diff --git a/comms/py-esptool/Makefile b/comms/py-esptool/Makefile
index d6063857361f..f563dc8bc2bd 100644
--- a/comms/py-esptool/Makefile
+++ b/comms/py-esptool/Makefile
@@ -1,54 +1,57 @@
 PORTNAME=	esptool
 DISTVERSIONPREFIX=	v
-DISTVERSION=	4.2.1
+DISTVERSION=	4.4
 CATEGORIES=	comms python
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	loader@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=	${PYTHON_PKGNAMEPREFIX}pyserial>=3.0:comms/py-pyserial@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}ecdsa>=0.16.0:security/py-ecdsa@${PY_FLAVOR}\
-		${PYTHON_PKGNAMEPREFIX}bitstring>=3.1.6:devel/py-bitstring@${PY_FLAVOR}\
+		${PYTHON_PKGNAMEPREFIX}bitstring>=3.1.6,<4:devel/py-bitstring@${PY_FLAVOR}\
 		${PYTHON_PKGNAMEPREFIX}cryptography>=2.1.4:security/py-cryptography@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}reedsolo>=1.5.3,<=1.5.4:devel/py-reedsolo@${PY_FLAVOR}
+		${PYTHON_PKGNAMEPREFIX}reedsolo>=1.5.3,<1.5.5:devel/py-reedsolo@${PY_FLAVOR}
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pyelftools>0:devel/py-pyelftools@${PY_FLAVOR}
 
 USES=		python:3.7+
 USE_GITHUB=	yes
-USE_PYTHON=	autoplist concurrent distutils
+USE_PYTHON=	autoplist concurrent 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}
 
 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} $${test}; done
+		do ${SETENV} ${TEST_ENV} ${PYTHON_CMD} -m pytest $${test}; done
 	@cd ${TEST_WRKSRC} && for chip in \
-		esp32 esp32c2 esp32c3 esp32s2 esp32s3 esp32s3beta2 esp32h2beta1; \
-		do ${SETENV} ${TEST_ENV} ${PYTHON_CMD} \
-		test/test_espefuse_host.py $${chip}; done
+		esp32 esp32c2 esp32c3 esp32s2 esp32s3 esp32s3beta2 esp32h2beta1 esp32c6; \
+		do ${SETENV} ${TEST_ENV} ${PYTHON_CMD} -m pytest \
+		test/test_espefuse.py --chip $${chip}; done
 .if exists(${ESPTOOL_SERIALPORT})
 	@cd ${TEST_WRKSRC} && ${SETENV} ${TEST_ENV} \
-		${PYTHON_CMD} test/test_esptool.py \
-		${ESPTOOL_SERIALPORT} ${ESPTOOL_CHIP} ${ESPTOOL_BAUDRATE}
+		${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 5798260d5507..f32f8e6ac318 100644
--- a/comms/py-esptool/distinfo
+++ b/comms/py-esptool/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1660207649
-SHA256 (espressif-esptool-v4.2.1_GH0.tar.gz) = cb2405dca03fd68394644e22479e03f85629656e8f14f8345b50fc758d61f7b3
-SIZE (espressif-esptool-v4.2.1_GH0.tar.gz) = 7271498
+TIMESTAMP = 1669170432
+SHA256 (espressif-esptool-v4.4_GH0.tar.gz) = 2d9eacbeda2f711cbd2d5a83d704a9068e42f649bef9ece05fad4a5ed30c7715
+SIZE (espressif-esptool-v4.4_GH0.tar.gz) = 7213588