespace OutlookAddin.Ribbon
             }
         }
 
+        public void OnInspectorRibbonLoad(IRibbonUI ribbon)
+        {
+            _inspectorRibbon = ribbon;
+        }
+
         public bool OnGetFileToEspoCrmEnabled(IRibbonControl control)
         {
             try
@@ -72,5 +85,48 @@ namespace OutlookAddin.Ribbon
         {
             Globals.ThisAddIn.AddInHost.LaunchSettings();
         }
+
+        public bool OnGetComposeFromCaseVisible(IRibbonControl control)
+        {
+            // Show only on outgoing (compose) mail inspectors.
+            try
+            {
+                var inspector = control?.Context as Outlook.Inspector;
+                if (inspector?.CurrentItem is Outlook.MailItem mail)
+                {
+                    return mail.Sent == false;
+                }
+            }
+            catch { /* fall through */ }
+            return true;
+        }
+
+        public void OnComposeFromCase(IRibbonControl control)
+        {
+            try
+            {
+                var inspector = control?.Context as Outlook.Inspector;
+                if (inspector?.CurrentItem is Outlook.MailItem mail)
+                {
+                    _ = Globals.ThisAddIn.AddInHost.LaunchComposeFromCaseAsync(mail);
+                }
+            }
+            catch (Exception ex)
+            {
+                Globals.ThisAddIn.AddInHost.Logger.Warning(ex, "OnComposeFromCase failed");
+            }
+        }
+
+        private static string LoadResource(string name)
+        {
+            using (var stream = Assembly.GetExecutingAssembly().GetManifestResourceStream(name))
+            {
+                if (stream == null) return string.Empty;
+                using (var reader = new StreamReader(stream))
+                {
+                    return reader.ReadToEnd();
+                }
+            }
+        }
     }
 }
diff --git a/src/OutlookAddin/Ribbon/InspectorRibbon.xml b/src/OutlookAddin/Ribbon/InspectorRibbon.xml
new file mode 100644
index 0000000..82f9600
--- /dev/null
+++ b/src/OutlookAddin/Ribbon/InspectorRibbon.xml
@@ -0,0 +1,19 @@
+<?xml version="1.0" encoding="UTF-8"?>
+<customUI xmlns="http://schemas.microsoft.com/office/2009/07/customui" onLoad="OnInspectorRibbonLoad">
+  <ribbon>
+    <tabs>
+      <tab idMso="TabNewMailMessage">
+        <group id="MarcusLawComposeGroup" label="Marcus-Law" insertBeforeMso="GroupClipboard">
+          <button id="ComposeFromCase"
+                  label="כתוב מתיק"
+                  screentip="פתח את המייל מתיק EspoCRM"
+                  supertip="בחר תיק EspoCRM כדי לאכלס את הנמענים ואת הכותרת של המייל הזה, וכדי שהמייל יתויק אוטומטית כששולחים אותו."
+                  size="large"
+                  imageMso="MailMergeStartLetters"
+                  onAction="OnComposeFromCase"
+                  getVisible="OnGetComposeFromCaseVisible" />
+        </group>
+      </tab>
+    </tabs>
+  </ribbon>
+</customUI>
diff --git a/src/OutlookAddin/Services/AddInHost.cs b/src/OutlookAddin/Services/AddInHost.cs
index 93031c9..349f1fe 100644
--- a/src/OutlookAddin/Services/AddInHost.cs
+++ b/src/OutlookAddin/Services/AddInHost.cs
@@ -37,12 +37,15 @@ namespace OutlookAddin.Services
         public IEspoCrmClient? CrmClient { get; private set; }
         public IFilingService? FilingService { get; private set; }
         public IMatchingService? MatchingService { get; private set; }
+        public ComposeService? ComposeService { get; private set; }
 
         private readonly Outlook.Application _outlookApp;
         private readonly MemoryCache _matchCache = new MemoryCache(new MemoryCacheOptions());
         private RetryQueueProcessor? _retryProcessor;
         private HttpClient? _httpClient;
         private SidebarController? _sidebarController;
+        private SentItemsWatcher? _sentItemsWatcher;
+        private NamedPipeListener? _pipeListener;
 
         public AddInHost(Outlook.Application outlookApp)
         {
@@ -56,6 +59,139 @@ namespace OutlookAddin.Services
             RetryQueue = new DiskRetryQueue(Logger);
 
             TryInitializeCrm();
+            InitializeSentItemsWatcher();
+            InitializeNamedPipeListener();
+            HookItemSend();
+        }
+
+        private void InitializeSentItemsWatcher()
+        {
+            try
+            {
+                _sentItemsWatcher = new SentItemsWatcher(_outlookApp, Logger);
+                _sentItemsWatcher.MailMatched += OnSentMailMatched;
+                _sentItemsWatcher.Initialize();
+            }
+            catch (Exception ex)
+            {
+                Logger.Error(ex, "AddInHost: SentItemsWatcher init failed");
+            }
+        }
+
+        private void InitializeNamedPipeListener()
+        {
+            try
+            {
+                _pipeListener = new NamedPipeListener(System.Windows.Threading.Dispatcher.CurrentDispatcher, Logger);
+                _pipeListener.MessageReceived += OnPipeMessage;
+                _pipeListener.Start();
+            }
+            catch (Exception ex)
+            {
+                Logger.Error(ex, "AddInHost: NamedPipeListener init failed");
+            }
+        }
+
+        private void HookItemSend()
+        {
+            try
+            {
+                _outlookApp.ItemSend += OnItemSend;
+            }
+            catch (Exception ex)
+            {
+                Logger.Error(ex, "AddInHost: ItemSend hook failed");
+            }
+        }
+
+        private void OnItemSend(object item, ref bool cancel)
+        {
+            try
+            {
+                if (item is not Outlook.MailItem mail) return;
+                var guid = ComposeService.ReadAddInGuid(mail);
+                var caseId = ComposeService.ReadEspoCaseId(mail);
+                if (string.IsNullOrWhiteSpace(guid) || string.IsNullOrWhiteSpace(caseId)) return;
+                var name = ComposeService.ReadEspoCaseName(mail) ?? caseId!;
+                var target = new FilingTarget("Case", caseId!, name);
+                _sentItemsWatcher?.Track(guid!, target);
+                Logger.Information("Outgoing mail tagged for auto-file (guid={Guid}, caseId={CaseId})", guid, caseId);
+            }
+            catch (Exception ex)
+            {
+                Logger.Warning(ex, "AddInHost.OnItemSend handler failed");
+            }
+        }
+
+        private async void OnSentMailMatched(object? sender, SentMailMatchedEventArgs e)
+        {
+            try
+            {
+                if (FilingService == null)
+                {
+                    Logger.Warning("Auto-file aborted — FilingService not configured");
+                    return;
+                }
+                var envelope = MailItemExtractor.Extract(e.Mail);
+                var summary = await FilingService.FileAsync(new[] { envelope }, e.Target).ConfigureAwait(true);
+                if (summary.FiledCount == 1)
+                {
+                    StampSingleCategory(e.Mail, "Filed: " + e.Target.ParentName);
+                    Logger.Information("Auto-filed sent mail to {Type}/{Id}", e.Target.ParentType, e.Target.ParentId);
+                }
+                else if (summary.QueuedCount == 1)
+                {
+                    Logger.Information("Auto-file queued for retry (target={Name})", e.Target.ParentName);
+                }
+                else
+                {
+                    Logger.Warning("Auto-file failed for sent mail (target={Name})", e.Target.ParentName);
+                }
+            }
+            catch (Exception ex)
+            {
+                Logger.Warning(ex, "OnSentMailMatched handler failed");
+            }
+        }
+
+        private void StampSingleCategory(Outlook.MailItem mail, string categoryName)
+        {
+            try
+            {
+                EnsureCategoryExists(categoryName);
+                var existing = mail.Categories ?? string.Empty;
+                if (existing.IndexOf(categoryName, StringComparison.Ordinal) >= 0) return;
+                mail.Categories = string.IsNullOrEmpty(existing) ? categoryName : existing + "; " + categoryName;
+                mail.Save();
+            }
+            catch (Exception ex)
+            {
+                Logger.Warning(ex, "StampSingleCategory failed");
+            }
+        }
+
+        private void OnPipeMessage(object? sender, string message)
+        {
+            // Message format (UTF-8 single line):
+            //   COMPOSE <caseId>
+            // Future commands may follow.
+            try
+            {
+                if (string.IsNullOrWhiteSpace(message)) return;
+                var trimmed = message.Trim();
+                if (trimmed.StartsWith("COMPOSE ", StringComparison.OrdinalIgnoreCase))
+                {
+                    var caseId = trimmed.Substring("COMPOSE ".Length).Trim();
+                    if (!string.IsNullOrWhiteSpace(caseId))
+                    {
+                        _ = LaunchComposeFromCaseByIdAsync(caseId);
+                    }
+                }
+            }
+            catch (Exception ex)
+            {
+                Logger.Warning(ex, "OnPipeMessage handler failed for {Message}", message);
+            }
         }
 
         /// <summary>
@@ -137,6 +273,7 @@ namespace OutlookAddin.Services
                 CrmClient = new EspoCrmClient(_httpClient, baseUrl.ToString(), creds.Username, creds.ApiKey, Logger);
                 FilingService = new FilingService(CrmClient, RetryQueue, Logger);
                 MatchingService = new MatchingService(CrmClient, _matchCache, Logger);
+                ComposeService = new ComposeService(CrmClient, Logger);
                 _retryProcessor = new RetryQueueProcessor(RetryQueue, CrmClient, Logger);
                 _retryProcessor.Start();
                 Logger.Information("AddInHost: CRM client initialized for {BaseUrl}", baseUrl);
@@ -159,6 +296,81 @@ namespace OutlookAddin.Services
             CrmClient = null;
             FilingService = null;
             MatchingService = null;
+            ComposeService = null;
+        }
+
+        /// <summary>
+        /// Entry point invoked by the Inspector "Compose from Case" ribbon
+        /// button. The MailItem comes from the open Inspector — populate it
+        /// with case details and stamp the tracking UserProperties.
+        /// </summary>
+        public async Task LaunchComposeFromCaseAsync(Outlook.MailItem mail)
+        {
+            if (mail == null) return;
+            if (!IsConfigured)
+            {
+                MessageBox.Show(
+                    "התוסף עדיין לא מוגדר. פתח את ההגדרות תחילה.",
+                    "Marcus-Law OutlookAddin",
+                    MessageBoxButton.OK,
+                    MessageBoxImage.Information);
+                return;
+            }
+
+            var vm = new ComposeFromCaseViewModel(CrmClient!, Logger);
+            var dialog = new ComposeFromCaseDialog(vm);
+            var ok = dialog.ShowDialog();
+            if (ok != true || vm.Result == null) return;
+
+            try
+            {
+                await ComposeService!.ApplyCaseToMailAsync(mail, vm.Result.Id, Settings.EspoCrmUrl).ConfigureAwait(true);
+            }
+            catch (Exception ex)
+            {
+                Logger.Error(ex, "LaunchComposeFromCaseAsync failed");
+                MessageBox.Show(
+                    "טעינת התיק נכשלה: " + ex.Message,
+                    "Marcus-Law OutlookAddin",
+                    MessageBoxButton.OK,
+                    MessageBoxImage.Error);
+            }
+        }
+
+        /// <summary>
+        /// Entry point for the URL-protocol handler (outlookaddin://compose?caseId=…).
+        /// Creates a brand new MailItem, populates it with case details, then
+        /// shows the Inspector so the user can compose+send.
+        /// </summary>
+        public async Task LaunchComposeFromCaseByIdAsync(string caseId)
+        {
+            if (!IsConfigured)
+            {
+                MessageBox.Show(
+                    "התוסף עדיין לא מוגדר. פתח את ההגדרות תחילה.",
+                    "Marcus-Law OutlookAddin",
+                    MessageBoxButton.OK,
+                    MessageBoxImage.Information);
+                return;
+            }
+
+            Outlook.MailItem? mail = null;
+            try
+            {
+                mail = (Outlook.MailItem)_outlookApp.CreateItem(Outlook.OlItemType.olMailItem);
+                await ComposeService!.ApplyCaseToMailAsync(mail, caseId, Settings.EspoCrmUrl).ConfigureAwait(true);
+                mail.Display(false);
+            }
+            catch (Exception ex)
+            {
+                Logger.Error(ex, "LaunchComposeFromCaseByIdAsync failed for caseId={CaseId}", caseId);
+                if (mail != null) try { Marshal.ReleaseComObject(mail); } catch { }
+                MessageBox.Show(
+                    "פתיחת המייל מתיק נכשלה: " + ex.Message,
+                    "Marcus-Law OutlookAddin",
+                    MessageBoxButton.OK,
+                    MessageBoxImage.Error);
+            }
         }
 
         /// <summary>
@@ -419,6 +631,9 @@ namespace OutlookAddin.Services
 
         public void Dispose()
         {
+            try { _outlookApp.ItemSend -= OnItemSend; } catch { }
+            try { _sentItemsWatcher?.Dispose(); } catch { }
+            try { _pipeListener?.Dispose(); } catch { }
             try { _sidebarController?.Dispose(); } catch { }
             try { _retryProcessor?.Dispose(); } catch { }
             try { _httpClient?.Dispose(); } catch { }
diff --git a/src/OutlookAddin/Services/ComposeService.cs b/src/OutlookAddin/Services/ComposeService.cs
new file mode 100644
index 0000000..cd635ba
--- /dev/null
+++ b/src/OutlookAddin/Services/ComposeService.cs
@@ -0,0 +1,162 @@
+using System;
+using System.Runtime.InteropServices;
+using System.Threading.Tasks;
+using MarcusLaw.OutlookAddin.Core.Models;
+using MarcusLaw.OutlookAddin.Core.Services;
+using Serilog;
+using Outlook = Microsoft.Office.Interop.Outlook;
+
+namespace OutlookAddin.Services
+{
+    /// <summary>
+    /// Drives the "Compose from Case" flow:
+    /// 1. Caller opens a MailItem (either via Inspector ribbon or by us
+    ///    creating a brand new MailItem via the URL protocol).
+    /// 2. Resolve full Case details (name, number, contacts) and the primary
+    ///    contact's email address.
+    /// 3. Populate the MailItem (To/Subject/footer) and stamp two
+    ///    UserProperties: <c>EspoCaseId</c> and <c>OutlookAddinGuid</c>.
+    /// 4. Display the MailItem so the user can edit/send.
+    /// </summary>
+    public sealed class ComposeService
+    {
+        private const string EspoCaseIdProperty = "EspoCaseId";
+        private const string EspoCaseNameProperty = "EspoCaseName";
+        private const string AddInGuidProperty = "OutlookAddinGuid";
+
+        private readonly IEspoCrmClient _client;
+        private readonly ILogger _logger;
+
+        public ComposeService(IEspoCrmClient client, ILogger logger)
+        {
+            _client = client ?? throw new ArgumentNullException(nameof(client));
+            _logger = logger ?? throw new ArgumentNullException(nameof(logger));
+        }
+
+        public async Task<ComposeResult> ApplyCaseToMailAsync(
+            Outlook.MailItem mail,
+            string caseId,
+            string baseCrmUrl)
+        {
+            if (mail == null) throw new ArgumentNullException(nameof(mail));
+            if (string.IsNullOrWhiteSpace(caseId)) throw new ArgumentException("caseId required", nameof(caseId));
+
+            var caseEntity = await _client.GetCaseAsync(caseId, "id,name,number,status,contactsIds,accountId").ConfigureAwait(true);
+            ContactEntity? primaryContact = null;
+            if (caseEntity.ContactsIds != null && caseEntity.ContactsIds.Count > 0)
+            {
+                try
+                {
+                    primaryContact = await _client.GetContactAsync(
+                        caseEntity.ContactsIds[0],
+                        "id,name,emailAddress",
+                        default).ConfigureAwait(true);
+                }
+                catch (Exception ex)
+                {
+                    _logger.Warning(ex, "ComposeService: failed to load primary contact for case {CaseId}", caseId);
+                }
+            }
+
+            var guid = Guid.NewGuid().ToString("N");
+            StampUserProperty(mail, EspoCaseIdProperty, caseEntity.Id);
+            StampUserProperty(mail, EspoCaseNameProperty, caseEntity.Name ?? caseEntity.Number ?? caseEntity.Id);
+            StampUserProperty(mail, AddInGuidProperty, guid);
+
+            try
+            {
+                if (!string.IsNullOrWhiteSpace(primaryContact?.EmailAddress))
+                {
+                    var existingTo = mail.To ?? string.Empty;
+                    if (!existingTo.Contains(primaryContact!.EmailAddress!))
+                    {
+                        mail.To = string.IsNullOrEmpty(existingTo)
+                            ? primaryContact.EmailAddress
+                            : existingTo + "; " + primaryContact.EmailAddress;
+                    }
+                }
+
+                var caseLabel = caseEntity.Number ?? caseEntity.Name ?? caseEntity.Id;
+                var existingSubject = mail.Subject ?? string.Empty;
+                if (!existingSubject.Contains("[" + caseLabel + "]"))
+                {
+                    mail.Subject = "[" + caseLabel + "] " + existingSubject;
+                }
+
+                var crmCaseUrl = baseCrmUrl?.TrimEnd('/') + "/#Case/view/" + caseEntity.Id;
+                var footer =
+                    "<br/><hr/><p style=\"direction:rtl;font-size:11px;color:#666;\">" +
+                    "תיק EspoCRM: " +
+                    "<a href=\"" + crmCaseUrl + "\">" + System.Net.WebUtility.HtmlEncode(caseLabel) + "</a>" +
+                    "</p>";
+                var html = mail.HTMLBody ?? string.Empty;
+                if (!html.Contains("#Case/view/" + caseEntity.Id))
+                {
+                    mail.HTMLBody = html + footer;
+                }
+            }
+            catch (Exception ex)
+            {
+                _logger.Warning(ex, "ComposeService: failed to populate MailItem for case {CaseId}", caseId);
+            }
+
+            try { mail.Save(); } catch { /* ignore */ }
+
+            return new ComposeResult(
+                guid,
+                new FilingTarget("Case", caseEntity.Id, caseEntity.Name ?? caseEntity.Id));
+        }
+
+        public static string? ReadEspoCaseId(Outlook.MailItem mail) => TryReadUserProperty(mail, EspoCaseIdProperty);
+        public static string? ReadEspoCaseName(Outlook.MailItem mail) => TryReadUserProperty(mail, EspoCaseNameProperty);
+        public static string? ReadAddInGuid(Outlook.MailItem mail) => TryReadUserProperty(mail, AddInGuidProperty);
+
+        private static void StampUserProperty(Outlook.MailItem mail, string name, string value)
+        {
+            Outlook.UserProperties? props = null;
+            Outlook.UserProperty? prop = null;
+            try
+            {
+                props = mail.UserProperties;
+                prop = props.Find(name) ?? props.Add(name, Outlook.OlUserPropertyType.olText, false);
+                prop.Value = value;
+            }
+            catch { /* ignore */ }
+            finally
+            {
+                if (prop != null && Marshal.IsComObject(prop)) Marshal.ReleaseComObject(prop);
+                if (props != null && Marshal.IsComObject(props)) Marshal.ReleaseComObject(props);
+            }
+        }
+
+        private static string? TryReadUserProperty(Outlook.MailItem mail, string name)
+        {
+            Outlook.UserProperties? props = null;
+            Outlook.UserProperty? prop = null;
+            try
+            {
+                props = mail.UserProperties;
+                prop = props?.Find(name);
+                return prop?.Value as string;
+            }
+            catch { return null; }
+            finally
+            {
+                if (prop != null && Marshal.IsComObject(prop)) Marshal.ReleaseComObject(prop);
+                if (props != null && Marshal.IsComObject(props)) Marshal.ReleaseComObject(props);
+            }
+        }
+    }
+
+    public sealed class ComposeResult
+    {
+        public string Guid { get; }
+        public FilingTarget Target { get; }
+
+        public ComposeResult(string guid, FilingTarget target)
+        {
+            Guid = guid;
+            Target = target;
+        }
+    }
+}
diff --git a/src/OutlookAddin/Services/NamedPipeListener.cs b/src/OutlookAddin/Services/NamedPipeListener.cs
new file mode 100644
index 0000000..34d48aa
--- /dev/null
+++ b/src/OutlookAddin/Services/NamedPipeListener.cs
@@ -0,0 +1,87 @@
+using System;
+using System.IO.Pipes;
+using System.Text;
+using System.Threading;
+using System.Threading.Tasks;
+using System.Windows.Threading;
+using Serilog;
+
+namespace OutlookAddin.Services
+{
+    /// <summary>
+    /// Hosts a named pipe (<c>\\.\pipe\MarcusLaw.OutlookAddin</c>) that the
+    /// out-of-process URL-protocol handler writes lines to. Each line is
+    /// dispatched to <see cref="MessageReceived"/> on the WPF UI thread so
+    /// callers can freely touch the Outlook COM model.
+    /// </summary>
+    public sealed class NamedPipeListener : IDisposable
+    {
+        public const string PipeName = "MarcusLaw.OutlookAddin";
+
+        private readonly CancellationTokenSource _cts = new CancellationTokenSource();
+        private readonly Dispatcher _dispatcher;
+        private readonly ILogger _logger;
+        private Task? _loop;
+
+        public event EventHandler<string>? MessageReceived;
+
+        public NamedPipeListener(Dispatcher dispatcher, ILogger logger)
+        {
+            _dispatcher = dispatcher ?? throw new ArgumentNullException(nameof(dispatcher));
+            _logger = logger ?? throw new ArgumentNullException(nameof(logger));
+        }
+
+        public void Start()
+        {
+            if (_loop != null) return;
+            _loop = Task.Run(() => RunAsync(_cts.Token));
+            _logger.Information("NamedPipeListener started ({Pipe})", PipeName);
+        }
+
+        private async Task RunAsync(CancellationToken ct)
+        {
+            while (!ct.IsCancellationRequested)
+            {
+                try
+                {
+                    using var server = new NamedPipeServerStream(
+                        PipeName,
+                        PipeDirection.InOut,
+                        maxNumberOfServerInstances: 1,
+                        PipeTransmissionMode.Byte,
+                        PipeOptions.Asynchronous);
+
+                    await server.WaitForConnectionAsync(ct).ConfigureAwait(false);
+
+                    using var reader = new System.IO.StreamReader(server, Encoding.UTF8, detectEncodingFromByteOrderMarks: false, bufferSize: 1024, leaveOpen: true);
+                    string? line;
+                    while ((line = await reader.ReadLineAsync().ConfigureAwait(false)) != null)
+                    {
+                        var captured = line;
+                        try
+                        {
+                            _dispatcher.BeginInvoke((Action)(() => MessageReceived?.Invoke(this, captured)));
+                        }
+                        catch (Exception ex)
+                        {
+                            _logger.Warning(ex, "NamedPipeListener dispatcher invoke failed");
+                        }
+                    }
+                }
+                catch (OperationCanceledException) { return; }
+                catch (Exception ex)
+                {
+                    _logger.Warning(ex, "NamedPipeListener loop iteration failed — retrying");
+                    try { await Task.Delay(TimeSpan.FromSeconds(2), ct).ConfigureAwait(false); }
+                    catch (OperationCanceledException) { return; }
+                }
+            }
+        }
+
+        public void Dispose()
+        {
+            try { _cts.Cancel(); } catch { /* ignore */ }
+            _cts.Dispose();
+        }
+    }
+}
diff --git a/src/OutlookAddin/Services/SentItemsWatcher.cs b/src/OutlookAddin/Services/SentItemsWatcher.cs
new file mode 100644
index 0000000..c21f101
--- /dev/null
+++ b/src/OutlookAddin/Services/SentItemsWatcher.cs
@@ -0,0 +1,179 @@
+using System;
+using System.Collections.Generic;
+using System.Runtime.InteropServices;
+using System.Threading;
+using MarcusLaw.OutlookAddin.Core.Models;
+using Serilog;
+using Outlook = Microsoft.Office.Interop.Outlook;
+
+namespace OutlookAddin.Services
+{
+    /// <summary>
+    /// Watches the user's default Sent Items folder for newly added mail
+    /// that carries our <c>OutlookAddinGuid</c> UserProperty. When a match
+    /// arrives, fires <see cref="MailFiled"/> with the resolved
+    /// <see cref="MailEnvelope"/> + target so the host can POST it to
+    /// EspoCRM.
+    ///
+    /// The MAPI provider (Outlook) only fires Items.ItemAdd while the
+    /// reference stays rooted, so we keep <see cref="_sentItems"/> in a
+    /// field — letting it be GC'd silently drops the subscription.
+    /// </summary>
+    public sealed class SentItemsWatcher : IDisposable
+    {
+        private readonly Outlook.Application _app;
+        private readonly ILogger _logger;
+        private readonly Dictionary<string, PendingItem> _pending = new Dictionary<string, PendingItem>();
+        private readonly Timer _expiryTimer;
+
+        private Outlook.Items? _sentItems;
+        private int _disposed;
+
+        public TimeSpan PendingTimeout { get; } = TimeSpan.FromMinutes(2);
+
+        public event EventHandler<SentMailMatchedEventArgs>? MailMatched;
+
+        public SentItemsWatcher(Outlook.Application app, ILogger logger)
+        {
+            _app = app ?? throw new ArgumentNullException(nameof(app));
+            _logger = logger ?? throw new ArgumentNullException(nameof(logger));
+            _expiryTimer = new Timer(_ => SweepExpired(), null, TimeSpan.FromSeconds(30), TimeSpan.FromSeconds(30));
+        }
+
+        public void Initialize()
+        {
+            try
+            {
+                var ns = _app.Session;
+                var folder = ns.GetDefaultFolder(Outlook.OlDefaultFolders.olFolderSentMail);
+                _sentItems = folder.Items;
+                _sentItems.ItemAdd += OnSentItemAdd;
+                _logger.Information("SentItemsWatcher attached to Sent Items folder");
+            }
+            catch (Exception ex)
+            {
+                _logger.Error(ex, "SentItemsWatcher.Initialize failed");
+            }
+        }
+
+        /// <summary>
+        /// Registers a guid → target mapping. When a Sent Items item with
+        /// the matching UserProperty arrives, the watcher fires
+        /// <see cref="MailMatched"/>.
+        /// </summary>
+        public void Track(string guid, FilingTarget target)
+        {
+            if (string.IsNullOrWhiteSpace(guid)) return;
+            lock (_pending)
+            {
+                _pending[guid] = new PendingItem(target, DateTimeOffset.UtcNow);
+            }
+        }
+
+        private void OnSentItemAdd(object item)
+        {
+            if (Volatile.Read(ref _disposed) != 0) return;
+            try
+            {
+                if (item is not Outlook.MailItem mail) return;
+
+                var guid = TryReadUserProperty(mail, "OutlookAddinGuid");
+                var caseId = TryReadUserProperty(mail, "EspoCaseId");
+                var caseName = TryReadUserProperty(mail, "EspoCaseName");
+                if (string.IsNullOrWhiteSpace(guid)) return;
+
+                PendingItem? pending = null;
+                lock (_pending)
+                {
+                    if (_pending.TryGetValue(guid!, out var p))
+                    {
+                        pending = p;
+                        _pending.Remove(guid!);
+                    }
+                }
+
+                var target = pending?.Target;
+                if (target == null && !string.IsNullOrWhiteSpace(caseId))
+                {
+                    target = new FilingTarget("Case", caseId!, caseName ?? caseId!);
+                }
+                if (target == null)
+                {
+                    _logger.Information("SentItemsWatcher: matched guid {Guid} has no target — skipping", guid);
+                    return;
+                }
+
+                MailMatched?.Invoke(this, new SentMailMatchedEventArgs(mail, target));
+            }
+            catch (Exception ex)
+            {
+                _logger.Warning(ex, "SentItemsWatcher.OnSentItemAdd failed");
+            }
+        }
+
+        private static string? TryReadUserProperty(Outlook.MailItem mail, string name)
+        {
+            Outlook.UserProperties? props = null;
+            Outlook.UserProperty? prop = null;
+            try
+            {
+                props = mail.UserProperties;
+                prop = props?.Find(name);
+                return prop?.Value as string;
+            }
+            catch { return null; }
+            finally
+            {
+                if (prop != null && Marshal.IsComObject(prop)) Marshal.ReleaseComObject(prop);
+                if (props != null && Marshal.IsComObject(props)) Marshal.ReleaseComObject(props);
+            }
+        }
+
+        private void SweepExpired()
+        {
+            if (Volatile.Read(ref _disposed) != 0) return;
+            var cutoff = DateTimeOffset.UtcNow - PendingTimeout;
+            lock (_pending)
+            {
+                var stale = new List<string>();
+                foreach (var kv in _pending)
+                {
+                    if (kv.Value.RegisteredAt < cutoff) stale.Add(kv.Key);
+                }
+                foreach (var k in stale) _pending.Remove(k);
+            }
+        }
+
+        public void Dispose()
+        {
+            if (Interlocked.Exchange(ref _disposed, 1) != 0) return;
+            try { if (_sentItems != null) _sentItems.ItemAdd -= OnSentItemAdd; } catch { /* ignore */ }
+            _sentItems = null;
+            try { _expiryTimer.Dispose(); } catch { /* ignore */ }
+        }
+
+        private sealed class PendingItem
+        {
+            public FilingTarget Target { get; }
+            public DateTimeOffset RegisteredAt { get; }
+
+            public PendingItem(FilingTarget target, DateTimeOffset at)
+            {
+                Target = target;
+                RegisteredAt = at;
+            }
+        }
+    }
+
+    public sealed class SentMailMatchedEventArgs : EventArgs
+    {
+        public Outlook.MailItem Mail { get; }
+        public FilingTarget Target { get; }
+
+        public SentMailMatchedEventArgs(Outlook.MailItem mail, FilingTarget target)
+        {
+            Mail = mail;
+            Target = target;
+        }
+    }
+}
diff --git a/src/OutlookAddinProtocolHandler/OutlookAddinProtocolHandler.csproj b/src/OutlookAddinProtocolHandler/OutlookAddinProtocolHandler.csproj
new file mode 100644
index 0000000..38e25c3
--- /dev/null
+++ b/src/OutlookAddinProtocolHandler/OutlookAddinProtocolHandler.csproj
@@ -0,0 +1,17 @@
+<Project Sdk="Microsoft.NET.Sdk">
+  <PropertyGroup>
+    <OutputType>WinExe</OutputType>
+    <TargetFramework>net48</TargetFramework>
+    <RootNamespace>OutlookAddinProtocolHandler</RootNamespace>
+    <AssemblyName>OutlookAddinProtocolHandler</AssemblyName>
+    <LangVersion>latest</LangVersion>
+    <Nullable>enable</Nullable>
+    <UseWindowsForms>true</UseWindowsForms>
+    <Company>Marcus-Law</Company>
+    <Product>OutlookAddinProtocolHandler</Product>
+  </PropertyGroup>
+
+  <ItemGroup>
+    <Reference Include="System.Web" />
+  </ItemGroup>
+</Project>
diff --git a/src/OutlookAddinProtocolHandler/Program.cs b/src/OutlookAddinProtocolHandler/Program.cs
new file mode 100644
index 0000000..5376683
--- /dev/null
+++ b/src/OutlookAddinProtocolHandler/Program.cs
@@ -0,0 +1,89 @@
+using System;
+using System.Collections.Specialized;
+using System.IO;
+using System.IO.Pipes;
+using System.Text;
+using System.Web;
+using System.Windows.Forms;
+
+namespace OutlookAddinProtocolHandler
+{
+    /// <summary>
+    /// Tiny shim launched when the user clicks an <c>outlookaddin://</c> URL.
+    /// Parses the URL and forwards a one-line command over the named pipe
+    /// owned by the in-process VSTO add-in. If Outlook isn't running, the
+    /// pipe connect will fail and we surface a MessageBox.
+    /// </summary>
+    public static class Program
+    {
+        private const string PipeName = "MarcusLaw.OutlookAddin";
+
+        [STAThread]
+        public static int Main(string[] args)
+        {
+            try
+            {
+                if (args.Length == 0)
+                {
+                    return Fail("השימוש: outlookaddin://compose?caseId=<id>");
+                }
+
+                var raw = args[0];
+                if (!raw.StartsWith("outlookaddin://", StringComparison.OrdinalIgnoreCase))
+                {
+                    return Fail("URL לא תקין: " + raw);
+                }
+
+                var uri = new Uri(raw);
+                var command = (uri.Host ?? "").ToLowerInvariant();
+                var query = HttpUtility.ParseQueryString(uri.Query ?? string.Empty);
+
+                switch (command)
+                {
+                    case "compose":
+                        return SendCompose(query);
+                    default:
+                        return Fail("פעולה לא ידועה: " + command);
+                }
+            }
+            catch (Exception ex)
+            {
+                return Fail("שגיאה: " + ex.Message);
+            }
+        }
+
+        private static int SendCompose(NameValueCollection query)
+        {
+            var caseId = query["caseId"];
+            if (string.IsNullOrWhiteSpace(caseId))
+            {
+                return Fail("חסר caseId בכתובת ה-URL");
+            }
+
+            var payload = "COMPOSE " + caseId.Trim() + "\n";
+            try
+            {
+                using var pipe = new NamedPipeClientStream(".", PipeName, PipeDirection.InOut);
+                pipe.Connect(timeout: 3000);
+                var bytes = Encoding.UTF8.GetBytes(payload);
+                pipe.Write(bytes, 0, bytes.Length);
+                pipe.Flush();
+                return 0;
+            }
+            catch (TimeoutException)
+            {
+                return Fail("Outlook אינו פתוח, או שהתוסף עדיין לא נטען.");
+            }
+            catch (IOException ex)
+            {
+                return Fail("תקלת תקשורת עם התוסף: " + ex.Message);
+            }
+        }
+
+        private static int Fail(string message)
+        {
+            MessageBox.Show(message, "Marcus-Law OutlookAddin", MessageBoxButtons.OK, MessageBoxIcon.Warning);
+            return 1;
+        }
+    }
+}
diff --git a/tools/install-protocol.ps1 b/tools/install-protocol.ps1
new file mode 100644
index 0000000..ce2af01
--- /dev/null
+++ b/tools/install-protocol.ps1
@@ -0,0 +1,41 @@
+# Registers the `outlookaddin://` URL protocol in HKCU so that
+# clicking a link like `outlookaddin://compose?caseId=…` launches the
+# OutlookAddinProtocolHandler.exe shim, which forwards the request over
+# a named pipe to the running VSTO add-in.
+#
+# Usage:
+#   .\install-protocol.ps1 -ExePath "C:\Path\To\OutlookAddinProtocolHandler.exe"
+#
+# Or, to derive the path automatically from a ClickOnce install:
+#   .\install-protocol.ps1
+
+[CmdletBinding()]
+param(
+    [string]$ExePath
+)
+
+$ErrorActionPreference = 'Stop'
+
+if (-not $ExePath) {
+    $candidate = Join-Path $env:LOCALAPPDATA "Apps\OutlookAddinProtocolHandler\OutlookAddinProtocolHandler.exe"
+    if (Test-Path $candidate) {
+        $ExePath = $candidate
+    } else {
+        throw "ExePath not supplied and default location not found: $candidate"
+    }
+}
+
+if (-not (Test-Path $ExePath)) {
+    throw "Protocol handler not found: $ExePath"
+}
+
+$root = "HKCU:\Software\Classes\outlookaddin"
+New-Item -Path $root -Force | Out-Null
+Set-ItemProperty -Path $root -Name "(default)" -Value "URL:OutlookAddin Protocol"
+Set-ItemProperty -Path $root -Name "URL Protocol" -Value ""
+
+$shellCmd = Join-Path $root "shell\open\command"
+New-Item -Path $shellCmd -Force | Out-Null
+Set-ItemProperty -Path $shellCmd -Name "(default)" -Value ("`"" + $ExePath + "`" `"%1`"")
+
+Write-Host "Registered outlookaddin:// -> $ExePath" -ForegroundColor Green
diff --git a/tools/uninstall-protocol.ps1 b/tools/uninstall-protocol.ps1
new file mode 100644
index 0000000..b7d6c89
--- /dev/null
+++ b/tools/uninstall-protocol.ps1
@@ -0,0 +1,3 @@
+$ErrorActionPreference = 'SilentlyContinue'
+Remove-Item -Path "HKCU:\Software\Classes\outlookaddin" -Recurse -Force
+Write-Host "Removed outlookaddin:// protocol registration" -ForegroundColor Yellow