diff --git a/misc/py-shell-gpt/Makefile b/misc/py-shell-gpt/Makefile
index eafdf56a9be7..5bdce031082a 100644
--- a/misc/py-shell-gpt/Makefile
+++ b/misc/py-shell-gpt/Makefile
@@ -1,42 +1,42 @@
 PORTNAME=	shell-gpt
-DISTVERSION=	1.4.4
+DISTVERSION=	1.4.5
 CATEGORIES=	misc python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 DISTNAME=	${PORTNAME:S/-/_/}-${DISTVERSION}
 
 MAINTAINER=	tagattie@FreeBSD.org
 COMMENT=	Command-line productivity tool powered by large language models
 WWW=		https://github.com/TheR1D/shell_gpt
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}hatchling>0:devel/py-hatchling@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}openai>=1.34.0<2.0.0:misc/py-openai@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}typer>=0.7.0<1.0.0:devel/py-typer@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}click>=7.1.1<9.0.0:devel/py-click@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}rich>=13.1.0<14.0.0:textproc/py-rich@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}rich>=13.1.0<15.0.0:textproc/py-rich@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}distro>=1.8.0<2.0.0:sysutils/py-distro@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}instructor>=0.4.5<1.0.0:misc/py-instructor@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}instructor>=1.0.0<2.0.0:misc/py-instructor@${PY_FLAVOR} \
 		curl:ftp/curl
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}requests-mock>=1.10.0<2.0.0:www/py-requests-mock@${PY_FLAVOR}
 
 USES=		python
 USE_PYTHON=	autoplist pep517 pytest
 
 BINARY_ALIAS=	python=${PYTHON_CMD}
 NO_ARCH=	yes
 
 PORTDOCS=	README.md
 
 OPTIONS_DEFINE=	DOCS LITELLM
 
 LITELLM_DESC=		Support various LLMs via LiteLLM
-LITELLM_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}litellm>=1.24.5<2.0.0:misc/py-litellm@${PY_FLAVOR}
+LITELLM_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}litellm>=1.42.5<2.0.0:misc/py-litellm@${PY_FLAVOR}
 
 post-install-DOCS-on:
 	@${MKDIR} ${STAGEDIR}${DOCSDIR}
 	${INSTALL_MAN} ${PORTDOCS:S|^|${WRKSRC}/|} ${STAGEDIR}${DOCSDIR}
 
 .include <bsd.port.mk>
diff --git a/misc/py-shell-gpt/distinfo b/misc/py-shell-gpt/distinfo
index aefd5ae5e71e..757c87505b06 100644
--- a/misc/py-shell-gpt/distinfo
+++ b/misc/py-shell-gpt/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1723426484
-SHA256 (shell_gpt-1.4.4.tar.gz) = 3384af581ba95b6d6da7004e1ede5be0884fe4a72783b408dca3c0ac3fff71e9
-SIZE (shell_gpt-1.4.4.tar.gz) = 36454
+TIMESTAMP = 1744804062
+SHA256 (shell_gpt-1.4.5.tar.gz) = 3656c58f370b436ede0d05d108ebda6f5f8107c07b8221ef1e68e53173253ecf
+SIZE (shell_gpt-1.4.5.tar.gz) = 36507