diff --git a/src/game/level_update.c b/src/game/level_update.c
index 630311b72..dad9e42c0 100644
--- a/src/game/level_update.c
+++ b/src/game/level_update.c
@@ -1250,14 +1250,6 @@ s32 update_level(void) {
 }
 
 s32 init_level(void) {
-    // reset cap flags
-    if (save_file_exists(gCurrSaveFileNum - 1)) {
-        save_file_clear_flags(SAVE_FLAG_CAP_ON_GROUND);
-        save_file_clear_flags(SAVE_FLAG_CAP_ON_KLEPTO);
-        save_file_clear_flags(SAVE_FLAG_CAP_ON_UKIKI);
-        save_file_clear_flags(SAVE_FLAG_CAP_ON_MR_BLIZZARD);
-    }
-
     reset_dialog_render_state();
 
     s32 val4 = 0;
diff --git a/src/game/mario.c b/src/game/mario.c
index e8bcc175d..7fef51e21 100644
--- a/src/game/mario.c
+++ b/src/game/mario.c
@@ -2051,11 +2051,12 @@ static void init_single_mario(struct MarioState* m) {
 
     m->invincTimer = 0;
 
-    if (save_file_get_flags() & (SAVE_FLAG_CAP_ON_GROUND | SAVE_FLAG_CAP_ON_KLEPTO | SAVE_FLAG_CAP_ON_UKIKI | SAVE_FLAG_CAP_ON_MR_BLIZZARD)) {
+    // always put the cap on head
+    /*if (save_file_get_flags() & (SAVE_FLAG_CAP_ON_GROUND | SAVE_FLAG_CAP_ON_KLEPTO | SAVE_FLAG_CAP_ON_UKIKI | SAVE_FLAG_CAP_ON_MR_BLIZZARD)) {
         m->flags = 0;
-    } else {
+    } else {*/
         m->flags = (MARIO_CAP_ON_HEAD | MARIO_NORMAL_CAP);
-    }
+    //}
 
     m->forwardVel = 0.0f;
     m->squishTimer = 0;
diff --git a/src/game/save_file.c b/src/game/save_file.c
index 788766539..1952624b9 100644
--- a/src/game/save_file.c
+++ b/src/game/save_file.c
@@ -603,6 +603,10 @@ s32 save_file_get_total_star_count(s32 fileIndex, s32 minCourse, s32 maxCourse)
 }
 
 void save_file_set_flags(u32 flags) {
+    // prevent saving any flag that would make the player hatless on level transition
+    flags &= ~(SAVE_FLAG_CAP_ON_GROUND | SAVE_FLAG_CAP_ON_KLEPTO | SAVE_FLAG_CAP_ON_MR_BLIZZARD | SAVE_FLAG_CAP_ON_UKIKI);
+    if (flags == 0) { return; }
+
     gSaveBuffer.files[gCurrSaveFileNum - 1][0].flags |= (flags | SAVE_FLAG_FILE_EXISTS);
     gSaveFileModified = TRUE;
     network_send_save_set_flag(gCurrSaveFileNum - 1, 0, 0, (flags | SAVE_FLAG_FILE_EXISTS));