diff --git a/src/file.c b/src/file.c
index c68c5fc..165bc9f 100644
--- a/src/file.c
+++ b/src/file.c
@@ -131,7 +131,7 @@ void file_write(const char *path, const StringArray *lines) {
 }
 
 void file_free(File *file) {
-  if (!file->error) {
+  if (!file->error && file->content != NULL) {
     free(file->content);
   }
 }
diff --git a/src/project.c b/src/project.c
index 91961b1..4eda19a 100644
--- a/src/project.c
+++ b/src/project.c
@@ -104,6 +104,12 @@ void project_init(Project *project, const char *project_path,
 
   project->sub_counts.length = project->frag_count;
 
+  for (unsigned int i = 0; i < project->frag_count; i++) {
+    for (unsigned int j = 0; j < MAX_SUB_FILE + 1; j++) {
+      project->fragment_shaders[i][j].content = NULL;
+    }
+  }
+
   for (unsigned int i = 0; i < project->frag_count; i++) {
     project->sub_counts.values[i] = 0;
     if (!read_fragment_shader_file(project, frag_prefix, i)) {
@@ -138,7 +144,9 @@ void project_reload(Project *project, void (*reload_callback)(unsigned int)) {
 
 void project_free(Project *project) {
   for (unsigned int i = 0; i < project->frag_count; i++) {
-    file_free(&project->fragment_shaders[i][0]);
+    for (unsigned int j = 0; j < MAX_SUB_FILE + 1; j++) {
+      file_free(&project->fragment_shaders[i][j]);
+    }
   }
 
   config_file_free(&project->config);