--- b/devel/py-watchdog/Makefile	
+++ b/devel/py-watchdog/Makefile	
@@ -1,5 +1,5 @@ 
 PORTNAME=	watchdog
-PORTVERSION=	0.10.6
+PORTVERSION=	2.1.5
 CATEGORIES=	devel python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
@@ -9,12 +9,10 @@ COMMENT=	Python API library to monitor file system events
 
 LICENSE=	APACHE20
 
-RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}argh>=0.26.1:devel/py-argh@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}eventlet>=0:net/py-eventlet@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}pathtools>=0.1.2:devel/py-pathtools@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}yaml>=3.11:devel/py-yaml@${PY_FLAVOR}
+RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}argh>=0.24.1:devel/py-argh@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}yaml>=3.10:devel/py-yaml@${PY_FLAVOR}
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pytest>0:devel/py-pytest@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}pytest-cov>0:devel/py-pytest-cov@${PY_FLAVOR}
+		${PYTHON_PKGNAMEPREFIX}flaky>0:devel/py-flaky@${PY_FLAVOR}
 
 USES=		python:3.6+
 USE_PYTHON=	autoplist concurrent distutils
@@ -25,10 +23,11 @@ NO_ARCH=	yes
 
 PORTDOCS=	*
 
+TEST_ENV=	PYTHONPATH=${STAGEDIR}${PYTHONPREFIX_SITELIBDIR}
+
 OPTIONS_DEFINE=	DOCS
 
-DOCS_BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pathtools>=0.1.2:devel/py-pathtools@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}sphinx>=0,1:textproc/py-sphinx@${PY_FLAVOR}
+DOCS_BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}sphinx>=0,1:textproc/py-sphinx@${PY_FLAVOR}
 
 post-build-DOCS-on:
 	(cd ${WRKSRC}/docs ; ${MAKE_CMD} SPHINXBUILD=sphinx-build-${PYTHON_VER} html)
@@ -39,6 +38,6 @@ post-install-DOCS-on:
 	${COPYTREE_SHARE} . ${STAGEDIR}${DOCSDIR} "-not -name .buildinfo")
 
 do-test:
-	@cd ${WRKSRC} && ${PYTHON_CMD} -m pytest -v -rs -o addopts= tests
+	@cd ${TEST_WRKSRC} && ${SETENV} ${TEST_ENV} ${PYTHON_CMD} -m pytest -v -rs -o addopts= tests
 
 .include <bsd.port.mk>
--- b/devel/py-watchdog/distinfo	
+++ b/devel/py-watchdog/distinfo	
@@ -1,3 +1,3 @@ 
-TIMESTAMP = 1612010670
-SHA256 (watchdog-0.10.6.tar.gz) = 1e1ea6d3d74feca5c62393525107aa45c5d4cd15199e2a5f62b1a6ca83679131
-SIZE (watchdog-0.10.6.tar.gz) = 99949
+TIMESTAMP = 1631895216
+SHA256 (watchdog-2.1.5.tar.gz) = 5563b005907613430ef3d4aaac9c78600dd5704e84764cb6deda4b3d72807f09
+SIZE (watchdog-2.1.5.tar.gz) = 114220
--- /dev/null	
+++ b/devel/py-watchdog/files/patch-src_watchdog_observers_kqueue.py	
@@ -0,0 +1,25 @@ 
+Restore original return value of "absolute_path" as is was done by "pathtools".
+
+Obtained from:
+https://github.com/gorakhargosh/watchdog/commit/b9774e9e6e8dcbb7d2e0786eb13ab30848ed1514
+
+--- src/watchdog/observers/kqueue.py.orig	2021-09-18 09:02:58 UTC
++++ src/watchdog/observers/kqueue.py
+@@ -76,8 +76,6 @@ import os
+ import os.path
+ import select
+ 
+-from pathlib import Path
+-
+ from watchdog.observers.api import (
+     BaseObserver,
+     EventEmitter,
+@@ -127,7 +125,7 @@ WATCHDOG_KQ_FFLAGS = (
+ 
+ 
+ def absolute_path(path):
+-    return Path(path).resolve()
++    return os.path.abspath(os.path.normpath(path))
+ 
+ # Flag tests.
+ 
--- /dev/null	
+++ b/devel/py-watchdog/files/patch-tests_test__emitter.py	
@@ -0,0 +1,26 @@ 
+Skip some checks for BSD
+
+* Test "test_delete_self()" was tested only on Darwin platforms in 0.10.6
+* Test "file_lifecyle" was introduced in 2.0.0
+
+Obtained from:
+https://github.com/gorakhargosh/watchdog/commit/b9774e9e6e8dcbb7d2e0786eb13ab30848ed1514
+
+--- tests/test_emitter.py.orig	2021-09-18 09:50:34 UTC
++++ tests/test_emitter.py
+@@ -355,6 +355,7 @@ def test_separate_consecutive_moves():
+ 
+ 
+ @pytest.mark.flaky(max_runs=5, min_passes=1, rerun_filter=rerun_filter)
++@pytest.mark.skipif(platform.is_bsd(), reason="BSD create another set of events for this test")
+ def test_delete_self():
+     mkdir(p('dir1'))
+     start_watching(p('dir1'))
+@@ -642,6 +643,7 @@ def test_move_nested_subdirectories_on_windows():
+ 
+ 
+ @pytest.mark.flaky(max_runs=5, min_passes=1, rerun_filter=rerun_filter)
++@pytest.mark.skipif(platform.is_bsd(), reason="BSD create another set of events for this test")
+ def test_file_lifecyle():
+     start_watching()
+