diff --git a/keyboard/ergodox_ez/keymaps/osx_de_experimental/keymap.c b/keyboard/ergodox_ez/keymaps/osx_de_experimental/keymap.c
index 5b8fd28a714..3974dacf65e 100644
--- a/keyboard/ergodox_ez/keymaps/osx_de_experimental/keymap.c
+++ b/keyboard/ergodox_ez/keymaps/osx_de_experimental/keymap.c
@@ -22,17 +22,17 @@
 #define NUMB 4
 #define EGOS 5
 
-#define M_TOGGLE_5 0
-#define M_DE_OSX_PLUS_CTRLALT 1
-#define SM_KISS 2
-#define SM_FROWN 3
-#define SM_CRY 4
-#define SM_SMILE 5
-#define SM_SMIRK 6
-#define M_LGUI_SHFT 7
-#define SM_HEART 8
-#define SM_LAUGH 9
-#define M_CTL_SFT_HASH 10
+#define SMLY_TOG_QUOT 0
+#define M_TOGGLE_5 1
+#define M_DE_OSX_PLUS_CTRLALT 2
+#define SM_KISS 3
+#define SM_FROWN 4
+#define SM_CRY 5
+#define SM_SMILE 6
+#define SM_SMIRK 7
+#define M_LGUI_SHFT 8
+#define SM_HEART 9
+#define SM_LAUGH 10
 #define SM_SAD 11
 #define M_DE_OSX_CIRC_CTRLCMD 12
 #define M_MEH_SH_ACUT 13
@@ -45,7 +45,7 @@ const uint16_t PROGMEM keymaps[][MATRIX_ROWS][MATRIX_COLS] = {
     KC_TAB, DE_OSX_Q, DE_OSX_W, DE_OSX_E, DE_OSX_R, DE_OSX_T, KC_LGUI, 
     KC_LALT, DE_OSX_A, DE_OSX_S, DE_OSX_D, DE_OSX_F, DE_OSX_G, 
     KC_LSFT, CTL_T(DE_OSX_Y), DE_OSX_X, DE_OSX_C, DE_OSX_V, DE_OSX_B, KC_LALT, 
-                  LT(SYMB,DE_OSX_LESS), M(M_DE_OSX_CIRC_CTRLCMD), M(M_DE_OSX_PLUS_CTRLALT), LSFT(KC_LCTRL), LT(SMLY,DE_OSX_QUOT), 
+                  LT(SYMB,DE_OSX_LESS), M(M_DE_OSX_CIRC_CTRLCMD), M(M_DE_OSX_PLUS_CTRLALT), LSFT(KC_LCTRL), M(SMLY_TOG_QUOT), 
                                               KC_HOME, KC_END, 
                                                      KC_PGUP, 
                                        KC_BSPC, KC_DEL, KC_PGDN, 
@@ -163,6 +163,23 @@ const macro_t *action_get_macro(keyrecord_t *record, uint8_t id, uint8_t opt)
 {
 static uint16_t start;
 switch(id) {
+case SMLY_TOG_QUOT:
+//Macro: SMLY_TOG_QUOT//-----------------------
+if (record->event.pressed) {
+			start = timer_read();
+           layer_state ^= (1<<SMLY);
+           layer_state &= (1<<SMLY);
+			return MACRO_NONE; 		} else {
+           layer_state ^= (1<<SMLY);
+           layer_state &= (1<<SMLY);
+			if (timer_elapsed(start) >150) {
+				return MACRO_NONE;
+			} else {
+				return MACRO(D(LSFT),T(BSLS),U(LSFT),END);
+			}
+		}
+
+break;
 case M_TOGGLE_5:
 //Macro: M_TOGGLE_5//-----------------------
  if (record->event.pressed){
@@ -225,7 +242,7 @@ case M_LGUI_SHFT:
 if (record->event.pressed){
 			return MACRO(D(LGUI),D(LSFT),END);
 		}else{
-			return MACRO(U(LGUI),U(LSFT),U(LGUI),U(LSFT),U(LGUI),U(LSFT),U(LGUI),U(LSFT),U(LGUI),U(LSFT),U(LGUI),U(LSFT),U(LGUI),U(LSFT),U(LGUI),U(LSFT),U(LGUI),U(LSFT),U(LGUI),U(LSFT),U(LGUI),U(LSFT),END);
+			return MACRO(U(LGUI),U(LSFT),U(LGUI),U(LSFT),U(LGUI),U(LSFT),U(LGUI),U(LSFT),U(LGUI),U(LSFT),U(LGUI),U(LSFT),U(LGUI),U(LSFT),U(LGUI),U(LSFT),U(LGUI),U(LSFT),U(LGUI),U(LSFT),U(LGUI),U(LSFT),U(LGUI),U(LSFT),U(LGUI),U(LSFT),END);
 		}
 
 break;
@@ -242,20 +259,6 @@ if (record->event.pressed) {
 			return MACRO(D(LSFT),T(DOT),U(LSFT),T(SLSH),D(LSFT),T(D),U(LSFT),END);
 		}
 
-break;
-case M_CTL_SFT_HASH:
-//Macro: M_CTL_SFT_HASH//-----------------------
-if (record->event.pressed) {
-			start = timer_read();
-			return MACRO(D(LCTRL),D(LSFT),END);
-		} else {
-			if (timer_elapsed(start) >150) {
-				return MACRO(U(LCTRL),U(LSFT),END);
-			} else {
-				return MACRO(U(LCTRL),U(LSFT),T(BSLS),END);
-			}
-		}
-
 break;
 case SM_SAD:
 //Macro: SM_SAD//-----------------------
@@ -322,13 +325,8 @@ switch (layer) {
         ergodox_right_led_2_on();
         
     break;
-    case SMLY:
-        
-        
-        ergodox_right_led_3_on();
-    break;
     case NUMB:
-        ergodox_right_led_1_on();
+        
         
         ergodox_right_led_3_on();
     break;
diff --git a/keyboard/ergodox_ez/keymaps/osx_de_experimental/osx_de_experimental_highres.png b/keyboard/ergodox_ez/keymaps/osx_de_experimental/osx_de_experimental_highres.png
index b1e9e763ea1..7fe2bb19d99 100644
Binary files a/keyboard/ergodox_ez/keymaps/osx_de_experimental/osx_de_experimental_highres.png and b/keyboard/ergodox_ez/keymaps/osx_de_experimental/osx_de_experimental_highres.png differ