diff --git a/ports/esp32/boards/ESP32_GENERIC_S3/sdkconfig.board b/ports/esp32/boards/ESP32_GENERIC_S3/sdkconfig.board
index a36b971162850..9839b0d300510 100644
--- a/ports/esp32/boards/ESP32_GENERIC_S3/sdkconfig.board
+++ b/ports/esp32/boards/ESP32_GENERIC_S3/sdkconfig.board
@@ -1,6 +1,5 @@
 CONFIG_ESPTOOLPY_FLASHMODE_QIO=y
 CONFIG_ESPTOOLPY_FLASHFREQ_80M=y
-CONFIG_ESPTOOLPY_AFTER_NORESET=y
 
 CONFIG_ESPTOOLPY_FLASHSIZE_4MB=
 CONFIG_ESPTOOLPY_FLASHSIZE_8MB=y
diff --git a/ports/esp32/boards/UM_FEATHERS2/sdkconfig.board b/ports/esp32/boards/UM_FEATHERS2/sdkconfig.board
index c2e1c2b3d3b7c..9ab58f215f2e6 100644
--- a/ports/esp32/boards/UM_FEATHERS2/sdkconfig.board
+++ b/ports/esp32/boards/UM_FEATHERS2/sdkconfig.board
@@ -1,6 +1,5 @@
 CONFIG_ESPTOOLPY_FLASHMODE_QIO=y
 CONFIG_ESPTOOLPY_FLASHFREQ_80M=y
-CONFIG_ESPTOOLPY_AFTER_NORESET=y
 
 CONFIG_SPIRAM_MEMTEST=
 
diff --git a/ports/esp32/boards/UM_FEATHERS2NEO/sdkconfig.board b/ports/esp32/boards/UM_FEATHERS2NEO/sdkconfig.board
index a624f7fd97fb1..6ef737212f23a 100644
--- a/ports/esp32/boards/UM_FEATHERS2NEO/sdkconfig.board
+++ b/ports/esp32/boards/UM_FEATHERS2NEO/sdkconfig.board
@@ -1,6 +1,5 @@
 CONFIG_ESPTOOLPY_FLASHMODE_QIO=y
 CONFIG_ESPTOOLPY_FLASHFREQ_80M=y
-CONFIG_ESPTOOLPY_AFTER_NORESET=y
 
 # LWIP
 CONFIG_LWIP_LOCAL_HOSTNAME="UMFeatherS2Neo"
diff --git a/ports/esp32/boards/UM_FEATHERS3/sdkconfig.board b/ports/esp32/boards/UM_FEATHERS3/sdkconfig.board
index c557141ebfc9b..3ca0c4b243e28 100644
--- a/ports/esp32/boards/UM_FEATHERS3/sdkconfig.board
+++ b/ports/esp32/boards/UM_FEATHERS3/sdkconfig.board
@@ -1,6 +1,5 @@
 CONFIG_ESPTOOLPY_FLASHMODE_QIO=y
 CONFIG_ESPTOOLPY_FLASHFREQ_80M=y
-CONFIG_ESPTOOLPY_AFTER_NORESET=y
 
 CONFIG_ESPTOOLPY_FLASHSIZE_4MB=
 CONFIG_ESPTOOLPY_FLASHSIZE_8MB=
diff --git a/ports/esp32/boards/UM_NANOS3/sdkconfig.board b/ports/esp32/boards/UM_NANOS3/sdkconfig.board
index 31d7528317a1d..2a39c64337b20 100644
--- a/ports/esp32/boards/UM_NANOS3/sdkconfig.board
+++ b/ports/esp32/boards/UM_NANOS3/sdkconfig.board
@@ -1,6 +1,5 @@
 CONFIG_ESPTOOLPY_FLASHMODE_QIO=y
 CONFIG_ESPTOOLPY_FLASHFREQ_80M=y
-CONFIG_ESPTOOLPY_AFTER_NORESET=y
 
 CONFIG_ESPTOOLPY_FLASHSIZE_4MB=
 CONFIG_ESPTOOLPY_FLASHSIZE_8MB=y
diff --git a/ports/esp32/boards/UM_PROS3/sdkconfig.board b/ports/esp32/boards/UM_PROS3/sdkconfig.board
index 0de84d57d01d9..5752e03e60013 100644
--- a/ports/esp32/boards/UM_PROS3/sdkconfig.board
+++ b/ports/esp32/boards/UM_PROS3/sdkconfig.board
@@ -1,6 +1,5 @@
 CONFIG_ESPTOOLPY_FLASHMODE_QIO=y
 CONFIG_ESPTOOLPY_FLASHFREQ_80M=y
-CONFIG_ESPTOOLPY_AFTER_NORESET=y
 
 CONFIG_ESPTOOLPY_FLASHSIZE_4MB=
 CONFIG_ESPTOOLPY_FLASHSIZE_8MB=
diff --git a/ports/esp32/boards/UM_TINYS2/sdkconfig.board b/ports/esp32/boards/UM_TINYS2/sdkconfig.board
index 0a2097e242141..c09731431b9e0 100644
--- a/ports/esp32/boards/UM_TINYS2/sdkconfig.board
+++ b/ports/esp32/boards/UM_TINYS2/sdkconfig.board
@@ -1,6 +1,5 @@
 CONFIG_ESPTOOLPY_FLASHMODE_QIO=y
 CONFIG_ESPTOOLPY_FLASHFREQ_80M=y
-CONFIG_ESPTOOLPY_AFTER_NORESET=y
 
 # LWIP
 CONFIG_LWIP_LOCAL_HOSTNAME="UMTinyS2"
diff --git a/ports/esp32/boards/UM_TINYS3/sdkconfig.board b/ports/esp32/boards/UM_TINYS3/sdkconfig.board
index d1689aaf394c8..d1d19761a0666 100644
--- a/ports/esp32/boards/UM_TINYS3/sdkconfig.board
+++ b/ports/esp32/boards/UM_TINYS3/sdkconfig.board
@@ -1,6 +1,5 @@
 CONFIG_ESPTOOLPY_FLASHMODE_QIO=y
 CONFIG_ESPTOOLPY_FLASHFREQ_80M=y
-CONFIG_ESPTOOLPY_AFTER_NORESET=y
 
 CONFIG_ESPTOOLPY_FLASHSIZE_4MB=
 CONFIG_ESPTOOLPY_FLASHSIZE_8MB=y
diff --git a/ports/esp32/boards/UM_TINYWATCHS3/sdkconfig.board b/ports/esp32/boards/UM_TINYWATCHS3/sdkconfig.board
index d73f4fe0bc012..1380e15ce8481 100644
--- a/ports/esp32/boards/UM_TINYWATCHS3/sdkconfig.board
+++ b/ports/esp32/boards/UM_TINYWATCHS3/sdkconfig.board
@@ -1,6 +1,5 @@
 CONFIG_ESPTOOLPY_FLASHMODE_QIO=y
 CONFIG_ESPTOOLPY_FLASHFREQ_80M=y
-CONFIG_ESPTOOLPY_AFTER_NORESET=y
 
 CONFIG_ESPTOOLPY_FLASHSIZE_4MB=
 CONFIG_ESPTOOLPY_FLASHSIZE_8MB=y
diff --git a/ports/esp32/modmachine.c b/ports/esp32/modmachine.c
index 759455a59a5d6..5e05a261b70c7 100644
--- a/ports/esp32/modmachine.c
+++ b/ports/esp32/modmachine.c
@@ -222,7 +222,19 @@ static mp_int_t mp_machine_reset_cause(void) {
 
 #if MICROPY_ESP32_USE_BOOTLOADER_RTC
 #include "soc/rtc_cntl_reg.h"
+#include "usb.h"
+#if CONFIG_IDF_TARGET_ESP32S3
+#include "esp32s3/rom/usb/usb_dc.h"
+#include "esp32s3/rom/usb/usb_persist.h"
+#include "esp32s3/rom/usb/chip_usb_dw_wrapper.h"
+#endif
+
 NORETURN static void machine_bootloader_rtc(void) {
+    #if CONFIG_IDF_TARGET_ESP32S3
+    usb_usj_mode();
+    usb_dc_prepare_persist();
+    chip_usb_set_persist_flags(USBDC_BOOT_DFU);
+    #endif
     REG_WRITE(RTC_CNTL_OPTION1_REG, RTC_CNTL_FORCE_DOWNLOAD_BOOT);
     esp_restart();
 }
diff --git a/ports/esp32/mpconfigport.h b/ports/esp32/mpconfigport.h
index dc7c8882c8802..15ff459374d82 100644
--- a/ports/esp32/mpconfigport.h
+++ b/ports/esp32/mpconfigport.h
@@ -207,7 +207,8 @@
 #endif
 
 #if MICROPY_HW_ENABLE_USBDEV
-#define MICROPY_SCHEDULER_STATIC_NODES      (1)
+#define MICROPY_SCHEDULER_STATIC_NODES        (1)
+#define MICROPY_HW_USB_CDC_DTR_RTS_BOOTLOADER (1)
 
 // Enable USB-CDC serial port
 #ifndef MICROPY_HW_USB_CDC
diff --git a/ports/esp32/usb.c b/ports/esp32/usb.c
index f3d8b3e2e372d..a21d0f2dcecb6 100644
--- a/ports/esp32/usb.c
+++ b/ports/esp32/usb.c
@@ -81,6 +81,18 @@ void usb_init(void) {
 
 }
 
+#if CONFIG_IDF_TARGET_ESP32S3
+void usb_usj_mode(void) {
+    // Switch the USB PHY back to Serial/Jtag mode, disabling OTG support
+    // This should be run before jumping to bootloader.
+    usb_del_phy(phy_hdl);
+    usb_phy_config_t phy_conf = {
+        .controller = USB_PHY_CTRL_SERIAL_JTAG,
+    };
+    usb_new_phy(&phy_conf, &phy_hdl);
+}
+#endif
+
 void mp_usbd_port_get_serial_number(char *serial_buf) {
     // use factory default MAC as serial ID
     uint8_t mac[8];
diff --git a/ports/esp32/usb.h b/ports/esp32/usb.h
index 5e5eea34e5694..2bfa3d31aff8b 100644
--- a/ports/esp32/usb.h
+++ b/ports/esp32/usb.h
@@ -29,5 +29,6 @@
 #define MICROPY_HW_USB_CDC_TX_TIMEOUT_MS (500)
 
 void usb_init(void);
+void usb_usj_mode(void);
 
 #endif // MICROPY_INCLUDED_ESP32_USB_H
diff --git a/shared/tinyusb/mp_usbd_cdc.c b/shared/tinyusb/mp_usbd_cdc.c
index c6a88e467d398..344e29fe289c1 100644
--- a/shared/tinyusb/mp_usbd_cdc.c
+++ b/shared/tinyusb/mp_usbd_cdc.c
@@ -138,9 +138,12 @@ void tud_sof_cb(uint32_t frame_count) {
 
 #endif
 
-#if MICROPY_HW_ENABLE_USBDEV && (MICROPY_HW_USB_CDC_1200BPS_TOUCH || MICROPY_HW_USB_CDC)
+#if MICROPY_HW_ENABLE_USBDEV && ( \
+    MICROPY_HW_USB_CDC_1200BPS_TOUCH || \
+    MICROPY_HW_USB_CDC || \
+    MICROPY_HW_USB_CDC_DTR_RTS_BOOTLOADER)
 
-#if MICROPY_HW_USB_CDC_1200BPS_TOUCH
+#if MICROPY_HW_USB_CDC_1200BPS_TOUCH || MICROPY_HW_USB_CDC_DTR_RTS_BOOTLOADER
 static mp_sched_node_t mp_bootloader_sched_node;
 
 static void usbd_cdc_run_bootloader_task(mp_sched_node_t *node) {
@@ -149,6 +152,13 @@ static void usbd_cdc_run_bootloader_task(mp_sched_node_t *node) {
 }
 #endif
 
+#if MICROPY_HW_USB_CDC_DTR_RTS_BOOTLOADER
+static struct {
+    bool dtr : 1;
+    bool rts : 1;
+} prev_line_state = {0};
+#endif
+
 void
 #if MICROPY_HW_USB_EXTERNAL_TINYUSB
 mp_usbd_line_state_cb
@@ -165,6 +175,15 @@ tud_cdc_line_state_cb
         tud_sof_cb_enable(true);
     }
     #endif
+    #if MICROPY_HW_USB_CDC_DTR_RTS_BOOTLOADER
+    if (dtr && !rts) {
+        if (prev_line_state.rts && !prev_line_state.dtr) {
+            mp_sched_schedule_node(&mp_bootloader_sched_node, usbd_cdc_run_bootloader_task);
+        }
+    }
+    prev_line_state.rts = rts;
+    prev_line_state.dtr = dtr;
+    #endif
     #if MICROPY_HW_USB_CDC_1200BPS_TOUCH
     if (dtr == false && rts == false) {
         // Device is disconnected.
diff --git a/shared/tinyusb/mp_usbd_cdc.h b/shared/tinyusb/mp_usbd_cdc.h
index 1abe0fa0a41b3..10c08567feb0e 100644
--- a/shared/tinyusb/mp_usbd_cdc.h
+++ b/shared/tinyusb/mp_usbd_cdc.h
@@ -31,6 +31,12 @@
 #define MICROPY_HW_USB_CDC_TX_TIMEOUT (500)
 #endif
 
+// This is typically only enabled on esp32
+// parts which have an internal usb peripheral.
+#ifndef MICROPY_HW_USB_CDC_DTR_RTS_BOOTLOADER
+#define MICROPY_HW_USB_CDC_DTR_RTS_BOOTLOADER (0)
+#endif
+
 uintptr_t mp_usbd_cdc_poll_interfaces(uintptr_t poll_flags);
 void tud_cdc_rx_cb(uint8_t itf);
 mp_uint_t mp_usbd_cdc_tx_strn(const char *str, mp_uint_t len);