diff --git a/keyboards/massdrop/alt/keymaps/default/keymap.c b/keyboards/massdrop/alt/keymaps/default/keymap.c
index 3f0b84e387..9d8387bb72 100644
--- a/keyboards/massdrop/alt/keymaps/default/keymap.c
+++ b/keyboards/massdrop/alt/keymaps/default/keymap.c
@@ -19,6 +19,7 @@ enum alt_keycodes {
     DBG_MTRX,           //DEBUG Toggle Matrix Prints
     DBG_KBD,            //DEBUG Toggle Keyboard Prints
     DBG_MOU,            //DEBUG Toggle Mouse Prints
+    MD_BOOT,            //Restart into bootloader after hold timeout
 };
 
 #define TG_NKRO MAGIC_TOGGLE_NKRO //Toggle 6KRO / NKRO mode
@@ -37,7 +38,7 @@ const uint16_t PROGMEM keymaps[][MATRIX_ROWS][MATRIX_COLS] = {
         KC_GRV,  KC_F1,   KC_F2,   KC_F3,   KC_F4,   KC_F5,   KC_F6,   KC_F7,   KC_F8,   KC_F9,   KC_F10,  KC_F11,  KC_F12,  KC_TRNS, KC_MUTE, \
         L_T_BR,  L_PSD,   L_BRI,   L_PSI,   KC_TRNS, KC_TRNS, KC_TRNS, U_T_AUTO,U_T_AGCR,KC_TRNS, KC_PSCR, KC_SLCK, KC_PAUS, KC_TRNS, KC_TRNS, \
         L_T_PTD, L_PTP,   L_BRD,   L_PTN,   KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS,          KC_TRNS, KC_VOLU, \
-        KC_TRNS, L_T_MD,  L_T_ONF, KC_TRNS, KC_TRNS, KC_TRNS, TG_NKRO, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS,          KC_PGUP, KC_VOLD, \
+        KC_TRNS, L_T_MD,  L_T_ONF, KC_TRNS, KC_TRNS, MD_BOOT, TG_NKRO, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS,          KC_PGUP, KC_VOLD, \
         KC_TRNS, KC_TRNS, KC_TRNS,                            KC_TRNS,                            KC_TRNS, KC_TRNS, KC_HOME, KC_PGDN, KC_END  \
     ),
     /*
@@ -68,6 +69,8 @@ void matrix_scan_user(void) {
 #define MODS_ALT  (keyboard_report->mods & MOD_BIT(KC_LALT) || keyboard_report->mods & MOD_BIT(KC_RALT))
 
 bool process_record_user(uint16_t keycode, keyrecord_t *record) {
+    static uint32_t key_timer;
+
     switch (keycode) {
         case L_BRI:
             if (record->event.pressed) {
@@ -194,6 +197,15 @@ bool process_record_user(uint16_t keycode, keyrecord_t *record) {
                 CDC_print("\r\n");
             }
             return false;
+        case MD_BOOT:
+            if (record->event.pressed) {
+                key_timer = timer_read32();
+            } else {
+                if (timer_elapsed32(key_timer) >= 500) {
+                    reset_keyboard();
+                }
+            }
+            return false;
         default:
             return true; //Process all other keycodes normally
     }
diff --git a/keyboards/massdrop/alt/keymaps/mac/keymap.c b/keyboards/massdrop/alt/keymaps/mac/keymap.c
new file mode 100644
index 0000000000..a8adbd3c8d
--- /dev/null
+++ b/keyboards/massdrop/alt/keymaps/mac/keymap.c
@@ -0,0 +1,212 @@
+#include QMK_KEYBOARD_H
+
+enum alt_keycodes {
+    L_BRI = SAFE_RANGE, //LED Brightness Increase
+    L_BRD,              //LED Brightness Decrease
+    L_PTN,              //LED Pattern Select Next
+    L_PTP,              //LED Pattern Select Previous
+    L_PSI,              //LED Pattern Speed Increase
+    L_PSD,              //LED Pattern Speed Decrease
+    L_T_MD,             //LED Toggle Mode
+    L_T_ONF,            //LED Toggle On / Off
+    L_ON,               //LED On
+    L_OFF,              //LED Off
+    L_T_BR,             //LED Toggle Breath Effect
+    L_T_PTD,            //LED Toggle Scrolling Pattern Direction
+    U_T_AUTO,           //USB Extra Port Toggle Auto Detect / Always Active
+    U_T_AGCR,           //USB Toggle Automatic GCR control
+    DBG_TOG,            //DEBUG Toggle On / Off
+    DBG_MTRX,           //DEBUG Toggle Matrix Prints
+    DBG_KBD,            //DEBUG Toggle Keyboard Prints
+    DBG_MOU,            //DEBUG Toggle Mouse Prints
+    MD_BOOT,            //Restart into bootloader after hold timeout
+};
+
+#define TG_NKRO MAGIC_TOGGLE_NKRO //Toggle 6KRO / NKRO mode
+
+keymap_config_t keymap_config;
+
+const uint16_t PROGMEM keymaps[][MATRIX_ROWS][MATRIX_COLS] = {
+    [0] = LAYOUT(
+        KC_ESC,  KC_1,    KC_2,    KC_3,    KC_4,    KC_5,    KC_6,    KC_7,    KC_8,    KC_9,    KC_0,    KC_MINS, KC_EQL,  KC_BSPC, KC_DEL,  \
+        KC_TAB,  KC_Q,    KC_W,    KC_E,    KC_R,    KC_T,    KC_Y,    KC_U,    KC_I,    KC_O,    KC_P,    KC_LBRC, KC_RBRC, KC_BSLS, KC_HOME, \
+        KC_CAPS, KC_A,    KC_S,    KC_D,    KC_F,    KC_G,    KC_H,    KC_J,    KC_K,    KC_L,    KC_SCLN, KC_QUOT,          KC_ENT,  KC_PGUP, \
+        KC_LSFT, KC_Z,    KC_X,    KC_C,    KC_V,    KC_B,    KC_N,    KC_M,    KC_COMM, KC_DOT,  KC_SLSH, KC_RSFT,          KC_UP,   KC_PGDN, \
+        KC_LCTL, KC_LALT, KC_LGUI,                            KC_SPC,                             KC_RGUI, MO(1),   KC_LEFT, KC_DOWN, KC_RGHT  \
+    ),
+    [1] = LAYOUT(
+        KC_GRV,  KC_F1,   KC_F2,   KC_F3,   KC_F4,   KC_F5,   KC_F6,   KC_F7,   KC_F8,   KC_F9,   KC_F10,  KC_F11,  KC_F12,  KC_TRNS, KC_MUTE, \
+        L_T_BR,  L_PSD,   L_BRI,   L_PSI,   KC_TRNS, KC_TRNS, KC_TRNS, U_T_AUTO,U_T_AGCR,KC_TRNS, KC_PSCR, KC_SLCK, KC_PAUS, KC_TRNS, KC_TRNS, \
+        L_T_PTD, L_PTP,   L_BRD,   L_PTN,   KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS,          KC_TRNS, KC_VOLU, \
+        KC_TRNS, L_T_MD,  L_T_ONF, KC_TRNS, KC_TRNS, MD_BOOT, TG_NKRO, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS,          KC_PGUP, KC_VOLD, \
+        KC_TRNS, KC_TRNS, KC_TRNS,                            KC_TRNS,                            KC_TRNS, KC_TRNS, KC_HOME, KC_PGDN, KC_END  \
+    ),
+    /*
+    [X] = LAYOUT(
+        KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, \
+        KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, \
+        KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS,          KC_TRNS, KC_TRNS, \
+        KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS,          KC_TRNS, KC_TRNS, \
+        KC_TRNS, KC_TRNS, KC_TRNS,                            KC_TRNS,                            KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS  \
+    ),
+    */
+};
+
+const uint16_t PROGMEM fn_actions[] = {
+
+};
+
+// Runs just one time when the keyboard initializes.
+void matrix_init_user(void) {
+};
+
+// Runs constantly in the background, in a loop.
+void matrix_scan_user(void) {
+};
+
+#define MODS_SHIFT  (keyboard_report->mods & MOD_BIT(KC_LSHIFT) || keyboard_report->mods & MOD_BIT(KC_RSHIFT))
+#define MODS_CTRL  (keyboard_report->mods & MOD_BIT(KC_LCTL) || keyboard_report->mods & MOD_BIT(KC_RCTRL))
+#define MODS_ALT  (keyboard_report->mods & MOD_BIT(KC_LALT) || keyboard_report->mods & MOD_BIT(KC_RALT))
+
+bool process_record_user(uint16_t keycode, keyrecord_t *record) {
+    static uint32_t key_timer;
+
+    switch (keycode) {
+        case L_BRI:
+            if (record->event.pressed) {
+                if (LED_GCR_STEP > LED_GCR_MAX - gcr_desired) gcr_desired = LED_GCR_MAX;
+                else gcr_desired += LED_GCR_STEP;
+                if (led_animation_breathing) gcr_breathe = gcr_desired;
+            }
+            return false;
+        case L_BRD:
+            if (record->event.pressed) {
+                if (LED_GCR_STEP > gcr_desired) gcr_desired = 0;
+                else gcr_desired -= LED_GCR_STEP;
+                if (led_animation_breathing) gcr_breathe = gcr_desired;
+            }
+            return false;
+        case L_PTN:
+            if (record->event.pressed) {
+                if (led_animation_id == led_setups_count - 1) led_animation_id = 0;
+                else led_animation_id++;
+            }
+            return false;
+        case L_PTP:
+            if (record->event.pressed) {
+                if (led_animation_id == 0) led_animation_id = led_setups_count - 1;
+                else led_animation_id--;
+            }
+            return false;
+        case L_PSI:
+            if (record->event.pressed) {
+                led_animation_speed += ANIMATION_SPEED_STEP;
+            }
+            return false;
+        case L_PSD:
+            if (record->event.pressed) {
+                led_animation_speed -= ANIMATION_SPEED_STEP;
+                if (led_animation_speed < 0) led_animation_speed = 0;
+            }
+            return false;
+        case L_T_MD:
+            if (record->event.pressed) {
+                led_lighting_mode++;
+                if (led_lighting_mode > LED_MODE_MAX_INDEX) led_lighting_mode = LED_MODE_NORMAL;
+            }
+            return false;
+        case L_T_ONF:
+            if (record->event.pressed) {
+                led_enabled = !led_enabled;
+                I2C3733_Control_Set(led_enabled);
+            }
+            return false;
+        case L_ON:
+            if (record->event.pressed) {
+                led_enabled = 1;
+                I2C3733_Control_Set(led_enabled);
+            }
+            return false;
+        case L_OFF:
+            if (record->event.pressed) {
+                led_enabled = 0;
+                I2C3733_Control_Set(led_enabled);
+            }
+            return false;
+        case L_T_BR:
+            if (record->event.pressed) {
+                led_animation_breathing = !led_animation_breathing;
+                if (led_animation_breathing)
+                {
+                    gcr_breathe = gcr_desired;
+                    led_animation_breathe_cur = BREATHE_MIN_STEP;
+                    breathe_dir = 1;
+                }
+            }
+            return false;
+        case L_T_PTD:
+            if (record->event.pressed) {
+                led_animation_direction = !led_animation_direction;
+            }
+            return false;
+        case U_T_AUTO:
+            if (record->event.pressed && MODS_SHIFT && MODS_CTRL) {
+                usb_extra_manual = !usb_extra_manual;
+                CDC_print("USB extra port manual mode ");
+                CDC_print(usb_extra_manual ? "enabled" : "disabled");
+                CDC_print("\r\n");
+            }
+            return false;
+        case U_T_AGCR:
+            if (record->event.pressed && MODS_SHIFT && MODS_CTRL) {
+                usb_gcr_auto = !usb_gcr_auto;
+                CDC_print("USB GCR auto mode ");
+                CDC_print(usb_gcr_auto ? "enabled" : "disabled");
+                CDC_print("\r\n");
+            }
+            return false;
+        case DBG_TOG:
+            if (record->event.pressed) {
+                debug_enable = !debug_enable;
+                CDC_print("Debug mode ");
+                CDC_print(debug_enable ? "enabled" : "disabled");
+                CDC_print("\r\n");
+            }
+            return false;
+        case DBG_MTRX:
+            if (record->event.pressed) {
+                debug_matrix = !debug_matrix;
+                CDC_print("Debug matrix ");
+                CDC_print(debug_matrix ? "enabled" : "disabled");
+                CDC_print("\r\n");
+            }
+            return false;
+        case DBG_KBD:
+            if (record->event.pressed) {
+                debug_keyboard = !debug_keyboard;
+                CDC_print("Debug keyboard ");
+                CDC_print(debug_keyboard ? "enabled" : "disabled");
+                CDC_print("\r\n");
+            }
+            return false;
+        case DBG_MOU:
+            if (record->event.pressed) {
+                debug_mouse = !debug_mouse;
+                CDC_print("Debug mouse ");
+                CDC_print(debug_mouse ? "enabled" : "disabled");
+                CDC_print("\r\n");
+            }
+            return false;
+        case MD_BOOT:
+            if (record->event.pressed) {
+                key_timer = timer_read32();
+            } else {
+                if (timer_elapsed32(key_timer) >= 500) {
+                    reset_keyboard();
+                }
+            }
+            return false;
+        default:
+            return true; //Process all other keycodes normally
+    }
+}
diff --git a/keyboards/massdrop/ctrl/keymaps/default/keymap.c b/keyboards/massdrop/ctrl/keymaps/default/keymap.c
index ac58f336e3..9bfb7fec58 100644
--- a/keyboards/massdrop/ctrl/keymaps/default/keymap.c
+++ b/keyboards/massdrop/ctrl/keymaps/default/keymap.c
@@ -19,6 +19,7 @@ enum ctrl_keycodes {
     DBG_MTRX,           //DEBUG Toggle Matrix Prints
     DBG_KBD,            //DEBUG Toggle Keyboard Prints
     DBG_MOU,            //DEBUG Toggle Mouse Prints
+    MD_BOOT,            //Restart into bootloader after hold timeout
 };
 
 #define TG_NKRO MAGIC_TOGGLE_NKRO //Toggle 6KRO / NKRO mode
@@ -39,7 +40,7 @@ const uint16_t PROGMEM keymaps[][MATRIX_ROWS][MATRIX_COLS] = {
         KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS,   KC_MPLY, KC_MSTP, KC_VOLU, \
         L_T_BR,  L_PSD,   L_BRI,   L_PSI,   KC_TRNS, KC_TRNS, KC_TRNS, U_T_AUTO,U_T_AGCR,KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS,   KC_MPRV, KC_MNXT, KC_VOLD, \
         L_T_PTD, L_PTP,   L_BRD,   L_PTN,   KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, \
-        KC_TRNS, L_T_MD,  L_T_ONF, KC_TRNS, KC_TRNS, KC_TRNS, TG_NKRO, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS,                              KC_TRNS, \
+        KC_TRNS, L_T_MD,  L_T_ONF, KC_TRNS, KC_TRNS, MD_BOOT, TG_NKRO, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS,                              KC_TRNS, \
         KC_TRNS, KC_TRNS, KC_TRNS,                  KC_TRNS,                             KC_TRNS, KC_TRNS, KC_TRNS, KC_TRNS,            KC_TRNS, KC_TRNS, KC_TRNS \
     ),
     /*
@@ -71,6 +72,8 @@ void matrix_scan_user(void) {
 #define MODS_ALT  (keyboard_report->mods & MOD_BIT(KC_LALT) || keyboard_report->mods & MOD_BIT(KC_RALT))
 
 bool process_record_user(uint16_t keycode, keyrecord_t *record) {
+    static uint32_t key_timer;
+
     switch (keycode) {
         case L_BRI:
             if (record->event.pressed) {
@@ -197,7 +200,16 @@ bool process_record_user(uint16_t keycode, keyrecord_t *record) {
                 CDC_print("\r\n");
             }
             return false;
+        case MD_BOOT:
+            if (record->event.pressed) {
+                key_timer = timer_read32();
+            } else {
+                if (timer_elapsed32(key_timer) >= 500) {
+                    reset_keyboard();
+                }
+            }
+            return false;
         default:
             return true; //Process all other keycodes normally
     }
-}
\ No newline at end of file
+}
diff --git a/keyboards/massdrop/ctrl/keymaps/mac/keymap.c b/keyboards/massdrop/ctrl/keymaps/mac/keymap.c
index 116aaa9a12..a03f891e8c 100644
--- a/keyboards/massdrop/ctrl/keymaps/mac/keymap.c
+++ b/keyboards/massdrop/ctrl/keymaps/mac/keymap.c
@@ -19,6 +19,7 @@ enum ctrl_keycodes {
     DBG_MTRX,           //DEBUG Toggle Matrix Prints
     DBG_KBD,            //DEBUG Toggle Keyboard Prints
     DBG_MOU,            //DEBUG Toggle Mouse Prints
+    MD_BOOT,            //Restart into bootloader after hold timeout
 };
 
 #define TG_NKRO MAGIC_TOGGLE_NKRO //Toggle 6KRO / NKRO mode
@@ -71,6 +72,8 @@ void matrix_scan_user(void) {
 #define MODS_ALT  (keyboard_report->mods & MOD_BIT(KC_LALT) || keyboard_report->mods & MOD_BIT(KC_RALT))
 
 bool process_record_user(uint16_t keycode, keyrecord_t *record) {
+    static uint32_t key_timer;
+
     switch (keycode) {
         case L_BRI:
             if (record->event.pressed) {
@@ -197,6 +200,15 @@ bool process_record_user(uint16_t keycode, keyrecord_t *record) {
                 CDC_print("\r\n");
             }
             return false;
+        case MD_BOOT:
+            if (record->event.pressed) {
+                key_timer = timer_read32();
+            } else {
+                if (timer_elapsed32(key_timer) >= 500) {
+                    reset_keyboard();
+                }
+            }
+            return false;
         default:
             return true; //Process all other keycodes normally
     }
diff --git a/tmk_core/common/arm_atsam/bootloader.c b/tmk_core/common/arm_atsam/bootloader.c
index 5155d9ff04..9701a62196 100644
--- a/tmk_core/common/arm_atsam/bootloader.c
+++ b/tmk_core/common/arm_atsam/bootloader.c
@@ -15,5 +15,35 @@
  */
 
 #include "bootloader.h"
+#include "samd51j18a.h"
 
-void bootloader_jump(void) {}
+//Set watchdog timer to reset. Directs the bootloader to stay in programming mode.
+void bootloader_jump(void)
+{
+    //Keyboards released with certain bootloader can not enter bootloader from app until workaround is created
+    uint8_t ver_no_jump[] = "v2.18Jun 22 2018 17:28:08";
+    uint8_t *ver_check = ver_no_jump;
+    uint8_t *boot_check = (uint8_t *)0x21A0;
+    while (*ver_check && *boot_check == *ver_check)
+    {
+        ver_check++;
+        boot_check++;
+    }
+    if (!*ver_check)
+    {
+        //Version match
+        //Software workaround would go here
+        return; //No software restart method implemented... must use hardware reset button
+    }
+
+    WDT->CTRLA.bit.ENABLE = 0;
+    while (WDT->SYNCBUSY.bit.ENABLE) {}
+    while (WDT->CTRLA.bit.ENABLE) {}
+    WDT->CONFIG.bit.WINDOW = 0;
+    WDT->CONFIG.bit.PER = 0;
+    WDT->EWCTRL.bit.EWOFFSET = 0;
+    WDT->CTRLA.bit.ENABLE = 1;
+    while (WDT->SYNCBUSY.bit.ENABLE) {}
+    while (!WDT->CTRLA.bit.ENABLE) {}
+    while (1) {} //Wait on timeout
+}
diff --git a/tmk_core/protocol/arm_atsam/d51_util.c b/tmk_core/protocol/arm_atsam/d51_util.c
index 91b58757cf..bb63a94814 100644
--- a/tmk_core/protocol/arm_atsam/d51_util.c
+++ b/tmk_core/protocol/arm_atsam/d51_util.c
@@ -41,8 +41,8 @@ void m15_print(uint32_t x)
 
 //Display unsigned 32-bit number through debug led
 //Read as follows: 1230 = [*]  [* *]  [* * *]  [**]  (note zero is fast double flash)
-#define DLED_ONTIME 600000
-#define DLED_PAUSE 1000000
+#define DLED_ONTIME 1000000
+#define DLED_PAUSE 1500000
 volatile uint32_t w;
 void dled_print(uint32_t x, uint8_t long_pause)
 {
diff --git a/tmk_core/protocol/arm_atsam/main_arm_atsam.c b/tmk_core/protocol/arm_atsam/main_arm_atsam.c
index e9514730ec..8cc7767038 100644
--- a/tmk_core/protocol/arm_atsam/main_arm_atsam.c
+++ b/tmk_core/protocol/arm_atsam/main_arm_atsam.c
@@ -225,6 +225,8 @@ int main(void)
     {
         if (usb_state == USB_STATE_POWERDOWN)
         {
+            uint32_t timer_led = timer_read32();
+
             led_on;
             if (led_enabled)
             {
@@ -233,7 +235,10 @@ int main(void)
                     I2C3733_Control_Set(0);
                 }
             }
-            while (usb_state == USB_STATE_POWERDOWN) {}
+            while (usb_state == USB_STATE_POWERDOWN)
+            {
+                if (timer_read32() - timer_led > 1000) led_off; //Good to indicate went to sleep, but only for a second
+            }
             if (led_enabled)
             {
                 for (drvid=0;drvid<ISSI3733_DRIVER_COUNT;drvid++)