diff --git a/devel/py-osprofiler/Makefile b/devel/py-osprofiler/Makefile
index c1064cc0ddab..b524c5ed6881 100644
--- a/devel/py-osprofiler/Makefile
+++ b/devel/py-osprofiler/Makefile
@@ -1,31 +1,31 @@
 PORTNAME=	osprofiler
-PORTVERSION=	4.3.0
+PORTVERSION=	4.4.0
 CATEGORIES=	devel python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	OpenStack Profiler Library
 WWW=		https://docs.openstack.org/osprofiler/latest/
 
 LICENSE=	APACHE20
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
-BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pbr>=2.0:devel/py-pbr@${PY_FLAVOR} \
+BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pbr>=6.1.1:devel/py-pbr@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}setuptools>=0:devel/py-setuptools@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}wheel>=0:devel/py-wheel@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}netaddr>=0.7.18:net/py-netaddr@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}oslo.concurrency>=3.26.0:devel/py-oslo.concurrency@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}oslo.config>=5.2.0:devel/py-oslo.config@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}oslo.serialization>=2.18.0:devel/py-oslo.serialization@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}oslo.utils>=3.33.0:devel/py-oslo.utils@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}prettytable>=0.7.2:devel/py-prettytable@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}requests>=2.14.2:www/py-requests@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}webob>=1.7.1:www/py-webob@${PY_FLAVOR}
 
 USES=		python
 USE_PYTHON=	autoplist concurrent pep517
 
 NO_ARCH=	yes
 
 .include <bsd.port.mk>
diff --git a/devel/py-osprofiler/distinfo b/devel/py-osprofiler/distinfo
index 46f73692994a..f14ef281cc1d 100644
--- a/devel/py-osprofiler/distinfo
+++ b/devel/py-osprofiler/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1748495781
-SHA256 (osprofiler-4.3.0.tar.gz) = 77a8da2b23bb5f9048054bd5ccc45d0ac84574ca8a88ef120b8fac6e8864e24c
-SIZE (osprofiler-4.3.0.tar.gz) = 95940
+TIMESTAMP = 1778096620
+SHA256 (osprofiler-4.4.0.tar.gz) = 6e08df7eef6afc0d2d027813d40e43cb228f0eb3eb3441d61495c2800ebfa320
+SIZE (osprofiler-4.4.0.tar.gz) = 96231
diff --git a/devel/py-osprofiler/files/patch-osprofiler_cmd_shell.py b/devel/py-osprofiler/files/patch-osprofiler_cmd_shell.py
index 2a28ddfefccc..9243a3c52673 100644
--- a/devel/py-osprofiler/files/patch-osprofiler_cmd_shell.py
+++ b/devel/py-osprofiler/files/patch-osprofiler_cmd_shell.py
@@ -1,13 +1,13 @@
---- osprofiler/cmd/shell.py.orig	2018-03-14 17:31:26 UTC
+--- osprofiler/cmd/shell.py.orig	2026-05-05 14:09:04 UTC
 +++ osprofiler/cmd/shell.py
-@@ -54,7 +54,9 @@ class OSProfilerShell(object):
-         return parser
- 
-     def _append_subcommands(self, parent_parser):
+@@ -54,7 +54,9 @@ class OSProfilerShell:
+     def _append_subcommands(
+         self, parent_parser: argparse.ArgumentParser
+     ) -> None:
 -        subcommands = parent_parser.add_subparsers(help="<subcommands>")
 +        # Fix CLI for Python 3.x
 +        subcommands = parent_parser.add_subparsers(help="<subcommands>", dest="too few arguments")
 +        subcommands.required = True
          for group_cls in commands.BaseCommand.__subclasses__():
-             group_parser = subcommands.add_parser(group_cls.group_name)
-             subcommand_parser = group_parser.add_subparsers()
+             if group_cls.group_name is None:
+                 continue