diff --git a/misc/py-crewai-cli/Makefile b/misc/py-crewai-cli/Makefile
index 88f5e5a9220d..090a30cdf671 100644
--- a/misc/py-crewai-cli/Makefile
+++ b/misc/py-crewai-cli/Makefile
@@ -1,60 +1,64 @@
 PORTNAME=	crewai-cli
-PORTVERSION=	1.15.7
+PORTVERSION=	1.15.20
 CATEGORIES=	misc python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 DISTNAME=	crewai_cli-${PORTVERSION}
 
 MAINTAINER=	yuri@FreeBSD.org
 COMMENT=	CrewAI: CLI
 WWW=		https://crewai.com \
 		https://docs.crewai.com \
 		https://github.com/crewAIInc/crewAI
 
 LICENSE=	MIT
 
 BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}hatchling>=0:devel/py-hatchling@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}appdirs>=1.4.4:devel/py-appdirs@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}certifi>=0:security/py-certifi@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}click>=8.1.7:devel/py-click@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}crewai-core>=1.15.7:misc/py-crewai-core@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}crewai-core>=1.15.20:misc/py-crewai-core@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}cryptography>=42.0:security/py-cryptography@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}httpx>=0.28.1:www/py-httpx@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}packaging>=23.0:devel/py-packaging@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pydantic-settings>=2.14.2:devel/py-pydantic-settings@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pydantic2>=2.11.9:devel/py-pydantic2@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pyjwt>=2.13.0:www/py-pyjwt@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}python-dotenv>=1.2.2:www/py-python-dotenv@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}rich>=13.7.1:textproc/py-rich@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}textual>=7.5.0:textproc/py-textual@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}tomli-w>=1.1.0:textproc/py-tomli-w@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}tomli>=2.0.2:textproc/py-tomli@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}uv>=0.11.6:devel/py-uv@${PY_FLAVOR}
-TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}crewai>=1.5.0:misc/py-crewai@${PY_FLAVOR} \
+TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}anyio>0:devel/py-anyio@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}crewai>=1.15.20:misc/py-crewai@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-subprocess>=0:devel/py-pytest-subprocess@${PY_FLAVOR}
 
 USES=		python
 USE_PYTHON=	autoplist concurrent pep517 pytest
 
 NO_ARCH=	yes
 
 # Template files contain Jinja syntax and cannot be byte-compiled.
 PEP517_INSTALL_CMD=	${PYTHON_CMD} -m installer --no-compile-bytecode \
 			--destdir ${STAGEDIR} --prefix ${PREFIX} \
 			${BUILD_WRKSRC}/dist/${PORTNAME:C|[-_]+|_|g}-${DISTVERSION}*.whl
 
 TEST_ENV=	${MAKE_ENV} PYTHONPATH=${STAGEDIR}${PYTHONPREFIX_SITELIBDIR}
 TEST_WRKSRC=	${WRKSRC}/tests
-# ignore failing tests, see https://github.com/crewAIInc/crewAI/issues/6643
+# ignore failing tests, see https://github.com/crewAIInc/crewAI/issues/6643, they said that the fix is awaiting review in a pull request
+# adding the args --disable-plugin-autoload -p anyio causes tests to fail, see https://github.com/crewAIInc/crewAI/issues/7305
 TEST_ARGS=	--ignore=test_click_compatibility.py \
+		--ignore=test_cli.py \
 		--ignore=test_create_crew.py \
+		--ignore=test_create_unified.py \
 		--ignore=test_plus_api.py \
 		--ignore=test_run_crew.py \
 		--ignore=test_run_declarative_flow.py \
 		--ignore=skills/test_cli_commands.py \
 		--ignore=tools/test_main.py \
 		--deselect=tests/test_crew_run_tui.py::test_crew_done_keeps_memory_save_subscription_until_completion
 
-# tests as of 1.15.7: 523 passed, 1 deselected, 5 warnings in 9.56s
+# tests as of 1.15.20: 504 passed, 4 warnings in 18.61s
 
 .include <bsd.port.mk>
diff --git a/misc/py-crewai-cli/distinfo b/misc/py-crewai-cli/distinfo
index 3d82cd7767ff..cfc2d924f79d 100644
--- a/misc/py-crewai-cli/distinfo
+++ b/misc/py-crewai-cli/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1785096578
-SHA256 (crewai_cli-1.15.7.tar.gz) = cf50dc856694d85d1b2a4609c28918454019b2f5f01ac596a6b293bc6ab19465
-SIZE (crewai_cli-1.15.7.tar.gz) = 220301
+TIMESTAMP = 1788718641
+SHA256 (crewai_cli-1.15.20.tar.gz) = 21f1735ee7e6818f658f46d59844d6f04700af5398c632a3e0fd42c8e6180c93
+SIZE (crewai_cli-1.15.20.tar.gz) = 233643
diff --git a/misc/py-crewai-cli/files/patch-pyproject.toml b/misc/py-crewai-cli/files/patch-pyproject.toml
index 9fdd9c1ed3f0..13a46734a75c 100644
--- a/misc/py-crewai-cli/files/patch-pyproject.toml
+++ b/misc/py-crewai-cli/files/patch-pyproject.toml
@@ -1,32 +1,36 @@
+-- Loosen strict / pinned dependency constraints so the port can use the
+-- current versions of its dependencies in the FreeBSD Ports tree.  Upper
+-- bounds and exact pins are build/runtime policy, not API requirements.
+
 --- pyproject.toml.orig	2020-02-02 00:00:00 UTC
 +++ pyproject.toml
 @@ -8,19 +8,19 @@ authors = [
  ]
  requires-python = ">=3.10, <3.14"
  dependencies = [
--    "crewai-core==1.15.7",
-+    "crewai-core>=1.15.7",
+-    "crewai-core==1.15.20",
++    "crewai-core>=1.15.20",
      "click>=8.1.7,<9",
 -    "pydantic>=2.11.9,<2.13",
 -    "pydantic-settings>=2.14.2,<3",
 -    "appdirs~=1.4.4",
 +    "pydantic>=2.11.9",
 +    "pydantic-settings>=2.14.2",
 +    "appdirs>=1.4.4",
      "cryptography>=42.0",
 -    "httpx~=0.28.1",
 +    "httpx>=0.28.1",
      "pyjwt>=2.13.0,<3",
      "rich>=13.7.1",
 -    "tomli~=2.0.2",
 -    "tomli-w~=1.1.0",
 +    "tomli>=2.0.2",
 +    "tomli-w>=1.1.0",
      "packaging>=23.0",
 -    "python-dotenv>=1.2.2,<2",
 -    "uv~=0.11.6",
 +    "python-dotenv>=1.2.2",
 +    "uv>=0.11.6",
      "textual>=7.5.0",
      "certifi",
  ]