diff --git a/comms/py-esptool/Makefile b/comms/py-esptool/Makefile
index 65da3fc7a3bc..4ba710e64a53 100644
--- a/comms/py-esptool/Makefile
+++ b/comms/py-esptool/Makefile
@@ -1,62 +1,65 @@
 PORTNAME=	esptool
 DISTVERSIONPREFIX=	v
-DISTVERSION=	4.10.0
+DISTVERSION=	5.2.0
 CATEGORIES=	comms python
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
-MAINTAINER=	ports@FreeBSD.org
+MAINTAINER=	leres@FreeBSD.org
 COMMENT=	Utility to communicate with Espressif ESP8266 & ESP32 chips
 WWW=		https://github.com/espressif/esptool
 
 LICENSE=	GPLv2
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
-RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pyserial>=3.3:comms/py-pyserial@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}ecdsa>=0.16.0:security/py-ecdsa@${PY_FLAVOR} \
+RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}argcomplete>=3:devel/py-argcomplete@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}bitstring>=3.1.6:devel/py-bitstring@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}reedsolo>=1.5.3:devel/py-reedsolo@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}pyyaml>=5.1:devel/py-pyyaml@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}click>=3:devel/py-click@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}ecdsa>=0.16.0:security/py-ecdsa@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}intelhex>0:devel/py-intelhex@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}argcomplete>=3:devel/py-argcomplete@${PY_FLAVOR}
+		${PYTHON_PKGNAMEPREFIX}pyserial>=3.3:comms/py-pyserial@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}pyyaml>=5.1:devel/py-pyyaml@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}reedsolo>=1.5.3:devel/py-reedsolo@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}rich-click>0:devel/py-rich-click@${PY_FLAVOR}
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pyelftools>0:devel/py-pyelftools@${PY_FLAVOR}
 
 USES=		python
 USE_GITHUB=	yes
 USE_PYTHON=	autoplist concurrent cryptography distutils pytest
 
 GH_ACCOUNT=	espressif
 NO_ARCH=	yes
 
 # test/test_espefuse_host.py calls the python command
 # through subprocess Popen(), create an alias for it.
-BINARY_ALIAS=		python=${PYTHON_CMD}
-TEST_ENV=		${MAKE_ENV} PYTHONPATH=${STAGEDIR}${PYTHONPREFIX_SITELIBDIR}
-TEST_ENV+=		CRYPTOGRAPHY_OPENSSL_NO_LEGACY=1
+BINARY_ALIAS=	python=${PYTHON_CMD}
+TEST_ENV=	${MAKE_ENV} \
+		PYTHONPATH=${STAGEDIR}${PYTHONPREFIX_SITELIBDIR}
+TEST_ENV+=	CRYPTOGRAPHY_OPENSSL_NO_LEGACY=1
 
 ESPTOOL_BAUDRATE?=	115200
 ESPTOOL_CHIP?=		esp8266
 ESPTOOL_SERIALPORT?=	/dev/ttyU0
 
 do-test:
 	@cd ${TEST_WRKSRC} && for test in \
 		test/test_imagegen.py \
 		test/test_espsecure.py \
 		test/test_merge_bin.py \
 		test/test_image_info.py \
 		test/test_modules.py; \
 		do ${SETENV} ${TEST_ENV} ${PYTHON_CMD} -m pytest $${test}; done
 	@cd ${TEST_WRKSRC} && for chip in \
 		esp32 esp32c2 esp32c3 esp32c5 esp32c5beta3 esp32c6 esp32c61 \
 		esp32h2 esp32h2beta1 esp32p4 esp32s2 esp32s3 esp32s3beta2 \
 		esp32h21 esp32h4; \
 		do ${SETENV} ${TEST_ENV} ${PYTHON_CMD} -m pytest \
 		test/test_espefuse.py --chip $${chip}; done
 .if exists(${ESPTOOL_SERIALPORT})
 	@cd ${TEST_WRKSRC} && ${SETENV} ${TEST_ENV} \
 		${PYTHON_CMD} -m pytest test/test_esptool.py \
 		--port ${ESPTOOL_SERIALPORT} \
 		--chip ${ESPTOOL_CHIP} \
 		--baud ${ESPTOOL_BAUDRATE}
 .endif
 
 .include <bsd.port.mk>
diff --git a/comms/py-esptool/distinfo b/comms/py-esptool/distinfo
index 343a9e7dca20..a64a29bf6e7b 100644
--- a/comms/py-esptool/distinfo
+++ b/comms/py-esptool/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1766855295
-SHA256 (espressif-esptool-v4.10.0_GH0.tar.gz) = feabee2783407cb5657bf1c6770f385cf1378b7920a5ce89ef32d42c7ce5be3c
-SIZE (espressif-esptool-v4.10.0_GH0.tar.gz) = 5961194
+TIMESTAMP = 1779652335
+SHA256 (espressif-esptool-v5.2.0_GH0.tar.gz) = 74067faf6837f18af7acf6e61e0b9a4c0851bcc58a06ea846b14e5f30c000ecd
+SIZE (espressif-esptool-v5.2.0_GH0.tar.gz) = 6056496