diff --git a/devel/py-dulwich/Makefile b/devel/py-dulwich/Makefile
index f8e46e3db50e..76462d6bac6d 100644
--- a/devel/py-dulwich/Makefile
+++ b/devel/py-dulwich/Makefile
@@ -1,60 +1,60 @@
 PORTNAME=	dulwich
-PORTVERSION=	0.24.7
+PORTVERSION=	0.24.8
 CATEGORIES=	devel python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 DISTFILES=	dulwich-${PORTVERSION}${EXTRACT_SUFX}
 
 MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	Python Git Library
 WWW=		https://www.dulwich.io/ \
 		https://github.com/jelmer/dulwich
 
 LICENSE=	APACHE20 GPLv2+
 LICENSE_COMB=	dual
 LICENSE_FILE=	${WRKSRC}/COPYING
 
 BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}setuptools>=61:devel/py-setuptools@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}setuptools-rust>=0:devel/py-setuptools-rust@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}wheel>=0:devel/py-wheel@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}urllib3>=2.2.2,1:net/py-urllib3@${PY_FLAVOR}
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}fastimport>=0:devel/py-fastimport@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}gevent>=0:devel/py-gevent@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}geventhttpclient>=0:devel/py-geventhttpclient@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}setuptools>=17.1:devel/py-setuptools@${PY_FLAVOR}
 
 USES=		cargo cpe python shebangfix
 USE_PYTHON=	autoplist concurrent pep517 unittest
 
 CARGO_BUILD=	no
 CARGO_INSTALL=	no
 
 CPE_VENDOR=	dulwich_project
 
 SHEBANG_FILES=	examples/*.py
 
 OPTIONS_DEFINE=	DOCS EXAMPLES FASTIMPORT PARAMIKO
 FASTIMPORT_DESC=Git fastimport support
 PARAMIKO_DESC=	SSH2 support
 
 FASTIMPORT_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}fastimport>=0:devel/py-fastimport@${PY_FLAVOR}
 PARAMIKO_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}paramiko>=0:security/py-paramiko@${PY_FLAVOR}
 
 .include <bsd.port.pre.mk>
 
 .if ${PYTHON_REL} < 31200
-RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}typing-extensions>=4.0:devel/py-typing-extensions@${PY_FLAVOR}
+RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}typing-extensions>=4.6.0:devel/py-typing-extensions@${PY_FLAVOR}
 .endif
 
 post-install:
 	${FIND} ${STAGEDIR}${PYTHON_SITELIBDIR} -name '*.so' -exec ${STRIP_CMD} {} +
 
 post-install-DOCS-on:
 	${MKDIR} ${STAGEDIR}${DOCSDIR}/
 	${INSTALL_DATA} ${WRKSRC}/docs/tutorial/*.txt ${STAGEDIR}${DOCSDIR}/
 
 post-install-EXAMPLES-on:
 	${MKDIR} ${STAGEDIR}${EXAMPLESDIR}/
 	${INSTALL_DATA} ${WRKSRC}/examples/*.py ${STAGEDIR}${EXAMPLESDIR}/
 
 .include <bsd.port.post.mk>
diff --git a/devel/py-dulwich/Makefile.crates b/devel/py-dulwich/Makefile.crates
index 745d2e0c9f33..1ff6407b7a1b 100644
--- a/devel/py-dulwich/Makefile.crates
+++ b/devel/py-dulwich/Makefile.crates
@@ -1,19 +1,20 @@
 CARGO_CRATES=	autocfg-1.5.0 \
 		heck-0.5.0 \
 		indoc-2.0.6 \
 		libc-0.2.177 \
 		memchr-2.7.6 \
 		memoffset-0.9.1 \
 		once_cell-1.21.3 \
 		portable-atomic-1.11.1 \
 		proc-macro2-1.0.101 \
 		pyo3-0.27.0 \
 		pyo3-build-config-0.27.0 \
 		pyo3-ffi-0.27.0 \
 		pyo3-macros-0.27.0 \
 		pyo3-macros-backend-0.27.0 \
 		quote-1.0.41 \
+		similar-2.7.0 \
 		syn-2.0.107 \
 		target-lexicon-0.13.3 \
 		unicode-ident-1.0.19 \
 		unindent-0.2.4
diff --git a/devel/py-dulwich/distinfo b/devel/py-dulwich/distinfo
index b25c8c131584..712bdb43f035 100644
--- a/devel/py-dulwich/distinfo
+++ b/devel/py-dulwich/distinfo
@@ -1,41 +1,43 @@
-TIMESTAMP = 1761446612
-SHA256 (dulwich-0.24.7.tar.gz) = f10bffa1395a8dedc3d38ac05164f761ae838a6a18f9a09a966f27dd651850d4
-SIZE (dulwich-0.24.7.tar.gz) = 968411
+TIMESTAMP = 1762586792
+SHA256 (dulwich-0.24.8.tar.gz) = c9f4748bbcca56fb57458c71c0d30e2351ac15e0583d428c739c09228be68f05
+SIZE (dulwich-0.24.8.tar.gz) = 998526
 SHA256 (rust/crates/autocfg-1.5.0.crate) = c08606f8c3cbf4ce6ec8e28fb0014a2c086708fe954eaa885384a6165172e7e8
 SIZE (rust/crates/autocfg-1.5.0.crate) = 18729
 SHA256 (rust/crates/heck-0.5.0.crate) = 2304e00983f87ffb38b55b444b5e3b60a884b5d30c0fca7d82fe33449bbe55ea
 SIZE (rust/crates/heck-0.5.0.crate) = 11517
 SHA256 (rust/crates/indoc-2.0.6.crate) = f4c7245a08504955605670dbf141fceab975f15ca21570696aebe9d2e71576bd
 SIZE (rust/crates/indoc-2.0.6.crate) = 17164
 SHA256 (rust/crates/libc-0.2.177.crate) = 2874a2af47a2325c2001a6e6fad9b16a53b802102b528163885171cf92b15976
 SIZE (rust/crates/libc-0.2.177.crate) = 792045
 SHA256 (rust/crates/memchr-2.7.6.crate) = f52b00d39961fc5b2736ea853c9cc86238e165017a493d1d5c8eac6bdc4cc273
 SIZE (rust/crates/memchr-2.7.6.crate) = 97616
 SHA256 (rust/crates/memoffset-0.9.1.crate) = 488016bfae457b036d996092f6cb448677611ce4449e970ceaf42695203f218a
 SIZE (rust/crates/memoffset-0.9.1.crate) = 9032
 SHA256 (rust/crates/once_cell-1.21.3.crate) = 42f5e15c9953c5e4ccceeb2e7382a716482c34515315f7b03532b8b4e8393d2d
 SIZE (rust/crates/once_cell-1.21.3.crate) = 34534
 SHA256 (rust/crates/portable-atomic-1.11.1.crate) = f84267b20a16ea918e43c6a88433c2d54fa145c92a811b5b047ccbe153674483
 SIZE (rust/crates/portable-atomic-1.11.1.crate) = 185506
 SHA256 (rust/crates/proc-macro2-1.0.101.crate) = 89ae43fd86e4158d6db51ad8e2b80f313af9cc74f5c0e03ccb87de09998732de
 SIZE (rust/crates/proc-macro2-1.0.101.crate) = 53886
 SHA256 (rust/crates/pyo3-0.27.0.crate) = fa8e48c12afdeb26aa4be4e5c49fb5e11c3efa0878db783a960eea2b9ac6dd19
 SIZE (rust/crates/pyo3-0.27.0.crate) = 1172080
 SHA256 (rust/crates/pyo3-build-config-0.27.0.crate) = bc1989dbf2b60852e0782c7487ebf0b4c7f43161ffe820849b56cf05f945cee1
 SIZE (rust/crates/pyo3-build-config-0.27.0.crate) = 35562
 SHA256 (rust/crates/pyo3-ffi-0.27.0.crate) = c808286da7500385148930152e54fb6883452033085bf1f857d85d4e82ca905c
 SIZE (rust/crates/pyo3-ffi-0.27.0.crate) = 78505
 SHA256 (rust/crates/pyo3-macros-0.27.0.crate) = 83a0543c16be0d86cf0dbf2e2b636ece9fd38f20406bb43c255e0bc368095f92
 SIZE (rust/crates/pyo3-macros-0.27.0.crate) = 8916
 SHA256 (rust/crates/pyo3-macros-backend-0.27.0.crate) = 2a00da2ce064dcd582448ea24a5a26fa9527e0483103019b741ebcbe632dcd29
 SIZE (rust/crates/pyo3-macros-backend-0.27.0.crate) = 82461
 SHA256 (rust/crates/quote-1.0.41.crate) = ce25767e7b499d1b604768e7cde645d14cc8584231ea6b295e9c9eb22c02e1d1
 SIZE (rust/crates/quote-1.0.41.crate) = 31408
+SHA256 (rust/crates/similar-2.7.0.crate) = bbbb5d9659141646ae647b42fe094daf6c6192d1620870b449d9557f748b2daa
+SIZE (rust/crates/similar-2.7.0.crate) = 53928
 SHA256 (rust/crates/syn-2.0.107.crate) = 2a26dbd934e5451d21ef060c018dae56fc073894c5a7896f882928a76e6d081b
 SIZE (rust/crates/syn-2.0.107.crate) = 301716
 SHA256 (rust/crates/target-lexicon-0.13.3.crate) = df7f62577c25e07834649fc3b39fafdc597c0a3527dc1c60129201ccfcbaa50c
 SIZE (rust/crates/target-lexicon-0.13.3.crate) = 28498
 SHA256 (rust/crates/unicode-ident-1.0.19.crate) = f63a545481291138910575129486daeaf8ac54aee4387fe7906919f7830c7d9d
 SIZE (rust/crates/unicode-ident-1.0.19.crate) = 47480
 SHA256 (rust/crates/unindent-0.2.4.crate) = 7264e107f553ccae879d21fbea1d6724ac785e8c3bfc762137959b5802826ef3
 SIZE (rust/crates/unindent-0.2.4.crate) = 7422