diff --git a/devices/ble_hci/common-hal/_bleio/__init__.c b/devices/ble_hci/common-hal/_bleio/__init__.c
index d8a222ecfe..a22bcfb082 100644
--- a/devices/ble_hci/common-hal/_bleio/__init__.c
+++ b/devices/ble_hci/common-hal/_bleio/__init__.c
@@ -57,6 +57,11 @@ bool vm_used_ble;
 //     }
 // }
 
+void bleio_user_reset() {
+    // HCI doesn't support the BLE workflow so just do a full reset.
+    bleio_reset();
+}
+
 // Turn off BLE on a reset or reload.
 void bleio_reset() {
     // Create a UUID object for all CCCD's.
diff --git a/main.c b/main.c
index a3cc01d165..17fe8167f2 100644
--- a/main.c
+++ b/main.c
@@ -277,10 +277,10 @@ STATIC void cleanup_after_vm(supervisor_allocation *heap, mp_obj_t exception) {
     memorymonitor_reset();
     #endif
 
-    filesystem_flush();
-    stop_mp();
-    free_memory(heap);
-    supervisor_move_memory();
+    // Disable user related BLE state that uses the micropython heap.
+    #if CIRCUITPY_BLEIO
+    bleio_user_reset();
+    #endif
 
     #if CIRCUITPY_CANIO
     common_hal_canio_reset();
@@ -297,6 +297,12 @@ STATIC void cleanup_after_vm(supervisor_allocation *heap, mp_obj_t exception) {
     #endif
     reset_port();
     reset_board();
+
+    // Free the heap last because other modules may reference heap memory and need to shut down.
+    filesystem_flush();
+    stop_mp();
+    free_memory(heap);
+    supervisor_move_memory();
 }
 
 STATIC void print_code_py_status_message(safe_mode_t safe_mode) {
@@ -645,6 +651,12 @@ STATIC bool run_code_py(safe_mode_t safe_mode, bool first_run, bool *simulate_re
 
     // Done waiting, start the board back up.
 
+    // We delay resetting BLE until after the wait in case we're transferring
+    // more files over.
+    #if CIRCUITPY_BLEIO
+    bleio_reset();
+    #endif
+
     // free code allocation if unused
     if ((next_code_options & next_code_stickiness_situation) == 0) {
         free_memory(next_code_allocation);
@@ -888,6 +900,7 @@ int __attribute__((used)) main(void) {
     serial_init();
 
     #if CIRCUITPY_BLEIO
+    bleio_reset();
     supervisor_bluetooth_enable_workflow();
     supervisor_start_bluetooth();
     #endif
diff --git a/ports/espressif/common-hal/_bleio/Adapter.c b/ports/espressif/common-hal/_bleio/Adapter.c
index d72f9dbf02..943e44e7cd 100644
--- a/ports/espressif/common-hal/_bleio/Adapter.c
+++ b/ports/espressif/common-hal/_bleio/Adapter.c
@@ -574,6 +574,9 @@ void common_hal_bleio_adapter_start_advertising(bleio_adapter_obj_t *self, bool
 }
 
 void common_hal_bleio_adapter_stop_advertising(bleio_adapter_obj_t *self) {
+    if (!common_hal_bleio_adapter_get_advertising(self)) {
+        return;
+    }
     int err_code = ble_gap_ext_adv_stop(0);
     self->user_advertising = false;
 
diff --git a/ports/espressif/common-hal/_bleio/__init__.c b/ports/espressif/common-hal/_bleio/__init__.c
index 7eba47d6a1..e25f9b0ef1 100644
--- a/ports/espressif/common-hal/_bleio/__init__.c
+++ b/ports/espressif/common-hal/_bleio/__init__.c
@@ -42,6 +42,17 @@
 // #include "common-hal/_bleio/bonding.h"
 #include "common-hal/_bleio/ble_events.h"
 
+void bleio_user_reset() {
+    // Stop any user scanning or advertising.
+    common_hal_bleio_adapter_stop_scan(&common_hal_bleio_adapter_obj);
+    common_hal_bleio_adapter_stop_advertising(&common_hal_bleio_adapter_obj);
+
+    ble_event_remove_heap_handlers();
+
+    // Maybe start advertising the BLE workflow.
+    supervisor_bluetooth_background();
+}
+
 // Turn off BLE on a reset or reload.
 void bleio_reset() {
     // Set this explicitly to save data.
diff --git a/ports/espressif/common-hal/_bleio/ble_events.c b/ports/espressif/common-hal/_bleio/ble_events.c
index 1ccd72cb61..a072a80623 100644
--- a/ports/espressif/common-hal/_bleio/ble_events.c
+++ b/ports/espressif/common-hal/_bleio/ble_events.c
@@ -31,6 +31,7 @@
 #include <stdbool.h>
 #include <stdio.h>
 
+#include "py/gc.h"
 #include "py/misc.h"
 #include "py/mpstate.h"
 #include "py/runtime.h"
@@ -44,6 +45,17 @@ void ble_event_reset(void) {
     MP_STATE_VM(ble_event_handler_entries) = NULL;
 }
 
+void ble_event_remove_heap_handlers(void) {
+    ble_event_handler_entry_t *it = MP_STATE_VM(ble_event_handler_entries);
+    while (it != NULL) {
+        // If the param is on the heap, then delete the handler.
+        if (HEAP_PTR(it->param)) {
+            ble_event_remove_handler(it->func, it->param);
+        }
+        it = it->next;
+    }
+}
+
 void ble_event_add_handler_entry(ble_event_handler_entry_t *entry,
     ble_gap_event_fn *func, void *param) {
     ble_event_handler_entry_t *it = MP_STATE_VM(ble_event_handler_entries);
diff --git a/ports/espressif/common-hal/_bleio/ble_events.h b/ports/espressif/common-hal/_bleio/ble_events.h
index 03ff351118..cc6c9e92f7 100644
--- a/ports/espressif/common-hal/_bleio/ble_events.h
+++ b/ports/espressif/common-hal/_bleio/ble_events.h
@@ -40,6 +40,7 @@ typedef struct ble_event_handler_entry {
 } ble_event_handler_entry_t;
 
 void ble_event_reset(void);
+void ble_event_remove_heap_handlers(void);
 void ble_event_add_handler(ble_gap_event_fn *func, void *param);
 void ble_event_remove_handler(ble_gap_event_fn *func, void *param);
 
diff --git a/ports/espressif/supervisor/port.c b/ports/espressif/supervisor/port.c
index 11709eda40..bf606ad159 100644
--- a/ports/espressif/supervisor/port.c
+++ b/ports/espressif/supervisor/port.c
@@ -283,10 +283,6 @@ void reset_port(void) {
     watchdog_reset();
     #endif
 
-    #if CIRCUITPY_BLEIO
-    bleio_reset();
-    #endif
-
     #if CIRCUITPY_WIFI
     wifi_reset();
     #endif
diff --git a/ports/nrf/bluetooth/ble_drv.c b/ports/nrf/bluetooth/ble_drv.c
index f5d2f96715..cf3f9382d7 100644
--- a/ports/nrf/bluetooth/ble_drv.c
+++ b/ports/nrf/bluetooth/ble_drv.c
@@ -35,6 +35,7 @@
 #include "nrf_sdm.h"
 #include "nrf_soc.h"
 #include "nrfx_power.h"
+#include "py/gc.h"
 #include "py/misc.h"
 #include "py/mpstate.h"
 
@@ -56,6 +57,17 @@ void ble_drv_reset() {
     sd_flash_operation_status = SD_FLASH_OPERATION_DONE;
 }
 
+void ble_drv_remove_heap_handlers(void) {
+    ble_drv_evt_handler_entry_t *it = MP_STATE_VM(ble_drv_evt_handler_entries);
+    while (it != NULL) {
+        // If the param is on the heap, then delete the handler.
+        if (HEAP_PTR(it->param)) {
+            ble_drv_remove_event_handler(it->func, it->param);
+        }
+        it = it->next;
+    }
+}
+
 void ble_drv_add_event_handler_entry(ble_drv_evt_handler_entry_t *entry, ble_drv_evt_handler_t func, void *param) {
     ble_drv_evt_handler_entry_t *it = MP_STATE_VM(ble_drv_evt_handler_entries);
     while (it != NULL) {
diff --git a/ports/nrf/bluetooth/ble_drv.h b/ports/nrf/bluetooth/ble_drv.h
index e7649fceee..798e70e1fb 100644
--- a/ports/nrf/bluetooth/ble_drv.h
+++ b/ports/nrf/bluetooth/ble_drv.h
@@ -67,6 +67,7 @@ typedef struct ble_drv_evt_handler_entry {
 } ble_drv_evt_handler_entry_t;
 
 void ble_drv_reset(void);
+void ble_drv_remove_heap_handlers(void);
 void ble_drv_add_event_handler(ble_drv_evt_handler_t func, void *param);
 void ble_drv_remove_event_handler(ble_drv_evt_handler_t func, void *param);
 
diff --git a/ports/nrf/common-hal/_bleio/PacketBuffer.c b/ports/nrf/common-hal/_bleio/PacketBuffer.c
index f7d35cbdb5..38dcdd9041 100644
--- a/ports/nrf/common-hal/_bleio/PacketBuffer.c
+++ b/ports/nrf/common-hal/_bleio/PacketBuffer.c
@@ -380,9 +380,11 @@ mp_int_t common_hal_bleio_packet_buffer_write(bleio_packet_buffer_obj_t *self, c
                !mp_hal_is_interrupted()) {
             RUN_BACKGROUND_TASKS;
         }
+        if (mp_hal_is_interrupted()) {
+            return -1;
+        }
     }
-    if (self->conn_handle == BLE_CONN_HANDLE_INVALID ||
-        mp_hal_is_interrupted()) {
+    if (self->conn_handle == BLE_CONN_HANDLE_INVALID) {
         return -1;
     }
 
diff --git a/ports/nrf/common-hal/_bleio/__init__.c b/ports/nrf/common-hal/_bleio/__init__.c
index e02cf306af..1d59983896 100644
--- a/ports/nrf/common-hal/_bleio/__init__.c
+++ b/ports/nrf/common-hal/_bleio/__init__.c
@@ -94,6 +94,17 @@ void check_sec_status(uint8_t sec_status) {
     }
 }
 
+void bleio_user_reset() {
+    // Stop any user scanning or advertising.
+    common_hal_bleio_adapter_stop_scan(&common_hal_bleio_adapter_obj);
+    common_hal_bleio_adapter_stop_advertising(&common_hal_bleio_adapter_obj);
+
+    ble_drv_remove_heap_handlers();
+
+    // Maybe start advertising the BLE workflow.
+    supervisor_bluetooth_background();
+}
+
 // Turn off BLE on a reset or reload.
 void bleio_reset() {
     // Set this explicitly to save data.
diff --git a/ports/nrf/supervisor/port.c b/ports/nrf/supervisor/port.c
index 5c1139271d..0d1f71e886 100644
--- a/ports/nrf/supervisor/port.c
+++ b/ports/nrf/supervisor/port.c
@@ -246,10 +246,6 @@ void reset_port(void) {
 
     timers_reset();
 
-    #if CIRCUITPY_BLEIO
-    bleio_reset();
-    #endif
-
     #if CIRCUITPY_WATCHDOG
     watchdog_reset();
     #endif
diff --git a/py/gc.h b/py/gc.h
index ddd07fb4c0..b9036ff4ba 100644
--- a/py/gc.h
+++ b/py/gc.h
@@ -35,11 +35,16 @@
 #define WORDS_PER_BLOCK ((MICROPY_BYTES_PER_GC_BLOCK) / MP_BYTES_PER_OBJ_WORD)
 #define BYTES_PER_BLOCK (MICROPY_BYTES_PER_GC_BLOCK)
 
+#define HEAP_PTR(ptr) ( \
+    MP_STATE_MEM(gc_pool_start) != 0                     /* Not on the heap if it isn't inited */ \
+    && ptr >= (void *)MP_STATE_MEM(gc_pool_start)        /* must be above start of pool */ \
+    && ptr < (void *)MP_STATE_MEM(gc_pool_end)           /* must be below end of pool */ \
+    )
+
 // ptr should be of type void*
 #define VERIFY_PTR(ptr) ( \
     ((uintptr_t)(ptr) & (BYTES_PER_BLOCK - 1)) == 0          /* must be aligned on a block */ \
-    && ptr >= (void *)MP_STATE_MEM(gc_pool_start)        /* must be above start of pool */ \
-    && ptr < (void *)MP_STATE_MEM(gc_pool_end)           /* must be below end of pool */ \
+    && HEAP_PTR(ptr) \
     )
 
 void gc_init(void *start, void *end);
diff --git a/shared-bindings/_bleio/__init__.h b/shared-bindings/_bleio/__init__.h
index 55b527cfa5..f34df306b7 100644
--- a/shared-bindings/_bleio/__init__.h
+++ b/shared-bindings/_bleio/__init__.h
@@ -54,6 +54,11 @@ extern const mp_obj_type_t mp_type_bleio_BluetoothError;
 extern const mp_obj_type_t mp_type_bleio_RoleError;
 extern const mp_obj_type_t mp_type_bleio_SecurityError;
 
+// Resets all user created BLE state in preparation for the heap disappearing.
+// It will maintain BLE workflow and connections.
+void bleio_user_reset(void);
+
+// Completely resets the BLE stack including BLE connections.
 void bleio_reset(void);
 
 extern mp_obj_t bleio_set_adapter(mp_obj_t adapter_obj);