diff --git a/src/cli/io.c b/src/cli/io.c
index f31ddc01..5727d270 100644
--- a/src/cli/io.c
+++ b/src/cli/io.c
@@ -46,6 +46,10 @@ char* readFile(const char* path)
 
 void setRootDirectory(const char* path)
 {
+  if (rootDirectory != NULL)
+  {
+    free((void*)rootDirectory);
+  }
   rootDirectory = path;
 }
 
diff --git a/src/cli/vm.c b/src/cli/vm.c
index 3a62d0f7..a682911d 100644
--- a/src/cli/vm.c
+++ b/src/cli/vm.c
@@ -48,6 +48,7 @@ void runFile(WrenBindForeignMethodFn bindForeign, const char* path)
 
   wrenFreeVM(vm);
   free(source);
+  setRootDirectory(NULL);
 
   // Exit with an error code if the script failed.
   if (result == WREN_RESULT_COMPILE_ERROR) exit(65); // EX_DATAERR.