18 files changed, 189 insertions, 220 deletions

diff --git a/src/burn/engine/apply.cpp b/src/burn/engine/apply.cpp
index 4d527409..aad9e6eb 100644
--- a/src/burn/engine/apply.cpp
+++ b/src/burn/engine/apply.cpp
@@ -335,6 +335,7 @@ extern "C" void ApplyReset(
     {
         BURN_PACKAGE* pPackage = pPackages->rgPackages + i;
         pPackage->hrCacheResult = S_OK;
+        pPackage->fReachedExecution = FALSE;
         pPackage->transactionRegistrationState = BURN_PACKAGE_REGISTRATION_STATE_UNKNOWN;
     }
 }
@@ -433,7 +434,7 @@ LExit:
 
 extern "C" HRESULT ApplyUnregister(
     __in BURN_ENGINE_STATE* pEngineState,
-    __in BOOL fFailedOrRollback,
+    __in BOOL fFailed,
     __in BOOL fSuspend,
     __in BOOTSTRAPPER_APPLY_RESTART restart
     )
@@ -466,7 +467,7 @@ extern "C" HRESULT ApplyUnregister(
 
     // If apply failed in any way and we're going to be keeping the bundle registered then
     // execute any rollback dependency registration actions.
-    if (fFailedOrRollback && fKeepRegistration)
+    if (fFailed && fKeepRegistration)
     {
         // Execute any rollback registration actions.
         HRESULT hrRegistrationRollback = ExecuteDependentRegistrationActions(pEngineState->companionConnection.hPipe, &pEngineState->registration, pEngineState->plan.rgRollbackRegistrationActions, pEngineState->plan.cRollbackRegistrationActions);
@@ -587,11 +588,7 @@ extern "C" HRESULT ApplyCache(
     }
 
 LExit:
-    if (FAILED(hr))
-    {
-        DoRollbackCache(pUX, pPlan, hPipe, dwCheckpoint);
-        pContext->fRollback = TRUE;
-    }
+    pContext->dwCacheCheckpoint = dwCheckpoint;
 
     // Clean up any remanents in the cache.
     if (INVALID_HANDLE_VALUE != hPipe)
@@ -612,6 +609,16 @@ LExit:
     return hr;
 }
 
+extern "C" void ApplyCacheRollback(
+    __in BURN_USER_EXPERIENCE* pUX,
+    __in BURN_PLAN* pPlan,
+    __in HANDLE hPipe,
+    __in BURN_APPLY_CONTEXT* pContext
+    )
+{
+    DoRollbackCache(pUX, pPlan, hPipe, pContext->dwCacheCheckpoint);
+}
+
 extern "C" HRESULT ApplyExecute(
     __in BURN_ENGINE_STATE* pEngineState,
     __in BURN_APPLY_CONTEXT* pApplyContext,
@@ -687,7 +694,6 @@ extern "C" HRESULT ApplyExecute(
                     IgnoreRollbackError(hrRollback, "Failed commit transaction from disable rollback");
                 }
 
-                pApplyContext->fRollback = TRUE;
                 break;
             }
 
@@ -708,7 +714,6 @@ extern "C" HRESULT ApplyExecute(
             // If the rollback boundary is vital, end execution here.
             if (pRollbackBoundary && pRollbackBoundary->fVital)
             {
-                pApplyContext->fRollback = TRUE;
                 break;
             }
 
@@ -2110,41 +2115,44 @@ static void DoRollbackCache(
     )
 {
     HRESULT hr = S_OK;
-    DWORD iCheckpoint = 0;
+    BURN_PACKAGE* pPackage = NULL;
+    DWORD dwLastCheckpoint = 0;
 
-    // Scan to last checkpoint.
-    for (DWORD i = 0; i < pPlan->cRollbackCacheActions; ++i)
+    // Rollback cache actions.
+    for (DWORD i = pPlan->cRollbackCacheActions; i > 0; --i)
     {
-        BURN_CACHE_ACTION* pRollbackCacheAction = &pPlan->rgRollbackCacheActions[i];
+        BURN_CACHE_ACTION* pRollbackCacheAction = &pPlan->rgRollbackCacheActions[i - 1];
 
-        if (BURN_CACHE_ACTION_TYPE_CHECKPOINT == pRollbackCacheAction->type && pRollbackCacheAction->checkpoint.dwId == dwCheckpoint)
+        switch (pRollbackCacheAction->type)
         {
-            iCheckpoint = i;
+        case BURN_CACHE_ACTION_TYPE_CHECKPOINT:
+            dwLastCheckpoint = pRollbackCacheAction->checkpoint.dwId;
             break;
-        }
-    }
 
-    // Rollback cache actions.
-    if (iCheckpoint)
-    {
-        // i has to be a signed integer so it doesn't get decremented to 0xFFFFFFFF.
-        for (int i = iCheckpoint - 1; i >= 0; --i)
-        {
-            BURN_CACHE_ACTION* pRollbackCacheAction = &pPlan->rgRollbackCacheActions[i];
+        case BURN_CACHE_ACTION_TYPE_ROLLBACK_PACKAGE:
+            pPackage = pRollbackCacheAction->rollbackPackage.pPackage;
 
-            switch (pRollbackCacheAction->type)
+            // If the package was executed then it's up to ApplyExecute to rollback its cache.
+            if (!pPackage->fReachedExecution)
             {
-            case BURN_CACHE_ACTION_TYPE_CHECKPOINT:
-                break;
-
-            case BURN_CACHE_ACTION_TYPE_ROLLBACK_PACKAGE:
-                hr = CleanPackage(hPipe, pRollbackCacheAction->rollbackPackage.pPackage);
-                break;
-
-            default:
-                AssertSz(FALSE, "Invalid rollback cache action.");
-                break;
+                if (!pPackage->fCached) // only rollback when it wasn't already cached.
+                {
+                    if (dwLastCheckpoint <= dwCheckpoint) // only rollback when it was attempted to be cached.
+                    {
+                        hr = CleanPackage(hPipe, pPackage);
+                    }
+                }
+                else if (pPackage->fCanAffectRegistration)
+                {
+                    // Don't let this already cached package cause the registration to be kept if the bundle failed and wasn't already registered.
+                    pPackage->cacheRegistrationState = BURN_PACKAGE_REGISTRATION_STATE_IGNORED;
+                }
             }
+            break;
+
+        default:
+            AssertSz(FALSE, "Invalid rollback cache action.");
+            break;
         }
     }
 }
@@ -2180,9 +2188,11 @@ static HRESULT DoExecuteAction(
             *ppCheckpoint = &pExecuteAction->checkpoint;
             break;
 
-        case BURN_EXECUTE_ACTION_TYPE_WAIT_SYNCPOINT:
+        case BURN_EXECUTE_ACTION_TYPE_WAIT_CACHE_PACKAGE:
+            pExecuteAction->waitCachePackage.pPackage->fReachedExecution = TRUE;
+
             // wait for cache sync-point
-            rghWait[0] = pExecuteAction->syncpoint.hEvent;
+            rghWait[0] = pExecuteAction->waitCachePackage.pPackage->hCacheEvent;
             rghWait[1] = pContext->pApplyContext->hCacheThread;
             switch (::WaitForMultipleObjects(rghWait[1] ? 2 : 1, rghWait, FALSE, INFINITE))
             {
@@ -2354,10 +2364,17 @@ static HRESULT DoRollbackActions(
                 ExitFunction1(hr = S_OK);
 
             case BURN_EXECUTE_ACTION_TYPE_UNCACHE_PACKAGE:
-                // TODO: This used to be skipped if the package was already cached.
-                //       Need to figure out new logic for when (if?) to skip it.
-                hr = CleanPackage(pEngineState->companionConnection.hPipe, pRollbackAction->uncachePackage.pPackage);
-                IgnoreRollbackError(hr, "Failed to uncache package for rollback.");
+                if (!pRollbackAction->uncachePackage.pPackage->fCached) // only rollback when it wasn't already cached.
+                {
+                    hr = CleanPackage(pEngineState->companionConnection.hPipe, pRollbackAction->uncachePackage.pPackage);
+                    IgnoreRollbackError(hr, "Failed to uncache package for rollback.");
+                }
+                else if (pRollbackAction->uncachePackage.pPackage->fCanAffectRegistration)
+                {
+                    // Don't let this already cached package cause the registration to be kept if the bundle failed and wasn't already registered.
+                    pRollbackAction->uncachePackage.pPackage->cacheRegistrationState = BURN_PACKAGE_REGISTRATION_STATE_IGNORED;
+                }
+
                 break;
 
             default:
diff --git a/src/burn/engine/apply.h b/src/burn/engine/apply.h
index 39580297..45270f92 100644
--- a/src/burn/engine/apply.h
+++ b/src/burn/engine/apply.h
@@ -71,7 +71,7 @@ HRESULT ApplyRegister(
     );
 HRESULT ApplyUnregister(
     __in BURN_ENGINE_STATE* pEngineState,
-    __in BOOL fFailedOrRollback,
+    __in BOOL fFailed,
     __in BOOL fSuspend,
     __in BOOTSTRAPPER_APPLY_RESTART restart
     );
@@ -83,6 +83,12 @@ HRESULT ApplyCache(
     __in HANDLE hPipe,
     __in BURN_APPLY_CONTEXT* pContext
     );
+void ApplyCacheRollback(
+    __in BURN_USER_EXPERIENCE* pUX,
+    __in BURN_PLAN* pPlan,
+    __in HANDLE hPipe,
+    __in BURN_APPLY_CONTEXT* pContext
+    );
 HRESULT ApplyExecute(
     __in BURN_ENGINE_STATE* pEngineState,
     __in BURN_APPLY_CONTEXT* pApplyContext,
diff --git a/src/burn/engine/core.cpp b/src/burn/engine/core.cpp
index 601f29a0..aab49cb7 100644
--- a/src/burn/engine/core.cpp
+++ b/src/burn/engine/core.cpp
@@ -467,6 +467,7 @@ extern "C" HRESULT CorePlan(
     pEngineState->plan.wzBundleId = pEngineState->registration.sczId;
     pEngineState->plan.wzBundleProviderKey = pEngineState->registration.sczId;
     pEngineState->plan.fDisableRollback = pEngineState->fDisableRollback;
+    pEngineState->plan.fBundleAlreadyRegistered = pEngineState->registration.fInstalled;
 
     hr = PlanSetVariables(action, &pEngineState->variables);
     ExitOnFailure(hr, "Failed to update action.");
@@ -613,6 +614,7 @@ extern "C" HRESULT CoreApply(
     BURN_APPLY_CONTEXT applyContext = { };
     BOOL fDeleteApplyCs = FALSE;
     BURN_CACHE_THREAD_CONTEXT cacheThreadContext = { };
+    BOOL fRollbackCache = FALSE;
     DWORD dwPhaseCount = 0;
     BOOTSTRAPPER_APPLYCOMPLETE_ACTION applyCompleteAction = BOOTSTRAPPER_APPLYCOMPLETE_ACTION_NONE;
 
@@ -713,6 +715,8 @@ extern "C" HRESULT CoreApply(
         applyContext.hCacheThread = ::CreateThread(NULL, 0, CacheThreadProc, &cacheThreadContext, 0, NULL);
         ExitOnNullWithLastError(applyContext.hCacheThread, hr, "Failed to create cache thread.");
 
+        fRollbackCache = TRUE;
+
         // If we're not caching in parallel, wait for the cache thread to terminate.
         if (!pEngineState->fParallelCacheAndExecute)
         {
@@ -740,23 +744,32 @@ extern "C" HRESULT CoreApply(
         }
     }
 
-    // If something went wrong or force restarted, skip cleaning.
-    if (FAILED(hr) || applyContext.fRollback || fSuspend || BOOTSTRAPPER_APPLY_RESTART_INITIATED == restart)
+    if (fSuspend || BOOTSTRAPPER_APPLY_RESTART_INITIATED == restart)
     {
-        ExitFunction();
+        // Leave cache alone.
+        fRollbackCache = FALSE;
     }
-
-    // Clean.
-    if (pEngineState->plan.cCleanActions)
+    else if (SUCCEEDED(hr))
     {
-        ApplyClean(&pEngineState->userExperience, &pEngineState->plan, pEngineState->companionConnection.hPipe);
+        // Clean.
+        fRollbackCache = FALSE;
+
+        if (pEngineState->plan.cCleanActions)
+        {
+            ApplyClean(&pEngineState->userExperience, &pEngineState->plan, pEngineState->companionConnection.hPipe);
+        }
     }
 
 LExit:
+    if (fRollbackCache)
+    {
+        ApplyCacheRollback(&pEngineState->userExperience, &pEngineState->plan, pEngineState->companionConnection.hCachePipe, &applyContext);
+    }
+
     // Unregister.
     if (fRegistered)
     {
-        ApplyUnregister(pEngineState, FAILED(hr) || applyContext.fRollback, fSuspend, restart);
+        ApplyUnregister(pEngineState, FAILED(hr), fSuspend, restart);
     }
 
     if (fElevated)
diff --git a/src/burn/engine/core.h b/src/burn/engine/core.h
index 9f779366..27cb2e25 100644
--- a/src/burn/engine/core.h
+++ b/src/burn/engine/core.h
@@ -138,8 +138,8 @@ typedef struct _BURN_APPLY_CONTEXT
 {
     CRITICAL_SECTION csApply;
     DWORD cOverallProgressTicks;
-    BOOL fRollback;
     HANDLE hCacheThread;
+    DWORD dwCacheCheckpoint;
 } BURN_APPLY_CONTEXT;
 
 
diff --git a/src/burn/engine/exeengine.cpp b/src/burn/engine/exeengine.cpp
index c0ba93e0..13d4f6c6 100644
--- a/src/burn/engine/exeengine.cpp
+++ b/src/burn/engine/exeengine.cpp
@@ -268,20 +268,12 @@ extern "C" HRESULT ExeEnginePlanAddPackage(
     __in BURN_PACKAGE* pPackage,
     __in BURN_PLAN* pPlan,
     __in BURN_LOGGING* pLog,
-    __in BURN_VARIABLES* pVariables,
-    __in_opt HANDLE hCacheEvent
+    __in BURN_VARIABLES* pVariables
     )
 {
     HRESULT hr = S_OK;
     BURN_EXECUTE_ACTION* pAction = NULL;
 
-    // add wait for cache
-    if (hCacheEvent)
-    {
-        hr = PlanExecuteCacheSyncAndRollback(pPlan, pPackage, hCacheEvent);
-        ExitOnFailure(hr, "Failed to plan package cache syncpoint");
-    }
-
     hr = DependencyPlanPackage(pdwInsertSequence, pPackage, pPlan);
     ExitOnFailure(hr, "Failed to plan package dependency actions.");
 
diff --git a/src/burn/engine/exeengine.h b/src/burn/engine/exeengine.h
index e032ea01..4fec2dd9 100644
--- a/src/burn/engine/exeengine.h
+++ b/src/burn/engine/exeengine.h
@@ -28,8 +28,7 @@ HRESULT ExeEnginePlanAddPackage(
     __in BURN_PACKAGE* pPackage,
     __in BURN_PLAN* pPlan,
     __in BURN_LOGGING* pLog,
-    __in BURN_VARIABLES* pVariables,
-    __in_opt HANDLE hCacheEvent
+    __in BURN_VARIABLES* pVariables
     );
 HRESULT ExeEngineExecutePackage(
     __in BURN_EXECUTE_ACTION* pExecuteAction,
diff --git a/src/burn/engine/msiengine.cpp b/src/burn/engine/msiengine.cpp
index 3e96e5f9..a579fa17 100644
--- a/src/burn/engine/msiengine.cpp
+++ b/src/burn/engine/msiengine.cpp
@@ -915,8 +915,7 @@ extern "C" HRESULT MsiEnginePlanAddPackage(
     __in BURN_PACKAGE* pPackage,
     __in BURN_PLAN* pPlan,
     __in BURN_LOGGING* pLog,
-    __in BURN_VARIABLES* pVariables,
-    __in_opt HANDLE hCacheEvent
+    __in BURN_VARIABLES* pVariables
     )
 {
     HRESULT hr = S_OK;
@@ -943,13 +942,6 @@ extern "C" HRESULT MsiEnginePlanAddPackage(
         }
     }
 
-    // add wait for cache
-    if (hCacheEvent)
-    {
-        hr = PlanExecuteCacheSyncAndRollback(pPlan, pPackage, hCacheEvent);
-        ExitOnFailure(hr, "Failed to plan package cache syncpoint");
-    }
-
     hr = DependencyPlanPackage(NULL, pPackage, pPlan);
     ExitOnFailure(hr, "Failed to plan package dependency actions.");
 
diff --git a/src/burn/engine/msiengine.h b/src/burn/engine/msiengine.h
index 8b5bcdd0..e4155a62 100644
--- a/src/burn/engine/msiengine.h
+++ b/src/burn/engine/msiengine.h
@@ -49,8 +49,7 @@ HRESULT MsiEnginePlanAddPackage(
     __in BURN_PACKAGE* pPackage,
     __in BURN_PLAN* pPlan,
     __in BURN_LOGGING* pLog,
-    __in BURN_VARIABLES* pVariables,
-    __in_opt HANDLE hCacheEvent
+    __in BURN_VARIABLES* pVariables
     );
 HRESULT MsiEngineBeginTransaction(
     __in BURN_ROLLBACK_BOUNDARY* pRollbackBoundary
diff --git a/src/burn/engine/mspengine.cpp b/src/burn/engine/mspengine.cpp
index 6d58d324..4a82598f 100644
--- a/src/burn/engine/mspengine.cpp
+++ b/src/burn/engine/mspengine.cpp
@@ -57,8 +57,7 @@ static HRESULT PlanTargetProduct(
     __in BURN_VARIABLES* pVariables,
     __in BOOTSTRAPPER_ACTION_STATE actionState,
     __in BURN_PACKAGE* pPackage,
-    __in BURN_MSPTARGETPRODUCT* pTargetProduct,
-    __in_opt HANDLE hCacheEvent
+    __in BURN_MSPTARGETPRODUCT* pTargetProduct
     );
 
 
@@ -504,21 +503,11 @@ extern "C" HRESULT MspEnginePlanAddPackage(
     __in BURN_PACKAGE* pPackage,
     __in BURN_PLAN* pPlan,
     __in BURN_LOGGING* pLog,
-    __in BURN_VARIABLES* pVariables,
-    __in_opt HANDLE hCacheEvent
+    __in BURN_VARIABLES* pVariables
     )
 {
     HRESULT hr = S_OK;
 
-    // TODO: need to handle the case where this patch adds itself to an earlier patch's list of target products. That would
-    //       essentially bump this patch earlier in the plan and we need to make sure this patch is downloaded.
-    // add wait for cache
-    if (hCacheEvent)
-    {
-        hr = PlanExecuteCacheSyncAndRollback(pPlan, pPackage, hCacheEvent);
-        ExitOnFailure(hr, "Failed to plan package cache syncpoint");
-    }
-
     hr = DependencyPlanPackage(NULL, pPackage, pPlan);
     ExitOnFailure(hr, "Failed to plan package dependency actions.");
 
@@ -536,13 +525,13 @@ extern "C" HRESULT MspEnginePlanAddPackage(
 
         if (BOOTSTRAPPER_ACTION_STATE_NONE != pTargetProduct->execute)
         {
-            hr = PlanTargetProduct(display, pUserExperience, FALSE, pPlan, pLog, pVariables, pTargetProduct->execute, pPackage, pTargetProduct, hCacheEvent);
+            hr = PlanTargetProduct(display, pUserExperience, FALSE, pPlan, pLog, pVariables, pTargetProduct->execute, pPackage, pTargetProduct);
             ExitOnFailure(hr, "Failed to plan target product.");
         }
 
         if (BOOTSTRAPPER_ACTION_STATE_NONE != pTargetProduct->rollback)
         {
-            hr = PlanTargetProduct(display, pUserExperience, TRUE, pPlan, pLog, pVariables, pTargetProduct->rollback, pPackage, pTargetProduct, hCacheEvent);
+            hr = PlanTargetProduct(display, pUserExperience, TRUE, pPlan, pLog, pVariables, pTargetProduct->rollback, pPackage, pTargetProduct);
             ExitOnFailure(hr, "Failed to plan rollback target product.");
         }
     }
@@ -1089,8 +1078,7 @@ static HRESULT PlanTargetProduct(
     __in BURN_VARIABLES* pVariables,
     __in BOOTSTRAPPER_ACTION_STATE actionState,
     __in BURN_PACKAGE* pPackage,
-    __in BURN_MSPTARGETPRODUCT* pTargetProduct,
-    __in_opt HANDLE hCacheEvent
+    __in BURN_MSPTARGETPRODUCT* pTargetProduct
     )
 {
     HRESULT hr = S_OK;
@@ -1153,16 +1141,17 @@ static HRESULT PlanTargetProduct(
     }
     else
     {
-        if (!fRollback && hCacheEvent)
+        if (!fRollback && pPackage->hCacheEvent)
         {
-            // Since a previouse MSP target action is being updated with the new MSP, 
+            // TODO: need to properly handle rolling back the caching of the package since this causes cache and execute plans to get out of sync.
+            // Since a previous MSP target action is being updated with the new MSP,
             // insert a wait syncpoint to before this action since we need to cache the current MSI before using it.
             BURN_EXECUTE_ACTION* pWaitSyncPointAction = NULL;
             hr = PlanInsertExecuteAction(dwInsertSequence, pPlan, &pWaitSyncPointAction);
             ExitOnFailure(hr, "Failed to insert execute action.");
 
-            pWaitSyncPointAction->type = BURN_EXECUTE_ACTION_TYPE_WAIT_SYNCPOINT;
-            pWaitSyncPointAction->syncpoint.hEvent = hCacheEvent;
+            pWaitSyncPointAction->type = BURN_EXECUTE_ACTION_TYPE_WAIT_CACHE_PACKAGE;
+            pWaitSyncPointAction->waitCachePackage.pPackage = pPackage;
 
             // Since we inserted an action before the MSP target action that we will be updating, need to update the pointer.
             pAction = pPlan->rgExecuteActions + (dwInsertSequence + 1);
diff --git a/src/burn/engine/mspengine.h b/src/burn/engine/mspengine.h
index 79998030..a8835d7b 100644
--- a/src/burn/engine/mspengine.h
+++ b/src/burn/engine/mspengine.h
@@ -57,8 +57,7 @@ HRESULT MspEnginePlanAddPackage(
     __in BURN_PACKAGE* pPackage,
     __in BURN_PLAN* pPlan,
     __in BURN_LOGGING* pLog,
-    __in BURN_VARIABLES* pVariables,
-    __in_opt HANDLE hCacheEvent
+    __in BURN_VARIABLES* pVariables
     );
 HRESULT MspEngineExecutePackage(
     __in_opt HWND hwndParent,
diff --git a/src/burn/engine/msuengine.cpp b/src/burn/engine/msuengine.cpp
index 6003123b..d6722bbf 100644
--- a/src/burn/engine/msuengine.cpp
+++ b/src/burn/engine/msuengine.cpp
@@ -192,20 +192,12 @@ extern "C" HRESULT MsuEnginePlanAddPackage(
     __in BURN_PACKAGE* pPackage,
     __in BURN_PLAN* pPlan,
     __in BURN_LOGGING* pLog,
-    __in BURN_VARIABLES* pVariables,
-    __in HANDLE hCacheEvent
+    __in BURN_VARIABLES* pVariables
     )
 {
     HRESULT hr = S_OK;
     BURN_EXECUTE_ACTION* pAction = NULL;
 
-    // add wait for cache
-    if (hCacheEvent)
-    {
-        hr = PlanExecuteCacheSyncAndRollback(pPlan, pPackage, hCacheEvent);
-        ExitOnFailure(hr, "Failed to plan package cache syncpoint");
-    }
-
     hr = DependencyPlanPackage(NULL, pPackage, pPlan);
     ExitOnFailure(hr, "Failed to plan package dependency actions.");
 
diff --git a/src/burn/engine/msuengine.h b/src/burn/engine/msuengine.h
index fda7a5ab..23dd5301 100644
--- a/src/burn/engine/msuengine.h
+++ b/src/burn/engine/msuengine.h
@@ -27,8 +27,7 @@ HRESULT MsuEnginePlanAddPackage(
     __in BURN_PACKAGE* pPackage,
     __in BURN_PLAN* pPlan,
     __in BURN_LOGGING* pLog,
-    __in BURN_VARIABLES* pVariables,
-    __in HANDLE hCacheEvent
+    __in BURN_VARIABLES* pVariables
     );
 HRESULT MsuEngineExecutePackage(
     __in BURN_EXECUTE_ACTION* pExecuteAction,
diff --git a/src/burn/engine/package.h b/src/burn/engine/package.h
index 89a3d6e9..94f27c23 100644
--- a/src/burn/engine/package.h
+++ b/src/burn/engine/package.h
@@ -240,8 +240,10 @@ typedef struct _BURN_PACKAGE
     BURN_DEPENDENCY_ACTION dependencyExecute;   // only valid during Plan.
     BURN_DEPENDENCY_ACTION dependencyRollback;  // only valid during Plan.
     BOOL fDependencyManagerWasHere;             // only valid during Plan.
+    HANDLE hCacheEvent;                         // only valid during Plan.
     LPWSTR sczCacheFolder;                      // only valid during Apply.
     HRESULT hrCacheResult;                      // only valid during Apply.
+    BOOL fReachedExecution;                     // only valid during Apply.
 
     BURN_PACKAGE_REGISTRATION_STATE cacheRegistrationState;          // initialized during Detect, updated during Apply.
     BURN_PACKAGE_REGISTRATION_STATE installRegistrationState;        // initialized during Detect, updated during Apply.
diff --git a/src/burn/engine/plan.cpp b/src/burn/engine/plan.cpp
index f0ae2a44..d1f07508 100644
--- a/src/burn/engine/plan.cpp
+++ b/src/burn/engine/plan.cpp
@@ -55,7 +55,6 @@ static HRESULT ProcessPackage(
     __in BURN_LOGGING* pLog,
     __in BURN_VARIABLES* pVariables,
     __in BOOTSTRAPPER_DISPLAY display,
-    __inout HANDLE* phSyncpointEvent,
     __inout BURN_ROLLBACK_BOUNDARY** ppRollbackBoundary
     );
 static HRESULT ProcessPackageRollbackBoundary(
@@ -77,23 +76,16 @@ static HRESULT AddRegistrationAction(
     );
 static HRESULT AddCachePackage(
     __in BURN_PLAN* pPlan,
-    __in BURN_PACKAGE* pPackage,
-    __out HANDLE* phSyncpointEvent
+    __in BURN_PACKAGE* pPackage
     );
 static HRESULT AddCachePackageHelper(
     __in BURN_PLAN* pPlan,
-    __in BURN_PACKAGE* pPackage,
-    __out HANDLE* phSyncpointEvent
+    __in BURN_PACKAGE* pPackage
     );
 static HRESULT AddCacheSlipstreamMsps(
     __in BURN_PLAN* pPlan,
     __in BURN_PACKAGE* pPackage
     );
-static BOOL AlreadyPlannedCachePackage(
-    __in BURN_PLAN* pPlan,
-    __in_z LPCWSTR wzPackageId,
-    __out HANDLE* phSyncpointEvent
-    );
 static DWORD GetNextCheckpointId(
     __in BURN_PLAN* pPlan
     );
@@ -765,7 +757,6 @@ static HRESULT PlanPackagesHelper(
     HRESULT hr = S_OK;
     BOOL fBundlePerMachine = pPlan->fPerMachine; // bundle is per-machine if plan starts per-machine.
     BURN_ROLLBACK_BOUNDARY* pRollbackBoundary = NULL;
-    HANDLE hSyncpointEvent = NULL;
 
     // Initialize the packages.
     for (DWORD i = 0; i < cPackages; ++i)
@@ -796,7 +787,7 @@ static HRESULT PlanPackagesHelper(
         DWORD iPackage = (BOOTSTRAPPER_ACTION_UNINSTALL == pPlan->action) ? cPackages - 1 - i : i;
         BURN_PACKAGE* pPackage = rgPackages + iPackage;
 
-        hr = ProcessPackage(fBundlePerMachine, pUX, pPlan, pPackage, pLog, pVariables, display, &hSyncpointEvent, &pRollbackBoundary);
+        hr = ProcessPackage(fBundlePerMachine, pUX, pPlan, pPackage, pLog, pVariables, display, &pRollbackBoundary);
         ExitOnFailure(hr, "Failed to process package.");
     }
 
@@ -902,7 +893,6 @@ static HRESULT ProcessPackage(
     __in BURN_LOGGING* pLog,
     __in BURN_VARIABLES* pVariables,
     __in BOOTSTRAPPER_DISPLAY display,
-    __inout HANDLE* phSyncpointEvent,
     __inout BURN_ROLLBACK_BOUNDARY** ppRollbackBoundary
     )
 {
@@ -926,14 +916,14 @@ static HRESULT ProcessPackage(
         if (BOOTSTRAPPER_REQUEST_STATE_NONE != pPackage->requested)
         {
             // If the package is in a requested state, plan it.
-            hr = PlanExecutePackage(fBundlePerMachine, display, pUX, pPlan, pPackage, pLog, pVariables, phSyncpointEvent);
+            hr = PlanExecutePackage(fBundlePerMachine, display, pUX, pPlan, pPackage, pLog, pVariables);
             ExitOnFailure(hr, "Failed to plan execute package.");
         }
         else
         {
             if (ForceCache(pPlan, pPackage))
             {
-                hr = AddCachePackage(pPlan, pPackage, phSyncpointEvent);
+                hr = AddCachePackage(pPlan, pPackage);
                 ExitOnFailure(hr, "Failed to plan cache package.");
 
                 if (pPackage->fPerMachine)
@@ -1072,8 +1062,7 @@ extern "C" HRESULT PlanExecutePackage(
     __in BURN_PLAN* pPlan,
     __in BURN_PACKAGE* pPackage,
     __in BURN_LOGGING* pLog,
-    __in BURN_VARIABLES* pVariables,
-    __inout HANDLE* phSyncpointEvent
+    __in BURN_VARIABLES* pVariables
     )
 {
     HRESULT hr = S_OK;
@@ -1088,7 +1077,7 @@ extern "C" HRESULT PlanExecutePackage(
 
     if (fRequestedCache || NeedsCache(pPackage, TRUE))
     {
-        hr = AddCachePackage(pPlan, pPackage, phSyncpointEvent);
+        hr = AddCachePackage(pPlan, pPackage);
         ExitOnFailure(hr, "Failed to plan cache package.");
     }
     else if (!pPackage->fCached && NeedsCache(pPackage, FALSE))
@@ -1128,19 +1117,19 @@ extern "C" HRESULT PlanExecutePackage(
     switch (pPackage->type)
     {
     case BURN_PACKAGE_TYPE_EXE:
-        hr = ExeEnginePlanAddPackage(NULL, pPackage, pPlan, pLog, pVariables, *phSyncpointEvent);
+        hr = ExeEnginePlanAddPackage(NULL, pPackage, pPlan, pLog, pVariables);
         break;
 
     case BURN_PACKAGE_TYPE_MSI:
-        hr = MsiEnginePlanAddPackage(display, pUserExperience, pPackage, pPlan, pLog, pVariables, *phSyncpointEvent);
+        hr = MsiEnginePlanAddPackage(display, pUserExperience, pPackage, pPlan, pLog, pVariables);
         break;
 
     case BURN_PACKAGE_TYPE_MSP:
-        hr = MspEnginePlanAddPackage(display, pUserExperience, pPackage, pPlan, pLog, pVariables, *phSyncpointEvent);
+        hr = MspEnginePlanAddPackage(display, pUserExperience, pPackage, pPlan, pLog, pVariables);
         break;
 
     case BURN_PACKAGE_TYPE_MSU:
-        hr = MsuEnginePlanAddPackage(pPackage, pPlan, pLog, pVariables, *phSyncpointEvent);
+        hr = MsuEnginePlanAddPackage(pPackage, pPlan, pLog, pVariables);
         break;
 
     default:
@@ -1453,7 +1442,7 @@ extern "C" HRESULT PlanRelatedBundlesComplete(
                 }
             }
 
-            hr = ExeEnginePlanAddPackage(pdwInsertIndex, &pRelatedBundle->package, pPlan, pLog, pVariables, NULL);
+            hr = ExeEnginePlanAddPackage(pdwInsertIndex, &pRelatedBundle->package, pPlan, pLog, pVariables);
             ExitOnFailure(hr, "Failed to add to plan related bundle: %ls", pRelatedBundle->package.sczId);
 
             // Calculate package states based on reference count for addon and patch related bundles.
@@ -1583,28 +1572,30 @@ LExit:
 
 extern "C" HRESULT PlanExecuteCacheSyncAndRollback(
     __in BURN_PLAN* pPlan,
-    __in BURN_PACKAGE* pPackage,
-    __in HANDLE hCacheEvent
+    __in BURN_PACKAGE* pPackage
     )
 {
     HRESULT hr = S_OK;
     BURN_EXECUTE_ACTION* pAction = NULL;
 
-    hr = PlanAppendExecuteAction(pPlan, &pAction);
-    ExitOnFailure(hr, "Failed to append wait action for caching.");
-
-    pAction->type = BURN_EXECUTE_ACTION_TYPE_WAIT_SYNCPOINT;
-    pAction->syncpoint.hEvent = hCacheEvent;
-
-    hr = PlanAppendRollbackAction(pPlan, &pAction);
-    ExitOnFailure(hr, "Failed to append rollback action.");
+    if (!pPlan->fBundleAlreadyRegistered)
+    {
+        hr = PlanAppendRollbackAction(pPlan, &pAction);
+        ExitOnFailure(hr, "Failed to append rollback action.");
 
-    pAction->type = BURN_EXECUTE_ACTION_TYPE_UNCACHE_PACKAGE;
-    pAction->uncachePackage.pPackage = pPackage;
+        pAction->type = BURN_EXECUTE_ACTION_TYPE_UNCACHE_PACKAGE;
+        pAction->uncachePackage.pPackage = pPackage;
+    }
 
     hr = PlanExecuteCheckpoint(pPlan);
     ExitOnFailure(hr, "Failed to append execute checkpoint for cache rollback.");
 
+    hr = PlanAppendExecuteAction(pPlan, &pAction);
+    ExitOnFailure(hr, "Failed to append wait action for caching.");
+
+    pAction->type = BURN_EXECUTE_ACTION_TYPE_WAIT_CACHE_PACKAGE;
+    pAction->waitCachePackage.pPackage = pPackage;
+
 LExit:
     return hr;
 }
@@ -1885,6 +1876,7 @@ static void ResetPlannedPackageState(
     pPackage->fDependencyManagerWasHere = FALSE;
     pPackage->expectedCacheRegistrationState = BURN_PACKAGE_REGISTRATION_STATE_UNKNOWN;
     pPackage->expectedInstallRegistrationState = BURN_PACKAGE_REGISTRATION_STATE_UNKNOWN;
+    pPackage->hCacheEvent = NULL;
 
     ReleaseNullStr(pPackage->sczCacheFolder);
 
@@ -2046,8 +2038,7 @@ LExit:
 
 static HRESULT AddCachePackage(
     __in BURN_PLAN* pPlan,
-    __in BURN_PACKAGE* pPackage,
-    __out HANDLE* phSyncpointEvent
+    __in BURN_PACKAGE* pPackage
     )
 {
     HRESULT hr = S_OK;
@@ -2059,7 +2050,7 @@ static HRESULT AddCachePackage(
         ExitOnFailure(hr, "Failed to plan slipstream patches for package.");
     }
 
-    hr = AddCachePackageHelper(pPlan, pPackage, phSyncpointEvent);
+    hr = AddCachePackageHelper(pPlan, pPackage);
     ExitOnFailure(hr, "Failed to plan cache package.");
 
 LExit:
@@ -2068,8 +2059,7 @@ LExit:
 
 static HRESULT AddCachePackageHelper(
     __in BURN_PLAN* pPlan,
-    __in BURN_PACKAGE* pPackage,
-    __out HANDLE* phSyncpointEvent
+    __in BURN_PACKAGE* pPackage
     )
 {
     AssertSz(pPackage->sczCacheId && *pPackage->sczCacheId, "AddCachePackageHelper() expects the package to have a cache id.");
@@ -2083,8 +2073,7 @@ static HRESULT AddCachePackageHelper(
         ExitFunction();
     }
 
-    BOOL fPlanned = AlreadyPlannedCachePackage(pPlan, pPackage->sczId, phSyncpointEvent);
-    if (fPlanned)
+    if (pPackage->hCacheEvent) // Only cache the package once.
     {
         ExitFunction();
     }
@@ -2100,12 +2089,15 @@ static HRESULT AddCachePackageHelper(
     pCacheAction->type = BURN_CACHE_ACTION_TYPE_CHECKPOINT;
     pCacheAction->checkpoint.dwId = dwCheckpoint;
 
-    // Only plan the cache rollback if the package is also going to be uninstalled;
-    // otherwise, future operations like repair will not be able to locate the cached package.
-    BOOL fPlanCacheRollback = (BOOTSTRAPPER_ACTION_STATE_UNINSTALL == pPackage->rollback);
-
-    if (fPlanCacheRollback)
+    if (!pPlan->fBundleAlreadyRegistered)
     {
+        // Create a package cache rollback action *before* the checkpoint.
+        hr = AppendRollbackCacheAction(pPlan, &pCacheAction);
+        ExitOnFailure(hr, "Failed to append rollback cache action.");
+
+        pCacheAction->type = BURN_CACHE_ACTION_TYPE_ROLLBACK_PACKAGE;
+        pCacheAction->rollbackPackage.pPackage = pPackage;
+
         hr = AppendRollbackCacheAction(pPlan, &pCacheAction);
         ExitOnFailure(hr, "Failed to append rollback cache action.");
 
@@ -2124,7 +2116,10 @@ static HRESULT AddCachePackageHelper(
     pCacheAction->syncpoint.hEvent = ::CreateEventW(NULL, TRUE, FALSE, NULL);
     ExitOnNullWithLastError(pCacheAction->syncpoint.hEvent, hr, "Failed to create syncpoint event.");
 
-    *phSyncpointEvent = pCacheAction->syncpoint.hEvent;
+    pPackage->hCacheEvent = pCacheAction->syncpoint.hEvent;
+
+    hr = PlanExecuteCacheSyncAndRollback(pPlan, pPackage);
+    ExitOnFailure(hr, "Failed to plan package cache syncpoint");
 
     pPackage->fPlannedCache = TRUE;
     if (pPackage->fCanAffectRegistration)
@@ -2142,7 +2137,6 @@ static HRESULT AddCacheSlipstreamMsps(
     )
 {
     HRESULT hr = S_OK;
-    HANDLE hIgnored = NULL;
 
     AssertSz(BURN_PACKAGE_TYPE_MSI == pPackage->type, "Only MSI packages can have slipstream patches.");
 
@@ -2151,7 +2145,7 @@ static HRESULT AddCacheSlipstreamMsps(
         BURN_PACKAGE* pMspPackage = pPackage->Msi.rgSlipstreamMsps[i].pMspPackage;
         AssertSz(BURN_PACKAGE_TYPE_MSP == pMspPackage->type, "Only MSP packages can be slipstream patches.");
 
-        hr = AddCachePackageHelper(pPlan, pMspPackage, &hIgnored);
+        hr = AddCachePackageHelper(pPlan, pMspPackage);
         ExitOnFailure(hr, "Failed to plan slipstream MSP: %ls", pMspPackage->sczId);
     }
 
@@ -2159,36 +2153,6 @@ LExit:
     return hr;
 }
 
-static BOOL AlreadyPlannedCachePackage(
-    __in BURN_PLAN* pPlan,
-    __in_z LPCWSTR wzPackageId,
-    __out HANDLE* phSyncpointEvent
-    )
-{
-    BOOL fPlanned = FALSE;
-
-    for (DWORD iCacheAction = 0; iCacheAction < pPlan->cCacheActions; ++iCacheAction)
-    {
-        BURN_CACHE_ACTION* pCacheAction = pPlan->rgCacheActions + iCacheAction;
-
-        if (BURN_CACHE_ACTION_TYPE_PACKAGE == pCacheAction->type)
-        {
-            if (CSTR_EQUAL == ::CompareStringW(LOCALE_NEUTRAL, 0, pCacheAction->package.pPackage->sczId, -1, wzPackageId, -1))
-            {
-                if (iCacheAction + 1 < pPlan->cCacheActions && BURN_CACHE_ACTION_TYPE_SIGNAL_SYNCPOINT == pPlan->rgCacheActions[iCacheAction + 1].type)
-                {
-                    *phSyncpointEvent = pPlan->rgCacheActions[iCacheAction + 1].syncpoint.hEvent;
-                }
-
-                fPlanned = TRUE;
-                break;
-            }
-        }
-    }
-
-    return fPlanned;
-}
-
 static DWORD GetNextCheckpointId(
     __in BURN_PLAN* pPlan
     )
@@ -2635,8 +2599,8 @@ static void ExecuteActionLog(
         LogStringLine(PlanDumpLevel, "%ls action[%u]: ROLLBACK_BOUNDARY id: %ls, vital: %ls", wzBase, iAction, pAction->rollbackBoundary.pRollbackBoundary->sczId, pAction->rollbackBoundary.pRollbackBoundary->fVital ? L"yes" : L"no");
         break;
 
-    case BURN_EXECUTE_ACTION_TYPE_WAIT_SYNCPOINT:
-        LogStringLine(PlanDumpLevel, "%ls action[%u]: WAIT_SYNCPOINT event handle: 0x%p", wzBase, iAction, pAction->syncpoint.hEvent);
+    case BURN_EXECUTE_ACTION_TYPE_WAIT_CACHE_PACKAGE:
+        LogStringLine(PlanDumpLevel, "%ls action[%u]: WAIT_CACHE_PACKAGE id: %ls, event handle: 0x%p", wzBase, iAction, pAction->waitCachePackage.pPackage->sczId, pAction->waitCachePackage.pPackage->hCacheEvent);
         break;
 
     case BURN_EXECUTE_ACTION_TYPE_UNCACHE_PACKAGE:
diff --git a/src/burn/engine/plan.h b/src/burn/engine/plan.h
index 00ab5516..6db464e1 100644
--- a/src/burn/engine/plan.h
+++ b/src/burn/engine/plan.h
@@ -48,7 +48,7 @@ enum BURN_EXECUTE_ACTION_TYPE
 {
     BURN_EXECUTE_ACTION_TYPE_NONE,
     BURN_EXECUTE_ACTION_TYPE_CHECKPOINT,
-    BURN_EXECUTE_ACTION_TYPE_WAIT_SYNCPOINT,
+    BURN_EXECUTE_ACTION_TYPE_WAIT_CACHE_PACKAGE,
     BURN_EXECUTE_ACTION_TYPE_UNCACHE_PACKAGE,
     BURN_EXECUTE_ACTION_TYPE_EXE_PACKAGE,
     BURN_EXECUTE_ACTION_TYPE_MSI_PACKAGE,
@@ -151,8 +151,8 @@ typedef struct _BURN_EXECUTE_ACTION
         BURN_EXECUTE_ACTION_CHECKPOINT checkpoint;
         struct
         {
-            HANDLE hEvent;
-        } syncpoint;
+            BURN_PACKAGE* pPackage;
+        } waitCachePackage;
         struct
         {
             BURN_PACKAGE* pPackage;
@@ -240,6 +240,7 @@ typedef struct _BURN_PLAN
     BOOL fAffectedMachineState;
     BOOL fIgnoreAllDependents;
     LPWSTR sczLayoutDirectory;
+    BOOL fBundleAlreadyRegistered;
 
     DWORD64 qwCacheSizeTotal;
 
@@ -377,8 +378,7 @@ HRESULT PlanExecutePackage(
     __in BURN_PLAN* pPlan,
     __in BURN_PACKAGE* pPackage,
     __in BURN_LOGGING* pLog,
-    __in BURN_VARIABLES* pVariables,
-    __inout HANDLE* phSyncpointEvent
+    __in BURN_VARIABLES* pVariables
     );
 HRESULT PlanDefaultRelatedBundleRequestState(
     __in BOOTSTRAPPER_RELATION_TYPE commandRelationType,
@@ -410,8 +410,7 @@ HRESULT PlanCleanPackage(
     );
 HRESULT PlanExecuteCacheSyncAndRollback(
     __in BURN_PLAN* pPlan,
-    __in BURN_PACKAGE* pPackage,
-    __in HANDLE hCacheEvent
+    __in BURN_PACKAGE* pPackage
     );
 HRESULT PlanExecuteCheckpoint(
     __in BURN_PLAN* pPlan
diff --git a/src/burn/test/BurnUnitTest/PlanTest.cpp b/src/burn/test/BurnUnitTest/PlanTest.cpp
index 23192349..3cb42c5f 100644
--- a/src/burn/test/BurnUnitTest/PlanTest.cpp
+++ b/src/burn/test/BurnUnitTest/PlanTest.cpp
@@ -67,7 +67,12 @@ namespace Bootstrapper
 
             fRollback = TRUE;
             dwIndex = 0;
+            ValidateCacheRollbackPackage(pPlan, fRollback, dwIndex++, L"PackageA");
             ValidateCacheCheckpoint(pPlan, fRollback, dwIndex++, 1);
+            ValidateCacheRollbackPackage(pPlan, fRollback, dwIndex++, L"PackageB");
+            ValidateCacheCheckpoint(pPlan, fRollback, dwIndex++, 9);
+            ValidateCacheRollbackPackage(pPlan, fRollback, dwIndex++, L"PackageC");
+            ValidateCacheCheckpoint(pPlan, fRollback, dwIndex++, 14);
             Assert::Equal(dwIndex, pPlan->cRollbackCacheActions);
 
             Assert::Equal(107082ull, pPlan->qwEstimatedSize);
@@ -77,8 +82,8 @@ namespace Bootstrapper
             dwIndex = 0;
             DWORD dwExecuteCheckpointId = 2;
             ValidateExecuteRollbackBoundary(pPlan, fRollback, dwIndex++, L"WixDefaultBoundary", TRUE, FALSE);
-            ValidateExecuteWaitSyncpoint(pPlan, fRollback, dwIndex++, pPlan->rgCacheActions[2].syncpoint.hEvent);
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
+            ValidateExecuteWaitCachePackage(pPlan, fRollback, dwIndex++, L"PackageA");
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
             ValidateExecutePackageProvider(pPlan, fRollback, dwIndex++, L"PackageA", BURN_DEPENDENCY_ACTION_REGISTER);
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
@@ -90,18 +95,18 @@ namespace Bootstrapper
             ValidateExecuteRollbackBoundary(pPlan, fRollback, dwIndex++, L"rbaOCA08D8ky7uBOK71_6FWz1K3TuQ", TRUE, TRUE);
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
             ValidateExecuteBeginMsiTransaction(pPlan, fRollback, dwIndex++, L"rbaOCA08D8ky7uBOK71_6FWz1K3TuQ");
-            ValidateExecuteWaitSyncpoint(pPlan, fRollback, dwIndex++, pPlan->rgCacheActions[5].syncpoint.hEvent);
             dwExecuteCheckpointId += 1; // cache checkpoints
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
+            ValidateExecuteWaitCachePackage(pPlan, fRollback, dwIndex++, L"PackageB");
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
             ValidateExecutePackageProvider(pPlan, fRollback, dwIndex++, L"PackageB", BURN_DEPENDENCY_ACTION_REGISTER);
             ValidateExecuteMsiPackage(pPlan, fRollback, dwIndex++, L"PackageB", BOOTSTRAPPER_ACTION_STATE_INSTALL, BURN_MSI_PROPERTY_INSTALL, INSTALLUILEVEL_NONE, FALSE, 0);
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
             ValidateExecutePackageDependency(pPlan, fRollback, dwIndex++, L"PackageB", L"{E6469F05-BDC8-4EB8-B218-67412543EFAA}", BURN_DEPENDENCY_ACTION_REGISTER);
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
-            ValidateExecuteWaitSyncpoint(pPlan, fRollback, dwIndex++, pPlan->rgCacheActions[8].syncpoint.hEvent);
             dwExecuteCheckpointId += 1; // cache checkpoints
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
+            ValidateExecuteWaitCachePackage(pPlan, fRollback, dwIndex++, L"PackageC");
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
             ValidateExecutePackageProvider(pPlan, fRollback, dwIndex++, L"PackageC", BURN_DEPENDENCY_ACTION_REGISTER);
             ValidateExecuteMsiPackage(pPlan, fRollback, dwIndex++, L"PackageC", BOOTSTRAPPER_ACTION_STATE_INSTALL, BURN_MSI_PROPERTY_INSTALL, INSTALLUILEVEL_NONE, FALSE, 0);
@@ -304,6 +309,7 @@ namespace Bootstrapper
 
             fRollback = TRUE;
             dwIndex = 0;
+            ValidateCacheRollbackPackage(pPlan, fRollback, dwIndex++, L"PackageA");
             ValidateCacheCheckpoint(pPlan, fRollback, dwIndex++, 1);
             Assert::Equal(dwIndex, pPlan->cRollbackCacheActions);
 
@@ -314,8 +320,8 @@ namespace Bootstrapper
             dwIndex = 0;
             DWORD dwExecuteCheckpointId = 2;
             ValidateExecuteRollbackBoundary(pPlan, fRollback, dwIndex++, L"WixDefaultBoundary", TRUE, FALSE);
-            ValidateExecuteWaitSyncpoint(pPlan, fRollback, dwIndex++, pPlan->rgCacheActions[2].syncpoint.hEvent);
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
+            ValidateExecuteWaitCachePackage(pPlan, fRollback, dwIndex++, L"PackageA");
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
             ValidateExecutePackageProvider(pPlan, fRollback, dwIndex++, L"PackageA", BURN_DEPENDENCY_ACTION_REGISTER);
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
@@ -385,6 +391,8 @@ namespace Bootstrapper
 
             fRollback = TRUE;
             dwIndex = 0;
+            ValidateCacheRollbackPackage(pPlan, fRollback, dwIndex++, L"PackageA");
+            ValidateCacheCheckpoint(pPlan, fRollback, dwIndex++, 1);
             Assert::Equal(dwIndex, pPlan->cRollbackCacheActions);
 
             Assert::Equal(33743ull, pPlan->qwEstimatedSize);
@@ -394,8 +402,8 @@ namespace Bootstrapper
             dwIndex = 0;
             DWORD dwExecuteCheckpointId = 2;
             ValidateExecuteRollbackBoundary(pPlan, fRollback, dwIndex++, L"WixDefaultBoundary", TRUE, FALSE);
-            ValidateExecuteWaitSyncpoint(pPlan, fRollback, dwIndex++, pPlan->rgCacheActions[2].syncpoint.hEvent);
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
+            ValidateExecuteWaitCachePackage(pPlan, fRollback, dwIndex++, L"PackageA");
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
             Assert::Equal(dwIndex, pPlan->cExecuteActions);
@@ -454,6 +462,7 @@ namespace Bootstrapper
 
             fRollback = TRUE;
             dwIndex = 0;
+            ValidateCacheRollbackPackage(pPlan, fRollback, dwIndex++, L"PackageA");
             ValidateCacheCheckpoint(pPlan, fRollback, dwIndex++, 1);
             Assert::Equal(dwIndex, pPlan->cRollbackCacheActions);
 
@@ -464,8 +473,8 @@ namespace Bootstrapper
             dwIndex = 0;
             DWORD dwExecuteCheckpointId = 2;
             ValidateExecuteRollbackBoundary(pPlan, fRollback, dwIndex++, L"WixDefaultBoundary", TRUE, FALSE);
-            ValidateExecuteWaitSyncpoint(pPlan, fRollback, dwIndex++, pPlan->rgCacheActions[2].syncpoint.hEvent);
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
+            ValidateExecuteWaitCachePackage(pPlan, fRollback, dwIndex++, L"PackageA");
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
             ValidateExecutePackageProvider(pPlan, fRollback, dwIndex++, L"PackageA", BURN_DEPENDENCY_ACTION_REGISTER);
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
@@ -731,14 +740,13 @@ namespace Bootstrapper
             ValidateCacheCheckpoint(pPlan, fRollback, dwIndex++, 3);
             ValidateCachePackage(pPlan, fRollback, dwIndex++, L"PatchA");
             ValidateCacheSignalSyncpoint(pPlan, fRollback, dwIndex++);
-            ValidateCacheCheckpoint(pPlan, fRollback, dwIndex++, 4);
+            ValidateCacheCheckpoint(pPlan, fRollback, dwIndex++, 5);
             ValidateCachePackage(pPlan, fRollback, dwIndex++, L"PackageA");
             ValidateCacheSignalSyncpoint(pPlan, fRollback, dwIndex++);
             Assert::Equal(dwIndex, pPlan->cCacheActions);
 
             fRollback = TRUE;
             dwIndex = 0;
-            ValidateCacheCheckpoint(pPlan, fRollback, dwIndex++, 4);
             Assert::Equal(dwIndex, pPlan->cRollbackCacheActions);
 
             Assert::Equal(3055111ull, pPlan->qwEstimatedSize);
@@ -749,11 +757,14 @@ namespace Bootstrapper
             DWORD dwExecuteCheckpointId = 2;
             BURN_EXECUTE_ACTION* pExecuteAction = NULL;
             ValidateExecuteRollbackBoundary(pPlan, fRollback, dwIndex++, L"WixDefaultBoundary", TRUE, FALSE);
-            ValidateExecuteWaitSyncpoint(pPlan, fRollback, dwIndex++, pPlan->rgCacheActions[2].syncpoint.hEvent);
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
-            ValidateExecuteWaitSyncpoint(pPlan, fRollback, dwIndex++, pPlan->rgCacheActions[8].syncpoint.hEvent);
-            dwExecuteCheckpointId += 2; // cache checkpoints
+            dwExecuteCheckpointId += 1; // cache checkpoints
+            ValidateExecuteWaitCachePackage(pPlan, fRollback, dwIndex++, L"NetFx48Web");
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
+            dwExecuteCheckpointId += 1; // cache checkpoints
+            ValidateExecuteWaitCachePackage(pPlan, fRollback, dwIndex++, L"PatchA");
+            ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
+            ValidateExecuteWaitCachePackage(pPlan, fRollback, dwIndex++, L"PackageA");
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
             ValidateExecutePackageProvider(pPlan, fRollback, dwIndex++, L"PackageA", BURN_DEPENDENCY_ACTION_REGISTER);
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
@@ -761,8 +772,6 @@ namespace Bootstrapper
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
             ValidateExecutePackageDependency(pPlan, fRollback, dwIndex++, L"PackageA", L"{22D1DDBA-284D-40A7-BD14-95EA07906F21}", BURN_DEPENDENCY_ACTION_REGISTER);
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
-            ValidateExecuteWaitSyncpoint(pPlan, fRollback, dwIndex++, pPlan->rgCacheActions[5].syncpoint.hEvent);
-            ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
             ValidateExecutePackageProvider(pPlan, fRollback, dwIndex++, L"PatchA", BURN_DEPENDENCY_ACTION_REGISTER);
             pExecuteAction = ValidateDeletedExecuteMspTarget(pPlan, fRollback, dwIndex++, L"PatchA", BOOTSTRAPPER_ACTION_STATE_INSTALL, L"{5FF7F534-3FFC-41E0-80CD-E6361E5E7B7B}", TRUE, BURN_MSI_PROPERTY_INSTALL, INSTALLUILEVEL_NONE, FALSE, TRUE);
@@ -777,10 +786,10 @@ namespace Bootstrapper
             dwIndex = 0;
             dwExecuteCheckpointId = 2;
             ValidateExecuteRollbackBoundary(pPlan, fRollback, dwIndex++, L"WixDefaultBoundary", TRUE, FALSE);
-            ValidateExecuteUncachePackage(pPlan, fRollback, dwIndex++, L"NetFx48Web");
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
-            dwExecuteCheckpointId += 2; // cache checkpoints
-            ValidateExecuteUncachePackage(pPlan, fRollback, dwIndex++, L"PackageA");
+            dwExecuteCheckpointId += 1; // cache checkpoints
+            ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
+            dwExecuteCheckpointId += 1; // cache checkpoints
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
             ValidateExecutePackageProvider(pPlan, fRollback, dwIndex++, L"PackageA", BURN_DEPENDENCY_ACTION_UNREGISTER);
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
@@ -789,8 +798,6 @@ namespace Bootstrapper
             ValidateExecutePackageDependency(pPlan, fRollback, dwIndex++, L"PackageA", L"{22D1DDBA-284D-40A7-BD14-95EA07906F21}", BURN_DEPENDENCY_ACTION_UNREGISTER);
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
-            ValidateExecuteUncachePackage(pPlan, fRollback, dwIndex++, L"PatchA");
-            ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
             ValidateExecutePackageProvider(pPlan, fRollback, dwIndex++, L"PatchA", BURN_DEPENDENCY_ACTION_UNREGISTER);
             ValidateExecuteCheckpoint(pPlan, fRollback, dwIndex++, dwExecuteCheckpointId++);
             pExecuteAction = ValidateDeletedExecuteMspTarget(pPlan, fRollback, dwIndex++, L"PatchA", BOOTSTRAPPER_ACTION_STATE_UNINSTALL, L"{5FF7F534-3FFC-41E0-80CD-E6361E5E7B7B}", TRUE, BURN_MSI_PROPERTY_UNINSTALL, INSTALLUILEVEL_NONE, FALSE, TRUE);
@@ -1414,16 +1421,16 @@ namespace Bootstrapper
             Assert::Equal<BOOL>(FALSE, pAction->fDeleted);
         }
 
-        void ValidateExecuteWaitSyncpoint(
+        void ValidateExecuteWaitCachePackage(
             __in BURN_PLAN* pPlan,
             __in BOOL fRollback,
             __in DWORD dwIndex,
-            __in HANDLE hEvent
+            __in_z LPCWSTR wzPackageId
             )
         {
             BURN_EXECUTE_ACTION* pAction = ValidateExecuteActionExists(pPlan, fRollback, dwIndex);
-            Assert::Equal<DWORD>(BURN_EXECUTE_ACTION_TYPE_WAIT_SYNCPOINT, pAction->type);
-            Assert::Equal((DWORD_PTR)hEvent, (DWORD_PTR)pAction->syncpoint.hEvent);
+            Assert::Equal<DWORD>(BURN_EXECUTE_ACTION_TYPE_WAIT_CACHE_PACKAGE, pAction->type);
+            NativeAssert::StringEqual(wzPackageId, pAction->waitCachePackage.pPackage->sczId);
             Assert::Equal<BOOL>(FALSE, pAction->fDeleted);
         }
 
diff --git a/src/test/burn/WixToolsetTest.BurnE2E/DependencyTests.cs b/src/test/burn/WixToolsetTest.BurnE2E/DependencyTests.cs
index d563bbe7..08370631 100644
--- a/src/test/burn/WixToolsetTest.BurnE2E/DependencyTests.cs
+++ b/src/test/burn/WixToolsetTest.BurnE2E/DependencyTests.cs
@@ -79,7 +79,7 @@ namespace WixToolsetTest.BurnE2E
             packageA.VerifyInstalled(false);
         }
 
-        [Fact(Skip = "https://github.com/wixtoolset/issues/issues/exea")]
+        [Fact]
         public void CanKeepUpgradedPackageAfterUninstallUpgradedBundle()
         {
             var testRegistryValueExe = "ExeA";
diff --git a/src/test/burn/WixToolsetTest.BurnE2E/FailureTests.cs b/src/test/burn/WixToolsetTest.BurnE2E/FailureTests.cs
index a11a5eb6..d8428a54 100644
--- a/src/test/burn/WixToolsetTest.BurnE2E/FailureTests.cs
+++ b/src/test/burn/WixToolsetTest.BurnE2E/FailureTests.cs
@@ -64,7 +64,7 @@ namespace WixToolsetTest.BurnE2E
             packageB.VerifyInstalled(false);
         }
 
-        [Fact(Skip = "https://github.com/wixtoolset/issues/issues/5750")]
+        [Fact]
         public void CanCancelExecuteWhileCaching()
         {
             var packageA = this.CreatePackageInstaller("PackageA");