diff --git a/SeaHaven.DataServices/Helpers/PendingUpliftCancellation.cs b/SeaHaven.DataServices/Helpers/PendingUpliftCancellation.cs
new file mode 100644
index 0000000..1a4e3c4
--- /dev/null
+++ b/SeaHaven.DataServices/Helpers/PendingUpliftCancellation.cs
@@ -0,0 +1,79 @@
+using Data.SeaHavenIndustries;
+using Data.SeaHavenIndustries.Enums;
+using Microsoft.EntityFrameworkCore;
+
+namespace SeaHaven.DataServices.Helpers
+{
+    /// <summary>
+    /// The single rule and write for "a work order that becomes Canceled cancels its pending
+    /// uplifts in the same action". Every path that can cancel a work order (board update,
+    /// the cancel endpoint, CRM webhook and reconciliation) asks <see cref="Applies"/> and
+    /// stages the cancellation into its own unit of work, so the uplift change and its own
+    /// audit row commit, or roll back, with the work order's status change.
+    /// </summary>
+    public static class PendingUpliftCancellation
+    {
+        public const string AuditAction = "uplift_cancel";
+        public const string CancelledStatus = "Withdrawn";
+
+        private static readonly string[] PendingStatuses = { "Pending", "ChangesRequested" };
+
+        /// <summary>True when a lifecycle change moves a work order into Canceled.</summary>
+        public static bool Applies(LifecycleStatus? before, LifecycleStatus? after)
+            => before != LifecycleStatus.Canceled && after == LifecycleStatus.Canceled;
+
+        /// <summary>
+        /// Uplift requests that belong to a work order: on a live dispatch that the work
+        /// order owns or is linked to.
+        /// </summary>
+        internal static IQueryable<DispatchUpliftRequest> ForWorkOrder(ApplicationDbContext context, int workOrderId)
+            => context.DispatchUpliftRequests.Where(u =>
+                (u.IsDeleted == null || u.IsDeleted == false)
+                && u.Dispatch != null
+                && (u.Dispatch.IsDeleted == null || u.Dispatch.IsDeleted == false)
+                && (
+                    u.Dispatch.WorkOrderId == workOrderId
+                    || u.Dispatch.DispatchWorkOrders!.Any(link => link.WorkOrderId == workOrderId)));
+
+        /// <summary>
+        /// Stages (does not save) the cancellation of every pending uplift on the work order,
+        /// with one audit row per uplift. Returns how many uplifts were cancelled.
+        /// </summary>
+        internal static async Task<int> StageAsync(
+            ApplicationDbContext context,
+            int workOrderId,
+            string? actorId,
+            string actorType,
+            DateTime now,
+            CancellationToken cancellationToken)
+        {
+            var pending = await ForWorkOrder(context, workOrderId)
+                .Include(u => u.Dispatch)
+                .Where(u => PendingStatuses.Contains(u.Status))
+                .ToListAsync(cancellationToken);
+
+            foreach (var request in pending)
+            {
+                var previous = request.Status;
+                request.Status = CancelledStatus;
+                request.DecidedAt = now;
+                request.DecidedByUserId = actorId;
+                request.LastModificationTime = now;
+
+                context.WorkOrderAuditLogs.Add(new WorkOrderAuditLog
+                {
+                    WorkOrderId = workOrderId,
+                    UserId = actorId,
+                    FieldName = $"Dispatch {request.Dispatch!.DispatchNumber} Uplift",
+                    OldValue = previous,
+                    NewValue = CancelledStatus,
+                    Action = AuditAction,
+                    ActorType = actorType,
+                    CreatedAt = now,
+                });
+            }
+
+            return pending.Count;
+        }
+    }
+}
diff --git a/SeaHaven.DataServices/Implementation/UpliftDataService.cs b/SeaHaven.DataServices/Implementation/UpliftDataService.cs
index 0c3706c..3f9cf21 100644
--- a/SeaHaven.DataServices/Implementation/UpliftDataService.cs
+++ b/SeaHaven.DataServices/Implementation/UpliftDataService.cs
@@ -455,15 +455,18 @@ namespace SeaHaven.DataServices.Implementation
                 .SumAsync(cancellationToken);
         }
 
-        public Task<List<DispatchUpliftRequest>> GetPendingForWorkOrderAsync(
+        public Task<int> StageCancelPendingForWorkOrderAsync(
             int workOrderId,
+            string? actorId,
+            DateTime now,
             CancellationToken cancellationToken)
-        {
-            return ForWorkOrder(workOrderId)
-                .Include(u => u.Dispatch)
-                .Where(u => u.Status == "Pending" || u.Status == "ChangesRequested")
-                .ToListAsync(cancellationToken);
-        }
+            => PendingUpliftCancellation.StageAsync(
+                _context,
+                workOrderId,
+                actorId,
+                actorType: "internal",
+                now,
+                cancellationToken);
 
         public async Task<bool> HasActiveAsync(int dispatchId, CancellationToken cancellationToken)
         {
@@ -524,15 +527,7 @@ namespace SeaHaven.DataServices.Implementation
         }
 
         private IQueryable<DispatchUpliftRequest> ForWorkOrder(int workOrderId)
-        {
-            return _context.DispatchUpliftRequests.Where(u =>
-                (u.IsDeleted == null || u.IsDeleted == false)
-                && u.Dispatch != null
-                && (u.Dispatch.IsDeleted == null || u.Dispatch.IsDeleted == false)
-                && (
-                    u.Dispatch.WorkOrderId == workOrderId
-                    || u.Dispatch.DispatchWorkOrders!.Any(link => link.WorkOrderId == workOrderId)));
-        }
+            => PendingUpliftCancellation.ForWorkOrder(_context, workOrderId);
 
         public async Task StageAsync(DispatchUpliftRequest request, CancellationToken cancellationToken)
         {
diff --git a/SeaHaven.DataServices/Implementation/WorkOrderWebhookDataService.cs b/SeaHaven.DataServices/Implementation/WorkOrderWebhookDataService.cs
index f32ebd0..49cdc7b 100644
--- a/SeaHaven.DataServices/Implementation/WorkOrderWebhookDataService.cs
+++ b/SeaHaven.DataServices/Implementation/WorkOrderWebhookDataService.cs
@@ -1,6 +1,8 @@
 using Data.SeaHavenIndustries;
+using Data.SeaHavenIndustries.Enums;
 using Microsoft.EntityFrameworkCore;
 using Microsoft.EntityFrameworkCore.Storage;
+using SeaHaven.DataServices.Helpers;
 using SeaHaven.DataServices.Interfaces;
 
 namespace SeaHaven.DataServices.Implementation
@@ -112,8 +114,22 @@ namespace SeaHaven.DataServices.Implementation
                 workOrder.WorkerOrderTitle = mutation.Title ?? mutation.Description;
                 workOrder.Description = mutation.Description;
                 workOrder.Status = mutation.IsCancelled ? "Cancelled" : mutation.Status;
+                var lifecycleBefore = workOrder.LifecycleStatus;
                 if (mutation.LifecycleStatus.HasValue)
                     workOrder.LifecycleStatus = mutation.LifecycleStatus.Value;
+
+                // A CRM cancellation cancels the work order's pending uplifts in this same save.
+                if (workOrder.Id > 0
+                    && PendingUpliftCancellation.Applies(lifecycleBefore, workOrder.LifecycleStatus))
+                {
+                    await PendingUpliftCancellation.StageAsync(
+                        _context,
+                        workOrder.Id,
+                        actorId: null,
+                        actorType: AuditActorType.Sync.ToString(),
+                        mutation.ProcessedAt.UtcDateTime,
+                        cancellationToken);
+                }
                 workOrder.Severity = mutation.Severity;
                 workOrder.Priority = mutation.Priority;
                 workOrder.ExternalAssignedTo = mutation.AssignedTo;
diff --git a/SeaHaven.DataServices/Interfaces/IUpliftDataService.cs b/SeaHaven.DataServices/Interfaces/IUpliftDataService.cs
index 4dfe871..1053202 100644
--- a/SeaHaven.DataServices/Interfaces/IUpliftDataService.cs
+++ b/SeaHaven.DataServices/Interfaces/IUpliftDataService.cs
@@ -32,7 +32,13 @@ namespace SeaHaven.DataServices.Interfaces
         // SH-207: queue-wide pending exposure for the approvals header (sum of
         // RequestedNTE over non-deleted Pending requests on non-deleted dispatches).
         Task<decimal> GetPendingExposureTotalAsync(CancellationToken cancellationToken);
-        Task<List<DispatchUpliftRequest>> GetPendingForWorkOrderAsync(int workOrderId, CancellationToken cancellationToken);
+        // Stages (does not save) the cancellation of the work order's pending uplifts, each
+        // with its own audit row, for the caller's unit of work. See PendingUpliftCancellation.
+        Task<int> StageCancelPendingForWorkOrderAsync(
+            int workOrderId,
+            string? actorId,
+            DateTime now,
+            CancellationToken cancellationToken);
         // SH-101: active = Pending or ChangesRequested (the only states that block a new request).
         Task<bool> HasActiveAsync(int dispatchId, CancellationToken cancellationToken);
         Task<DispatchUpliftRequest?> GetActiveRequestAsync(int dispatchId, CancellationToken cancellationToken);
diff --git a/SeaHaven.Services/Implementation/WorkOrderBoardUpdateService.cs b/SeaHaven.Services/Implementation/WorkOrderBoardUpdateService.cs
index d34c6fb..3a194fc 100644
--- a/SeaHaven.Services/Implementation/WorkOrderBoardUpdateService.cs
+++ b/SeaHaven.Services/Implementation/WorkOrderBoardUpdateService.cs
@@ -139,8 +139,7 @@ namespace SeaHaven.Services.Implementation
                 // Cancelling the work order cancels its pending uplift in the same action: the
                 // withdrawal and its own audit entry are staged here and committed by the same
                 // save as the status change.
-                if (lifecycleBefore != LifecycleStatus.Canceled
-                    && workOrder.LifecycleStatus == LifecycleStatus.Canceled)
+                if (PendingUpliftCancellation.Applies(lifecycleBefore, workOrder.LifecycleStatus))
                 {
                     await _upliftService.WithdrawPendingForWorkOrderAsync(workOrderId, actorId, ct);
                 }
diff --git a/SeaHaven.Services/Implementation/WorkOrderUpliftService.cs b/SeaHaven.Services/Implementation/WorkOrderUpliftService.cs
index 0980e0d..79da4a2 100644
--- a/SeaHaven.Services/Implementation/WorkOrderUpliftService.cs
+++ b/SeaHaven.Services/Implementation/WorkOrderUpliftService.cs
@@ -345,37 +345,11 @@ namespace SeaHaven.Services.Implementation
             string? actorId,
             CancellationToken cancellationToken)
         {
-            var pending = await _upliftData.GetPendingForWorkOrderAsync(workOrderId, cancellationToken);
-            if (pending.Count == 0)
-                return;
-
-            var now = _timeProvider.GetUtcNow().UtcDateTime;
-            foreach (var req in pending)
-            {
-                if (!UpliftStatus.CanTransition(req.Status, UpliftStatus.Withdrawn))
-                    continue;
-
-                var dispatch = req.Dispatch ?? await _dispatchData.GetByIdAsync(req.DispatchId);
-                if (dispatch == null)
-                    continue;
-
-                var previous = UpliftStatus.ToCanonical(req.Status);
-                req.Status = UpliftStatus.Withdrawn;
-                req.DecidedAt = now;
-                req.DecidedByUserId = actorId;
-                req.LastModificationTime = now;
-
-                await StageAuditAsync(
-                    dispatch,
-                    workOrderId,
-                    actorId,
-                    previous,
-                    UpliftStatus.Withdrawn,
-                    "uplift_cancel",
-                    now,
-                    cancellationToken,
-                    isStatusTransition: true);
-            }
+            await _upliftData.StageCancelPendingForWorkOrderAsync(
+                workOrderId,
+                actorId,
+                _timeProvider.GetUtcNow().UtcDateTime,
+                cancellationToken);
         }
 
         private async Task<WorkOrderUpliftDto> PersistCreatedAsync(
diff --git a/SeaHavenIndustries.Tests/WorkOrderBoardCancelServiceTests.cs b/SeaHavenIndustries.Tests/WorkOrderBoardCancelServiceTests.cs
index 01e93df..76e521a 100644
--- a/SeaHavenIndustries.Tests/WorkOrderBoardCancelServiceTests.cs
+++ b/SeaHavenIndustries.Tests/WorkOrderBoardCancelServiceTests.cs
@@ -461,7 +461,7 @@ public class WorkOrderBoardCancelServiceTests
         public Task<decimal> SumAutoApprovedAmountForWorkOrderAsync(int workOrderId, CancellationToken cancellationToken) => throw new NotSupportedException();
         public Task<IReadOnlyList<WorkOrderUpliftExposureData>> GetApprovedExposureForWorkOrdersAsync(IReadOnlyCollection<int> workOrderIds, CancellationToken cancellationToken) => throw new NotSupportedException();
         public Task<decimal> GetPendingExposureTotalAsync(CancellationToken cancellationToken) => throw new NotSupportedException();
-        public Task<List<DispatchUpliftRequest>> GetPendingForWorkOrderAsync(int workOrderId, CancellationToken cancellationToken) => throw new NotSupportedException();
+        public Task<int> StageCancelPendingForWorkOrderAsync(int workOrderId, string? actorId, DateTime now, CancellationToken cancellationToken) => throw new NotSupportedException();
         public Task<bool> HasActiveAsync(int dispatchId, CancellationToken cancellationToken) => throw new NotSupportedException();
         public Task<DispatchUpliftRequest?> GetActiveRequestAsync(int dispatchId, CancellationToken cancellationToken) => throw new NotSupportedException();
         public Task<DispatchUpliftRequest?> GetByRequestKeyAsync(int dispatchId, string requestKey, CancellationToken cancellationToken) => throw new NotSupportedException();
diff --git a/SeaHavenIndustries.Tests/WorkOrderBoardPatchCancelUpliftTests.cs b/SeaHavenIndustries.Tests/WorkOrderBoardPatchCancelUpliftTests.cs
index e2ad1f3..c2f68aa 100644
--- a/SeaHavenIndustries.Tests/WorkOrderBoardPatchCancelUpliftTests.cs
+++ b/SeaHavenIndustries.Tests/WorkOrderBoardPatchCancelUpliftTests.cs
@@ -40,7 +40,7 @@ public sealed class WorkOrderBoardPatchCancelUpliftTests
 
     // Saved in stages: the work order and its primary dispatch reference each other, which a
     // relational provider cannot insert in one statement batch.
-    private static async Task SeedWorkOrderAsync(ApplicationDbContext context)
+    internal static async Task SeedWorkOrderAsync(ApplicationDbContext context)
     {
         context.Accounts.Add(new Accounts { Id = 1, Name = "Acme Corp", IsDeleted = false });
         context.Users.Add(new ApplicationUser { Id = "actor-1", UserName = "actor-1" });
@@ -50,6 +50,7 @@ public sealed class WorkOrderBoardPatchCancelUpliftTests
         {
             Id = 1,
             InternalWONumber = "10000000001",
+            ExternalWorkOrderId = "123",
             LifecycleStatus = LifecycleStatus.Incomplete,
             Status = "Incomplete",
             AccountId = 1,
@@ -73,7 +74,7 @@ public sealed class WorkOrderBoardPatchCancelUpliftTests
         await context.SaveChangesAsync();
     }
 
-    private static DispatchUpliftRequest Uplift(int id, string status, decimal amount) => new()
+    internal static DispatchUpliftRequest Uplift(int id, string status, decimal amount) => new()
     {
         Id = id,
         DispatchId = 10,
@@ -231,7 +232,7 @@ public sealed class WorkOrderBoardPatchCancelUpliftTests
         }
     }
 
-    private sealed class SqliteRowVersionDbContext : ApplicationDbContext
+    internal sealed class SqliteRowVersionDbContext : ApplicationDbContext
     {
         public SqliteRowVersionDbContext(DbContextOptions<ApplicationDbContext> options)
             : base(options)
diff --git a/SeaHavenIndustries.Tests/WorkOrderCrmCancelUpliftTests.cs b/SeaHavenIndustries.Tests/WorkOrderCrmCancelUpliftTests.cs
new file mode 100644
index 0000000..f8ae2a1
--- /dev/null
+++ b/SeaHavenIndustries.Tests/WorkOrderCrmCancelUpliftTests.cs
@@ -0,0 +1,222 @@
+using System.Data.Common;
+using Data.SeaHavenIndustries;
+using Data.SeaHavenIndustries.Enums;
+using Microsoft.Data.Sqlite;
+using Microsoft.EntityFrameworkCore;
+using Microsoft.EntityFrameworkCore.Diagnostics;
+using SeaHaven.DataServices.Implementation;
+using SeaHaven.DataServices.Interfaces;
+using SeaHaven.Services.Implementation;
+using SeaHaven.Services.Interfaces;
+using Xunit;
+
+namespace SeaHavenIndustries.Tests;
+
+/// <summary>
+/// A work order cancelled by the CRM (webhook or reconciliation, both persisted by the
+/// webhook data service) cancels its pending uplift in the same save, with an audit entry
+/// of its own, exactly as a cancel from the board does.
+/// </summary>
+public sealed class WorkOrderCrmCancelUpliftTests
+{
+    private static readonly DateTimeOffset ProcessedAt = new(2026, 7, 24, 12, 1, 0, TimeSpan.Zero);
+
+    private static WorkOrderWebhookMutation CrmMutation(string eventType, bool cancelled) => new()
+    {
+        DeliveryId = $"delivery-{eventType}",
+        EventType = eventType,
+        OccurredAt = ProcessedAt.AddMinutes(-1),
+        UpdatedAt = ProcessedAt.AddMinutes(-1),
+        ProcessedAt = ProcessedAt,
+        BodySha256 = $"hash-{eventType}",
+        VersionHash = $"hash-{eventType}",
+        ExternalWorkOrderId = "123",
+        WorkerOrderNumber = "00000000123",
+        Source = "procurement",
+        IsStateEvent = true,
+        Customer = "Acme Corp",
+        Status = "Open",
+        IsCancelled = cancelled,
+        LifecycleStatus = cancelled ? LifecycleStatus.Canceled : LifecycleStatus.Pending,
+    };
+
+    private static async Task<DbContextOptions<ApplicationDbContext>> SeedInMemoryAsync(
+        params DispatchUpliftRequest[] uplifts)
+    {
+        var options = new DbContextOptionsBuilder<ApplicationDbContext>()
+            .UseInMemoryDatabase(Guid.NewGuid().ToString())
+            .Options;
+        await using var seed = new ApplicationDbContext(options);
+        await WorkOrderBoardPatchCancelUpliftTests.SeedWorkOrderAsync(seed);
+        seed.DispatchUpliftRequests.AddRange(uplifts);
+        await seed.SaveChangesAsync();
+        return options;
+    }
+
+    [Fact]
+    public async Task CrmCancel_CancelsPendingUpliftWithItsOwnSyncAuditAndLeavesDecidedUpliftsAlone()
+    {
+        var options = await SeedInMemoryAsync(
+            WorkOrderBoardPatchCancelUpliftTests.Uplift(100, "Pending", 700m),
+            WorkOrderBoardPatchCancelUpliftTests.Uplift(101, "Approved", 600m),
+            WorkOrderBoardPatchCancelUpliftTests.Uplift(102, "NoApprovalRequired", 300m),
+            WorkOrderBoardPatchCancelUpliftTests.Uplift(103, "Rejected", 900m));
+
+        await using (var context = new ApplicationDbContext(options))
+        {
+            var result = await new WorkOrderWebhookDataService(context)
+                .ApplyAsync(CrmMutation("work_order.cancelled", cancelled: true), CancellationToken.None);
+            Assert.Equal(WorkOrderWebhookPersistenceStatus.Applied, result.Status);
+        }
+
+        await using var verify = new ApplicationDbContext(options);
+        Assert.Equal(LifecycleStatus.Canceled, verify.workOrders.Single().LifecycleStatus);
+
+        var cancelled = verify.DispatchUpliftRequests.Single(u => u.Id == 100);
+        Assert.Equal(UpliftStatus.Withdrawn, cancelled.Status);
+        Assert.Equal(ProcessedAt.UtcDateTime, cancelled.DecidedAt);
+        Assert.Null(cancelled.DecidedByUserId);
+
+        Assert.Equal(UpliftStatus.Approved, verify.DispatchUpliftRequests.Single(u => u.Id == 101).Status);
+        Assert.Equal(UpliftStatus.NoApprovalRequired, verify.DispatchUpliftRequests.Single(u => u.Id == 102).Status);
+        Assert.Equal(UpliftStatus.Rejected, verify.DispatchUpliftRequests.Single(u => u.Id == 103).Status);
+        Assert.Equal(1900m, verify.Dispatches.Single().NTEAmount);
+
+        var upliftAudit = Assert.Single(verify.WorkOrderAuditLogs);
+        Assert.Equal("uplift_cancel", upliftAudit.Action);
+        Assert.Equal(1, upliftAudit.WorkOrderId);
+        Assert.Equal(AuditActorType.Sync.ToString(), upliftAudit.ActorType);
+        Assert.Null(upliftAudit.UserId);
+        Assert.Equal("Dispatch DIS-10 Uplift", upliftAudit.FieldName);
+        Assert.Equal(UpliftStatus.Pending, upliftAudit.OldValue);
+        Assert.Equal(UpliftStatus.Withdrawn, upliftAudit.NewValue);
+    }
+
+    [Fact]
+    public async Task CrmUpdateThatDoesNotCancel_LeavesPendingUpliftPending()
+    {
+        var options = await SeedInMemoryAsync(
+            WorkOrderBoardPatchCancelUpliftTests.Uplift(100, "Pending", 700m));
+
+        await using (var context = new ApplicationDbContext(options))
+        {
+            await new WorkOrderWebhookDataService(context)
+                .ApplyAsync(CrmMutation("work_order.updated", cancelled: false), CancellationToken.None);
+        }
+
+        await using var verify = new ApplicationDbContext(options);
+        Assert.Equal(LifecycleStatus.Pending, verify.workOrders.Single().LifecycleStatus);
+        Assert.Equal(UpliftStatus.Pending, verify.DispatchUpliftRequests.Single().Status);
+        Assert.Empty(verify.WorkOrderAuditLogs);
+    }
+
+    [Fact]
+    public async Task ReconciliationCancel_CancelsPendingUplift()
+    {
+        var options = await SeedInMemoryAsync(
+            WorkOrderBoardPatchCancelUpliftTests.Uplift(100, "Pending", 700m));
+
+        await using (var context = new ApplicationDbContext(options))
+        {
+            var service = WorkOrderReconciliationTests.CreateService(
+                new[]
+                {
+                    new ProcurementWorkOrder
+                    {
+                        WorkOrderId = "123",
+                        WoStatus = "cancelled",
+                        Customer = "Acme Corp",
+                        UpdatedAt = ProcessedAt,
+                    }
+                },
+                new WorkOrderWebhookDataService(context));
+            Assert.True(await service.RunPendingAsync(CancellationToken.None));
+        }
+
+        await using var verify = new ApplicationDbContext(options);
+        Assert.Equal(LifecycleStatus.Canceled, verify.workOrders.Single().LifecycleStatus);
+        Assert.Equal(UpliftStatus.Withdrawn, verify.DispatchUpliftRequests.Single().Status);
+        var upliftAudit = Assert.Single(verify.WorkOrderAuditLogs, log => log.Action == "uplift_cancel");
+        Assert.Equal(AuditActorType.Sync.ToString(), upliftAudit.ActorType);
+    }
+
+    [Fact]
+    public async Task CrmCancel_FailureBeforeCommit_RollsBackWorkOrderAndUpliftTogether()
+    {
+        await using var connection = new SqliteConnection("DataSource=:memory:");
+        await connection.OpenAsync();
+        var writes = new UpdateRecorder();
+        var failCommit = new FailCommitInterceptor();
+        var options = new DbContextOptionsBuilder<ApplicationDbContext>()
+            .UseSqlite(connection)
+            .AddInterceptors(writes, failCommit)
+            .Options;
+
+        await using (var seed = new WorkOrderBoardPatchCancelUpliftTests.SqliteRowVersionDbContext(options))
+        {
+            await seed.Database.EnsureCreatedAsync();
+            await WorkOrderBoardPatchCancelUpliftTests.SeedWorkOrderAsync(seed);
+            seed.DispatchUpliftRequests.Add(WorkOrderBoardPatchCancelUpliftTests.Uplift(100, "Pending", 700m));
+            await seed.SaveChangesAsync();
+        }
+
+        writes.Armed = true;
+        failCommit.Armed = true;
+        await using (var context = new WorkOrderBoardPatchCancelUpliftTests.SqliteRowVersionDbContext(options))
+        {
+            await Assert.ThrowsAnyAsync<InvalidOperationException>(() => new WorkOrderWebhookDataService(context)
+                .ApplyAsync(CrmMutation("work_order.cancelled", cancelled: true), CancellationToken.None));
+        }
+
+        // The work order and uplift updates both ran inside the save's transaction before
+        // the commit failed; neither may survive it.
+        Assert.True(writes.UpdatedUplift);
+        Assert.True(writes.UpdatedWorkOrder);
+
+        writes.Armed = false;
+        failCommit.Armed = false;
+        await using var verify = new WorkOrderBoardPatchCancelUpliftTests.SqliteRowVersionDbContext(options);
+        Assert.Equal(LifecycleStatus.Incomplete, (await verify.workOrders.AsNoTracking().SingleAsync()).LifecycleStatus);
+        Assert.Equal(UpliftStatus.Pending, (await verify.DispatchUpliftRequests.AsNoTracking().SingleAsync()).Status);
+        Assert.False(await verify.WorkOrderAuditLogs.AnyAsync());
+    }
+
+    private sealed class UpdateRecorder : DbCommandInterceptor
+    {
+        public bool Armed { get; set; }
+        public bool UpdatedUplift { get; private set; }
+        public bool UpdatedWorkOrder { get; private set; }
+
+        public override ValueTask<InterceptionResult<DbDataReader>> ReaderExecutingAsync(
+            DbCommand command,
+            CommandEventData eventData,
+            InterceptionResult<DbDataReader> result,
+            CancellationToken cancellationToken = default)
+        {
+            if (Armed && command.Transaction is not null)
+            {
+                UpdatedUplift |= command.CommandText.Contains("UPDATE \"DispatchUpliftRequests\"");
+                UpdatedWorkOrder |= command.CommandText.Contains("UPDATE \"workOrders\"");
+            }
+
+            return base.ReaderExecutingAsync(command, eventData, result, cancellationToken);
+        }
+    }
+
+    private sealed class FailCommitInterceptor : DbTransactionInterceptor
+    {
+        public bool Armed { get; set; }
+
+        public override ValueTask<InterceptionResult> TransactionCommittingAsync(
+            DbTransaction transaction,
+            TransactionEventData eventData,
+            InterceptionResult result,
+            CancellationToken cancellationToken = default)
+        {
+            if (Armed)
+                throw new InvalidOperationException("Simulated failure before the commit");
+
+            return base.TransactionCommittingAsync(transaction, eventData, result, cancellationToken);
+        }
+    }
+}
diff --git a/SeaHavenIndustries.Tests/WorkOrderReconciliationTests.cs b/SeaHavenIndustries.Tests/WorkOrderReconciliationTests.cs
index 331ab47..fd37400 100644
--- a/SeaHavenIndustries.Tests/WorkOrderReconciliationTests.cs
+++ b/SeaHavenIndustries.Tests/WorkOrderReconciliationTests.cs
@@ -216,6 +216,16 @@ public sealed class WorkOrderReconciliationTests
         Assert.Equal("winner", (await context.workOrders.SingleAsync()).WorkerOrderTitle);
     }
 
+    internal static WorkOrderReconciliationService CreateService(
+        IReadOnlyList<ProcurementWorkOrder> workOrders,
+        IWorkOrderWebhookDataService data) =>
+        Create(
+            new MockClient(
+                new[] { new ProcurementPage<ProcurementWorkOrder>(workOrders, null) },
+                new()),
+            data,
+            new RecordingJobs());
+
     private static WorkOrderReconciliationService Create(
         IProcurementWorkOrderClient client,
         IWorkOrderWebhookDataService workOrders,