diff --git a/devel/py-esptool/Makefile b/devel/py-esptool/Makefile
index 176e175cea2..fb9e6087268 100644
--- a/devel/py-esptool/Makefile
+++ b/devel/py-esptool/Makefile
@@ -1,9 +1,9 @@
 COMMENT=	ESP8266 and ESP32 ROM bootloader communication tool
 
-MODPY_DISTV=	4.8.1
+MODPY_DISTV=	4.9.0
+# v5+ requires new deps (including rich_click, not in ports)
 DISTNAME=	esptool-${MODPY_DISTV}
 PKGNAME=	py-${DISTNAME}
-REVISION=	0
 
 CATEGORIES=	devel
 HOMEPAGE=	https://github.com/espressif/esptool
diff --git a/devel/py-esptool/distinfo b/devel/py-esptool/distinfo
index 7749b94e5d4..f923a7c9de7 100644
--- a/devel/py-esptool/distinfo
+++ b/devel/py-esptool/distinfo
@@ -1,2 +1,2 @@
-SHA256 (esptool-4.8.1.tar.gz) = 3E7ya2WeGo3LAZFHwOptlJgLNN6Z++CRIceUHIslRTE=
-SIZE (esptool-4.8.1.tar.gz) = 409512
+SHA256 (esptool-4.9.0.tar.gz) = 9ja0VS84c835TPry1cN/VAfx8z33NkPv7lE4ZzELao4=
+SIZE (esptool-4.9.0.tar.gz) = 460440
diff --git a/devel/py-esptool/pkg/PLIST b/devel/py-esptool/pkg/PLIST
index 223b740bd9a..3e5df18581e 100644
--- a/devel/py-esptool/pkg/PLIST
+++ b/devel/py-esptool/pkg/PLIST
@@ -182,6 +182,23 @@ lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h2/emulate_efuse_co
 lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h2/fields.py
 lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h2/mem_definition.py
 lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h2/operations.py
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h21/
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h21/__init__.py
+${MODPY_COMMENT}lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h21/${MODPY_PYCACHE}/
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h21/${MODPY_PYCACHE}__init__.${MODPY_PYC_MAGIC_TAG}${MODPY_PYOEXTENSION}
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h21/${MODPY_PYCACHE}__init__.${MODPY_PYC_MAGIC_TAG}pyc
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h21/${MODPY_PYCACHE}emulate_efuse_controller.${MODPY_PYC_MAGIC_TAG}${MODPY_PYOEXTENSION}
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h21/${MODPY_PYCACHE}emulate_efuse_controller.${MODPY_PYC_MAGIC_TAG}pyc
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h21/${MODPY_PYCACHE}fields.${MODPY_PYC_MAGIC_TAG}${MODPY_PYOEXTENSION}
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h21/${MODPY_PYCACHE}fields.${MODPY_PYC_MAGIC_TAG}pyc
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h21/${MODPY_PYCACHE}mem_definition.${MODPY_PYC_MAGIC_TAG}${MODPY_PYOEXTENSION}
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h21/${MODPY_PYCACHE}mem_definition.${MODPY_PYC_MAGIC_TAG}pyc
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h21/${MODPY_PYCACHE}operations.${MODPY_PYC_MAGIC_TAG}${MODPY_PYOEXTENSION}
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h21/${MODPY_PYCACHE}operations.${MODPY_PYC_MAGIC_TAG}pyc
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h21/emulate_efuse_controller.py
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h21/fields.py
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h21/mem_definition.py
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h21/operations.py
 lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h2beta1/
 lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h2beta1/__init__.py
 ${MODPY_COMMENT}lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h2beta1/${MODPY_PYCACHE}/
@@ -199,6 +216,23 @@ lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h2beta1/emulate_efu
 lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h2beta1/fields.py
 lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h2beta1/mem_definition.py
 lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h2beta1/operations.py
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h4/
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h4/__init__.py
+${MODPY_COMMENT}lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h4/${MODPY_PYCACHE}/
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h4/${MODPY_PYCACHE}__init__.${MODPY_PYC_MAGIC_TAG}${MODPY_PYOEXTENSION}
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h4/${MODPY_PYCACHE}__init__.${MODPY_PYC_MAGIC_TAG}pyc
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h4/${MODPY_PYCACHE}emulate_efuse_controller.${MODPY_PYC_MAGIC_TAG}${MODPY_PYOEXTENSION}
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h4/${MODPY_PYCACHE}emulate_efuse_controller.${MODPY_PYC_MAGIC_TAG}pyc
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h4/${MODPY_PYCACHE}fields.${MODPY_PYC_MAGIC_TAG}${MODPY_PYOEXTENSION}
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h4/${MODPY_PYCACHE}fields.${MODPY_PYC_MAGIC_TAG}pyc
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h4/${MODPY_PYCACHE}mem_definition.${MODPY_PYC_MAGIC_TAG}${MODPY_PYOEXTENSION}
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h4/${MODPY_PYCACHE}mem_definition.${MODPY_PYC_MAGIC_TAG}pyc
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h4/${MODPY_PYCACHE}operations.${MODPY_PYC_MAGIC_TAG}${MODPY_PYOEXTENSION}
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h4/${MODPY_PYCACHE}operations.${MODPY_PYC_MAGIC_TAG}pyc
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h4/emulate_efuse_controller.py
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h4/fields.py
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h4/mem_definition.py
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32h4/operations.py
 lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32p4/
 lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32p4/__init__.py
 ${MODPY_COMMENT}lib/python${MODPY_VERSION}/site-packages/espefuse/efuse/esp32p4/${MODPY_PYCACHE}/
@@ -278,6 +312,9 @@ lib/python${MODPY_VERSION}/site-packages/espefuse/efuse_defs/esp32c5beta3.yaml
 lib/python${MODPY_VERSION}/site-packages/espefuse/efuse_defs/esp32c6.yaml
 lib/python${MODPY_VERSION}/site-packages/espefuse/efuse_defs/esp32c61.yaml
 lib/python${MODPY_VERSION}/site-packages/espefuse/efuse_defs/esp32h2.yaml
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse_defs/esp32h21.yaml
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse_defs/esp32h2_v0.0_v1.1.yaml
+lib/python${MODPY_VERSION}/site-packages/espefuse/efuse_defs/esp32h4.yaml
 lib/python${MODPY_VERSION}/site-packages/espefuse/efuse_defs/esp32p4.yaml
 lib/python${MODPY_VERSION}/site-packages/espefuse/efuse_defs/esp32s2.yaml
 lib/python${MODPY_VERSION}/site-packages/espefuse/efuse_defs/esp32s3.yaml
@@ -354,10 +391,14 @@ lib/python${MODPY_VERSION}/site-packages/esptool/targets/${MODPY_PYCACHE}esp32c6
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/${MODPY_PYCACHE}esp32c6beta.${MODPY_PYC_MAGIC_TAG}pyc
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/${MODPY_PYCACHE}esp32h2.${MODPY_PYC_MAGIC_TAG}${MODPY_PYOEXTENSION}
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/${MODPY_PYCACHE}esp32h2.${MODPY_PYC_MAGIC_TAG}pyc
+lib/python${MODPY_VERSION}/site-packages/esptool/targets/${MODPY_PYCACHE}esp32h21.${MODPY_PYC_MAGIC_TAG}${MODPY_PYOEXTENSION}
+lib/python${MODPY_VERSION}/site-packages/esptool/targets/${MODPY_PYCACHE}esp32h21.${MODPY_PYC_MAGIC_TAG}pyc
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/${MODPY_PYCACHE}esp32h2beta1.${MODPY_PYC_MAGIC_TAG}${MODPY_PYOEXTENSION}
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/${MODPY_PYCACHE}esp32h2beta1.${MODPY_PYC_MAGIC_TAG}pyc
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/${MODPY_PYCACHE}esp32h2beta2.${MODPY_PYC_MAGIC_TAG}${MODPY_PYOEXTENSION}
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/${MODPY_PYCACHE}esp32h2beta2.${MODPY_PYC_MAGIC_TAG}pyc
+lib/python${MODPY_VERSION}/site-packages/esptool/targets/${MODPY_PYCACHE}esp32h4.${MODPY_PYC_MAGIC_TAG}${MODPY_PYOEXTENSION}
+lib/python${MODPY_VERSION}/site-packages/esptool/targets/${MODPY_PYCACHE}esp32h4.${MODPY_PYC_MAGIC_TAG}pyc
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/${MODPY_PYCACHE}esp32p4.${MODPY_PYC_MAGIC_TAG}${MODPY_PYOEXTENSION}
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/${MODPY_PYCACHE}esp32p4.${MODPY_PYC_MAGIC_TAG}pyc
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/${MODPY_PYCACHE}esp32s2.${MODPY_PYC_MAGIC_TAG}${MODPY_PYOEXTENSION}
@@ -377,8 +418,10 @@ lib/python${MODPY_VERSION}/site-packages/esptool/targets/esp32c6.py
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/esp32c61.py
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/esp32c6beta.py
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/esp32h2.py
+lib/python${MODPY_VERSION}/site-packages/esptool/targets/esp32h21.py
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/esp32h2beta1.py
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/esp32h2beta2.py
+lib/python${MODPY_VERSION}/site-packages/esptool/targets/esp32h4.py
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/esp32p4.py
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/esp32s2.py
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/esp32s3.py
@@ -386,6 +429,7 @@ lib/python${MODPY_VERSION}/site-packages/esptool/targets/esp32s3beta2.py
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/esp8266.py
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/stub_flasher/
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/stub_flasher/1/
+lib/python${MODPY_VERSION}/site-packages/esptool/targets/stub_flasher/1/.DS_Store
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/stub_flasher/1/README.md
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/stub_flasher/1/esp32.json
 lib/python${MODPY_VERSION}/site-packages/esptool/targets/stub_flasher/1/esp32c2.json