diff --git a/locale/ID.po b/locale/ID.po
index 33767f674f904..21a16f4314b4d 100644
--- a/locale/ID.po
+++ b/locale/ID.po
@@ -4538,7 +4538,7 @@ msgstr ""
 #~ msgstr "Berjalan di mode aman(safe mode)! Auto-reload tidak aktif.\n"
 
 #~ msgid "Running in safe mode! Not running saved code.\n"
-#~ msgstr ""
+#~ msgstr "Berjalan di mode aman(safe mode)! Tidak menjalankan kode yang disimpan.\n"
 #~ "Berjalan di mode aman(safe mode)! tidak menjalankan kode yang tersimpan.\n"
 
 #~ msgid "'async for' or 'async with' outside async function"
diff --git a/locale/circuitpython.pot b/locale/circuitpython.pot
index c04405b99fd44..a6e71b519c497 100644
--- a/locale/circuitpython.pot
+++ b/locale/circuitpython.pot
@@ -710,13 +710,7 @@ msgid "CircuitPython core code crashed hard. Whoops!\n"
 msgstr ""
 
 #: supervisor/shared/safe_mode.c
-msgid ""
-"CircuitPython is in safe mode because you pressed the reset button during "
-"boot. Press again to exit safe mode.\n"
-msgstr ""
-
-#: supervisor/shared/safe_mode.c
-msgid "CircuitPython was unable to allocate the heap.\n"
+msgid "CircuitPython was unable to allocate the heap."
 msgstr ""
 
 #: shared-module/bitbangio/SPI.c
@@ -1634,10 +1628,6 @@ msgstr ""
 msgid "Not playing"
 msgstr ""
 
-#: main.c
-msgid "Not running saved code.\n"
-msgstr ""
-
 #: shared-bindings/_bleio/__init__.c
 msgid "Not settable"
 msgstr ""
@@ -1950,7 +1940,7 @@ msgid "Row entry must be digitalio.DigitalInOut"
 msgstr ""
 
 #: main.c
-msgid "Running in safe mode! "
+msgid "Running in safe mode! Not running saved code.\n"
 msgstr ""
 
 #: shared-module/sdcardio/SDCard.c
@@ -2071,13 +2061,13 @@ msgstr ""
 #: supervisor/shared/safe_mode.c
 msgid ""
 "The CircuitPython heap was corrupted because the stack was too small.\n"
-"Please increase the stack size if you know how, or if not:"
+"Increase the stack size if you know how. If not:"
 msgstr ""
 
 #: supervisor/shared/safe_mode.c
 msgid ""
 "The `microcontroller` module was used to boot into safe mode. Press reset to "
-"exit safe mode.\n"
+"exit safe mode."
 msgstr ""
 
 #: shared-bindings/rgbmatrix/RGBMatrix.c
@@ -2088,7 +2078,7 @@ msgstr ""
 msgid ""
 "The microcontroller's power dipped. Make sure your power supply provides\n"
 "enough power for the whole circuit and press reset (after ejecting "
-"CIRCUITPY).\n"
+"CIRCUITPY)."
 msgstr ""
 
 #: shared-module/audiomixer/MixerVoice.c
@@ -2382,7 +2372,12 @@ msgid "Writes not supported on Characteristic"
 msgstr ""
 
 #: supervisor/shared/safe_mode.c
-msgid "You are in safe mode: something unanticipated happened.\n"
+msgid "You are in safe mode because:\n"
+msgstr ""
+
+#: supervisor/shared/safe_mode.c
+msgid ""
+"You pressed the reset button during boot. Press again to exit safe mode."
 msgstr ""
 
 #: supervisor/shared/safe_mode.c
diff --git a/locale/de_DE.po b/locale/de_DE.po
index 3aaf33b57bfaf..641baa8e04974 100644
--- a/locale/de_DE.po
+++ b/locale/de_DE.po
@@ -732,8 +732,8 @@ msgstr ""
 "zu verlassen.\n"
 
 #: supervisor/shared/safe_mode.c
-msgid "CircuitPython was unable to allocate the heap.\n"
-msgstr "CircuitPython war es nicht möglich heap-Speicher zu allozieren.\n"
+msgid "CircuitPython was unable to allocate the heap."
+msgstr "CircuitPython war es nicht möglich heap-Speicher zu allozieren."
 
 #: shared-module/bitbangio/SPI.c
 msgid "Clock pin init failed."
diff --git a/locale/en_GB.po b/locale/en_GB.po
index 7fbac0439c8fb..ae8e3ff102ef9 100644
--- a/locale/en_GB.po
+++ b/locale/en_GB.po
@@ -729,8 +729,8 @@ msgstr ""
 "boot. Press again to exit safe mode.\n"
 
 #: supervisor/shared/safe_mode.c
-msgid "CircuitPython was unable to allocate the heap.\n"
-msgstr "CircuitPython was unable to allocate the heap.\n"
+msgid "CircuitPython was unable to allocate the heap."
+msgstr "CircuitPython was unable to allocate the heap."
 
 #: shared-module/bitbangio/SPI.c
 msgid "Clock pin init failed."
diff --git a/locale/es.po b/locale/es.po
index 096d413b074d1..7349726454a5c 100644
--- a/locale/es.po
+++ b/locale/es.po
@@ -738,8 +738,8 @@ msgstr ""
 "durante el arranque. Presione nuevamente para salir del modo seguro.\n"
 
 #: supervisor/shared/safe_mode.c
-msgid "CircuitPython was unable to allocate the heap.\n"
-msgstr "CircuitPython no puedo encontrar el montículo.\n"
+msgid "CircuitPython was unable to allocate the heap."
+msgstr "CircuitPython no puedo encontrar el montículo."
 
 #: shared-module/bitbangio/SPI.c
 msgid "Clock pin init failed."
@@ -4777,7 +4777,7 @@ msgstr "zi debe ser una forma (n_section,2)"
 #~ msgstr "Ejecutando en modo seguro! La auto-recarga esta deshabilitada.\n"
 
 #~ msgid "Running in safe mode! Not running saved code.\n"
-#~ msgstr ""
+#~ msgstr "Ejecutando en modo seguro!  No ejecutando el código almacenado.\n"
 #~ "Ejecutando en modo seguro! No se esta ejecutando el código guardado.\n"
 
 #~ msgid "__init__() should return None, not '%s'"
diff --git a/locale/fr.po b/locale/fr.po
index c422a12a51f9f..30be3b6cbee34 100644
--- a/locale/fr.po
+++ b/locale/fr.po
@@ -745,8 +745,8 @@ msgstr ""
 "mode sans échec.\n"
 
 #: supervisor/shared/safe_mode.c
-msgid "CircuitPython was unable to allocate the heap.\n"
-msgstr "CircuitPython n'as pu faire l'allocation de la pile.\n"
+msgid "CircuitPython was unable to allocate the heap."
+msgstr "CircuitPython n'as pu faire l'allocation de la pile."
 
 #: shared-module/bitbangio/SPI.c
 msgid "Clock pin init failed."
diff --git a/locale/hi.po b/locale/hi.po
index 369280fd9d485..566ed31686817 100644
--- a/locale/hi.po
+++ b/locale/hi.po
@@ -716,7 +716,7 @@ msgid ""
 msgstr ""
 
 #: supervisor/shared/safe_mode.c
-msgid "CircuitPython was unable to allocate the heap.\n"
+msgid "CircuitPython was unable to allocate the heap."
 msgstr ""
 
 #: shared-module/bitbangio/SPI.c
diff --git a/locale/ja.po b/locale/ja.po
index 5bb6460559af2..b1ce5591fdcbf 100644
--- a/locale/ja.po
+++ b/locale/ja.po
@@ -727,8 +727,8 @@ msgstr ""
 "度押すとセーフモードを終了します。\n"
 
 #: supervisor/shared/safe_mode.c
-msgid "CircuitPython was unable to allocate the heap.\n"
-msgstr "CircuitPythonはヒープを確保できませんでした\n"
+msgid "CircuitPython was unable to allocate the heap."
+msgstr "CircuitPythonはヒープを確保できませんでした"
 
 #: shared-module/bitbangio/SPI.c
 msgid "Clock pin init failed."
@@ -1966,8 +1966,8 @@ msgid "Row entry must be digitalio.DigitalInOut"
 msgstr "Rowの各要素は digitalio.DigitalInOut でなければなりません"
 
 #: main.c
-msgid "Running in safe mode! "
-msgstr "セーフモードで実行中！ "
+msgid "Running in safe mode! Not running saved code.\n"
+msgstr "セーフモードで実行中！ 保存されたコードは実行していません。\n"
 
 #: shared-module/sdcardio/SDCard.c
 msgid "SD card CSD format not supported"
diff --git a/locale/nl.po b/locale/nl.po
index 475ba432bf5b8..ff030620eb6a3 100644
--- a/locale/nl.po
+++ b/locale/nl.po
@@ -725,8 +725,8 @@ msgstr ""
 "het opstarten. Druk nogmaals om veilige modus te verlaten\n"
 
 #: supervisor/shared/safe_mode.c
-msgid "CircuitPython was unable to allocate the heap.\n"
-msgstr "CircuitPython kon het heap geheugen niet toewijzen.\n"
+msgid "CircuitPython was unable to allocate the heap."
+msgstr "CircuitPython kon het heap geheugen niet toewijzen."
 
 #: shared-module/bitbangio/SPI.c
 msgid "Clock pin init failed."
diff --git a/locale/pl.po b/locale/pl.po
index c419e6aaaa1e2..0a8d30f604c20 100644
--- a/locale/pl.po
+++ b/locale/pl.po
@@ -725,8 +725,8 @@ msgstr ""
 "przycisk resetowania. Naciśnij ponownie, aby wyjść z trybu awaryjnego.\n"
 
 #: supervisor/shared/safe_mode.c
-msgid "CircuitPython was unable to allocate the heap.\n"
-msgstr "CircuitPython nie mógł przydzielić sterty.\n"
+msgid "CircuitPython was unable to allocate the heap."
+msgstr "CircuitPython nie mógł przydzielić sterty."
 
 #: shared-module/bitbangio/SPI.c
 msgid "Clock pin init failed."
diff --git a/locale/pt_BR.po b/locale/pt_BR.po
index dc95cee04751e..8e854609b7ada 100644
--- a/locale/pt_BR.po
+++ b/locale/pt_BR.po
@@ -743,8 +743,8 @@ msgstr ""
 "de segurança.\n"
 
 #: supervisor/shared/safe_mode.c
-msgid "CircuitPython was unable to allocate the heap.\n"
-msgstr "O CircuitPython não conseguiu alocar o heap.\n"
+msgid "CircuitPython was unable to allocate the heap."
+msgstr "O CircuitPython não conseguiu alocar o heap."
 
 #: shared-module/bitbangio/SPI.c
 msgid "Clock pin init failed."
@@ -4818,7 +4818,7 @@ msgstr "zi deve estar na forma (n_section, 2)"
 #~ msgstr "Rodando em modo seguro! Atualização automática está desligada.\n"
 
 #~ msgid "Running in safe mode! Not running saved code.\n"
-#~ msgstr "Rodando em modo seguro! Não está executando o código salvo.\n"
+#~ msgstr "Rodando em modo seguro! O código salvo não está em execução.\n"
 
 #~ msgid "__init__() should return None, not '%s'"
 #~ msgstr "O __init__() deve retornar Nenhum, não '%s'"
diff --git a/locale/sv.po b/locale/sv.po
index 4d511c50cdf63..aaef6de777e8d 100644
--- a/locale/sv.po
+++ b/locale/sv.po
@@ -731,8 +731,8 @@ msgstr ""
 "under start. Tryck igen för att lämna säkert läge.\n"
 
 #: supervisor/shared/safe_mode.c
-msgid "CircuitPython was unable to allocate the heap.\n"
-msgstr "CircuitPython kunde inte allokera heap.\n"
+msgid "CircuitPython was unable to allocate the heap."
+msgstr "CircuitPython kunde inte allokera heap."
 
 #: shared-module/bitbangio/SPI.c
 msgid "Clock pin init failed."
diff --git a/locale/zh_Latn_pinyin.po b/locale/zh_Latn_pinyin.po
index 2978380792999..4a31b32cfa4c8 100644
--- a/locale/zh_Latn_pinyin.po
+++ b/locale/zh_Latn_pinyin.po
@@ -732,8 +732,8 @@ msgstr ""
 "chóng zhì ànniǔ. Zài àn yīcì tuìchū ānquán móshì.\n"
 
 #: supervisor/shared/safe_mode.c
-msgid "CircuitPython was unable to allocate the heap.\n"
-msgstr "CircuitPython wúfǎ fēnpèi duī.\n"
+msgid "CircuitPython was unable to allocate the heap."
+msgstr "CircuitPython wúfǎ fēnpèi duī."
 
 #: shared-module/bitbangio/SPI.c
 msgid "Clock pin init failed."
diff --git a/main.c b/main.c
index 48373b6834884..6904980ae95df 100755
--- a/main.c
+++ b/main.c
@@ -261,18 +261,20 @@ STATIC void print_code_py_status_message(safe_mode_t safe_mode) {
         serial_write_compressed(translate("Auto-reload is off.\n"));
     }
     if (safe_mode != NO_SAFE_MODE) {
-        serial_write_compressed(translate("Running in safe mode! "));
-        serial_write_compressed(translate("Not running saved code.\n"));
+        serial_write_compressed(translate("Running in safe mode! Not running saved code.\n"));
     }
 }
 
 STATIC bool run_code_py(safe_mode_t safe_mode) {
     bool serial_connected_at_start = serial_connected();
+    bool printed_safe_mode_message = false;
     #if CIRCUITPY_AUTORELOAD_DELAY_MS > 0
-    serial_write("\n");
-    print_code_py_status_message(safe_mode);
-    print_safe_mode_message(safe_mode);
-    serial_write("\n");
+    if (serial_connected_at_start) {
+        serial_write("\r\n");
+        print_code_py_status_message(safe_mode);
+        print_safe_mode_message(safe_mode);
+        printed_safe_mode_message = true;
+    }
     #endif
 
     pyexec_result_t result;
@@ -383,8 +385,11 @@ STATIC bool run_code_py(safe_mode_t safe_mode) {
                 print_code_py_status_message(safe_mode);
             }
 
-            print_safe_mode_message(safe_mode);
-            serial_write("\n");
+            if (!printed_safe_mode_message) {
+                print_safe_mode_message(safe_mode);
+                printed_safe_mode_message = true;
+            }
+            serial_write("\r\n");
             serial_write_compressed(translate("Press any key to enter the REPL. Use CTRL-D to reload.\n"));
             printed_press_any_key = true;
         }
@@ -521,7 +526,6 @@ STATIC void __attribute__ ((noinline)) run_boot_py(safe_mode_t safe_mode) {
     usb_set_defaults();
 #endif
 
-    // TODO(tannewt): Re-add support for flashing boot error output.
     if (ok_to_run) {
         bool found_boot = maybe_run_list(boot_py_filenames, NULL);
         (void) found_boot;
diff --git a/ports/atmel-samd/mpconfigport.mk b/ports/atmel-samd/mpconfigport.mk
index 060b17daf5979..8d0ff41768339 100644
--- a/ports/atmel-samd/mpconfigport.mk
+++ b/ports/atmel-samd/mpconfigport.mk
@@ -21,7 +21,7 @@ endif
 INTERNAL_LIBM = 1
 
 # Number of USB endpoint pairs.
-USB_NUM_EP = 8
+USB_NUM_ENDPOINT_PAIRS = 8
 
 CIRCUITPY_ROTARYIO_SOFTENCODER = 1
 
diff --git a/ports/cxd56/mpconfigport.mk b/ports/cxd56/mpconfigport.mk
index 5dbc71825df0c..edc8e6ddf5c1c 100644
--- a/ports/cxd56/mpconfigport.mk
+++ b/ports/cxd56/mpconfigport.mk
@@ -1,7 +1,7 @@
 USB_HIGHSPEED = 1
 
 # Number of USB endpoint pairs.
-USB_NUM_EP = 6
+USB_NUM_ENDPOINT_PAIRS = 6
 
 # Define an equivalent for MICROPY_LONGINT_IMPL, to pass to $(MPY-TOOL) in py/mkrules.mk
 # $(MPY-TOOL) needs to know what kind of longint to use (if any) to freeze long integers.
diff --git a/ports/esp32s2/mpconfigport.mk b/ports/esp32s2/mpconfigport.mk
index 2671c3055801b..a8dded05deb37 100644
--- a/ports/esp32s2/mpconfigport.mk
+++ b/ports/esp32s2/mpconfigport.mk
@@ -27,11 +27,6 @@ CIRCUITPY_ROTARYIO = 1
 CIRCUITPY_NVM = 1
 CIRCUITPY_PS2IO ?= 1
 CIRCUITPY_TOUCHIO_USE_NATIVE ?= 1
-# We don't have enough endpoints to include MIDI.
-CIRCUITPY_USB_MIDI ?= 0
-CIRCUITPY_USB_HID ?= 1
-# We have borrowed the VENDOR nomenclature from tinyusb. VENDOR AKA WEBUSB
-CIRCUITPY_USB_VENDOR ?= 0
 CIRCUITPY_WIFI = 1
 CIRCUITPY_WATCHDOG ?= 1
 
@@ -39,4 +34,14 @@ CIRCUITPY_ESPIDF = 1
 
 CIRCUITPY_MODULE ?= none
 
-USB_NUM_EP = 5
+# From the ESP32-S2 datasheet:
+#
+# Endpoint number 0 always present (bi-directional, consisting of EP0 IN and EP0 OUT)
+# Six additional endpoints (endpoint numbers 1 to 6), configurable as IN or OUT
+# Maximum of five IN endpoints concurrently active at any time (including EP0 IN)
+#
+# Due to the limited number of endpoints, some USB devices will be off by default.
+# For instance MIDI is available, but the device is turned off. It can be turned on
+# only if something else is turned off, such as HID.
+USB_NUM_ENDPOINT_PAIRS = 7
+USB_NUM_IN_ENDPOINTS = 5
diff --git a/ports/litex/mpconfigport.mk b/ports/litex/mpconfigport.mk
index d99b303f6d2c9..ce6ed08841682 100644
--- a/ports/litex/mpconfigport.mk
+++ b/ports/litex/mpconfigport.mk
@@ -7,7 +7,7 @@ MPY_TOOL_LONGINT_IMPL = -mlongint-impl=mpz
 INTERNAL_LIBM = 1
 
 # Number of USB endpoint pairs.
-USB_NUM_EP = 16
+USB_NUM_ENDPOINT_PAIRS = 16
 
 # Longints can be implemented as mpz, as longlong, or not
 LONGINT_IMPL = MPZ
diff --git a/ports/mimxrt10xx/mpconfigport.mk b/ports/mimxrt10xx/mpconfigport.mk
index 31b0dbfdac908..ac5e7fc8eda5f 100644
--- a/ports/mimxrt10xx/mpconfigport.mk
+++ b/ports/mimxrt10xx/mpconfigport.mk
@@ -17,7 +17,7 @@ INTERNAL_LIBM = 1
 USB_HIGHSPEED = 1
 
 # Number of USB endpoint pairs.
-USB_NUM_EP = 8
+USB_NUM_ENDPOINT_PAIRS = 8
 
 INTERNAL_FLASH_FILESYSTEM = 1
 
diff --git a/ports/nrf/mpconfigport.mk b/ports/nrf/mpconfigport.mk
index b00a051479e86..b355b8f652613 100644
--- a/ports/nrf/mpconfigport.mk
+++ b/ports/nrf/mpconfigport.mk
@@ -10,7 +10,7 @@ MPY_TOOL_LONGINT_IMPL = -mlongint-impl=mpz
 INTERNAL_LIBM = 1
 
 # Number of USB endpoint pairs.
-USB_NUM_EP = 8
+USB_NUM_ENDPOINT_PAIRS = 8
 
 # All nRF ports have longints.
 LONGINT_IMPL = MPZ
diff --git a/ports/raspberrypi/mpconfigport.mk b/ports/raspberrypi/mpconfigport.mk
index 75c5d227f00c9..8bc70ed638d60 100644
--- a/ports/raspberrypi/mpconfigport.mk
+++ b/ports/raspberrypi/mpconfigport.mk
@@ -49,6 +49,6 @@ CIRCUITPY_AUDIOMIXER = 1
 INTERNAL_LIBM = 1
 
 # Number of USB endpoint pairs.
-USB_NUM_EP = 8
+USB_NUM_ENDPOINT_PAIRS = 8
 
 INTERNAL_FLASH_FILESYSTEM = 1
diff --git a/ports/stm/boards/espruino_pico/mpconfigboard.mk b/ports/stm/boards/espruino_pico/mpconfigboard.mk
index efbbaa22e2df3..bc415f07ec8f8 100644
--- a/ports/stm/boards/espruino_pico/mpconfigboard.mk
+++ b/ports/stm/boards/espruino_pico/mpconfigboard.mk
@@ -22,6 +22,8 @@ CIRCUITPY_AUDIOPWMIO = 0
 CIRCUITPY_BUSDEVICE = 0
 CIRCUITPY_BITMAPTOOLS = 0
 CIRCUITPY_FRAMEBUFFERIO = 0
+CIRCUITPY_MIDI = 0
+CIRCUITPY_MSGPACK = 0
 CIRCUITPY_ULAB = 0
 CIRCUITPY_VECTORIO = 0
 
diff --git a/ports/stm/boards/pyb_nano_v2/mpconfigboard.mk b/ports/stm/boards/pyb_nano_v2/mpconfigboard.mk
index 5824e65a29f4d..99af948d7bb7e 100644
--- a/ports/stm/boards/pyb_nano_v2/mpconfigboard.mk
+++ b/ports/stm/boards/pyb_nano_v2/mpconfigboard.mk
@@ -16,3 +16,5 @@ LD_FILE = boards/STM32F411_fs.ld
 # Too big for the flash
 CIRCUITPY_AUDIOCORE = 0
 CIRCUITPY_AUDIOPWMIO = 0
+CIRCUITPY_MIDI = 0
+CIRCUITPY_MSGPACK = 0
diff --git a/ports/stm/boards/stm32f411ve_discovery/mpconfigboard.mk b/ports/stm/boards/stm32f411ve_discovery/mpconfigboard.mk
index 3180fbd0845e0..04c8cc2d4503a 100644
--- a/ports/stm/boards/stm32f411ve_discovery/mpconfigboard.mk
+++ b/ports/stm/boards/stm32f411ve_discovery/mpconfigboard.mk
@@ -15,3 +15,5 @@ LD_FILE = boards/STM32F411_fs.ld
 # Too big for the flash
 CIRCUITPY_AUDIOCORE = 0
 CIRCUITPY_AUDIOPWMIO = 0
+CIRCUITPY_MIDI = 0
+CIRCUITPY_MSGPACK = 0
diff --git a/ports/stm/mpconfigport.mk b/ports/stm/mpconfigport.mk
index ae021426dfded..551d2661d4046 100644
--- a/ports/stm/mpconfigport.mk
+++ b/ports/stm/mpconfigport.mk
@@ -7,7 +7,7 @@ ifeq ($(MCU_VARIANT),$(filter $(MCU_VARIANT),STM32F405xx STM32F407xx))
         CIRCUITPY_FRAMEBUFFERIO ?= 1
         CIRCUITPY_SDIOIO ?= 1
         # Number of USB endpoint pairs.
-        USB_NUM_EP = 4
+        USB_NUM_ENDPOINT_PAIRS = 4
 endif
 
 ifeq ($(MCU_SERIES),F4)
@@ -24,10 +24,7 @@ ifeq ($(MCU_SERIES),F4)
         CIRCUITPY_NVM ?= 0
         CIRCUITPY_ROTARYIO ?= 0
         CIRCUITPY_RTC ?= 0
-        CIRCUITPY_USB_MIDI ?= 0
-        CIRCUITPY_USB_HID ?= 0
-
-        USB_NUM_EP = 4
+        USB_NUM_ENDPOINT_PAIRS = 4
 endif
 
 ifeq ($(MCU_SERIES),H7)
@@ -44,10 +41,8 @@ ifeq ($(MCU_SERIES),H7)
 	CIRCUITPY_PWMIO ?= 0
         CIRCUITPY_ROTARYIO ?= 0
         CIRCUITPY_RTC ?= 0
-        CIRCUITPY_USB_HID ?= 0
-        CIRCUITPY_USB_MIDI ?= 0
 
-        USB_NUM_EP = 9
+        USB_NUM_ENDPOINT_PAIRS = 9
 endif
 
 ifeq ($(MCU_SERIES),F7)
@@ -62,8 +57,6 @@ ifeq ($(MCU_SERIES),F7)
         CIRCUITPY_NVM ?= 0
         CIRCUITPY_ROTARYIO ?= 0
         CIRCUITPY_RTC ?= 0
-        CIRCUITPY_USB_HID ?= 0
-        CIRCUITPY_USB_MIDI ?= 0
 
-        USB_NUM_EP = 6
+        USB_NUM_ENDPOINT_PAIRS = 6
 endif
diff --git a/py/circuitpy_mpconfig.mk b/py/circuitpy_mpconfig.mk
index c7b83dba2104b..eec52ca5fc894 100644
--- a/py/circuitpy_mpconfig.mk
+++ b/py/circuitpy_mpconfig.mk
@@ -338,8 +338,18 @@ CFLAGS += -DCIRCUITPY_UHEAP=$(CIRCUITPY_UHEAP)
 CIRCUITPY_USB ?= 1
 CFLAGS += -DCIRCUITPY_USB=$(CIRCUITPY_USB)
 
-# Compute this value once, so the shell command is not reinvoked many times.
-USB_NUM_EP_8_OR_GREATER := $(shell expr $(USB_NUM_EP) '>=' 8)
+# Compute these value once, so the shell command is not reinvoked many times.
+USB_NUM_ENDPOINT_PAIRS_5_OR_GREATER := $(shell expr $(USB_NUM_ENDPOINT_PAIRS) '>=' 5)
+USB_NUM_ENDPOINT_PAIRS_8_OR_GREATER := $(shell expr $(USB_NUM_ENDPOINT_PAIRS) '>=' 8)
+
+# Some chips may not support the same number of IN or OUT endpoints as pairs.
+# For instance, the ESP32-S2 only supports 5 IN endpoints at once, even though
+# it has 7 endpoint pairs.
+USB_NUM_IN_ENDPOINTS ?= $(USB_NUM_ENDPOINT_PAIRS)
+CFLAGS += -DUSB_NUM_IN_ENDPOINTS=$(USB_NUM_IN_ENDPOINTS)
+
+USB_NUM_OUT_ENDPOINTS ?= $(USB_NUM_ENDPOINT_PAIRS)
+CFLAGS += -DUSB_NUM_OUT_ENDPOINTS=$(USB_NUM_OUT_ENDPOINTS)
 
 CIRCUITPY_USB_CDC ?= 1
 CFLAGS += -DCIRCUITPY_USB_CDC=$(CIRCUITPY_USB_CDC)
@@ -348,20 +358,21 @@ CFLAGS += -DCIRCUITPY_USB_CDC_CONSOLE_ENABLED_DEFAULT=$(CIRCUITPY_USB_CDC_CONSOL
 CIRCUITPY_USB_CDC_DATA_ENABLED_DEFAULT ?= 0
 CFLAGS += -DCIRCUITPY_USB_CDC_DATA_ENABLED_DEFAULT=$(CIRCUITPY_USB_CDC_DATA_ENABLED_DEFAULT)
 
+# HID is available by default, but is not turned on if there are fewer than 5 endpoints.
 CIRCUITPY_USB_HID ?= 1
 CFLAGS += -DCIRCUITPY_USB_HID=$(CIRCUITPY_USB_HID)
-CIRCUITPY_USB_HID_ENABLED_DEFAULT = $(CIRCUITPY_USB_HID)
+CIRCUITPY_USB_HID_ENABLED_DEFAULT ?= $(USB_NUM_ENDPOINT_PAIRS_5_OR_GREATER)
 CFLAGS += -DCIRCUITPY_USB_HID_ENABLED_DEFAULT=$(CIRCUITPY_USB_HID_ENABLED_DEFAULT)
 
-# MIDI is usually available if there are at least 8 endpoints.
-CIRCUITPY_USB_MIDI ?= $(USB_NUM_EP_8_OR_GREATER)
+# MIDI is available by default, but is not turned on if there are fewer than 8 endpoints.
+CIRCUITPY_USB_MIDI ?= 1
 CFLAGS += -DCIRCUITPY_USB_MIDI=$(CIRCUITPY_USB_MIDI)
-CIRCUITPY_USB_MIDI_ENABLED_DEFAULT = $(CIRCUITPY_USB_MIDI)
+CIRCUITPY_USB_MIDI_ENABLED_DEFAULT ?= $(USB_NUM_ENDPOINT_PAIRS_8_OR_GREATER)
 CFLAGS += -DCIRCUITPY_USB_MIDI_ENABLED_DEFAULT=$(CIRCUITPY_USB_MIDI_ENABLED_DEFAULT)
 
 CIRCUITPY_USB_MSC ?= 1
 CFLAGS += -DCIRCUITPY_USB_MSC=$(CIRCUITPY_USB_MSC)
-CIRCUITPY_USB_MSC_ENABLED_DEFAULT = $(CIRCUITPY_USB_MSC)
+CIRCUITPY_USB_MSC_ENABLED_DEFAULT ?= $(CIRCUITPY_USB_MSC)
 CFLAGS += -DCIRCUITPY_USB_MSC_ENABLED_DEFAULT=$(CIRCUITPY_USB_MSC_ENABLED_DEFAULT)
 
 # Defaulting this to OFF initially because it has only been tested on a
@@ -370,10 +381,10 @@ CFLAGS += -DCIRCUITPY_USB_MSC_ENABLED_DEFAULT=$(CIRCUITPY_USB_MSC_ENABLED_DEFAUL
 CIRCUITPY_USB_VENDOR ?= 0
 CFLAGS += -DCIRCUITPY_USB_VENDOR=$(CIRCUITPY_USB_VENDOR)
 
-ifndef USB_NUM_EP
-$(error "USB_NUM_EP (number of USB endpoint pairs)must be defined")
+ifndef USB_NUM_ENDPOINT_PAIRS
+$(error "USB_NUM_ENDPOINT_PAIRS (number of USB endpoint pairs)must be defined")
 endif
-CFLAGS += -DUSB_NUM_EP=$(USB_NUM_EP)
+CFLAGS += -DUSB_NUM_ENDPOINT_PAIRS=$(USB_NUM_ENDPOINT_PAIRS)
 
 # For debugging.
 CIRCUITPY_USTACK ?= 0
diff --git a/shared-bindings/storage/__init__.c b/shared-bindings/storage/__init__.c
index 754b6866c879f..f19aaa4396468 100644
--- a/shared-bindings/storage/__init__.c
+++ b/shared-bindings/storage/__init__.c
@@ -176,7 +176,13 @@ MP_DEFINE_CONST_FUN_OBJ_0(storage_disable_usb_drive_obj, storage_disable_usb_dri
 //|     """Enabled presenting ``CIRCUITPY`` as a USB mass storage device.
 //|     By default, the device is enabled and ``CIRCUITPY`` is visible,
 //|     so you do not normally need to call this function.
-//|     Can be called in ``boot.py``, before USB is connected."""
+//|     Can be called in ``boot.py``, before USB is connected.
+//|
+//|     If you enable too many devices at once, you will run out of USB endpoints.
+//|     The number of available endpoints varies by microcontroller.
+//|     CircuitPython will go into safe mode after running boot.py to inform you if
+//|     not enough endpoints are available.
+//|     """
 //|     ...
 //|
 STATIC mp_obj_t storage_enable_usb_drive(void) {
diff --git a/shared-bindings/usb_cdc/__init__.c b/shared-bindings/usb_cdc/__init__.c
index 557c06a3ec35b..f16373fa7324a 100644
--- a/shared-bindings/usb_cdc/__init__.c
+++ b/shared-bindings/usb_cdc/__init__.c
@@ -82,7 +82,13 @@ MP_DEFINE_CONST_FUN_OBJ_0(usb_cdc_disable_obj, usb_cdc_disable);
 //|     :param console bool: Enable or disable the `console` USB serial device.
 //|       True to enable; False to disable. Enabled by default.
 //|     :param data bool: Enable or disable the `data` USB serial device.
-//|       True to enable; False to disable. *Disabled* by default."""
+//|       True to enable; False to disable. *Disabled* by default.
+//|
+//|     If you enable too many devices at once, you will run out of USB endpoints.
+//|     The number of available endpoints varies by microcontroller.
+//|     CircuitPython will go into safe mode after running boot.py to inform you if
+//|     not enough endpoints are available.
+//|     """
 //|     ...
 //|
 STATIC mp_obj_t usb_cdc_enable(size_t n_args, const mp_obj_t *pos_args, mp_map_t *kw_args) {
diff --git a/shared-bindings/usb_hid/__init__.c b/shared-bindings/usb_hid/__init__.c
index 8e85cc67f03c7..f5a7c1cf725d3 100644
--- a/shared-bindings/usb_hid/__init__.c
+++ b/shared-bindings/usb_hid/__init__.c
@@ -37,12 +37,21 @@
 //|
 
 //| devices: Tuple[Device, ...]
-//| """Tuple of all active HID device interfaces."""
+//| """Tuple of all active HID device interfaces.
+//| The default set of devices is ``Device.KEYBOARD, Device.MOUSE, Device.CONSUMER_CONTROL``,
+//| On boards where `usb_hid` is disabled by default, `devices` is an empty tuple.
+//| """
 //|
 
 //| def disable() -> None:
 //|     """Do not present any USB HID devices to the host computer.
-//|     Can be called in ``boot.py``, before USB is connected."""
+//|     Can be called in ``boot.py``, before USB is connected.
+//|     The HID composite device is normally enabled by default,
+//|     but on some boards with limited endpoints, including STM32F4,
+//|     it is disabled by default. You must turn off another USB device such
+//|     as `usb_cdc` or `storage` to free up endpoints for use by `usb_hid`.
+//|     """
+//|
 STATIC mp_obj_t usb_hid_disable(void) {
     if (!common_hal_usb_hid_disable()) {
         mp_raise_RuntimeError(translate("Cannot change USB devices now"));
@@ -59,6 +68,11 @@ MP_DEFINE_CONST_FUN_OBJ_0(usb_hid_disable_obj, usb_hid_disable);
 //|       If `devices` is empty, HID is disabled. The order of the ``Devices``
 //|       may matter to the host. For instance, for MacOS, put the mouse device
 //|       before any Gamepad or Digitizer HID device or else it will not work.
+//|
+//|     If you enable too many devices at once, you will run out of USB endpoints.
+//|     The number of available endpoints varies by microcontroller.
+//|     CircuitPython will go into safe mode after running boot.py to inform you if
+//|     not enough endpoints are available.
 //|     """
 //|     ...
 //|
diff --git a/shared-bindings/usb_midi/__init__.c b/shared-bindings/usb_midi/__init__.c
index a3ed06dd8c71d..9c583fb78e556 100644
--- a/shared-bindings/usb_midi/__init__.c
+++ b/shared-bindings/usb_midi/__init__.c
@@ -45,7 +45,8 @@
 
 //| def disable() -> None:
 //|     """Disable presenting a USB MIDI device to the host.
-//|     The device is normally enabled by default.
+//|     The device is normally enabled by default, but on some boards with limited endpoints
+//|     including ESP32-S2 and certain STM boards, it is disabled by default.
 //|     Can be called in ``boot.py``, before USB is connected."""
 //|     ...
 //|
@@ -60,7 +61,13 @@ MP_DEFINE_CONST_FUN_OBJ_0(usb_midi_disable_obj, usb_midi_disable);
 //| def enable() -> None:
 //|     """Enable presenting a USB MIDI device to the host.
 //|     The device is enabled by default, so you do not normally need to call this function.
-//|     Can be called in ``boot.py``, before USB is connected."""
+//|     Can be called in ``boot.py``, before USB is connected.
+//|
+//|     If you enable too many devices at once, you will run out of USB endpoints.
+//|     The number of available endpoints varies by microcontroller.
+//|     CircuitPython will go into safe mode after running boot.py to inform you if
+//|     not enough endpoints are available.
+//|     """
 //|     ...
 //|
 STATIC mp_obj_t usb_midi_enable(void) {
diff --git a/shared-module/storage/__init__.c b/shared-module/storage/__init__.c
index b1d038a7d30de..cbe72c6f161a2 100644
--- a/shared-module/storage/__init__.c
+++ b/shared-module/storage/__init__.c
@@ -93,14 +93,18 @@ size_t storage_usb_descriptor_length(void) {
 
 static const char storage_interface_name[] = USB_INTERFACE_NAME " Mass Storage";
 
-size_t storage_usb_add_descriptor(uint8_t *descriptor_buf, uint8_t *current_interface, uint8_t *current_endpoint, uint8_t *current_interface_string) {
+size_t storage_usb_add_descriptor(uint8_t *descriptor_buf, descriptor_counts_t *descriptor_counts, uint8_t *current_interface_string) {
     memcpy(descriptor_buf, usb_msc_descriptor_template, sizeof(usb_msc_descriptor_template));
-    descriptor_buf[MSC_INTERFACE_INDEX] = *current_interface;
-    (*current_interface)++;
-
-    descriptor_buf[MSC_IN_ENDPOINT_INDEX] = 0x80 | (USB_MSC_EP_NUM_IN ? USB_MSC_EP_NUM_IN : *current_endpoint);
-    descriptor_buf[MSC_OUT_ENDPOINT_INDEX] = USB_MSC_EP_NUM_OUT ? USB_MSC_EP_NUM_OUT : *current_endpoint;
-    (*current_endpoint)++;
+    descriptor_buf[MSC_INTERFACE_INDEX] = descriptor_counts->current_interface;
+    descriptor_counts->current_interface++;
+
+    descriptor_buf[MSC_IN_ENDPOINT_INDEX] =
+        0x80 | (USB_MSC_EP_NUM_IN ? USB_MSC_EP_NUM_IN : descriptor_counts->current_endpoint);
+    descriptor_counts->num_in_endpoints++;
+    descriptor_buf[MSC_OUT_ENDPOINT_INDEX] =
+        USB_MSC_EP_NUM_OUT ? USB_MSC_EP_NUM_OUT : descriptor_counts->current_endpoint;
+    descriptor_counts->num_out_endpoints++;
+    descriptor_counts->current_endpoint++;
 
     usb_add_interface_string(*current_interface_string, storage_interface_name);
     descriptor_buf[MSC_INTERFACE_STRING_INDEX] = *current_interface_string;
diff --git a/shared-module/storage/__init__.h b/shared-module/storage/__init__.h
index addc8e3d05d77..a07e2c2e0e720 100644
--- a/shared-module/storage/__init__.h
+++ b/shared-module/storage/__init__.h
@@ -28,12 +28,13 @@
 #define SHARED_MODULE_STORAGE___INIT___H
 
 #include "py/mpconfig.h"
+#include "supervisor/usb.h"
 
 #if CIRCUITPY_USB
 bool storage_usb_enabled(void);
 void storage_usb_set_defaults(void);
 size_t storage_usb_descriptor_length(void);
-size_t storage_usb_add_descriptor(uint8_t *descriptor_buf, uint8_t *current_interface, uint8_t *current_endpoint, uint8_t *current_interface_string);
+size_t storage_usb_add_descriptor(uint8_t *descriptor_buf, descriptor_counts_t *descriptor_counts, uint8_t *current_interface_string);
 #endif
 
 #endif // SHARED_MODULE_STORAGE___INIT___H
diff --git a/shared-module/usb_cdc/__init__.c b/shared-module/usb_cdc/__init__.c
index 446c65931e038..c5da1f41e0379 100644
--- a/shared-module/usb_cdc/__init__.c
+++ b/shared-module/usb_cdc/__init__.c
@@ -173,37 +173,39 @@ size_t usb_cdc_descriptor_length(void) {
     return sizeof(usb_cdc_descriptor_template);
 }
 
-size_t usb_cdc_add_descriptor(uint8_t *descriptor_buf, uint8_t *current_interface, uint8_t *current_endpoint, uint8_t *current_interface_string, bool console) {
+size_t usb_cdc_add_descriptor(uint8_t *descriptor_buf, descriptor_counts_t *descriptor_counts, uint8_t *current_interface_string, bool console) {
     memcpy(descriptor_buf, usb_cdc_descriptor_template, sizeof(usb_cdc_descriptor_template));
 
     // Store comm interface number.
-    descriptor_buf[CDC_FIRST_INTERFACE_INDEX] = *current_interface;
-    descriptor_buf[CDC_COMM_INTERFACE_INDEX] = *current_interface;
-    descriptor_buf[CDC_UNION_MASTER_INTERFACE_INDEX] = *current_interface;
-    (*current_interface)++;
+    descriptor_buf[CDC_FIRST_INTERFACE_INDEX] = descriptor_counts->current_interface;
+    descriptor_buf[CDC_COMM_INTERFACE_INDEX] = descriptor_counts->current_interface;
+    descriptor_buf[CDC_UNION_MASTER_INTERFACE_INDEX] = descriptor_counts->current_interface;
+    descriptor_counts->current_interface++;
 
     // Now store data interface number.
-    descriptor_buf[CDC_CALL_MANAGEMENT_DATA_INTERFACE_INDEX] = *current_interface;
-    descriptor_buf[CDC_UNION_SLAVE_INTERFACE_INDEX] = *current_interface;
-    descriptor_buf[CDC_DATA_INTERFACE_INDEX] = *current_interface;
-    (*current_interface)++;
+    descriptor_buf[CDC_CALL_MANAGEMENT_DATA_INTERFACE_INDEX] = descriptor_counts->current_interface;
+    descriptor_buf[CDC_UNION_SLAVE_INTERFACE_INDEX] = descriptor_counts->current_interface;
+    descriptor_buf[CDC_DATA_INTERFACE_INDEX] = descriptor_counts->current_interface;
+    descriptor_counts->current_interface++;
 
     descriptor_buf[CDC_CONTROL_IN_ENDPOINT_INDEX] = 0x80 | (
         console
-        ? (USB_CDC_EP_NUM_NOTIFICATION ? USB_CDC_EP_NUM_NOTIFICATION : *current_endpoint)
-        : (USB_CDC2_EP_NUM_NOTIFICATION ? USB_CDC2_EP_NUM_NOTIFICATION : *current_endpoint));
-    (*current_endpoint)++;
-
-    descriptor_buf[CDC_DATA_OUT_ENDPOINT_INDEX] =
-        console
-        ? (USB_CDC_EP_NUM_DATA_OUT ? USB_CDC_EP_NUM_DATA_OUT : *current_endpoint)
-        : (USB_CDC2_EP_NUM_DATA_OUT ? USB_CDC2_EP_NUM_DATA_OUT : *current_endpoint);
+        ? (USB_CDC_EP_NUM_NOTIFICATION ? USB_CDC_EP_NUM_NOTIFICATION : descriptor_counts->current_endpoint)
+        : (USB_CDC2_EP_NUM_NOTIFICATION ? USB_CDC2_EP_NUM_NOTIFICATION : descriptor_counts->current_endpoint));
+    descriptor_counts->num_in_endpoints++;
+    descriptor_counts->current_endpoint++;
 
     descriptor_buf[CDC_DATA_IN_ENDPOINT_INDEX] = 0x80 | (
         console
-        ? (USB_CDC_EP_NUM_DATA_IN ? USB_CDC_EP_NUM_DATA_IN : *current_endpoint)
-        : (USB_CDC2_EP_NUM_DATA_IN ? USB_CDC2_EP_NUM_DATA_IN : *current_endpoint));
-    (*current_endpoint)++;
+        ? (USB_CDC_EP_NUM_DATA_IN ? USB_CDC_EP_NUM_DATA_IN : descriptor_counts->current_endpoint)
+        : (USB_CDC2_EP_NUM_DATA_IN ? USB_CDC2_EP_NUM_DATA_IN : descriptor_counts->current_endpoint));
+    descriptor_counts->num_in_endpoints++;
+    descriptor_buf[CDC_DATA_OUT_ENDPOINT_INDEX] =
+        console
+        ? (USB_CDC_EP_NUM_DATA_OUT ? USB_CDC_EP_NUM_DATA_OUT : descriptor_counts->current_endpoint)
+        : (USB_CDC2_EP_NUM_DATA_OUT ? USB_CDC2_EP_NUM_DATA_OUT : descriptor_counts->current_endpoint);
+    descriptor_counts->num_out_endpoints++;
+    descriptor_counts->current_endpoint++;
 
     usb_add_interface_string(*current_interface_string,
         console ? console_cdc_comm_interface_name : data_cdc_comm_interface_name);
diff --git a/shared-module/usb_cdc/__init__.h b/shared-module/usb_cdc/__init__.h
index ae39143017816..5195c964e25e8 100644
--- a/shared-module/usb_cdc/__init__.h
+++ b/shared-module/usb_cdc/__init__.h
@@ -29,6 +29,7 @@
 
 #include "py/mpconfig.h"
 #include "py/objtuple.h"
+#include "supervisor/usb.h"
 
 bool usb_cdc_console_enabled(void);
 bool usb_cdc_data_enabled(void);
@@ -36,6 +37,6 @@ bool usb_cdc_data_enabled(void);
 void usb_cdc_set_defaults(void);
 
 size_t usb_cdc_descriptor_length(void);
-size_t usb_cdc_add_descriptor(uint8_t *descriptor_buf, uint8_t *current_interface, uint8_t *current_endpoint, uint8_t *current_interface_string, bool repl);
+size_t usb_cdc_add_descriptor(uint8_t *descriptor_buf, descriptor_counts_t *descriptor_counts, uint8_t *current_interface_string, bool console);
 
 #endif /* SHARED_MODULE_USB_CDC___INIT___H */
diff --git a/shared-module/usb_hid/__init__.c b/shared-module/usb_hid/__init__.c
index c1df75b9d813c..a92fd0c725254 100644
--- a/shared-module/usb_hid/__init__.c
+++ b/shared-module/usb_hid/__init__.c
@@ -113,11 +113,11 @@ size_t usb_hid_descriptor_length(void) {
 static const char usb_hid_interface_name[] = USB_INTERFACE_NAME " HID";
 
 // This is the interface descriptor, not the report descriptor.
-size_t usb_hid_add_descriptor(uint8_t *descriptor_buf, uint8_t *current_interface, uint8_t *current_endpoint, uint8_t *current_interface_string, uint16_t report_descriptor_length) {
+size_t usb_hid_add_descriptor(uint8_t *descriptor_buf, descriptor_counts_t *descriptor_counts, uint8_t *current_interface_string, uint16_t report_descriptor_length) {
     memcpy(descriptor_buf, usb_hid_descriptor_template, sizeof(usb_hid_descriptor_template));
 
-    descriptor_buf[HID_DESCRIPTOR_INTERFACE_INDEX] = *current_interface;
-    (*current_interface)++;
+    descriptor_buf[HID_DESCRIPTOR_INTERFACE_INDEX] = descriptor_counts->current_interface;
+    descriptor_counts->current_interface++;
 
     usb_add_interface_string(*current_interface_string, usb_hid_interface_name);
     descriptor_buf[HID_DESCRIPTOR_INTERFACE_STRING_INDEX] = *current_interface_string;
@@ -126,9 +126,13 @@ size_t usb_hid_add_descriptor(uint8_t *descriptor_buf, uint8_t *current_interfac
     descriptor_buf[HID_DESCRIPTOR_LENGTH_INDEX] = report_descriptor_length & 0xFF;
     descriptor_buf[HID_DESCRIPTOR_LENGTH_INDEX + 1] = (report_descriptor_length >> 8);
 
-    descriptor_buf[HID_IN_ENDPOINT_INDEX] = 0x80 | (USB_HID_EP_NUM_IN ? USB_HID_EP_NUM_IN : *current_endpoint);
-    descriptor_buf[HID_OUT_ENDPOINT_INDEX] = USB_HID_EP_NUM_OUT ? USB_HID_EP_NUM_OUT : *current_endpoint;
-    (*current_endpoint)++;
+    descriptor_buf[HID_IN_ENDPOINT_INDEX] =
+        0x80 | (USB_HID_EP_NUM_IN ? USB_HID_EP_NUM_IN : descriptor_counts->current_endpoint);
+    descriptor_counts->num_in_endpoints++;
+    descriptor_buf[HID_OUT_ENDPOINT_INDEX] =
+        USB_HID_EP_NUM_OUT ? USB_HID_EP_NUM_OUT : descriptor_counts->current_endpoint;
+    descriptor_counts->num_out_endpoints++;
+    descriptor_counts->current_endpoint++;
 
     return sizeof(usb_hid_descriptor_template);
 }
diff --git a/shared-module/usb_hid/__init__.h b/shared-module/usb_hid/__init__.h
index 24a4d57a69230..5069effd3d857 100644
--- a/shared-module/usb_hid/__init__.h
+++ b/shared-module/usb_hid/__init__.h
@@ -28,13 +28,14 @@
 #define SHARED_MODULE_USB_HID___INIT___H
 
 #include "shared-module/usb_hid/Device.h"
+#include "supervisor/usb.h"
 
 extern usb_hid_device_obj_t usb_hid_devices[];
 
 bool usb_hid_enabled(void);
 void usb_hid_set_defaults(void);
 
-size_t usb_hid_add_descriptor(uint8_t *descriptor_buf, uint8_t *current_interface, uint8_t *current_endpoint, uint8_t *current_interface_string, uint16_t report_descriptor_length);
+size_t usb_hid_add_descriptor(uint8_t *descriptor_buf, descriptor_counts_t *descriptor_counts, uint8_t *current_interface_string, uint16_t report_descriptor_length);
 size_t usb_hid_descriptor_length(void);
 size_t usb_hid_report_descriptor_length(void);
 
diff --git a/shared-module/usb_midi/__init__.c b/shared-module/usb_midi/__init__.c
index c258d35c23a64..ac2e05adcb849 100644
--- a/shared-module/usb_midi/__init__.c
+++ b/shared-module/usb_midi/__init__.c
@@ -175,36 +175,38 @@ static const char midi_audio_control_interface_name[] = USB_INTERFACE_NAME " Aud
 static const char midi_in_jack_name[] = USB_INTERFACE_NAME " usb_midi.ports[0]";
 static const char midi_out_jack_name[] = USB_INTERFACE_NAME " usb_midi.ports[0]";
 
-size_t usb_midi_add_descriptor(uint8_t *descriptor_buf, uint8_t *current_interface, uint8_t *current_endpoint, uint8_t *current_interface_string) {
+size_t usb_midi_add_descriptor(uint8_t *descriptor_buf, descriptor_counts_t *descriptor_counts, uint8_t *current_interface_string) {
     memcpy(descriptor_buf, usb_midi_descriptor_template, sizeof(usb_midi_descriptor_template));
 
-    descriptor_buf[MIDI_AUDIO_CONTROL_INTERFACE_NUMBER_INDEX] = *current_interface;
-    (*current_interface)++;
+    descriptor_buf[MIDI_AUDIO_CONTROL_INTERFACE_NUMBER_INDEX] = descriptor_counts->current_interface;
+    descriptor_counts->current_interface++;
 
     descriptor_buf[MIDI_STREAMING_IN_ENDPOINT_INDEX] =
-        0x80 | (USB_MIDI_EP_NUM_IN ? USB_MIDI_EP_NUM_IN : *current_endpoint);
+        0x80 | (USB_MIDI_EP_NUM_IN ? USB_MIDI_EP_NUM_IN : descriptor_counts->current_endpoint);
+    descriptor_counts->num_in_endpoints++;
     descriptor_buf[MIDI_STREAMING_OUT_ENDPOINT_INDEX] =
-        USB_MIDI_EP_NUM_OUT ? USB_MIDI_EP_NUM_OUT : *current_endpoint;
-    (*current_endpoint)++;
+        USB_MIDI_EP_NUM_OUT ? USB_MIDI_EP_NUM_OUT : descriptor_counts->current_endpoint;
+    descriptor_counts->num_out_endpoints++;
+    descriptor_counts->current_endpoint++;
 
-    descriptor_buf[MIDI_STREAMING_INTERFACE_NUMBER_INDEX] = *current_interface;
-    descriptor_buf[MIDI_STREAMING_INTERFACE_NUMBER_INDEX_2] = *current_interface;
-    (*current_interface)++;
+    descriptor_buf[MIDI_STREAMING_INTERFACE_NUMBER_INDEX] = descriptor_counts->current_interface;
+    descriptor_buf[MIDI_STREAMING_INTERFACE_NUMBER_INDEX_2] = descriptor_counts->current_interface;
+    descriptor_counts->current_interface++;
 
     usb_add_interface_string(*current_interface_string, midi_streaming_interface_name);
-    descriptor_buf[MIDI_STREAMING_INTERFACE_STRING_INDEX] = *current_interface;
+    descriptor_buf[MIDI_STREAMING_INTERFACE_STRING_INDEX] = *current_interface_string;
     (*current_interface_string)++;
 
     usb_add_interface_string(*current_interface_string, midi_audio_control_interface_name);
-    descriptor_buf[MIDI_AUDIO_CONTROL_INTERFACE_STRING_INDEX] = *current_interface;
+    descriptor_buf[MIDI_AUDIO_CONTROL_INTERFACE_STRING_INDEX] = *current_interface_string;
     (*current_interface_string)++;
 
     usb_add_interface_string(*current_interface_string, midi_in_jack_name);
-    descriptor_buf[MIDI_IN_JACK_STRING_INDEX] = *current_interface;
+    descriptor_buf[MIDI_IN_JACK_STRING_INDEX] = *current_interface_string;
     (*current_interface_string)++;
 
     usb_add_interface_string(*current_interface_string, midi_out_jack_name);
-    descriptor_buf[MIDI_OUT_JACK_STRING_INDEX] = *current_interface;
+    descriptor_buf[MIDI_OUT_JACK_STRING_INDEX] = *current_interface_string;
     (*current_interface_string)++;
 
     return sizeof(usb_midi_descriptor_template);
diff --git a/shared-module/usb_midi/__init__.h b/shared-module/usb_midi/__init__.h
index 9ab61e12dbe06..8cc430efe338e 100644
--- a/shared-module/usb_midi/__init__.h
+++ b/shared-module/usb_midi/__init__.h
@@ -27,11 +27,13 @@
 #ifndef SHARED_MODULE_USB_MIDI___INIT___H
 #define SHARED_MODULE_USB_MIDI___INIT___H
 
+#include "supervisor/usb.h"
+
 bool usb_midi_enabled(void);
 void usb_midi_set_defaults(void);
 void usb_midi_setup_ports(void);
 
 size_t usb_midi_descriptor_length(void);
-size_t usb_midi_add_descriptor(uint8_t *descriptor_buf, uint8_t *current_interface, uint8_t *current_endpoint, uint8_t *current_interface_string);
+size_t usb_midi_add_descriptor(uint8_t *descriptor_buf, descriptor_counts_t *descriptor_counts, uint8_t *current_interface_string);
 
 #endif /* SHARED_MODULE_USB_MIDI___INIT___H */
diff --git a/supervisor/shared/safe_mode.c b/supervisor/shared/safe_mode.c
index 661fd79af8397..ec85ea9d43eb1 100644
--- a/supervisor/shared/safe_mode.c
+++ b/supervisor/shared/safe_mode.c
@@ -117,13 +117,17 @@ void __attribute__((noinline,)) reset_into_safe_mode(safe_mode_t reason) {
 
 
 
-#define FILE_AN_ISSUE translate("\nPlease file an issue with the contents of your CIRCUITPY drive at \nhttps://github.com/adafruit/circuitpython/issues\n")
-
 void print_safe_mode_message(safe_mode_t reason) {
     if (reason == NO_SAFE_MODE) {
         return;
     }
-    serial_write("\n");
+
+    serial_write("\r\n");
+    serial_write_compressed(translate("You are in safe mode because:\n"));
+
+    const compressed_string_t *message = NULL;
+
+    // First check for safe mode reasons that do not necessarily reflect bugs.
 
     switch (reason) {
         case USER_SAFE_MODE:
@@ -133,40 +137,40 @@ void print_safe_mode_message(safe_mode_t reason) {
             serial_write_compressed(BOARD_USER_SAFE_MODE_ACTION);
             serial_write_compressed(translate("To exit, please reset the board without "));
             serial_write_compressed(BOARD_USER_SAFE_MODE_ACTION);
-            #else
-            break;
             #endif
-            return;
+            break;
         case MANUAL_SAFE_MODE:
-            serial_write_compressed(translate("CircuitPython is in safe mode because you pressed the reset button during boot. Press again to exit safe mode.\n"));
-            return;
+            message = translate("You pressed the reset button during boot. Press again to exit safe mode.");
+            break;
         case PROGRAMMATIC_SAFE_MODE:
-            serial_write_compressed(translate("The `microcontroller` module was used to boot into safe mode. Press reset to exit safe mode.\n"));
-            return;
-        default:
+            message = translate("The `microcontroller` module was used to boot into safe mode. Press reset to exit safe mode.");
             break;
-    }
-
-    serial_write_compressed(translate("You are in safe mode: something unanticipated happened.\n"));
-    switch (reason) {
         case BROWNOUT:
-            serial_write_compressed(translate("The microcontroller's power dipped. Make sure your power supply provides\nenough power for the whole circuit and press reset (after ejecting CIRCUITPY).\n"));
-            return;
-        case HEAP_OVERWRITTEN:
-            serial_write_compressed(translate("The CircuitPython heap was corrupted because the stack was too small.\nPlease increase the stack size if you know how, or if not:"));
-            serial_write_compressed(FILE_AN_ISSUE);
-            return;
-        case NO_HEAP:
-            serial_write_compressed(translate("CircuitPython was unable to allocate the heap.\n"));
-            serial_write_compressed(FILE_AN_ISSUE);
-            return;
+            message = translate("The microcontroller's power dipped. Make sure your power supply provides\nenough power for the whole circuit and press reset (after ejecting CIRCUITPY).");
+            break;
+        case USB_TOO_MANY_ENDPOINTS:
+            message = translate("USB devices need more endpoints than are available.");
+            break;
+        case USB_TOO_MANY_INTERFACE_NAMES:
+            message = translate("USB devices specify too many interface names.");
+            break;
+        case WATCHDOG_RESET:
+            message = translate("Watchdog timer expired.");
+            break;
         default:
             break;
     }
 
+    if (message) {
+        serial_write_compressed(message);
+        serial_write("\r\n");
+        return;
+    }
+
+    // Something worse happened.
+
     serial_write_compressed(translate("CircuitPython core code crashed hard. Whoops!\n"));
 
-    const compressed_string_t *message = NULL;
     switch (reason) {
         case HARD_CRASH:
             message = translate("Crash into the HardFault_Handler.");
@@ -177,6 +181,12 @@ void print_safe_mode_message(safe_mode_t reason) {
         case MICROPY_FATAL_ERROR:
             message = translate("Fatal error.");
             break;
+        case NO_HEAP:
+            message = translate("CircuitPython was unable to allocate the heap.");
+            break;
+        case HEAP_OVERWRITTEN:
+            message = translate("The CircuitPython heap was corrupted because the stack was too small.\nIncrease the stack size if you know how. If not:");
+            break;
         case GC_ALLOC_OUTSIDE_VM:
             message = translate("Attempted heap allocation when VM not running.");
             break;
@@ -193,19 +203,10 @@ void print_safe_mode_message(safe_mode_t reason) {
         case MEM_MANAGE:
             message = translate("Invalid memory access.");
             break;
-        case WATCHDOG_RESET:
-            message = translate("Watchdog timer expired.");
-            break;
-        case USB_TOO_MANY_ENDPOINTS:
-            message = translate("USB devices need more endpoints than are available.");
-            break;
-        case USB_TOO_MANY_INTERFACE_NAMES:
-            message = translate("USB devices specify too many interface names.");
-            break;
         default:
             message = translate("Unknown reason.");
             break;
     }
     serial_write_compressed(message);
-    serial_write_compressed(FILE_AN_ISSUE);
+    serial_write_compressed(translate("\nPlease file an issue with the contents of your CIRCUITPY drive at \nhttps://github.com/adafruit/circuitpython/issues\n"));
 }
diff --git a/supervisor/shared/usb/usb_desc.c b/supervisor/shared/usb/usb_desc.c
index f1d2ac719692c..bad0d84523374 100644
--- a/supervisor/shared/usb/usb_desc.c
+++ b/supervisor/shared/usb/usb_desc.c
@@ -184,9 +184,16 @@ static void usb_build_configuration_descriptor(void) {
     configuration_descriptor[CONFIG_TOTAL_LENGTH_HI_INDEX] = (total_descriptor_length >> 8) & 0xFF;
 
     // Number interfaces and endpoints.
-    // Endpoint 0 is already used for USB control, so start with 1.
-    uint8_t current_interface = 0;
-    uint8_t current_endpoint = 1;
+    // Endpoint 0 is already used for USB control,
+    // so start with 1 for the current endpoint and for the number of in and out endpoints
+    // already in use.
+
+    descriptor_counts_t descriptor_counts = {
+        .current_interface = 0,
+        .current_endpoint = 1,
+        .num_in_endpoints = 1,
+        .num_out_endpoints = 1,
+    };
 
     uint8_t *descriptor_buf_remaining = configuration_descriptor + sizeof(configuration_descriptor_template);
 
@@ -194,12 +201,13 @@ static void usb_build_configuration_descriptor(void) {
     if (usb_cdc_console_enabled()) {
         // Concatenate and fix up the CDC REPL descriptor.
         descriptor_buf_remaining += usb_cdc_add_descriptor(
-            descriptor_buf_remaining, &current_interface, &current_endpoint, &current_interface_string, true);
+            descriptor_buf_remaining, &descriptor_counts, &current_interface_string, true /*console*/);
+
     }
     if (usb_cdc_data_enabled()) {
         // Concatenate and fix up the CDC data descriptor.
         descriptor_buf_remaining += usb_cdc_add_descriptor(
-            descriptor_buf_remaining, &current_interface, &current_endpoint, &current_interface_string, false);
+            descriptor_buf_remaining, &descriptor_counts, &current_interface_string, false /*console*/);
     }
     #endif
 
@@ -207,14 +215,14 @@ static void usb_build_configuration_descriptor(void) {
     if (storage_usb_enabled()) {
         // Concatenate and fix up the MSC descriptor.
         descriptor_buf_remaining += storage_usb_add_descriptor(
-            descriptor_buf_remaining, &current_interface, &current_endpoint, &current_interface_string);
+            descriptor_buf_remaining, &descriptor_counts, &current_interface_string);
     }
     #endif
 
     #if CIRCUITPY_USB_HID
     if (usb_hid_enabled()) {
         descriptor_buf_remaining += usb_hid_add_descriptor(
-            descriptor_buf_remaining, &current_interface, &current_endpoint, &current_interface_string,
+            descriptor_buf_remaining, &descriptor_counts, &current_interface_string,
             usb_hid_report_descriptor_length());
     }
     #endif
@@ -223,18 +231,19 @@ static void usb_build_configuration_descriptor(void) {
     if (usb_midi_enabled()) {
         // Concatenate and fix up the MIDI descriptor.
         descriptor_buf_remaining += usb_midi_add_descriptor(
-            descriptor_buf_remaining, &current_interface, &current_endpoint, &current_interface_string);
+            descriptor_buf_remaining, &descriptor_counts, &current_interface_string);
     }
     #endif
 
     // Now we know how many interfaces have been used.
-    configuration_descriptor[CONFIG_NUM_INTERFACES_INDEX] = current_interface;
+    configuration_descriptor[CONFIG_NUM_INTERFACES_INDEX] = descriptor_counts.current_interface;
 
     // Did we run out of endpoints?
-    if (current_endpoint - 1 > USB_NUM_EP) {
+    if (descriptor_counts.current_endpoint > USB_NUM_ENDPOINT_PAIRS ||
+        descriptor_counts.num_in_endpoints > USB_NUM_IN_ENDPOINTS ||
+        descriptor_counts.num_out_endpoints > USB_NUM_OUT_ENDPOINTS) {
         reset_into_safe_mode(USB_TOO_MANY_ENDPOINTS);
     }
-
 }
 
 // str must not be on the heap.
diff --git a/supervisor/usb.h b/supervisor/usb.h
index 918da988975db..e0feb58ea86ee 100644
--- a/supervisor/usb.h
+++ b/supervisor/usb.h
@@ -50,6 +50,14 @@ void init_usb_hardware(void);
 // Temporary hook for code after init. Only used for RP2040.
 void post_usb_init(void);
 
+// Indexes and counts updated as descriptors are built.
+typedef struct {
+    size_t current_interface;
+    size_t current_endpoint;
+    size_t num_in_endpoints;
+    size_t num_out_endpoints;
+} descriptor_counts_t;
+
 // Shared implementation.
 bool usb_enabled(void);
 void usb_add_interface_string(uint8_t interface_string_index, const char str[]);