diff --git a/misc/py-litellm/Makefile b/misc/py-litellm/Makefile
index 5a6f83dbac38..2666f47c8b3b 100644
--- a/misc/py-litellm/Makefile
+++ b/misc/py-litellm/Makefile
@@ -1,48 +1,48 @@
 PORTNAME=	litellm
-DISTVERSION=	1.44.2
+DISTVERSION=	1.44.5
 CATEGORIES=	misc python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	tagattie@FreeBSD.org
 COMMENT=	Call all LLM APIs using the OpenAI format
 WWW=		https://github.com/BerriAI/litellm
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}poetry-core>0:devel/py-poetry-core@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}wheel>0:devel/py-wheel@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}openai>=1.40.0:misc/py-openai@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}python-dotenv>=0.2.0:www/py-python-dotenv@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}tiktoken>=0.7.0:textproc/py-tiktoken@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}importlib-metadata>=6.8.0:devel/py-importlib-metadata@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}tokenizers>0:textproc/py-tokenizers@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}click>0:devel/py-click@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}Jinja2>=3.1.2<4.0.0:devel/py-Jinja2@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}aiohttp>0:www/py-aiohttp@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}requests>=2.31.0<3.0.0:www/py-requests@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pydantic2>=2.0.0<3.0.0:devel/py-pydantic2@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}jsonschema>=4.22.0<5.0.0:devel/py-jsonschema@${PY_FLAVOR}
 
 USES=		python shebangfix
 USE_PYTHON=	autoplist concurrent pep517
 
 REINPLACE_ARGS=	-i ''
 NO_ARCH=	yes
 
 PORTDOCS=	README.md
 
 OPTIONS_DEFINE=	DOCS
 
 post-patch:
 	@${REINPLACE_CMD} -e 's|%%PYTHON_CMD%%|${PYTHON_CMD}|' \
 		${WRKSRC}/litellm/proxy/start.sh
 	@${FIND} ${WRKSRC}/litellm/proxy -type f \
 		\( -name '*.orig' -o -name '*.bak' \) -delete
 
 post-install-DOCS-on:
 	@${MKDIR} ${STAGEDIR}${DOCSDIR}
 	${INSTALL_MAN} ${PORTDOCS:S|^|${WRKSRC}/|} ${STAGEDIR}${DOCSDIR}
 
 .include <bsd.port.mk>
diff --git a/misc/py-litellm/distinfo b/misc/py-litellm/distinfo
index 7e16ad51ea37..76a40c801f4c 100644
--- a/misc/py-litellm/distinfo
+++ b/misc/py-litellm/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1724373433
-SHA256 (litellm-1.44.2.tar.gz) = b9290b1414caf6a955a5a493fb1b1dce95b2710a934e968c9ab04d0a3fba804c
-SIZE (litellm-1.44.2.tar.gz) = 8129040
+TIMESTAMP = 1724636554
+SHA256 (litellm-1.44.5.tar.gz) = 297dbf7d733c95aa54322874cc49de264f0f209d8bf9622672d21f8786a77920
+SIZE (litellm-1.44.5.tar.gz) = 8266887