diff --git a/devel/py-deepdiff/Makefile b/devel/py-deepdiff/Makefile
index cfd66efe40a8..d7ca589e0544 100644
--- a/devel/py-deepdiff/Makefile
+++ b/devel/py-deepdiff/Makefile
@@ -1,25 +1,28 @@
 PORTNAME=	deepdiff
-DISTVERSION=	5.8.1
+DISTVERSION=	6.6.1
 CATEGORIES=	devel python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	yuri@FreeBSD.org
 COMMENT=	Deep difference and search of any Python object/data
 WWW=		https://github.com/seperman/deepdiff
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
-RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}ordered-set>=4.1.0:devel/py-ordered-set@${PY_FLAVOR}
-TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pytest>0:devel/py-pytest@${PY_FLAVOR}
+RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}ordered-set>=4.0.2:devel/py-ordered-set@${PY_FLAVOR}
+TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pytest>0:devel/py-pytest@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}jsonpickle>0:devel/py-jsonpickle@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}pydantic>0:devel/py-pydantic@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}types-PyYAML>=0:devel/py-types-PyYAML@${PY_FLAVOR}
 
 USES=		python
 USE_PYTHON=	distutils autoplist
 
 NO_ARCH=	yes
 
 do-test: # some tests fail, see https://github.com/seperman/deepdiff/issues/323
 	@cd ${WRKSRC} && ${SETENV} ${TEST_ENV} ${PYTHON_CMD} -m pytest
 
 .include <bsd.port.mk>
diff --git a/devel/py-deepdiff/distinfo b/devel/py-deepdiff/distinfo
index 49c1e951e612..03ec673c7ee9 100644
--- a/devel/py-deepdiff/distinfo
+++ b/devel/py-deepdiff/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1653954572
-SHA256 (deepdiff-5.8.1.tar.gz) = 8d4eb2c4e6cbc80b811266419cb71dd95a157094a3947ccf937a94d44943c7b8
-SIZE (deepdiff-5.8.1.tar.gz) = 385498
+TIMESTAMP = 1697832765
+SHA256 (deepdiff-6.6.1.tar.gz) = 75c75b1511f0e48edef2b70d785a9c32b2631666b465fa8c32270a77a7b950b5
+SIZE (deepdiff-6.6.1.tar.gz) = 402840