diff --git a/www/py-werkzeug/Makefile b/www/py-werkzeug/Makefile
index afe32e3378eb..f6cc33242e49 100644
--- a/www/py-werkzeug/Makefile
+++ b/www/py-werkzeug/Makefile
@@ -1,7 +1,7 @@
 # Created by: Moggie <moggie@elasticmind.net>
 
 PORTNAME=	werkzeug
-PORTVERSION=	1.0.1
+PORTVERSION=	2.0.0
 CATEGORIES=	www python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
@@ -23,10 +23,10 @@ NO_ARCH=	yes
 OPTIONS_DEFINE=	EXAMPLES WATCHDOG
 WATCHDOG_DESC=	Monitor filesystem events
 
-WATCHDOG_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}watchdog>=0.8:devel/py-watchdog@${PY_FLAVOR}
+WATCHDOG_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}watchdog>=0:devel/py-watchdog@${PY_FLAVOR}
 
 post-install-EXAMPLES-on:
-	@${MKDIR} ${STAGEDIR}${EXAMPLESDIR}
-	(cd ${WRKSRC}/examples/ && ${COPYTREE_SHARE} . ${STAGEDIR}${EXAMPLESDIR})
+	${MKDIR} ${STAGEDIR}${EXAMPLESDIR}
+	cd ${WRKSRC}/examples/ && ${COPYTREE_SHARE} . ${STAGEDIR}${EXAMPLESDIR}
 
 .include <bsd.port.mk>
diff --git a/www/py-werkzeug/distinfo b/www/py-werkzeug/distinfo
index 3635ac7c7820..d3975a60243c 100644
--- a/www/py-werkzeug/distinfo
+++ b/www/py-werkzeug/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1585752057
-SHA256 (Werkzeug-1.0.1.tar.gz) = 6c80b1e5ad3665290ea39320b91e1be1e0d5f60652b964a3070216de83d2e47c
-SIZE (Werkzeug-1.0.1.tar.gz) = 904455
+TIMESTAMP = 1620928643
+SHA256 (Werkzeug-2.0.0.tar.gz) = 3389bbfe6d40c6dd25e6d3f974155163c8b3de5bbda6a89342d4ab93fae80ba0
+SIZE (Werkzeug-2.0.0.tar.gz) = 892229
diff --git a/www/py-werkzeug/pkg-plist b/www/py-werkzeug/pkg-plist
index 03e98a2378bc..e026201975c7 100644
--- a/www/py-werkzeug/pkg-plist
+++ b/www/py-werkzeug/pkg-plist
@@ -1,3 +1,4 @@
+%%PORTEXAMPLES%%%%EXAMPLESDIR%%/README.rst
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/coolmagic/__init__.py
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/coolmagic/application.py
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/coolmagic/helpers.py
@@ -9,10 +10,10 @@
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/coolmagic/utils.py
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/coolmagic/views/__init__.py
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/coolmagic/views/static.py
+%%PORTEXAMPLES%%%%EXAMPLESDIR%%/couchy/README
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/couchy/__init__.py
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/couchy/application.py
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/couchy/models.py
-%%PORTEXAMPLES%%%%EXAMPLESDIR%%/couchy/README
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/couchy/static/style.css
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/couchy/templates/display.html
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/couchy/templates/layout.html
@@ -56,8 +57,8 @@
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/manage-shorty.py
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/manage-simplewiki.py
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/manage-webpylike.py
-%%PORTEXAMPLES%%%%EXAMPLESDIR%%/partial/complex_routing.py
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/partial/README
+%%PORTEXAMPLES%%%%EXAMPLESDIR%%/partial/complex_routing.py
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/plnt/__init__.py
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/plnt/database.py
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/plnt/shared/style.css
@@ -68,7 +69,6 @@
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/plnt/utils.py
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/plnt/views.py
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/plnt/webapp.py
-%%PORTEXAMPLES%%%%EXAMPLESDIR%%/README.rst
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/shortly/shortly.py
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/shortly/static/style.css
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/shortly/templates/404.html
@@ -107,3 +107,4 @@
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/upload.py
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/webpylike/example.py
 %%PORTEXAMPLES%%%%EXAMPLESDIR%%/webpylike/webpylike.py
+%%PORTEXAMPLES%%%%EXAMPLESDIR%%/wsecho.py