diff --git a/.gitmodules b/.gitmodules
index b0a12ffe205e0..510991a5a391e 100644
--- a/.gitmodules
+++ b/.gitmodules
@@ -143,7 +143,7 @@
 [submodule "ports/espressif/esp-idf"]
 	path = ports/espressif/esp-idf
 	url = https://github.com/adafruit/esp-idf.git
-	branch = circuitpython-v5.1.3
+	branch = circuitpython-v5.2.2
 [submodule "ports/espressif/esp-protocols"]
 	path = ports/espressif/esp-protocols
 	url = https://github.com/espressif/esp-protocols.git
diff --git a/devices/ble_hci/common-hal/_bleio/__init__.c b/devices/ble_hci/common-hal/_bleio/__init__.c
index 6cdc37f435c3b..9663e70699807 100644
--- a/devices/ble_hci/common-hal/_bleio/__init__.c
+++ b/devices/ble_hci/common-hal/_bleio/__init__.c
@@ -37,6 +37,9 @@ bool vm_used_ble;
 //     }
 // }
 
+void common_hal_bleio_init(void) {
+}
+
 void bleio_user_reset() {
     // HCI doesn't support the BLE workflow so just do a full reset.
     bleio_reset();
diff --git a/locale/circuitpython.pot b/locale/circuitpython.pot
index 0e3878bc3d8c9..feb9457088c67 100644
--- a/locale/circuitpython.pot
+++ b/locale/circuitpython.pot
@@ -113,7 +113,7 @@ msgstr ""
 #: ports/raspberrypi/common-hal/rp2pio/StateMachine.c
 #: ports/raspberrypi/common-hal/usb_host/Port.c
 #: shared-bindings/digitalio/DigitalInOut.c
-#: shared-bindings/microcontroller/Pin.c
+#: shared-bindings/microcontroller/Pin.c shared-module/max3421e/Max3421E.c
 msgid "%q in use"
 msgstr ""
 
@@ -1114,10 +1114,12 @@ msgstr ""
 msgid "Input/output error"
 msgstr ""
 
+#: ports/espressif/common-hal/_bleio/__init__.c
 #: ports/nordic/common-hal/_bleio/__init__.c
 msgid "Insufficient authentication"
 msgstr ""
 
+#: ports/espressif/common-hal/_bleio/__init__.c
 #: ports/nordic/common-hal/_bleio/__init__.c
 msgid "Insufficient encryption"
 msgstr ""
@@ -1154,6 +1156,7 @@ msgstr ""
 #: ports/atmel-samd/common-hal/alarm/pin/PinAlarm.c
 #: ports/atmel-samd/common-hal/countio/Counter.c
 #: ports/atmel-samd/common-hal/frequencyio/FrequencyIn.c
+#: ports/atmel-samd/common-hal/max3421e/Max3421E.c
 #: ports/atmel-samd/common-hal/ps2io/Ps2.c
 #: ports/atmel-samd/common-hal/pulseio/PulseIn.c
 #: ports/atmel-samd/common-hal/rotaryio/IncrementalEncoder.c
@@ -1285,6 +1288,10 @@ msgstr ""
 msgid "MAC address was invalid"
 msgstr ""
 
+#: ports/espressif/common-hal/_bleio/Characteristic.c
+msgid "MITM security not supported"
+msgstr ""
+
 #: shared-bindings/is31fl3741/IS31FL3741.c
 msgid "Mapping must be a tuple"
 msgstr ""
@@ -2139,6 +2146,7 @@ msgstr ""
 msgid "Unknown BLE error: %d"
 msgstr ""
 
+#: ports/espressif/common-hal/max3421e/Max3421E.c
 #: ports/raspberrypi/common-hal/wifi/__init__.c
 #, c-format
 msgid "Unknown error code %d"
@@ -3810,7 +3818,7 @@ msgstr ""
 msgid "pop from empty %q"
 msgstr ""
 
-#: shared-bindings/socketpool/Socket.c shared-bindings/ssl/SSLSocket.c
+#: shared-bindings/socketpool/Socket.c
 msgid "port must be >= 0"
 msgstr ""
 
diff --git a/main.c b/main.c
index 3988bc9e7dc0e..a463fbe4afe6b 100644
--- a/main.c
+++ b/main.c
@@ -1006,10 +1006,6 @@ int __attribute__((used)) main(void) {
     supervisor_status_bar_init();
     #endif
 
-    #if CIRCUITPY_BLEIO
-    // Early init so that a reset press can cause BLE public advertising.
-    supervisor_bluetooth_init();
-    #endif
 
     #if !INTERNAL_FLASH_FILESYSTEM
     // Set up anything that might need to get done before we try to use SPI flash
@@ -1027,6 +1023,12 @@ int __attribute__((used)) main(void) {
         set_safe_mode(SAFE_MODE_NO_CIRCUITPY);
     }
 
+    #if CIRCUITPY_BLEIO
+    // Early init so that a reset press can cause BLE public advertising. Need the filesystem to
+    // read settings.toml.
+    supervisor_bluetooth_init();
+    #endif
+
     #if CIRCUITPY_ALARM
     // Record which alarm woke us up, if any.
     // common_hal_alarm_record_wake_alarm() should return a static, non-heap object
diff --git a/ports/espressif/Makefile b/ports/espressif/Makefile
index 17641f683a79a..629376add113e 100644
--- a/ports/espressif/Makefile
+++ b/ports/espressif/Makefile
@@ -229,11 +229,13 @@ LDFLAGS += \
 	-Tesp32c6.rom.newlib.ld \
 	-Tesp32c6.rom.coexist.ld \
 	-Tesp32c6.rom.heap.ld \
+	-Tesp32c6.rom.systimer.ld \
 	-Tesp32c6.rom.wdt.ld
 else ifeq ($(IDF_TARGET),esp32h2)
 LDFLAGS += \
 	-Tesp32h2.rom.heap.ld \
 	-Tesp32h2.rom.newlib.ld \
+	-Tesp32h2.rom.systimer.ld \
 	-Tesp32h2.rom.wdt.ld
 else ifeq ($(IDF_TARGET),esp32s2)
 LDFLAGS += \
diff --git a/ports/espressif/boards/adafruit_feather_esp32c6_4mbflash_nopsram/mpconfigboard.h b/ports/espressif/boards/adafruit_feather_esp32c6_4mbflash_nopsram/mpconfigboard.h
index c3d168ac16d20..969bf468574fe 100644
--- a/ports/espressif/boards/adafruit_feather_esp32c6_4mbflash_nopsram/mpconfigboard.h
+++ b/ports/espressif/boards/adafruit_feather_esp32c6_4mbflash_nopsram/mpconfigboard.h
@@ -11,7 +11,9 @@
 #define MICROPY_HW_BOARD_NAME       "Adafruit Feather ESP32-C6 4MB Flash No PSRAM"
 #define MICROPY_HW_MCU_NAME         "ESP32C6"
 
-#define MICROPY_HW_NEOPIXEL (&pin_GPIO9)
+// Don't use the neopixel for status because we can't use it at the same time as
+// the boot button.
+// #define MICROPY_HW_NEOPIXEL (&pin_GPIO9)
 
 #define MICROPY_HW_LED_STATUS (&pin_GPIO15)
 
diff --git a/ports/espressif/common-hal/_bleio/Adapter.c b/ports/espressif/common-hal/_bleio/Adapter.c
index 3c08f28ea4dae..0a8550408d895 100644
--- a/ports/espressif/common-hal/_bleio/Adapter.c
+++ b/ports/espressif/common-hal/_bleio/Adapter.c
@@ -39,6 +39,7 @@
 #include "common-hal/_bleio/Connection.h"
 
 #include "esp_bt.h"
+#include "esp_mac.h"
 #include "esp_nimble_hci.h"
 #include "nvs_flash.h"
 
@@ -48,11 +49,6 @@
 
 bleio_connection_internal_t bleio_connections[BLEIO_TOTAL_CONNECTION_COUNT];
 
-// static void bluetooth_adapter_background(void *data) {
-//     supervisor_bluetooth_background();
-//     bleio_background();
-// }
-
 bool ble_active = false;
 
 static void nimble_host_task(void *param) {
@@ -63,7 +59,7 @@ static void nimble_host_task(void *param) {
 static TaskHandle_t cp_task = NULL;
 
 static void _on_sync(void) {
-    int rc = ble_hs_util_ensure_addr(0);
+    int rc = ble_hs_util_ensure_addr(false);
     assert(rc == 0);
 
     xTaskNotifyGive(cp_task);
@@ -72,6 +68,8 @@ static void _on_sync(void) {
 // All examples have this. It'd make sense in a header.
 void ble_store_config_init(void);
 
+char default_ble_name[] = { 'C', 'I', 'R', 'C', 'U', 'I', 'T', 'P', 'Y', 0, 0, 0, 0, 0, 0, 0};
+
 void common_hal_bleio_adapter_set_enabled(bleio_adapter_obj_t *self, bool enabled) {
     const bool is_enabled = common_hal_bleio_adapter_get_enabled(self);
 
@@ -81,15 +79,6 @@ void common_hal_bleio_adapter_set_enabled(bleio_adapter_obj_t *self, bool enable
     }
 
     if (enabled) {
-        esp_err_t err = nvs_flash_init();
-        if (err == ESP_ERR_NVS_NO_FREE_PAGES || err == ESP_ERR_NVS_NEW_VERSION_FOUND) {
-            // NVS partition was truncated and needs to be erased
-            // Retry nvs_flash_init
-            ESP_ERROR_CHECK(nvs_flash_erase());
-            err = nvs_flash_init();
-        }
-        ESP_ERROR_CHECK(err);
-
         CHECK_ESP_RESULT(nimble_port_init());
 
         // ble_hs_cfg.reset_cb = blecent_on_reset;
@@ -104,8 +93,8 @@ void common_hal_bleio_adapter_set_enabled(bleio_adapter_obj_t *self, bool enable
         ble_hs_cfg.sm_our_key_dist |= BLE_SM_PAIR_KEY_DIST_ENC;
         ble_hs_cfg.sm_their_key_dist |= BLE_SM_PAIR_KEY_DIST_ENC;
 
-        ble_hs_cfg.sm_mitm = 1;
-        ble_hs_cfg.sm_sc = 1;
+        ble_hs_cfg.sm_mitm = 0;
+        ble_hs_cfg.sm_sc = 0;
         /* Stores the IRK */
         ble_hs_cfg.sm_our_key_dist |= BLE_SM_PAIR_KEY_DIST_ID;
         ble_hs_cfg.sm_their_key_dist |= BLE_SM_PAIR_KEY_DIST_ID;
@@ -122,7 +111,17 @@ void common_hal_bleio_adapter_set_enabled(bleio_adapter_obj_t *self, bool enable
         } else
         #endif
         {
-            ble_svc_gap_device_name_set("CIRCUITPY");
+            uint8_t mac[6];
+            esp_read_mac(mac, ESP_MAC_BT);
+            mp_int_t len = sizeof(default_ble_name) - 1;
+            default_ble_name[len - 6] = nibble_to_hex_lower[mac[3] >> 4 & 0xf];
+            default_ble_name[len - 5] = nibble_to_hex_lower[mac[3] & 0xf];
+            default_ble_name[len - 4] = nibble_to_hex_lower[mac[4] >> 4 & 0xf];
+            default_ble_name[len - 3] = nibble_to_hex_lower[mac[4] & 0xf];
+            default_ble_name[len - 2] = nibble_to_hex_lower[mac[5] >> 4 & 0xf];
+            default_ble_name[len - 1] = nibble_to_hex_lower[mac[5] & 0xf];
+            default_ble_name[len] = '\0'; // for now we add null for compatibility with C ASCIIZ strings
+            ble_svc_gap_device_name_set(default_ble_name);
         }
 
         // Clear all of the internal connection objects.
@@ -180,6 +179,14 @@ bool common_hal_bleio_adapter_set_address(bleio_adapter_obj_t *self, bleio_addre
     return result == 0;
 }
 
+uint16_t bleio_adapter_get_name(char *buf, uint16_t len) {
+    const char *name = ble_svc_gap_device_name();
+    uint16_t full_len = strlen(name);
+    memcpy(buf, name, MIN(full_len, len));
+
+    return full_len;
+}
+
 mp_obj_str_t *common_hal_bleio_adapter_get_name(bleio_adapter_obj_t *self) {
     const char *name = ble_svc_gap_device_name();
 
@@ -401,7 +408,8 @@ mp_obj_t common_hal_bleio_adapter_connect(bleio_adapter_obj_t *self, bleio_addre
             _connect_event, self));
 
     int error_code;
-    CHECK_NOTIFY(xTaskNotifyWait(0, 0, (uint32_t *)&error_code, 200));
+    // Wait an extra 50 ms to give the connect method the opportunity to time out.
+    CHECK_NOTIFY(xTaskNotifyWait(0, 0, (uint32_t *)&error_code, pdMS_TO_TICKS(timeout * 1000 + 50)));
     // Negative values are error codes, connection handle otherwise.
     if (error_code < 0) {
         CHECK_BLE_ERROR(-error_code);
@@ -487,6 +495,7 @@ static int _advertising_event(struct ble_gap_event *event, void *self_in) {
             #endif
             break;
     }
+    background_callback_add_core(&bleio_background_callback);
     return 0;
 }
 
@@ -499,6 +508,8 @@ uint32_t _common_hal_bleio_adapter_start_advertising(bleio_adapter_obj_t *self,
     if (ble_gap_adv_active() && !self->user_advertising) {
         return BLE_HS_EBUSY;
     }
+    // Override anonymous because it isn't working with the ESP-IDF.
+    anonymous = false;
 
     uint32_t rc;
 
@@ -521,12 +532,19 @@ uint32_t _common_hal_bleio_adapter_start_advertising(bleio_adapter_obj_t *self,
     bool extended = advertising_data_len > BLE_ADV_LEGACY_DATA_MAX_LEN ||
         scan_response_data_len > BLE_ADV_LEGACY_DATA_MAX_LEN;
 
+    bool scannable = scan_response_data_len > 0;
+    bool legacy_pdu = !extended && !anonymous;
+    if (legacy_pdu && connectable) {
+        // Connectable legacy advertisements are always scannable too.
+        scannable = true;
+    }
+
     struct ble_gap_ext_adv_params adv_params = {
         .connectable = connectable,
-        .scannable = scan_response_data_len > 0,
+        .scannable = scannable,
         .directed = directed_to != NULL,
         .high_duty_directed = high_duty_directed,
-        .legacy_pdu = !extended,
+        .legacy_pdu = legacy_pdu,
         .anonymous = anonymous,
         .include_tx_power = extended,
         .scan_req_notif = false,
@@ -712,14 +730,46 @@ mp_obj_t common_hal_bleio_adapter_get_connections(bleio_adapter_obj_t *self) {
     return self->connection_objs;
 }
 
+#define NIMBLE_NVS_PEER_SEC_KEY                  "peer_sec"
+#define NIMBLE_NVS_OUR_SEC_KEY                   "our_sec"
+#define NIMBLE_NVS_CCCD_SEC_KEY                  "cccd_sec"
+#define NIMBLE_NVS_PEER_RECORDS_KEY              "p_dev_rec"
+#define NIMBLE_NVS_NAMESPACE                     "nimble_bond"
+
+// Implement bonding control ourselves when the adapter isn't enabled so that it
+// can run when BLE is off.
 void common_hal_bleio_adapter_erase_bonding(bleio_adapter_obj_t *self) {
-    ble_store_clear();
+    if (common_hal_bleio_adapter_get_enabled(self)) {
+        ble_store_clear();
+    } else {
+        nvs_handle_t nimble_handle;
+        esp_err_t err = nvs_open(NIMBLE_NVS_NAMESPACE, NVS_READWRITE, &nimble_handle);
+        if (err != ESP_OK) {
+            return;
+        }
+        nvs_erase_all(nimble_handle);
+        nvs_commit(nimble_handle);
+        nvs_close(nimble_handle);
+    }
 }
 
 bool common_hal_bleio_adapter_is_bonded_to_central(bleio_adapter_obj_t *self) {
-    int count;
-    ble_store_util_count(BLE_STORE_OBJ_TYPE_PEER_SEC, &count);
-    return count > 0;
+    if (common_hal_bleio_adapter_get_enabled(self)) {
+        int count;
+        ble_store_util_count(BLE_STORE_OBJ_TYPE_PEER_SEC, &count);
+        return count > 0;
+    }
+    nvs_handle_t nimble_handle;
+    esp_err_t err = nvs_open(NIMBLE_NVS_NAMESPACE, NVS_READONLY, &nimble_handle);
+    if (err != ESP_OK) {
+        return false;
+    }
+    err = nvs_find_key(nimble_handle, "peer_sec_1", NULL);
+    nvs_close(nimble_handle);
+    if (err == ESP_OK) {
+        return true;
+    }
+    return false;
 }
 
 void bleio_adapter_gc_collect(bleio_adapter_obj_t *adapter) {
diff --git a/ports/espressif/common-hal/_bleio/Characteristic.c b/ports/espressif/common-hal/_bleio/Characteristic.c
index 4df80a53d991e..a095add66736b 100644
--- a/ports/espressif/common-hal/_bleio/Characteristic.c
+++ b/ports/espressif/common-hal/_bleio/Characteristic.c
@@ -17,7 +17,6 @@
 
 #include "common-hal/_bleio/Adapter.h"
 #include "common-hal/_bleio/Service.h"
-// #include "common-hal/_bleio/bonding.h"
 
 
 static int characteristic_on_ble_gap_evt(struct ble_gap_event *event, void *param);
@@ -57,6 +56,22 @@ void common_hal_bleio_characteristic_construct(bleio_characteristic_obj_t *self,
     if ((props & CHAR_PROP_WRITE_NO_RESPONSE) != 0) {
         self->flags |= BLE_GATT_CHR_F_WRITE_NO_RSP;
     }
+    if (read_perm == SECURITY_MODE_ENC_WITH_MITM || write_perm == SECURITY_MODE_ENC_WITH_MITM ||
+        read_perm == SECURITY_MODE_SIGNED_WITH_MITM || write_perm == SECURITY_MODE_SIGNED_WITH_MITM) {
+        mp_raise_NotImplementedError(MP_ERROR_TEXT("MITM security not supported"));
+    }
+    if (read_perm == SECURITY_MODE_ENC_NO_MITM) {
+        self->flags |= BLE_GATT_CHR_F_READ_ENC;
+    }
+    if (read_perm == SECURITY_MODE_SIGNED_NO_MITM) {
+        self->flags |= BLE_GATT_CHR_F_READ_AUTHEN;
+    }
+    if (write_perm == SECURITY_MODE_ENC_NO_MITM) {
+        self->flags |= BLE_GATT_CHR_F_WRITE_ENC;
+    }
+    if (write_perm == SECURITY_MODE_SIGNED_NO_MITM) {
+        self->flags |= BLE_GATT_CHR_F_WRITE_AUTHEN;
+    }
 
     if (initial_value_bufinfo != NULL) {
         // Copy the initial value if it's on the heap. Otherwise it's internal and we may not be able
@@ -72,6 +87,12 @@ void common_hal_bleio_characteristic_construct(bleio_characteristic_obj_t *self,
             self->current_value = initial_value_bufinfo->buf;
             assert(self->current_value_len == max_length);
         }
+    } else {
+        self->current_value = port_malloc(max_length, false);
+        if (self->current_value != NULL) {
+            self->current_value_alloc = max_length;
+            self->current_value_len = 0;
+        }
     }
 
     if (gc_alloc_possible()) {
@@ -294,6 +315,7 @@ int bleio_characteristic_access_cb(uint16_t conn_handle, uint16_t attr_handle,
                         bleio_packet_buffer_extend(MP_OBJ_FROM_PTR(self->observer), conn_handle, self->current_value, self->current_value_len);
                     }
                 }
+                background_callback_add_core(&bleio_background_callback);
                 return rc;
             }
             return BLE_ATT_ERR_UNLIKELY;
diff --git a/ports/espressif/common-hal/_bleio/Connection.c b/ports/espressif/common-hal/_bleio/Connection.c
index ea30b1865f595..5957cd5edcf68 100644
--- a/ports/espressif/common-hal/_bleio/Connection.c
+++ b/ports/espressif/common-hal/_bleio/Connection.c
@@ -91,14 +91,18 @@ int bleio_connection_event_cb(struct ble_gap_event *event, void *connection_in)
         case BLE_GAP_EVENT_NOTIFY_TX:
             MP_FALLTHROUGH;
         case BLE_GAP_EVENT_SUBSCRIBE:
-            return ble_event_run_handlers(event);
+            int status = ble_event_run_handlers(event);
+            background_callback_add_core(&bleio_background_callback);
+            return status;
 
         default:
             #if CIRCUITPY_VERBOSE_BLE
             mp_printf(&mp_plat_print, "Unhandled connection event: %d\n", event->type);
             #endif
-            return 0;
+            break;
     }
+
+    background_callback_add_core(&bleio_background_callback);
     return 0;
 }
 
diff --git a/ports/espressif/common-hal/_bleio/PacketBuffer.c b/ports/espressif/common-hal/_bleio/PacketBuffer.c
index e6886811966de..8640bf7e42b7f 100644
--- a/ports/espressif/common-hal/_bleio/PacketBuffer.c
+++ b/ports/espressif/common-hal/_bleio/PacketBuffer.c
@@ -92,6 +92,8 @@ static int queue_next_write(bleio_packet_buffer_obj_t *self) {
             // Allocate an mbuf because the functions below consume it.
             struct os_mbuf *om = ble_hs_mbuf_from_flat(self->outgoing[self->pending_index], self->pending_size);
             if (om == NULL) {
+                // We may not have any more mbufs if BLE busy. It isn't a problem (yet) so we'll
+                // just skip queueing for now.
                 return BLE_HS_ENOMEM;
             }
             size_t pending_size = self->pending_size;
@@ -157,7 +159,7 @@ void _common_hal_bleio_packet_buffer_construct(
     bleio_packet_buffer_obj_t *self, bleio_characteristic_obj_t *characteristic,
     uint32_t *incoming_buffer, size_t incoming_buffer_size,
     uint32_t *outgoing_buffer1, uint32_t *outgoing_buffer2, size_t max_packet_size,
-    void *static_handler_entry) {
+    ble_event_handler_t *static_handler_entry) {
     self->characteristic = characteristic;
     self->client = self->characteristic->service->is_remote;
     self->max_packet_size = max_packet_size;
@@ -331,7 +333,8 @@ mp_int_t common_hal_bleio_packet_buffer_write(bleio_packet_buffer_obj_t *self, c
 
     // If no writes are queued then sneak in this data.
     if (!self->packet_queued) {
-        CHECK_NIMBLE_ERROR(queue_next_write(self));
+        // This will queue up the packet even if it can't send immediately.
+        queue_next_write(self);
     }
     return num_bytes_written;
 }
diff --git a/ports/espressif/common-hal/_bleio/PacketBuffer.h b/ports/espressif/common-hal/_bleio/PacketBuffer.h
index e17a6c7425211..0ab084c5b0175 100644
--- a/ports/espressif/common-hal/_bleio/PacketBuffer.h
+++ b/ports/espressif/common-hal/_bleio/PacketBuffer.h
@@ -8,6 +8,7 @@
 
 #include "py/ringbuf.h"
 #include "shared-bindings/_bleio/Characteristic.h"
+#include "common-hal/_bleio/ble_events.h"
 
 typedef struct {
     mp_obj_base_t base;
@@ -28,4 +29,6 @@ typedef struct {
     bool packet_queued;
 } bleio_packet_buffer_obj_t;
 
+typedef ble_event_handler_entry_t ble_event_handler_t;
+
 void bleio_packet_buffer_extend(bleio_packet_buffer_obj_t *self, uint16_t conn_handle, const uint8_t *buffer, size_t len);
diff --git a/ports/espressif/common-hal/_bleio/__init__.c b/ports/espressif/common-hal/_bleio/__init__.c
index 0d99a97c23c4f..eb51e9f456700 100644
--- a/ports/espressif/common-hal/_bleio/__init__.c
+++ b/ports/espressif/common-hal/_bleio/__init__.c
@@ -19,9 +19,13 @@
 #include "supervisor/shared/bluetooth/bluetooth.h"
 
 #include "common-hal/_bleio/__init__.h"
-// #include "common-hal/_bleio/bonding.h"
 #include "common-hal/_bleio/ble_events.h"
 
+#include "nvs_flash.h"
+
+
+background_callback_t bleio_background_callback;
+
 void bleio_user_reset() {
     // Stop any user scanning or advertising.
     common_hal_bleio_adapter_stop_scan(&common_hal_bleio_adapter_obj);
@@ -36,7 +40,6 @@ void bleio_user_reset() {
 // Turn off BLE on a reset or reload.
 void bleio_reset() {
     // Set this explicitly to save data.
-    common_hal_bleio_adapter_obj.base.type = &bleio_adapter_type;
     if (!common_hal_bleio_adapter_get_enabled(&common_hal_bleio_adapter_obj)) {
         return;
     }
@@ -52,7 +55,26 @@ void bleio_reset() {
 // It currently only has properties and no state. Inited by bleio_reset
 bleio_adapter_obj_t common_hal_bleio_adapter_obj;
 
-void bleio_background(void) {
+void bleio_background(void *data) {
+    (void)data;
+    supervisor_bluetooth_background();
+}
+
+void common_hal_bleio_init(void) {
+    common_hal_bleio_adapter_obj.base.type = &bleio_adapter_type;
+
+    esp_err_t err = nvs_flash_init();
+    if (err == ESP_ERR_NVS_NO_FREE_PAGES || err == ESP_ERR_NVS_NEW_VERSION_FOUND) {
+        // NVS partition was truncated and needs to be erased
+        // Retry nvs_flash_init
+        ESP_ERROR_CHECK(nvs_flash_erase());
+        err = nvs_flash_init();
+    }
+    ESP_ERROR_CHECK(err);
+
+
+    bleio_background_callback.fun = bleio_background;
+    bleio_background_callback.data = NULL;
 }
 
 void common_hal_bleio_gc_collect(void) {
@@ -77,7 +99,7 @@ void check_nimble_error(int rc, const char *file, size_t line) {
             mp_raise_ConnectionError(MP_ERROR_TEXT("Not connected"));
             return;
         default:
-            #if CIRCUITPY_VERBOSE_BLE
+            #if CIRCUITPY_VERBOSE_BLE || CIRCUITPY_DEBUG
             if (file) {
                 mp_raise_bleio_BluetoothError(MP_ERROR_TEXT("Unknown system firmware error at %s:%d: %d"), file, line, rc);
             }
@@ -104,7 +126,7 @@ void check_ble_error(int error_code, const char *file, size_t line) {
             mp_raise_bleio_SecurityError(MP_ERROR_TEXT("Insufficient encryption"));
             return;
         default:
-            #if CIRCUITPY_VERBOSE_BLE
+            #if CIRCUITPY_VERBOSE_BLE || CIRCUITPY_DEBUG
             if (file) {
                 mp_raise_bleio_BluetoothError(MP_ERROR_TEXT("Unknown BLE error at %s:%d: %d"), file, line, error_code);
             }
diff --git a/ports/espressif/common-hal/_bleio/__init__.h b/ports/espressif/common-hal/_bleio/__init__.h
index 146281a9f8dc1..1852bd870a6dc 100644
--- a/ports/espressif/common-hal/_bleio/__init__.h
+++ b/ports/espressif/common-hal/_bleio/__init__.h
@@ -6,9 +6,13 @@
 
 #pragma once
 
+#include "supervisor/background_callback.h"
+
 #include "freertos/FreeRTOS.h" // IWYU pragma: keep; for BaseType_t
 
-void bleio_background(void);
+void bleio_background(void *data);
+
+extern background_callback_t bleio_background_callback;
 
 // typedef struct {
 //     ble_gap_enc_key_t own_enc;
diff --git a/ports/espressif/esp-idf b/ports/espressif/esp-idf
index 0b28b79fafa75..d58f9ce0b4799 160000
--- a/ports/espressif/esp-idf
+++ b/ports/espressif/esp-idf
@@ -1 +1 @@
-Subproject commit 0b28b79fafa75d36348d84d9eaccdbcd73220571
+Subproject commit d58f9ce0b4799e63490917b7bfc1300a10bc1f43
diff --git a/ports/espressif/mpconfigport.mk b/ports/espressif/mpconfigport.mk
index f9d0260acb8f6..95ff29fc1e23a 100644
--- a/ports/espressif/mpconfigport.mk
+++ b/ports/espressif/mpconfigport.mk
@@ -201,6 +201,9 @@ CIRCUITPY_GIFIO ?= $(CIRCUITPY_DISPLAYIO)
 CIRCUITPY_JPEGIO ?= $(CIRCUITPY_DISPLAYIO)
 CIRCUITPY_QRIO ?= $(CIRCUITPY_ESPCAMERA)
 
+CIRCUITPY_BLE_FILE_SERVICE ?= $(CIRCUITPY_BLEIO)
+CIRCUITPY_SERIAL_BLE ?= $(CIRCUITPY_BLEIO)
+
 # Features dependent on other features
 ifneq ($(CIRCUITPY_USB_DEVICE),0)
 CIRCUITPY_BUILD_EXTENSIONS ?= bin,uf2
diff --git a/ports/nordic/common-hal/_bleio/Adapter.h b/ports/nordic/common-hal/_bleio/Adapter.h
index 5a4a147d32a72..5bc1805d0727c 100644
--- a/ports/nordic/common-hal/_bleio/Adapter.h
+++ b/ports/nordic/common-hal/_bleio/Adapter.h
@@ -20,6 +20,8 @@
 #define BLEIO_TOTAL_CONNECTION_COUNT 5
 #endif
 
+#define BLEIO_HANDLE_INVALID BLE_CONN_HANDLE_INVALID
+
 extern bleio_connection_internal_t bleio_connections[BLEIO_TOTAL_CONNECTION_COUNT];
 
 typedef struct {
diff --git a/ports/nordic/common-hal/_bleio/PacketBuffer.c b/ports/nordic/common-hal/_bleio/PacketBuffer.c
index 3e0a0a56a4f88..f3058f6c23d9c 100644
--- a/ports/nordic/common-hal/_bleio/PacketBuffer.c
+++ b/ports/nordic/common-hal/_bleio/PacketBuffer.c
@@ -194,7 +194,7 @@ void _common_hal_bleio_packet_buffer_construct(
     bleio_packet_buffer_obj_t *self, bleio_characteristic_obj_t *characteristic,
     uint32_t *incoming_buffer, size_t incoming_buffer_size,
     uint32_t *outgoing_buffer1, uint32_t *outgoing_buffer2, size_t max_packet_size,
-    void *static_handler_entry) {
+    ble_event_handler_t *static_handler_entry) {
 
     self->characteristic = characteristic;
     self->client = self->characteristic->service->is_remote;
diff --git a/ports/nordic/common-hal/_bleio/PacketBuffer.h b/ports/nordic/common-hal/_bleio/PacketBuffer.h
index c55efd0293b60..a8573b048fa7d 100644
--- a/ports/nordic/common-hal/_bleio/PacketBuffer.h
+++ b/ports/nordic/common-hal/_bleio/PacketBuffer.h
@@ -11,6 +11,8 @@
 #include "py/ringbuf.h"
 #include "shared-bindings/_bleio/Characteristic.h"
 
+#include "bluetooth/ble_drv.h"
+
 typedef struct {
     mp_obj_base_t base;
     bleio_characteristic_obj_t *characteristic;
@@ -29,3 +31,5 @@ typedef struct {
     bool client;
     bool packet_queued;
 } bleio_packet_buffer_obj_t;
+
+typedef ble_drv_evt_handler_entry_t ble_event_handler_t;
diff --git a/ports/nordic/common-hal/_bleio/__init__.c b/ports/nordic/common-hal/_bleio/__init__.c
index 33e12eb3680fa..705bc14539536 100644
--- a/ports/nordic/common-hal/_bleio/__init__.c
+++ b/ports/nordic/common-hal/_bleio/__init__.c
@@ -74,6 +74,9 @@ void check_sec_status(uint8_t sec_status) {
     }
 }
 
+void common_hal_bleio_init(void) {
+}
+
 void bleio_user_reset() {
     // Stop any user scanning or advertising.
     common_hal_bleio_adapter_stop_scan(&common_hal_bleio_adapter_obj);
diff --git a/ports/silabs/common-hal/_bleio/PacketBuffer.c b/ports/silabs/common-hal/_bleio/PacketBuffer.c
index 96a7462f6c4ed..6cb3e58121cbb 100644
--- a/ports/silabs/common-hal/_bleio/PacketBuffer.c
+++ b/ports/silabs/common-hal/_bleio/PacketBuffer.c
@@ -145,7 +145,7 @@ void _common_hal_bleio_packet_buffer_construct(
     uint32_t *outgoing_buffer1,
     uint32_t *outgoing_buffer2,
     size_t max_packet_size,
-    void *static_handler_entry) {
+    ble_event_handler_t static_handler_entry) {
 
     bleio_characteristic_properties_t temp_prop;
     self->characteristic = characteristic;
diff --git a/ports/silabs/common-hal/_bleio/PacketBuffer.h b/ports/silabs/common-hal/_bleio/PacketBuffer.h
index f79eda6cf3a6e..c00db915f9465 100644
--- a/ports/silabs/common-hal/_bleio/PacketBuffer.h
+++ b/ports/silabs/common-hal/_bleio/PacketBuffer.h
@@ -57,6 +57,9 @@ typedef struct {
     uint8_t len;
 } bleio_packet_buffer_obj_list_t;
 
+// Unused
+typedef void *ble_event_handler_t;
+
 extern bool packet_buffer_on_ble_evt(uint16_t attribute,
     uint8_t *data,
     uint16_t len);
diff --git a/ports/silabs/common-hal/_bleio/__init__.c b/ports/silabs/common-hal/_bleio/__init__.c
index b5d9270af56c3..6191a88904a91 100644
--- a/ports/silabs/common-hal/_bleio/__init__.c
+++ b/ports/silabs/common-hal/_bleio/__init__.c
@@ -51,6 +51,9 @@ const osMutexAttr_t bluetooth_connection_mutex_attr = {
     .cb_size = osMutexCbSize
 };
 
+void common_hal_bleio_init(void) {
+}
+
 void bleio_user_reset() {
     // Stop any user scanning or advertising.
     common_hal_bleio_adapter_stop_scan(&common_hal_bleio_adapter_obj);
diff --git a/shared-bindings/_bleio/Adapter.h b/shared-bindings/_bleio/Adapter.h
index c6b7aeefc9609..0bc6f051ff3f5 100644
--- a/shared-bindings/_bleio/Adapter.h
+++ b/shared-bindings/_bleio/Adapter.h
@@ -35,6 +35,7 @@ uint16_t bleio_adapter_get_name(char *buf, uint16_t len);
 extern mp_obj_str_t *common_hal_bleio_adapter_get_name(bleio_adapter_obj_t *self);
 extern void common_hal_bleio_adapter_set_name(bleio_adapter_obj_t *self, const char *name);
 
+// Returns 0 if ok, otherwise a BLE stack specific error code.
 extern uint32_t _common_hal_bleio_adapter_start_advertising(bleio_adapter_obj_t *self,
     bool connectable, bool anonymous, uint32_t timeout, float interval,
     const uint8_t *advertising_data, uint16_t advertising_data_len,
diff --git a/shared-bindings/_bleio/PacketBuffer.h b/shared-bindings/_bleio/PacketBuffer.h
index 25d7127a67ec5..e9e642e2677e8 100644
--- a/shared-bindings/_bleio/PacketBuffer.h
+++ b/shared-bindings/_bleio/PacketBuffer.h
@@ -10,15 +10,24 @@
 
 extern const mp_obj_type_t bleio_packet_buffer_type;
 
+// Maximum size of a packet.
+#ifdef BLE_GATTS_VAR_ATTR_LEN_MAX
+#define BLEIO_PACKET_BUFFER_MAX_PACKET_SIZE BLE_GATTS_VAR_ATTR_LEN_MAX
+#else
+#define BLEIO_PACKET_BUFFER_MAX_PACKET_SIZE 512
+#endif
+
 void common_hal_bleio_packet_buffer_construct(
     bleio_packet_buffer_obj_t *self, bleio_characteristic_obj_t *characteristic,
     size_t buffer_size, size_t max_packet_size);
-// Allocation free
+// Allocation free version for BLE workflow use.
+#if CIRCUITPY_SERIAL_BLE || CIRCUITPY_BLE_FILE_SERVICE
 void _common_hal_bleio_packet_buffer_construct(
     bleio_packet_buffer_obj_t *self, bleio_characteristic_obj_t *characteristic,
     uint32_t *incoming_buffer, size_t incoming_buffer_size,
     uint32_t *outgoing_buffer1, uint32_t *outgoing_buffer2, size_t outgoing_buffer_size,
-    void *static_handler_entry);
+    ble_event_handler_t *static_handler_entry);
+#endif
 mp_int_t common_hal_bleio_packet_buffer_write(bleio_packet_buffer_obj_t *self, const uint8_t *data, size_t len, uint8_t *header, size_t header_len);
 mp_int_t common_hal_bleio_packet_buffer_readinto(bleio_packet_buffer_obj_t *self, uint8_t *data, size_t len);
 mp_int_t common_hal_bleio_packet_buffer_get_incoming_packet_length(bleio_packet_buffer_obj_t *self);
diff --git a/shared-bindings/_bleio/__init__.c b/shared-bindings/_bleio/__init__.c
index 2643a59618a63..c0cd439f7d924 100644
--- a/shared-bindings/_bleio/__init__.c
+++ b/shared-bindings/_bleio/__init__.c
@@ -82,6 +82,7 @@ NORETURN void mp_raise_bleio_SecurityError(mp_rom_error_text_t fmt, ...) {
 // Called when _bleio is imported.
 static mp_obj_t bleio___init__(void) {
 // HCI cannot be enabled on import, because we need to setup the HCI adapter first.
+    common_hal_bleio_init();
     #if !CIRCUITPY_BLEIO_HCI
     common_hal_bleio_adapter_set_enabled(&common_hal_bleio_adapter_obj, true);
     #endif
diff --git a/shared-bindings/_bleio/__init__.h b/shared-bindings/_bleio/__init__.h
index 0feb538d81d82..faf11ea1d0637 100644
--- a/shared-bindings/_bleio/__init__.h
+++ b/shared-bindings/_bleio/__init__.h
@@ -39,6 +39,10 @@ void bleio_user_reset(void);
 // Completely resets the BLE stack including BLE connections.
 void bleio_reset(void);
 
+// Init any state needed before calling any bleio functions including those
+// having to do with bonding. This doesn't enable the BLE adapter though.
+void common_hal_bleio_init(void);
+
 extern mp_obj_t bleio_set_adapter(mp_obj_t adapter_obj);
 
 NORETURN void mp_raise_bleio_BluetoothError(mp_rom_error_text_t msg, ...);
diff --git a/supervisor/shared/bluetooth/bluetooth.c b/supervisor/shared/bluetooth/bluetooth.c
index b1b116b9c01f9..877fbc6ef262d 100644
--- a/supervisor/shared/bluetooth/bluetooth.c
+++ b/supervisor/shared/bluetooth/bluetooth.c
@@ -12,6 +12,7 @@
 #include "shared-bindings/_bleio/Adapter.h"
 #if defined(CIRCUITPY_BOOT_BUTTON)
 #include "shared-bindings/digitalio/DigitalInOut.h"
+#include "shared-bindings/time/__init__.h"
 #endif
 #include "shared-bindings/microcontroller/Processor.h"
 #include "shared-bindings/microcontroller/ResetReason.h"
@@ -28,18 +29,21 @@
 
 #if CIRCUITPY_BLE_FILE_SERVICE
 #include "supervisor/shared/bluetooth/file_transfer.h"
-#include "bluetooth/ble_drv.h"
 #endif
 
 #if CIRCUITPY_SERIAL_BLE
 #include "supervisor/shared/bluetooth/serial.h"
-#include "bluetooth/ble_drv.h"
 #endif
 
 #if CIRCUITPY_STATUS_BAR
 #include "supervisor/shared/status_bar.h"
 #endif
 
+#if CIRCUITPY_WEB_WORKFLOW && CIRCUITPY_WIFI && CIRCUITPY_OS_GETENV
+#include "shared-module/os/__init__.h"
+#endif
+
+
 // This standard advertisement advertises the CircuitPython editing service and a CIRCUITPY short name.
 const uint8_t public_advertising_data[] = { 0x02, 0x01, 0x06, // 0-2 Flags
                                             0x02, 0x0a, 0xec,  // 3-5 TX power level -20
@@ -138,7 +142,7 @@ static void supervisor_bluetooth_start_advertising(void) {
     _private_advertising = true;
     // Advertise with less power when doing so publicly to reduce who can hear us. This will make it
     // harder for someone with bad intentions to pair from a distance.
-    if (!bonded || boot_in_discovery_mode) {
+    if (!bonded && boot_in_discovery_mode) {
         tx_power = -20;
         adv = public_advertising_data;
         adv_len = sizeof(public_advertising_data);
@@ -169,7 +173,7 @@ static void supervisor_bluetooth_start_advertising(void) {
         tx_power,
         NULL);
     // This may fail if we are already advertising.
-    advertising = status == NRF_SUCCESS;
+    advertising = status == 0;
 }
 
 #endif  // CIRCUITPY_BLE_FILE_SERVICE || CIRCUITPY_SERIAL_BLE
@@ -193,26 +197,18 @@ void supervisor_bluetooth_init(void) {
         return;
     }
 
+    common_hal_bleio_init();
     if (ble_mode == 0) {
         port_set_saved_word(BLE_DISCOVERY_DATA_GUARD | (0x01 << 8));
     }
     // Wait for a while to allow for reset.
 
-    #ifdef CIRCUITPY_BOOT_BUTTON
-    digitalio_digitalinout_obj_t boot_button;
-    common_hal_digitalio_digitalinout_construct(&boot_button, CIRCUITPY_BOOT_BUTTON);
-    common_hal_digitalio_digitalinout_switch_to_input(&boot_button, PULL_UP);
-    #endif
     #if CIRCUITPY_STATUS_LED
     status_led_init();
     #endif
     uint64_t start_ticks = supervisor_ticks_ms64();
     uint64_t diff = 0;
     if (ble_mode != 0) {
-        #ifdef CIRCUITPY_STATUS_LED
-        new_status_color(0x0000ff);
-        #endif
-        common_hal_bleio_adapter_erase_bonding(&common_hal_bleio_adapter_obj);
         boot_in_discovery_mode = true;
         reset_state = 0x0;
     }
@@ -221,7 +217,14 @@ void supervisor_bluetooth_init(void) {
     // Checking here allows us to have the status LED solidly on even if no button was
     // pressed.
     bool bonded = common_hal_bleio_adapter_is_bonded_to_central(&common_hal_bleio_adapter_obj);
-    if (!bonded) {
+    bool wifi_workflow_active = false;
+    #if CIRCUITPY_WEB_WORKFLOW && CIRCUITPY_WIFI && CIRCUITPY_OS_GETENV
+    char _api_password[64];
+    const size_t api_password_len = sizeof(_api_password) - 1;
+    os_getenv_err_t result = common_hal_os_getenv_str("CIRCUITPY_WEB_API_PASSWORD", _api_password + 1, api_password_len);
+    wifi_workflow_active = result == GETENV_OK;
+    #endif
+    if (!bonded && !wifi_workflow_active) {
         boot_in_discovery_mode = true;
     }
     #endif
@@ -235,14 +238,23 @@ void supervisor_bluetooth_init(void) {
             new_status_color(BLACK);
         }
         #endif
+        // Init the boot button every time in case it is used for LEDs.
         #ifdef CIRCUITPY_BOOT_BUTTON
-        if (!common_hal_digitalio_digitalinout_get_value(&boot_button)) {
+        digitalio_digitalinout_obj_t boot_button;
+        common_hal_digitalio_digitalinout_construct(&boot_button, CIRCUITPY_BOOT_BUTTON);
+        common_hal_digitalio_digitalinout_switch_to_input(&boot_button, PULL_UP);
+        common_hal_time_delay_ms(1);
+        bool button_pressed = !common_hal_digitalio_digitalinout_get_value(&boot_button);
+        common_hal_digitalio_digitalinout_deinit(&boot_button);
+        if (button_pressed) {
             boot_in_discovery_mode = true;
-            break;
         }
         #endif
         diff = supervisor_ticks_ms64() - start_ticks;
     }
+    if (boot_in_discovery_mode) {
+        common_hal_bleio_adapter_erase_bonding(&common_hal_bleio_adapter_obj);
+    }
     #if CIRCUITPY_STATUS_LED
     new_status_color(BLACK);
     status_led_deinit();
diff --git a/supervisor/shared/bluetooth/file_transfer.c b/supervisor/shared/bluetooth/file_transfer.c
index de21d7e71e95b..aa49c0a899a80 100644
--- a/supervisor/shared/bluetooth/file_transfer.c
+++ b/supervisor/shared/bluetooth/file_transfer.c
@@ -14,8 +14,6 @@
 #include "shared-bindings/_bleio/Service.h"
 #include "shared-bindings/_bleio/UUID.h"
 
-#include "bluetooth/ble_drv.h"
-
 #include "supervisor/fatfs.h"
 #include "supervisor/filesystem.h"
 #include "supervisor/shared/reload.h"
@@ -39,9 +37,9 @@ static mp_obj_t characteristic_list_items[2];
 #define PACKET_BUFFER_SIZE (2 * 10 + 512 + 12)
 // uint32_t so its aligned
 static uint32_t _buffer[PACKET_BUFFER_SIZE / 4 + 1];
-static uint32_t _outgoing1[BLE_GATTS_VAR_ATTR_LEN_MAX / 4];
-static uint32_t _outgoing2[BLE_GATTS_VAR_ATTR_LEN_MAX / 4];
-static ble_drv_evt_handler_entry_t static_handler_entry;
+static uint32_t _outgoing1[BLEIO_PACKET_BUFFER_MAX_PACKET_SIZE / 4];
+static uint32_t _outgoing2[BLEIO_PACKET_BUFFER_MAX_PACKET_SIZE / 4];
+static ble_event_handler_t static_handler_entry;
 static bleio_packet_buffer_obj_t _transfer_packet_buffer;
 
 void supervisor_start_bluetooth_file_transfer(void) {
@@ -60,6 +58,7 @@ void supervisor_start_bluetooth_file_transfer(void) {
     // Version number
     supervisor_ble_version_uuid.base.type = &bleio_uuid_type;
     common_hal_bleio_uuid_construct(&supervisor_ble_version_uuid, 0x0100, file_transfer_base_uuid);
+    supervisor_ble_version_characteristic.base.type = &bleio_characteristic_type;
     common_hal_bleio_characteristic_construct(&supervisor_ble_version_characteristic,
         &supervisor_ble_service,
         0,                                       // handle (for remote only)
@@ -81,6 +80,7 @@ void supervisor_start_bluetooth_file_transfer(void) {
     // Active filename.
     supervisor_ble_transfer_uuid.base.type = &bleio_uuid_type;
     common_hal_bleio_uuid_construct(&supervisor_ble_transfer_uuid, 0x0200, file_transfer_base_uuid);
+    supervisor_ble_transfer_characteristic.base.type = &bleio_characteristic_type;
     common_hal_bleio_characteristic_construct(&supervisor_ble_transfer_characteristic,
         &supervisor_ble_service,
         0,                                       // handle (for remote only)
@@ -88,15 +88,16 @@ void supervisor_start_bluetooth_file_transfer(void) {
         CHAR_PROP_READ | CHAR_PROP_WRITE_NO_RESPONSE | CHAR_PROP_NOTIFY,
         SECURITY_MODE_ENC_NO_MITM,
         SECURITY_MODE_ENC_NO_MITM,
-        BLE_GATTS_VAR_ATTR_LEN_MAX,                  // max length
+        BLEIO_PACKET_BUFFER_MAX_PACKET_SIZE,                  // max length
         false,                                       // fixed length
-        NULL,                                       // no initial valuen
+        NULL,                                       // no initial value
         NULL);
 
+    _transfer_packet_buffer.base.type = &bleio_packet_buffer_type;
     _common_hal_bleio_packet_buffer_construct(
         &_transfer_packet_buffer, &supervisor_ble_transfer_characteristic,
         _buffer, PACKET_BUFFER_SIZE,
-        _outgoing1, _outgoing2, BLE_GATTS_VAR_ATTR_LEN_MAX,
+        _outgoing1, _outgoing2, BLEIO_PACKET_BUFFER_MAX_PACKET_SIZE,
         &static_handler_entry);
 }
 
diff --git a/supervisor/shared/bluetooth/serial.c b/supervisor/shared/bluetooth/serial.c
index 179bd23cacfb5..3c8ae71eb4828 100644
--- a/supervisor/shared/bluetooth/serial.c
+++ b/supervisor/shared/bluetooth/serial.c
@@ -36,10 +36,13 @@ const uint8_t circuitpython_base_uuid[16] = {0x6e, 0x68, 0x74, 0x79, 0x50, 0x74,
 static mp_obj_list_t characteristic_list;
 static mp_obj_t characteristic_list_items[3];
 
-static uint32_t _outgoing1[BLE_GATTS_VAR_ATTR_LEN_MAX / 4];
-static uint32_t _outgoing2[BLE_GATTS_VAR_ATTR_LEN_MAX / 4];
-static ble_drv_evt_handler_entry_t rx_static_handler_entry;
-static ble_drv_evt_handler_entry_t tx_static_handler_entry;
+#if BLEIO_PACKET_BUFFER_MAX_PACKET_SIZE % 4 != 0
+#error "BLEIO_PACKET_BUFFER_MAX_PACKET_SIZE must be a multiple of 4"
+#endif
+static uint32_t _outgoing1[BLEIO_PACKET_BUFFER_MAX_PACKET_SIZE / 4];
+static uint32_t _outgoing2[BLEIO_PACKET_BUFFER_MAX_PACKET_SIZE / 4];
+static ble_event_handler_t rx_static_handler_entry;
+static ble_event_handler_t tx_static_handler_entry;
 static bleio_packet_buffer_obj_t _tx_packet_buffer;
 static uint32_t _incoming[64];
 static bleio_characteristic_buffer_obj_t _rx_buffer;
@@ -64,6 +67,7 @@ void supervisor_start_bluetooth_serial(void) {
     // RX
     supervisor_ble_circuitpython_rx_uuid.base.type = &bleio_uuid_type;
     common_hal_bleio_uuid_construct(&supervisor_ble_circuitpython_rx_uuid, 0x0002, circuitpython_base_uuid);
+    supervisor_ble_circuitpython_rx_characteristic.base.type = &bleio_characteristic_type;
     common_hal_bleio_characteristic_construct(&supervisor_ble_circuitpython_rx_characteristic,
         &supervisor_ble_circuitpython_service,
         0,                                       // handle (for remote only)
@@ -71,7 +75,7 @@ void supervisor_start_bluetooth_serial(void) {
         CHAR_PROP_WRITE | CHAR_PROP_WRITE_NO_RESPONSE,
         SECURITY_MODE_NO_ACCESS,
         SECURITY_MODE_ENC_NO_MITM,
-        BLE_GATTS_VAR_ATTR_LEN_MAX,                 // max length
+        BLEIO_PACKET_BUFFER_MAX_PACKET_SIZE,                 // max length
         false,                                      // fixed length
         NULL,                                      // no initial value
         NULL);
@@ -79,6 +83,7 @@ void supervisor_start_bluetooth_serial(void) {
     // TX
     supervisor_ble_circuitpython_tx_uuid.base.type = &bleio_uuid_type;
     common_hal_bleio_uuid_construct(&supervisor_ble_circuitpython_tx_uuid, 0x0003, circuitpython_base_uuid);
+    supervisor_ble_circuitpython_tx_characteristic.base.type = &bleio_characteristic_type;
     common_hal_bleio_characteristic_construct(&supervisor_ble_circuitpython_tx_characteristic,
         &supervisor_ble_circuitpython_service,
         0,                                       // handle (for remote only)
@@ -86,7 +91,7 @@ void supervisor_start_bluetooth_serial(void) {
         CHAR_PROP_NOTIFY,
         SECURITY_MODE_ENC_NO_MITM,
         SECURITY_MODE_NO_ACCESS,
-        BLE_GATTS_VAR_ATTR_LEN_MAX,                  // max length
+        BLEIO_PACKET_BUFFER_MAX_PACKET_SIZE,                  // max length
         false,                                       // fixed length
         NULL,                                       // no initial value
         NULL);
@@ -99,6 +104,7 @@ void supervisor_start_bluetooth_serial(void) {
 
     supervisor_ble_circuitpython_version_uuid.base.type = &bleio_uuid_type;
     common_hal_bleio_uuid_construct(&supervisor_ble_circuitpython_version_uuid, 0x0100, circuitpython_base_uuid);
+    supervisor_ble_circuitpython_version_characteristic.base.type = &bleio_characteristic_type;
     common_hal_bleio_characteristic_construct(&supervisor_ble_circuitpython_version_characteristic,
         &supervisor_ble_circuitpython_service,
         0,                                       // handle (for remote only)
@@ -115,13 +121,15 @@ void supervisor_start_bluetooth_serial(void) {
 
     // Use a PacketBuffer to transmit so that we glom characters to transmit
     // together and save BLE overhead.
+    _tx_packet_buffer.base.type = &bleio_packet_buffer_type;
     _common_hal_bleio_packet_buffer_construct(
         &_tx_packet_buffer, &supervisor_ble_circuitpython_tx_characteristic,
         NULL, 0,
-        _outgoing1, _outgoing2, BLE_GATTS_VAR_ATTR_LEN_MAX,
+        _outgoing1, _outgoing2, BLEIO_PACKET_BUFFER_MAX_PACKET_SIZE,
         &tx_static_handler_entry);
 
     // Use a CharacteristicBuffer for rx so we can read a single character at a time.
+    _rx_buffer.base.type = &bleio_characteristic_buffer_type;
     _common_hal_bleio_characteristic_buffer_construct(&_rx_buffer,
         &supervisor_ble_circuitpython_rx_characteristic,
         0.1f,
@@ -143,7 +151,7 @@ void supervisor_stop_bluetooth_serial(void) {
 }
 
 bool ble_serial_connected(void) {
-    return _tx_packet_buffer.conn_handle != BLE_CONN_HANDLE_INVALID;
+    return _tx_packet_buffer.conn_handle != BLEIO_HANDLE_INVALID;
 }
 
 uint32_t ble_serial_available(void) {
diff --git a/supervisor/shared/safe_mode.c b/supervisor/shared/safe_mode.c
index 81bcb749143de..30e5a23729bad 100644
--- a/supervisor/shared/safe_mode.c
+++ b/supervisor/shared/safe_mode.c
@@ -10,6 +10,7 @@
 
 #if defined(CIRCUITPY_BOOT_BUTTON)
 #include "shared-bindings/digitalio/DigitalInOut.h"
+#include "shared-bindings/time/__init__.h"
 #endif
 #include "shared-bindings/microcontroller/Processor.h"
 #include "shared-bindings/microcontroller/ResetReason.h"
@@ -64,11 +65,6 @@ safe_mode_t wait_for_safe_mode_reset(void) {
     #if CIRCUITPY_STATUS_LED
     status_led_init();
     #endif
-    #ifdef CIRCUITPY_BOOT_BUTTON
-    digitalio_digitalinout_obj_t boot_button;
-    common_hal_digitalio_digitalinout_construct(&boot_button, CIRCUITPY_BOOT_BUTTON);
-    common_hal_digitalio_digitalinout_switch_to_input(&boot_button, PULL_UP);
-    #endif
     uint64_t start_ticks = supervisor_ticks_ms64();
     uint64_t diff = 0;
     bool boot_in_safe_mode = false;
@@ -82,8 +78,15 @@ safe_mode_t wait_for_safe_mode_reset(void) {
             new_status_color(BLACK);
         }
         #endif
+        // Init the boot button every time in case it is used for LEDs.
         #ifdef CIRCUITPY_BOOT_BUTTON
-        if (!common_hal_digitalio_digitalinout_get_value(&boot_button)) {
+        digitalio_digitalinout_obj_t boot_button;
+        common_hal_digitalio_digitalinout_construct(&boot_button, CIRCUITPY_BOOT_BUTTON);
+        common_hal_digitalio_digitalinout_switch_to_input(&boot_button, PULL_UP);
+        common_hal_time_delay_ms(1);
+        bool button_pressed = !common_hal_digitalio_digitalinout_get_value(&boot_button);
+        common_hal_digitalio_digitalinout_deinit(&boot_button);
+        if (button_pressed) {
             boot_in_safe_mode = true;
             break;
         }