diff --git a/components/bootloader/Makefile.projbuild b/components/bootloader/Makefile.projbuild
index 35be94e4a3..9e7b17b65f 100644
--- a/components/bootloader/Makefile.projbuild
+++ b/components/bootloader/Makefile.projbuild
@@ -50,11 +50,14 @@ else ifdef CONFIG_SECURE_BOOTLOADER_ONE_TIME_FLASH
 
 # One time flashing requires user to run esptool.py command themselves,
 # and warning is printed about inability to reflash.
+#
+# The flashing command is deliberately printed without an auto-reset
+# step, so the device doesn't immediately reset to flash itself.
 
 bootloader: $(BOOTLOADER_BIN)
 	@echo $(SEPARATOR)
 	@echo "Bootloader built. One-time flash command is:"
-	@echo "$(ESPTOOLPY_WRITE_FLASH) $(BOOTLOADER_OFFSET) $(BOOTLOADER_BIN)"
+	@echo "$(subst hard_reset,no_reset,$(ESPTOOLPY_WRITE_FLASH)) $(BOOTLOADER_OFFSET) $(BOOTLOADER_BIN)"
 	@echo $(SEPARATOR)
 	@echo "* IMPORTANT: After first boot, BOOTLOADER CANNOT BE RE-FLASHED on same device"
 
diff --git a/components/esptool_py/Kconfig.projbuild b/components/esptool_py/Kconfig.projbuild
index 8bab51225e..dd2077cbb3 100644
--- a/components/esptool_py/Kconfig.projbuild
+++ b/components/esptool_py/Kconfig.projbuild
@@ -121,4 +121,61 @@ config ESPTOOLPY_FLASHSIZE
 	default "8MB" if ESPTOOLPY_FLASHSIZE_8MB
 	default "16MB" if ESPTOOLPY_FLASHSIZE_16MB
 
+config ESPTOOLPY_FLASHSIZE_DETECT
+    bool "Detect flash size when flashing bootloader"
+    default y
+    help
+        If this option is set, 'make flash' targets will automatically detect
+        the flash size and update the bootloader image when flashing.
+
+choice ESPTOOLPY_BEFORE
+    prompt "Before flashing"
+    default ESPTOOLPY_BEFORE_RESET
+    help
+        Configure whether esptool.py should reset the ESP32 before flashing.
+
+        Automatic resetting depends on the RTS & DTR signals being
+        wired from the serial port to the ESP32. Most USB development
+        boards do this internally.
+
+        The "Reset with ESP32R0 Windows workaround" option works
+        around an automatic reset bug in hardware, when using Windows
+        with some development boards. This fix only works if you're
+        using a silicon revision 0 ESP32.
+
+config ESPTOOLPY_BEFORE_RESET
+    bool "Reset to bootloader"
+config ESPTOOLPY_BEFORE_NORESET
+    bool "No reset"
+config ESPTOOLPY_BEFORE_ESP32R0
+    bool "Reset with ESP32R0 Windows workaround"
+endchoice
+
+config ESPTOOLPY_BEFORE
+    string
+    default "default_reset" if ESPTOOLPY_BEFORE_RESET
+    default "no_reset" if ESPTOOLPY_BEFORE_NORESET
+    default "esp32r0" if ESPTOOLPY_BEFORE_ESP32R0
+
+choice ESPTOOLPY_AFTER
+    prompt "After flashing"
+    default ESPTOOLPY_AFTER_RESET
+    help
+        Configure whether esptool.py should reset the ESP32 after flashing.
+
+        Automatic resetting depends on the RTS & DTR signals being
+        wired from the serial port to the ESP32. Most USB development
+        boards do this internally.
+
+config ESPTOOLPY_AFTER_RESET
+    bool "Reset after flashing"
+config ESPTOOLPY_AFTER_NORESET
+    bool "Stay in bootloader"
+endchoice
+
+config ESPTOOLPY_AFTER
+    string
+    default "hard_reset" if ESPTOOLPY_AFTER_RESET
+    default "no_reset" if ESPTOOLPY_AFTER_NORESET
+
 endmenu
diff --git a/components/esptool_py/Makefile.projbuild b/components/esptool_py/Makefile.projbuild
index b5992a4d96..88b5894731 100644
--- a/components/esptool_py/Makefile.projbuild
+++ b/components/esptool_py/Makefile.projbuild
@@ -13,7 +13,7 @@ PYTHON ?= $(call dequote,$(CONFIG_PYTHON))
 #
 ESPTOOLPY_SRC := $(COMPONENT_PATH)/esptool/esptool.py
 ESPTOOLPY := $(PYTHON) $(ESPTOOLPY_SRC) --chip esp32
-ESPTOOLPY_SERIAL := $(ESPTOOLPY) --port $(ESPPORT) --baud $(ESPBAUD)
+ESPTOOLPY_SERIAL := $(ESPTOOLPY) --port $(ESPPORT) --baud $(ESPBAUD) --before $(CONFIG_ESPTOOLPY_BEFORE) --after $(CONFIG_ESPTOOLPY_AFTER)
 
 # Supporting esptool command line tools
 ESPEFUSEPY := $(PYTHON) $(COMPONENT_PATH)/esptool/espefuse.py
@@ -21,10 +21,15 @@ ESPSECUREPY := $(PYTHON) $(COMPONENT_PATH)/esptool/espsecure.py
 export ESPSECUREPY  # is used in bootloader_support component
 
 ESPTOOL_FLASH_OPTIONS := --flash_mode $(ESPFLASHMODE) --flash_freq $(ESPFLASHFREQ) --flash_size $(ESPFLASHSIZE)
+ifdef CONFIG_ESPTOOLPY_FLASHSIZE_DETECT
+ESPTOOL_WRITE_FLASH_OPTIONS := --flash_mode $(ESPFLASHMODE) --flash_freq $(ESPFLASHFREQ) --flash_size detect
+else
+ESPTOOL_WRITE_FLASH_OPTIONS := $(ESPTOOL_FLASH_OPTIONS)
+endif
 
 ESPTOOL_ELF2IMAGE_OPTIONS :=
 
-ESPTOOLPY_WRITE_FLASH=$(ESPTOOLPY_SERIAL) write_flash $(if $(CONFIG_ESPTOOLPY_COMPRESSED),-z) $(ESPTOOL_FLASH_OPTIONS)
+ESPTOOLPY_WRITE_FLASH=$(ESPTOOLPY_SERIAL) write_flash $(if $(CONFIG_ESPTOOLPY_COMPRESSED),-z) $(ESPTOOL_WRITE_FLASH_OPTIONS)
 
 ESPTOOL_ALL_FLASH_ARGS += $(CONFIG_APP_OFFSET) $(APP_BIN)
 
diff --git a/components/esptool_py/esptool b/components/esptool_py/esptool
index adc914b91a..fe69994270 160000
--- a/components/esptool_py/esptool
+++ b/components/esptool_py/esptool
@@ -1 +1 @@
-Subproject commit adc914b91ac6d2cfd1ace56307b4374eb9439e14
+Subproject commit fe69994270e2a450aad3e94a409b58460b1a214f