diff --git a/net-mgmt/py-ciscoconfparse/Makefile b/net-mgmt/py-ciscoconfparse/Makefile
index 678a02c031a6..39c52cc33f90 100644
--- a/net-mgmt/py-ciscoconfparse/Makefile
+++ b/net-mgmt/py-ciscoconfparse/Makefile
@@ -1,32 +1,42 @@
 PORTNAME=	ciscoconfparse
-DISTVERSION=	1.9.28
+DISTVERSION=	1.9.52
 CATEGORIES=	net-mgmt python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	kai@FreeBSD.org
 COMMENT=	Parse, audit, query, build and modify Cisco IOS-style configurations
-WWW=		http://www.pennington.net/py/ciscoconfparse/
+WWW=		https://www.pennington.net/py/ciscoconfparse/
 
 LICENSE=	GPLv3+
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
+DEPRECATED=	Upstream repo archived on 5th March 2025. Please use net-mgmt/py-ciscoconfparse2 instead
+EXPIRATION_DATE=2026-11-30
+
 BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}poetry-core>=1.6.1:devel/py-poetry-core@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}packaging>=23.0:devel/py-packaging@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}wheel>=0.38.4:devel/py-wheel@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}deprecated>=1.2.14:devel/py-deprecated@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}dnspython>=2.4.2:dns/py-dnspython@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}dnspython>=2.4.2,1<3,1:dns/py-dnspython@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}hier-config>=2.2.3<3:net-mgmt/py-hier-config@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}loguru>=0.7.2:devel/py-loguru@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}passlib>=1.7.4:security/py-passlib@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}passlib>=1.7.4<2:security/py-passlib@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}toml>=0.10.2:textproc/py-toml@${PY_FLAVOR}
 
 USES=		python
 USE_PYTHON=	autoplist pep517 pytest
-# Test fails due missing file: fixtures/configs/sample_01.f5
-PYTEST_BROKEN_TESTS=	testParse_parse_syntax_f5_as_junos_nofactory_ioscfg_01
+# Test fails due missing files:
+# - fixtures/configs/sample_01.{asa,f5,ios,iosxr,junos,nxosf}
+PYTEST_BROKEN_TESTS=	testIPv6Obj_IPv4_embedded_in_IPv6_04 \
+			testParse_parse_syntax_f5_as_junos_nofactory_ioscfg_01 \
+			testParse_syntax \
+			testVal_JunosCfgLine_child_02 \
+			testVal_JunosCfgLine_child_03 \
+			testVal_JunosCfgLine_child_04
 
 TEST_ENV=	PYTHONPATH=${STAGEDIR}${PYTHONPREFIX_SITELIBDIR}
 
 NO_ARCH=	yes
 
 .include <bsd.port.mk>
diff --git a/net-mgmt/py-ciscoconfparse/distinfo b/net-mgmt/py-ciscoconfparse/distinfo
index 1f8cd87cc7ba..e1658aa19104 100644
--- a/net-mgmt/py-ciscoconfparse/distinfo
+++ b/net-mgmt/py-ciscoconfparse/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1699694157
-SHA256 (ciscoconfparse-1.9.28.tar.gz) = fdb64c57c4c10735a79e12bcb672237362edc83e0836f0f5ae5bb6188a9ead11
-SIZE (ciscoconfparse-1.9.28.tar.gz) = 480572
+TIMESTAMP = 1761990081
+SHA256 (ciscoconfparse-1.9.52.tar.gz) = 28b13af4f12aadf60b4ced921a72cc5e5514ce4a89aceba10a7239e2551d9a0a
+SIZE (ciscoconfparse-1.9.52.tar.gz) = 389869
diff --git a/net-mgmt/py-ciscoconfparse/files/patch-pyproject.toml b/net-mgmt/py-ciscoconfparse/files/patch-pyproject.toml
index 7e4fd764c245..8dea2a38ee01 100644
--- a/net-mgmt/py-ciscoconfparse/files/patch-pyproject.toml
+++ b/net-mgmt/py-ciscoconfparse/files/patch-pyproject.toml
@@ -1,25 +1,40 @@
-Just use poetry-core and remove directives that are unknown for it.
+* Use the more lightweight py-poetry-core.
 
-Avoid the installation of the test suite into the top of Python's site-lib.
+* Avoid the installation of the test suite into the top of Python's site-lib.
 
---- pyproject.toml.orig	2023-10-29 15:08:28 UTC
+* Relax some version requirements and set an upper bound for py-hier-config
+  because the 3.x release contains breaking changes.
+
+--- pyproject.toml.orig	2024-11-22 10:15:59 UTC
 +++ pyproject.toml
 @@ -2,9 +2,8 @@
  
  [build-system]
  # See -> PEP 517
 -requires = ["poetry>=1.5.1", "poetry-core>=1.6.1", "wheel>=0.38.4", "packaging>=23.0"]
 +requires = ["poetry-core>=1.6.1", "wheel>=0.38.4", "packaging>=23.0"]
  build-backend = "poetry.core.masonry.api"
 -requires-python = ">=3.8.0"
  
  ##############################################################################
  #
 @@ -38,7 +37,6 @@ packages = [
  packages = [
      # Syntax -> https://python-poetry.org/docs/pyproject/#packages
      { include = "ciscoconfparse/*" },
 -    { include = "tests/*" },
  ]
  # See -> https://python-poetry.org/docs/pyproject/#include-and-exclude
  include = [
+@@ -80,9 +78,9 @@ dnspython = "^2.4.2"
+ python = ">=3.8,<4.0.0"
+ passlib = "^1.7.4"
+ dnspython = "^2.4.2"
+-loguru = "0.7.2"
++loguru = ">=0.7.2"
+ toml = ">=0.10.2"
+-hier_config = "2.2.3"
++hier_config = ">=2.2.3,<3"
+ deprecated = ">=1.2.14"
+ 
+ [tool.poetry.urls]
diff --git a/net-mgmt/py-ciscoconfparse/files/patch-tests_conftest.py b/net-mgmt/py-ciscoconfparse/files/patch-tests_conftest.py
new file mode 100644
index 000000000000..bd921d5146d1
--- /dev/null
+++ b/net-mgmt/py-ciscoconfparse/files/patch-tests_conftest.py
@@ -0,0 +1,15 @@
+* Enable test suite compatibility with py-pytest 9+
+
+--- tests/conftest.py.orig	2026-08-21 16:06:50 UTC
++++ tests/conftest.py
+@@ -1424,10 +1424,6 @@ def parse_n01_factory(request):
+     yield parse_n01_factory
+
+
+-@pytest.mark.skipif(sys.version_info[0] >= 3, reason="No Python3 MockSSH support")
+-@pytest.mark.skipif(
+-    "windows" in platform.system().lower(), reason="No Windows MockSSH support"
+-)
+ @pytest.fixture(scope="session")
+ def cisco_sshd_mocked(request):
+     """Mock Cisco IOS SSH"""