diff --git a/internal/workflow/activities/cleanup.go b/internal/workflow/activities/cleanup.go
index de8cf7c7..9c8ff4ac 100644
--- a/internal/workflow/activities/cleanup.go
+++ b/internal/workflow/activities/cleanup.go
@@ -14,16 +14,18 @@ func NewCleanUpActivity() *CleanUpActivity {
 }
 
 type CleanUpActivityParams struct {
-	FullPath string
+	Paths []string
 }
 
 func (a *CleanUpActivity) Execute(ctx context.Context, params *CleanUpActivityParams) error {
-	if params == nil || params.FullPath == "" {
-		return fmt.Errorf("error processing parameters: missing or empty")
+	if params == nil {
+		return fmt.Errorf("error processing parameters: missing")
 	}
 
-	if err := os.RemoveAll(params.FullPath); err != nil {
-		return fmt.Errorf("error removing transfer directory: %v", err)
+	for _, p := range params.Paths {
+		if err := os.RemoveAll(p); err != nil {
+			return fmt.Errorf("error removing path: %v", err)
+		}
 	}
 
 	return nil
diff --git a/internal/workflow/processing.go b/internal/workflow/processing.go
index ffe3d7a9..f0b5aa05 100644
--- a/internal/workflow/processing.go
+++ b/internal/workflow/processing.go
@@ -457,8 +457,8 @@ func (w *ProcessingWorkflow) SessionHandler(sessCtx temporalsdk_workflow.Context
 		if tinfo.WatcherName != "" && !tinfo.IsDir {
 			// TODO: even if TempFile is defined, we should confirm that the file is
 			// locally available in disk, just in case we're in the context of a
-			// session retry where a different working is doing the work. In that
-			// case, the activity whould be executed again.
+			// session retry where a different worker is doing the work. In that
+			// case, the activity would be executed again.
 			if tinfo.TempFile == "" {
 				activityOpts := withActivityOptsForLongLivedRequest(sessCtx)
 				err := temporalsdk_workflow.ExecuteActivity(
@@ -475,6 +475,9 @@ func (w *ProcessingWorkflow) SessionHandler(sessCtx temporalsdk_workflow.Context
 		}
 	}
 
+	// Both of these values relate to temporary files on Enduro's processing Dir that never get cleaned-up.
+	var tempBlob, tempExtracted string
+	tempBlob = tinfo.TempFile
 	// Extract downloaded archive file contents.
 	{
 		if tinfo.WatcherName != "" && !tinfo.IsDir {
@@ -497,6 +500,7 @@ func (w *ProcessingWorkflow) SessionHandler(sessCtx temporalsdk_workflow.Context
 				tinfo.TempFile = result.ExtractPath
 				tinfo.StripTopLevelDir = false
 				tinfo.IsDir = true
+				tempExtracted = result.ExtractPath
 			}
 		}
 	}
@@ -523,11 +527,25 @@ func (w *ProcessingWorkflow) SessionHandler(sessCtx temporalsdk_workflow.Context
 
 	// Delete local temporary files.
 	defer func() {
+		// We need disconnected context here because when session gets released the cleanup
+		// activities get scheduled and then immediately canceled.
+		var filesToRemove []string
 		if tinfo.Bundle.FullPathBeforeStrip != "" {
-			activityOpts := withActivityOptsForLocalAction(sessCtx)
-			_ = temporalsdk_workflow.ExecuteActivity(activityOpts, activities.CleanUpActivityName, &activities.CleanUpActivityParams{
-				FullPath: tinfo.Bundle.FullPathBeforeStrip,
-			}).Get(activityOpts, nil)
+			filesToRemove = append(filesToRemove, tinfo.Bundle.FullPathBeforeStrip)
+		}
+		if tempBlob != "" {
+			filesToRemove = append(filesToRemove, tempBlob)
+		}
+		if tempExtracted != "" {
+			filesToRemove = append(filesToRemove, tempExtracted)
+		}
+		cleanUpCtx, cancel := temporalsdk_workflow.NewDisconnectedContext(sessCtx)
+		defer cancel()
+		activityOpts := withActivityOptsForLocalAction(cleanUpCtx)
+		if err := temporalsdk_workflow.ExecuteActivity(activityOpts, activities.CleanUpActivityName, &activities.CleanUpActivityParams{
+			Paths: filesToRemove,
+		}).Get(activityOpts, nil); err != nil {
+			w.logger.Error(err, "failed to clean up temporary files", "path", tempExtracted)
 		}
 	}()