diff --git a/devel/py-pyTooling/Makefile b/devel/py-pyTooling/Makefile
index 030909eefa2e..69cb31615f83 100644
--- a/devel/py-pyTooling/Makefile
+++ b/devel/py-pyTooling/Makefile
@@ -1,38 +1,38 @@
 PORTNAME=	pyTooling
 DISTVERSIONPREFIX=	v
-DISTVERSION=	6.4.0
+DISTVERSION=	6.6.0
 CATEGORIES=	devel
 #MASTER_SITES=	PYPI # requirements.txt is missing
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	yuri@FreeBSD.org
 COMMENT=	Collection of arbitrary classes, decorators, meta-classes, exceptions
 WWW=		https://pytooling.github.io/pyTooling/
 
 LICENSE=	APACHE20
 LICENSE_FILE=	${WRKSRC}/LICENSE.md
 
 BUILD_DEPENDS=	${PY_SETUPTOOLS} \
 		${PYTHON_PKGNAMEPREFIX}wheel>=0.40.0:devel/py-wheel@${PY_FLAVOR}
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}anytree>=2.8.0:devel/py-anytree@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}colorama>=0.4.6:devel/py-colorama@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}coverage>0:devel/py-coverage@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}igraph>0:math/py-igraph@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}itertree>0:devel/py-itertree@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}lxml>0:devel/py-lxml@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}mypy>=1.10:devel/py-mypy@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}networkx>=2.6:math/py-networkx@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-benchmark>=4.0.0:devel/py-pytest-benchmark@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-cov>0:devel/py-pytest-cov@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}ruamel.yaml>=0.17:devel/py-ruamel.yaml@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}treelib>0:devel/py-treelib@${PY_FLAVOR}
 
 USES=		python
-USE_PYTHON=	pep517 autoplist pytest # 98 tests fail, see https://github.com/pyTooling/pyTooling/issues/123
+USE_PYTHON=	pep517 autoplist pytest # 44 tests fail, see https://github.com/pyTooling/pyTooling/issues/123#issuecomment-2362275029
 USE_GITHUB=	yes
 
 NO_ARCH=	yes
 
 TEST_WRKSRC=	${WRKSRC}/tests
 
 .include <bsd.port.mk>
diff --git a/devel/py-pyTooling/distinfo b/devel/py-pyTooling/distinfo
index 986cce42ef7e..26be21289d1d 100644
--- a/devel/py-pyTooling/distinfo
+++ b/devel/py-pyTooling/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1720224103
-SHA256 (pyTooling-pyTooling-v6.4.0_GH0.tar.gz) = 790a7df3067275ab461f1deadc1c6cedaa0584354d4781a64ca888f58464ea95
-SIZE (pyTooling-pyTooling-v6.4.0_GH0.tar.gz) = 686129
+TIMESTAMP = 1726775247
+SHA256 (pyTooling-pyTooling-v6.6.0_GH0.tar.gz) = 5783818b97c63cb879d70f04094dfba5db837a164f7deb23c1a3fb946c15dee0
+SIZE (pyTooling-pyTooling-v6.6.0_GH0.tar.gz) = 696025
diff --git a/devel/py-pyTooling/files/patch-pyTooling_TerminalUI_____init____.py b/devel/py-pyTooling/files/patch-pyTooling_TerminalUI_____init____.py
new file mode 100644
index 000000000000..b84c80320fb0
--- /dev/null
+++ b/devel/py-pyTooling/files/patch-pyTooling_TerminalUI_____init____.py
@@ -0,0 +1,11 @@
+--- pyTooling/TerminalUI/__init__.py.orig	2024-09-19 21:15:21 UTC
++++ pyTooling/TerminalUI/__init__.py
+@@ -197,7 +197,7 @@ class TerminalBaseApplication(metaclass=ExtendedType, 
+ 		platform = Platform()
+ 		if platform.IsNativeWindows:
+ 			size = TerminalBaseApplication.__GetTerminalSizeOnWindows()
+-		elif (platform.IsNativeLinux or platform.IsNativeMacOS or platform.IsMinGW32OnWindows or platform.IsMinGW64OnWindows
++		elif (platform.IsNativeLinux or platform.IsNativeFreeBSD or platform.IsNativeMacOS or platform.IsMinGW32OnWindows or platform.IsMinGW64OnWindows
+ 					or platform.IsUCRT64OnWindows or platform.IsCygwin32OnWindows or platform.IsClang64OnWindows):
+ 			size = TerminalBaseApplication.__GetTerminalSizeOnLinux()
+ 		else:  # pragma: no cover
diff --git a/devel/py-pyTooling/files/patch-pyproject.toml b/devel/py-pyTooling/files/patch-pyproject.toml
index e2e375c4a552..9b471e9cf297 100644
--- a/devel/py-pyTooling/files/patch-pyproject.toml
+++ b/devel/py-pyTooling/files/patch-pyproject.toml
@@ -1,12 +1,12 @@
---- pyproject.toml.orig	2024-07-04 18:23:08 UTC
+--- pyproject.toml.orig	2024-09-18 22:07:19 UTC
 +++ pyproject.toml
 @@ -1,7 +1,7 @@ requires = [
  [build-system]
  requires = [
--  "setuptools ~= 70.0",
--  "wheel ~= 0.43",
+-  "setuptools ~= 75.1",
+-  "wheel ~= 0.44",
 +  "setuptools",
 +  "wheel",
-   "pyTooling ~= 6.3"
+   "pyTooling ~= 6.5"
  ]
  build-backend = "setuptools.build_meta"