diff --git a/cmd/launcher/svc_windows.go b/cmd/launcher/svc_windows.go
index 5dc5bb868..712439256 100644
--- a/cmd/launcher/svc_windows.go
+++ b/cmd/launcher/svc_windows.go
@@ -55,16 +55,14 @@ func runWindowsSvc(systemSlogger *multislogger.MultiSlogger, args []string) erro
 	logger := log.NewNopLogger()
 
 	if opts.RootDirectory != "" {
+		rootDirectoryChanged := false
+		optsRootDirectory := opts.RootDirectory
 		// check for old root directories before creating DB in case we've stomped over with windows MSI install
 		updatedRootDirectory := determineRootDirectory(systemSlogger.Logger, opts)
 		if updatedRootDirectory != opts.RootDirectory {
-			systemSlogger.Log(context.TODO(), slog.LevelInfo,
-				"old root directory contents detected, overriding opts.RootDirectory",
-				"opts_root_directory", opts.RootDirectory,
-				"updated_root_directory", updatedRootDirectory,
-			)
-
 			opts.RootDirectory = updatedRootDirectory
+			// cache that we did this so we can log to debug.json when set up below
+			rootDirectoryChanged = true
 		}
 
 		// Create a local logger. This logs to a known path, and aims to help diagnostics
@@ -80,6 +78,14 @@ func runWindowsSvc(systemSlogger *multislogger.MultiSlogger, args []string) erro
 
 		// also write system logs to localSloggerHandler
 		systemSlogger.AddHandler(localSloggerHandler)
+
+		if rootDirectoryChanged {
+			localSlogger.Log(context.TODO(), slog.LevelInfo,
+				"old root directory contents detected, overriding opts.RootDirectory",
+				"opts_root_directory", optsRootDirectory,
+				"updated_root_directory", updatedRootDirectory,
+			)
+		}
 	}
 
 	// Confirm that service configuration is up-to-date