fix(attachments): bind upload to Note.attachments to satisfy EspoCRM

The EspoCRM tenant now rejects role=Attachment uploads that carry
neither `field` nor `parentType` (400 "No `field` and `parentType`."),
which broke the entire save-attachments flow on v1.2.13 — every file,
including PDFs, failed at Step 1.

Bind the upload to the documented Attachment-Multiple example
parentType=Note, field=attachments. Note.attachments is a built-in
field with no allowed-file-types restriction, so all types pass
(including images) — unlike Document.file, which rejected images with
403. No parentId is set; the blob stays standalone and is still just
pushed to the network share.

Co-Authored-By: Claude Opus 4.8 (1M context) <noreply@anthropic.com>

.gitea/workflows/build.yml

@@ -258,15 +258,21 @@ jobs:
               & msbuild @msbuildArgs
               if ($LASTEXITCODE -ne 0) { throw "msbuild /t:Publish failed with $LASTEXITCODE" }
 
-              # Sanity check: did the VSTO publish target produce a .vsto file?
+              # Sanity check + rename to canonical OutlookAddin.vsto so the URL
-              $vsto = Get-ChildItem -Recurse -Filter '*.vsto' -Path publish | Select-Object -First 1
+              # matches PROVIDER_URL (hardcoded to .../OutlookAddin.vsto). Restrict
-              if (-not $vsto) { throw "msbuild /t:Publish completed but no .vsto file found under publish/" }
+              # to publish/ root -- there's a second .vsto inside Application Files
+              # that must keep its versioned name. Verify the renamed file exists
+              # before continuing; v1.2.11 shipped broken because a silent failure
+              # here left no OutlookAddin.vsto in the tar and 404'd the CDN.
+              $vsto = Get-ChildItem -File -Filter '*.vsto' -Path publish | Select-Object -First 1
+              if (-not $vsto) { throw "msbuild /t:Publish completed but no .vsto file found at publish/ root" }
               Write-Host "  produced $($vsto.FullName)"
-
-              # Rename to canonical OutlookAddin.vsto so the ClickOnce manifest
-              # URL matches PROVIDER_URL (which is hardcoded to .../OutlookAddin.vsto).
               if ($vsto.Name -ne 'OutlookAddin.vsto') {
-                  Rename-Item -LiteralPath $vsto.FullName -NewName 'OutlookAddin.vsto'
+                  Rename-Item -LiteralPath $vsto.FullName -NewName 'OutlookAddin.vsto' -ErrorAction Stop
+                  Write-Host "  renamed -> OutlookAddin.vsto"
+              }
+              if (-not (Test-Path 'publish/OutlookAddin.vsto')) {
+                  throw "post-rename: publish/OutlookAddin.vsto does not exist"
               }
 
               Write-Host "=== STEP F: stage protocol handler ==="

docs/AUTO-UPDATE-SETUP.md

@@ -315,16 +315,11 @@ git push origin v1.0.1
 ה-CI ירוץ אוטומטית כמו בשחרור הראשון.
 
 **אצל הלקוחות:**
-- ClickOnce בודק עדכון אוטומטית **כל 7 ימים** (הגדרה ב-csproj: `UpdateInterval=7`).
+- ה־VSTO runtime בודק את ה-`.vsto` manifest **בכל פתיחה של Outlook** (משוחזר מ-`<UpdatePeriodically>false</UpdatePeriodically>` ב-csproj החל מ-v1.2.9; קודם זה היה פעם ב-7 ימים). הבדיקה היא GET של ~6KB, ~100ms — בלתי מורגש בזמן הטעינה.
-- כדי **להאיץ** עדכון אצל לקוח מסויים:
+- ה-CI מציב `/p:MinimumRequiredVersion=<tag>` בכל build, אז מיד כשהבדיקה מזהה גרסה חדשה — ההתקנה נכפית בלי דיאלוג.
-  1. סגור את Outlook לגמרי.
+- **תרגום מעשי**: 30 שניות אחרי `git push --tags` ה-CI מסיים → תוך 2-3 דקות החבילה נדחפת ל-CDN → בכניסה הבאה של כל אחד מהלקוחות ל-Outlook הוא רץ על הגרסה החדשה. **בלי שום פעולה ידנית מצידם**.
-  2. פתח את Outlook שוב.
+- **הכפתור "בדוק עדכונים" בהגדרות** רק מודיע ("זמינה גרסה X — סגור ופתח Outlook"). הוא לא יכול להתקין מתוך תהליך Outlook רץ — `VSTOInstaller.exe` לא יכול לדרוס DLLs נעולים, וה-ApplicationDeployment API נכשל ב-`TrustNotGrantedException` בהקשר VSTO. ההתקנה תמיד קורית רק דרך ה-runtime בעלייה של Outlook. [פירוט בזיכרון: feedback_vsto_updater_api.md]
-  3. אם עברו לפחות 7 ימים מבדיקת ה-update הקודמת — יבדוק עכשיו ויעדכן.
+- **תקלה נדירה — לקוח שהותקן ידנית עם dev cert** (`HP-OFFICE1\<user>`, publicKeyToken `41d8d795775ea8cb`) לא יכול לעבור auto-update לגרסת prod cert (`Marcus-Law OutlookAddin`, publicKeyToken `c68d2b4c25051c5b`) — ClickOnce מתייחס אליהן כשתי אפליקציות שונות. **פעם אחת**: Apps & Features → uninstall של MarcusLaw.OutlookAddin → התקנה חדשה מ-`https://platform.dev.marcus-law.co.il/outlook-addin/OutlookAddin.vsto`. אחרי זה auto-update עובד.
-  4. אם לא — אפשר לנקות את ה-ClickOnce cache:
-     ```powershell
-     rundll32.exe dfshim.dll,CleanOnlineAppCache
-     ```
-     ואז לפתוח שוב את `https://platform.dev.marcus-law.co.il/outlook-addin/OutlookAddin.vsto`.
 
 ---
 

docs/PROJECT-BRIEFING.md

@@ -284,7 +284,7 @@ If the session is on the Linux dev server (`/home/chaim/espocrm-extensions/Outlo
    - Uploads `publish.tar.gz` to Gitea generic registry (`outlook-addin-publish/<version>/publish.tar.gz`)
    - Linux job downloads the tar.gz, builds a Docker image `outlook-addin-cdn:latest`, pushes to Gitea registry, calls Coolify to redeploy the CDN container
    - Posts to Mattermost channel `git-verelasim` with the install URL on success / a failure link on failure
-5. Lawyers' installed Add-in checks the deployment manifest at the install URL every 7 days (configured in csproj `<UpdateInterval>7</UpdateInterval>`) or whenever they click "בדוק עדכונים" in Settings → אודות.
+5. Lawyers' installed Add-in checks the deployment manifest at the install URL **on every Outlook startup** (csproj has `<UpdatePeriodically>false</UpdatePeriodically>` since v1.2.9 — earlier versions waited up to 7 days). The check is a single ~6 KB HTTP GET, ~100 ms. Combined with the CI setting `/p:MinimumRequiredVersion=<tag>` per build, this means every tagged release lands on every lawyer's PC the next time they open Outlook, silently and without prompts.
 
 **Semver policy:** PATCH for bug fixes (unilateral), MINOR for visible features (unilateral when warranted), MAJOR only with Chaim's explicit approval.
 

src/OutlookAddin.Core/Services/EspoCrmClient.cs

@@ -213,13 +213,29 @@ namespace MarcusLaw.OutlookAddin.Core.Services
             // is sent in the "file" field as a data-URI. The previous extra
             // "contents" alias was an undocumented legacy that strict tenants
             // reject with 400.
+            //
+            // We bind the upload to Note.attachments (parentType=Note,
+            // field=attachments). EspoCRM's attachment access checker now
+            // REJECTS a role=Attachment upload that carries neither `field`
+            // nor `parentType` ("No `field` and `parentType`." → 400) — the
+            // earlier "unbound blob" shape no longer passes. Note.attachments
+            // is the documented Attachment-Multiple example and a built-in
+            // field that carries NO "allowed file types" restriction, so every
+            // file type (PDF, JPEG, PNG, …) passes — unlike Document.file,
+            // which Marcus-Law limits to PDF/Word and which rejected images
+            // with 403 "Not allowed file type".
+            //
+            // We never set parentId / create a Note: the attachment stays a
+            // standalone blob whose id we immediately push to the network
+            // share. The (parentType, field) pair only satisfies the access
+            // checker and selects an unrestricted file-type policy.
             var payload = new Dictionary<string, object?>
             {
                 ["name"] = fileName,
                 ["type"] = mime,
                 ["role"] = "Attachment",
-                ["relatedType"] = "Document",
+                ["parentType"] = "Note",
-                ["field"] = "file",
+                ["field"] = "attachments",
                 ["file"] = dataUri
             };
 

src/OutlookAddin.UI/Dialogs/ComposeFromCaseDialog.xaml

@@ -1,9 +1,10 @@
 <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"
+        xmlns:conv="clr-namespace:MarcusLaw.OutlookAddin.UI.Converters"
         Title="כתוב מייל מתיק"
-        Height="480" Width="600"
+        Height="520" Width="680"
-        MinHeight="320" MinWidth="500"
+        MinHeight="360" MinWidth="540"
         FlowDirection="RightToLeft"
         WindowStartupLocation="CenterOwner"
         ShowInTaskbar="False"
@@ -11,6 +12,7 @@
         Background="#F8FAFC"
         FontFamily="Segoe UI, David, Frank Ruehl, Arial">
     <Window.Resources>
+        <conv:CaseStatusToHebrewConverter x:Key="CaseStatusHe" />
         <SolidColorBrush x:Key="Primary"      Color="#2563EB" />
         <SolidColorBrush x:Key="PrimaryHover" Color="#1D4ED8" />
         <SolidColorBrush x:Key="Border"       Color="#E2E8F0" />
@@ -134,24 +136,30 @@
         </Border>
 
         <Border Grid.Row="1" Style="{StaticResource Card}">
-            <ListBox ItemsSource="{Binding Cases}"
+            <DataGrid ItemsSource="{Binding Cases}"
-                     SelectedItem="{Binding SelectedCase}"
+                      SelectedItem="{Binding SelectedCase}"
-                     BorderThickness="0"
+                      AutoGenerateColumns="False"
-                     Background="Transparent"
+                      HeadersVisibility="Column"
-                     ItemContainerStyle="{StaticResource ResultItem}"
+                      GridLinesVisibility="Horizontal"
-                     Padding="4">
+                      HorizontalGridLinesBrush="#E2E8F0"
-                <ListBox.ItemTemplate>
+                      RowBackground="White"
-                    <DataTemplate>
+                      AlternatingRowBackground="#F8FAFC"
-                        <StackPanel>
+                      BorderThickness="0"
-                            <TextBlock FontSize="13">
+                      CanUserAddRows="False"
-                                <Run Text="[" /><Run Text="{Binding Number, Mode=OneWay}" /><Run Text="] " />
+                      CanUserDeleteRows="False"
-                                <Run Text="{Binding Name, Mode=OneWay}" FontWeight="SemiBold" />
+                      CanUserResizeRows="False"
-                            </TextBlock>
+                      CanUserReorderColumns="False"
-                            <TextBlock Text="{Binding Status}" Foreground="{StaticResource Muted}" FontSize="11" />
+                      SelectionMode="Single"
-                        </StackPanel>
+                      SelectionUnit="FullRow"
-                    </DataTemplate>
+                      IsReadOnly="True"
-                </ListBox.ItemTemplate>
+                      RowHeight="30">
-            </ListBox>
+                <DataGrid.Columns>
+                    <DataGridTextColumn Header="מס׳ תיק" Binding="{Binding Number}" Width="80" />
+                    <DataGridTextColumn Header="שם" Binding="{Binding Name}" Width="*" />
+                    <DataGridTextColumn Header="מס׳ בבית משפט" Binding="{Binding CourtCaseNumber}" Width="140" />
+                    <DataGridTextColumn Header="סטטוס" Binding="{Binding Status, Converter={StaticResource CaseStatusHe}}" Width="110" />
+                </DataGrid.Columns>
+            </DataGrid>
         </Border>
 
         <TextBlock Grid.Row="2" Text="{Binding StatusMessage}"

src/OutlookAddin.UI/ViewModels/ComposeFromCaseViewModel.cs

@@ -1,4 +1,5 @@
 using System;
+using System.Collections.Generic;
 using System.Collections.ObjectModel;
 using System.Threading;
 using System.Threading.Tasks;
@@ -74,20 +75,36 @@ namespace MarcusLaw.OutlookAddin.UI.ViewModels
                 ct.ThrowIfCancellationRequested();
 
                 Cases.Clear();
-                int kept = 0;
+                var caseHits = new List<EspoEntityRef>();
                 foreach (var hit in search.List)
                 {
-                    if (!string.Equals(hit.EntityType, "Case", StringComparison.OrdinalIgnoreCase)) continue;
+                    if (string.Equals(hit.EntityType, "Case", StringComparison.OrdinalIgnoreCase))
-                    Cases.Add(new CaseEntity
+                        caseHits.Add(hit);
-                    {
-                        Id = hit.Id,
-                        Name = hit.Name,
-                    });
-                    kept++;
                 }
-                StatusMessage = kept == 0
+
-                    ? "אין תוצאות מסוג תיק (Case)"
+                if (caseHits.Count == 0)
-                    : $"נמצאו {kept} תיקים";
+                {
+                    StatusMessage = "אין תוצאות מסוג תיק (Case)";
+                    return;
+                }
+
+                // GlobalSearch only returns id+name. Hydrate each hit with
+                // number+status (and the Hebrew case name when present) so the
+                // picker shows the same columns the file-attachments picker
+                // does.
+                var detailTasks = new List<Task<CaseEntity?>>(caseHits.Count);
+                foreach (var hit in caseHits)
+                {
+                    detailTasks.Add(LoadCaseRowAsync(hit, ct));
+                }
+                var details = await Task.WhenAll(detailTasks).ConfigureAwait(true);
+                ct.ThrowIfCancellationRequested();
+
+                foreach (var row in details)
+                {
+                    if (row != null) Cases.Add(row);
+                }
+                StatusMessage = $"נמצאו {Cases.Count} תיקים";
             }
             catch (OperationCanceledException) { /* superseded */ }
             catch (EspoCrmAuthorizationException)
@@ -101,6 +118,27 @@ namespace MarcusLaw.OutlookAddin.UI.ViewModels
             }
         }
 
+        private async Task<CaseEntity?> LoadCaseRowAsync(EspoEntityRef hit, CancellationToken ct)
+        {
+            var row = new CaseEntity { Id = hit.Id, Name = hit.Name };
+            if (string.IsNullOrEmpty(hit.Id)) return row;
+            try
+            {
+                var detail = await _client.GetCaseAsync(
+                    hit.Id, "id,name,number,status,cCourtCaseNumber", ct).ConfigureAwait(false);
+                row.Number = detail.Number;
+                row.Status = detail.Status;
+                row.CourtCaseNumber = detail.CourtCaseNumber;
+                if (!string.IsNullOrEmpty(detail.Name)) row.Name = detail.Name;
+            }
+            catch (OperationCanceledException) { throw; }
+            catch (Exception ex)
+            {
+                _logger.Warning(ex, "ComposeFromCase: hydrating case {CaseId} failed", hit.Id);
+            }
+            return row;
+        }
+
         [RelayCommand(CanExecute = nameof(CanSubmit))]
         private void Submit()
         {

src/OutlookAddin.UI/ViewModels/SaveAttachmentsViewModel.cs

@@ -107,6 +107,38 @@ namespace MarcusLaw.OutlookAddin.UI.ViewModels
             }
         }
 
+        /// <summary>
+        /// Seeds the case list with the cases already resolved for the mail's
+        /// sender (from the sidebar match) so the user doesn't have to search
+        /// for a client we've already identified. When exactly one case is
+        /// known we auto-select it (which kicks the subfolder/folder-path
+        /// resolve); with several we just show them and let the user pick.
+        /// The user can still type in the search box to override — that
+        /// repopulates <see cref="Cases"/> from a fresh server search.
+        /// </summary>
+        public void PreselectCases(IReadOnlyList<CaseEntity> cases)
+        {
+            if (cases == null || cases.Count == 0) return;
+
+            Cases.Clear();
+            foreach (var c in cases)
+            {
+                if (c == null || string.IsNullOrEmpty(c.Id)) continue;
+                Cases.Add(c);
+            }
+            if (Cases.Count == 0) return;
+
+            if (Cases.Count == 1)
+            {
+                SelectedCase = Cases[0];
+                StatusMessage = "התיק זוהה אוטומטית מהשולח";
+            }
+            else
+            {
+                StatusMessage = $"{Cases.Count} תיקים מקושרים לשולח — בחר/י תיק";
+            }
+        }
+
         private void ResetSubfolders()
         {
             Subfolders.Clear();

src/OutlookAddin/OutlookAddin.csproj

@@ -257,6 +257,9 @@
     <EmbeddedResource Include="Ribbon\InspectorRibbon.xml">
       <LogicalName>OutlookAddin.Ribbon.InspectorRibbon.xml</LogicalName>
     </EmbeddedResource>
+    <EmbeddedResource Include="Ribbon\ReadMailRibbon.xml">
+      <LogicalName>OutlookAddin.Ribbon.ReadMailRibbon.xml</LogicalName>
+    </EmbeddedResource>
     <EmbeddedResource Include="Images\klear-file.png">
       <LogicalName>OutlookAddin.Images.klear-file.png</LogicalName>
     </EmbeddedResource>

src/OutlookAddin/Properties/AssemblyInfo.cs

@@ -33,6 +33,6 @@ using System.Security;
 // You can specify all the values or you can default the Build and Revision Numbers 
 // by using the '*' as shown below:
 // [assembly: AssemblyVersion("1.0.*")]
-[assembly: AssemblyVersion("1.2.10.0")]
+[assembly: AssemblyVersion("1.2.14.0")]
-[assembly: AssemblyFileVersion("1.2.10.0")]
+[assembly: AssemblyFileVersion("1.2.14.0")]
 

src/OutlookAddin/Ribbon/ExplorerRibbon.cs

@@ -19,6 +19,7 @@ namespace OutlookAddin.Ribbon
     {
         private const string ExplorerResource = "OutlookAddin.Ribbon.ExplorerRibbon.xml";
         private const string InspectorResource = "OutlookAddin.Ribbon.InspectorRibbon.xml";
+        private const string ReadMailResource = "OutlookAddin.Ribbon.ReadMailRibbon.xml";
 
         // Every button whose `getEnabled` depends on the current Explorer
         // selection must be re-evaluated on every SelectionChange — Office
@@ -40,6 +41,8 @@ namespace OutlookAddin.Ribbon
                     return LoadResource(ExplorerResource);
                 case "Microsoft.Outlook.Mail.Compose":
                     return LoadResource(InspectorResource);
+                case "Microsoft.Outlook.Mail.Read":
+                    return LoadResource(ReadMailResource);
                 default:
                     return string.Empty;
             }
@@ -77,6 +80,51 @@ namespace OutlookAddin.Ribbon
             _inspectorRibbon = ribbon;
         }
 
+        // The read-mail inspector ribbon loads fresh for each opened message,
+        // so its getEnabled callback re-runs per window — no cached IRibbonUI
+        // or invalidation is needed here.
+        public void OnReadMailRibbonLoad(IRibbonUI ribbon)
+        {
+        }
+
+        /// <summary>
+        /// Enabled when the message open in this read inspector has at least
+        /// one attachment. Mirrors <see cref="OnGetSaveAttachmentsEnabled"/>
+        /// but reads the item from the Inspector context rather than the
+        /// Explorer selection.
+        /// </summary>
+        public bool OnGetSaveAttachmentsInspectorEnabled(IRibbonControl control)
+        {
+            try
+            {
+                var inspector = control?.Context as Outlook.Inspector;
+                if (inspector?.CurrentItem is not Outlook.MailItem mail) return false;
+                var attachments = mail.Attachments;
+                if (attachments == null) return false;
+                return attachments.Count > 0;
+            }
+            catch
+            {
+                return false;
+            }
+        }
+
+        public void OnSaveAttachmentsFromInspector(IRibbonControl control)
+        {
+            try
+            {
+                var inspector = control?.Context as Outlook.Inspector;
+                if (inspector?.CurrentItem is Outlook.MailItem mail)
+                {
+                    _ = Globals.ThisAddIn.AddInHost.LaunchSaveAttachmentsAsync(mail);
+                }
+            }
+            catch (Exception ex)
+            {
+                Globals.ThisAddIn.AddInHost.Logger.Warning(ex, "OnSaveAttachmentsFromInspector failed");
+            }
+        }
+
         public bool OnGetFileToEspoCrmEnabled(IRibbonControl control)
         {
             try
@@ -206,6 +254,7 @@ namespace OutlookAddin.Ribbon
                 {
                     case "FileToEspoCrm":        fileName = "klear-file.png";     break;
                     case "SaveAttachments":      fileName = "klear-attach.png";   break;
+                    case "SaveAttachmentsRead":  fileName = "klear-attach.png";   break;
                     case "ShowSidebar":          fileName = "klear-sidebar.png";  break;
                     case "OpenEspoCrmSettings":  fileName = "klear-settings.png"; break;
                     case "ComposeFromCase":      fileName = "klear-compose.png";  break;

src/OutlookAddin/Ribbon/ReadMailRibbon.xml

@@ -0,0 +1,19 @@
+<?xml version="1.0" encoding="UTF-8"?>
+<customUI xmlns="http://schemas.microsoft.com/office/2009/07/customui" onLoad="OnReadMailRibbonLoad">
+  <ribbon>
+    <tabs>
+      <tab idMso="TabReadMessage">
+        <group id="MarcusLawReadGroup" label="Klear">
+          <button id="SaveAttachmentsRead"
+                  label="שמור קבצים"
+                  screentip="שמור את הקבצים המצורפים בלבד"
+                  supertip="מעלה את הקבצים המצורפים של המייל הזה ל-Klear כ-Documents מקושרים לתיק שתבחר, בלי לתייק את המייל עצמו."
+                  size="large"
+                  getImage="OnGetImage"
+                  onAction="OnSaveAttachmentsFromInspector"
+                  getEnabled="OnGetSaveAttachmentsInspectorEnabled" />
+        </group>
+      </tab>
+    </tabs>
+  </ribbon>
+</customUI>

src/OutlookAddin/Services/AddInHost.cs

@@ -485,6 +485,13 @@ namespace OutlookAddin.Services
             // Subfolders are populated lazily once the user picks a case;
             // the default static set is already pre-loaded.
 
+            // If the sender already maps to a known client, seed the case
+            // list so the user sees the identified case pre-selected instead
+            // of having to search. Uses the same matching lookup the sidebar
+            // does (cached for 10 min), so this is normally instant. Any
+            // failure here is non-fatal — the dialog still opens empty.
+            await TryPreselectSenderCaseAsync(vm, envelope.From).ConfigureAwait(true);
+
             var dialog = new SaveAttachmentsDialog(vm);
             AttachOwnerToOutlook(dialog);
             var ok = dialog.ShowDialog();
@@ -541,6 +548,30 @@ namespace OutlookAddin.Services
             }
         }
 
+        /// <summary>
+        /// Looks up the mail sender against the CRM (reusing the sidebar's
+        /// cached match) and, when it resolves to one or more linked cases,
+        /// seeds the save-attachments dialog so the already-identified client
+        /// case shows up pre-selected. Best-effort: swallows any error.
+        /// </summary>
+        private async Task TryPreselectSenderCaseAsync(SaveAttachmentsViewModel vm, string? senderEmail)
+        {
+            if (MatchingService == null || string.IsNullOrWhiteSpace(senderEmail)) return;
+            try
+            {
+                var match = await MatchingService.LookupAsync(senderEmail!).ConfigureAwait(true);
+                // Ambiguous (same email on several contacts) → don't guess; let
+                // the user search. A clean match with linked cases → seed them.
+                if (match == null || match.IsAmbiguous) return;
+                if (match.RecentCases == null || match.RecentCases.Count == 0) return;
+                vm.PreselectCases(match.RecentCases);
+            }
+            catch (Exception ex)
+            {
+                Logger.Warning(ex, "Sender-case preselect for save-attachments failed (non-fatal)");
+            }
+        }
+
         private static void ShowAttachmentSummary(AttachmentSaveSummary summary, string caseLabel, string targetPath)
         {
             string message;

src/OutlookAddin/Services/ComposeService.cs

@@ -42,21 +42,7 @@ namespace OutlookAddin.Services
             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;
+            var recipientEmail = await ResolveRecipientEmailAsync(caseEntity, caseId).ConfigureAwait(true);
-            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);
@@ -65,14 +51,14 @@ namespace OutlookAddin.Services
 
             try
             {
-                if (!string.IsNullOrWhiteSpace(primaryContact?.EmailAddress))
+                if (!string.IsNullOrWhiteSpace(recipientEmail))
                 {
                     var existingTo = mail.To ?? string.Empty;
-                    if (!existingTo.Contains(primaryContact!.EmailAddress!))
+                    if (!existingTo.Contains(recipientEmail!))
                     {
                         mail.To = string.IsNullOrEmpty(existingTo)
-                            ? primaryContact.EmailAddress
+                            ? recipientEmail
-                            : existingTo + "; " + primaryContact.EmailAddress;
+                            : existingTo + "; " + recipientEmail;
                     }
                 }
 
@@ -107,6 +93,61 @@ namespace OutlookAddin.Services
                 new FilingTarget("Case", caseEntity.Id, caseEntity.Name ?? caseEntity.Id));
         }
 
+        /// <summary>
+        /// Find a usable recipient email for the case. EspoCRM's Case.contactsIds
+        /// is a many-to-many bag (primary + co-counsel + witnesses + …) and the
+        /// first entry isn't guaranteed to be the actual client — and even when
+        /// it is, the contact may have no emailAddress stored. So walk the list
+        /// and return the first non-empty address, then fall back to the
+        /// linked Account's email.
+        /// </summary>
+        private async Task<string?> ResolveRecipientEmailAsync(CaseEntity caseEntity, string caseId)
+        {
+            if (caseEntity.ContactsIds != null)
+            {
+                foreach (var contactId in caseEntity.ContactsIds)
+                {
+                    if (string.IsNullOrWhiteSpace(contactId)) continue;
+                    try
+                    {
+                        var contact = await _client.GetContactAsync(
+                            contactId,
+                            "id,name,emailAddress,emailAddressData",
+                            default).ConfigureAwait(true);
+                        if (!string.IsNullOrWhiteSpace(contact?.EmailAddress))
+                        {
+                            return contact!.EmailAddress;
+                        }
+                    }
+                    catch (Exception ex)
+                    {
+                        _logger.Warning(ex, "ComposeService: failed to load contact {ContactId} for case {CaseId}", contactId, caseId);
+                    }
+                }
+            }
+
+            if (!string.IsNullOrWhiteSpace(caseEntity.AccountId))
+            {
+                try
+                {
+                    var account = await _client.GetAccountAsync(
+                        caseEntity.AccountId!,
+                        "id,name,emailAddress",
+                        default).ConfigureAwait(true);
+                    if (!string.IsNullOrWhiteSpace(account?.EmailAddress))
+                    {
+                        return account!.EmailAddress;
+                    }
+                }
+                catch (Exception ex)
+                {
+                    _logger.Warning(ex, "ComposeService: failed to load account {AccountId} for case {CaseId}", caseEntity.AccountId, caseId);
+                }
+            }
+
+            return null;
+        }
+
         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);