diff --git a/security/py-cryptography/Makefile b/security/py-cryptography/Makefile
index 77c69b690f65..7957c4c9ac20 100644
--- a/security/py-cryptography/Makefile
+++ b/security/py-cryptography/Makefile
@@ -1,54 +1,54 @@
 PORTNAME=	cryptography
-PORTVERSION=	41.0.5
+PORTVERSION=	41.0.7
 PORTEPOCH=	1
 CATEGORIES=	security python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 DISTFILES=	${DISTNAME}${EXTRACT_SUFX}
 
 MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	Cryptographic recipes and primitives for Python developers
 WWW=		https://cryptography.io/en/latest/ \
 		https://github.com/pyca/cryptography
 
 LICENSE=	APACHE20 BSD3CLAUSE
 LICENSE_COMB=	dual
 LICENSE_FILE_APACHE20=	${WRKSRC}/LICENSE.APACHE
 LICENSE_FILE_BSD3CLAUSE=${WRKSRC}/LICENSE.BSD
 
 BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}cffi>=1.12:devel/py-cffi@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}setuptools>=61.0.0:devel/py-setuptools@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}setuptools-rust>=0.11.4:devel/py-setuptools-rust@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}wheel>=0:devel/py-wheel@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}cffi>=1.12:devel/py-cffi@${PY_FLAVOR}
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}bcrypt>=3.1.5:security/py-bcrypt@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}cryptography-vectors>=${PORTVERSION}:security/py-cryptography-vectors@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pretend>=0:devel/py-pretend@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-benchmark>=0:devel/py-pytest-benchmark@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-cov>=0:devel/py-pytest-cov@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-randomly>=0:devel/py-pytest-randomly@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-xdist>=0,1:devel/py-pytest-xdist@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}sqlite3>=0:databases/py-sqlite3@${PY_FLAVOR}
 
 USES=		cargo cpe python ssl
 USE_PYTHON=	autoplist concurrent pep517 pytest
 
 CARGO_BUILD=	no
 CARGO_CARGOLOCK=${WRKSRC}/src/rust/Cargo.lock
 CARGO_CARGOTOML=${WRKSRC}/src/rust/Cargo.toml
 CARGO_INSTALL=	no
 CARGO_TEST=	no
 CFLAGS+=	-I${OPENSSLINC}
 LDFLAGS+=	-L${OPENSSLLIB}
 TEST_ENV=	PYTHONPATH=${STAGEDIR}${PYTHON_SITELIBDIR}
 
 CPE_VENDOR=	cryptography_project
 
 OPTIONS_DEFINE=	SSH
 
 SSH_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}bcrypt>=3.1.5:security/py-bcrypt@${PY_FLAVOR}
 
 post-install:
 	${FIND} ${STAGEDIR}${PYTHON_SITELIBDIR} -name '*.so' -exec ${STRIP_CMD} {} +
 
 .include <bsd.port.mk>
diff --git a/security/py-cryptography/Makefile.crates b/security/py-cryptography/Makefile.crates
index 4fdecb814ffa..c32db9c8fb3e 100644
--- a/security/py-cryptography/Makefile.crates
+++ b/security/py-cryptography/Makefile.crates
@@ -1,53 +1,54 @@
 CARGO_CRATES=	Inflector-0.11.4 \
 		aliasable-0.1.3 \
 		asn1-0.15.2 \
 		asn1_derive-0.15.2 \
 		autocfg-1.1.0 \
 		base64-0.13.1 \
 		bitflags-1.3.2 \
+		bitflags-2.4.1 \
 		cc-1.0.79 \
 		cfg-if-1.0.0 \
 		foreign-types-0.3.2 \
 		foreign-types-shared-0.1.1 \
 		indoc-1.0.9 \
 		libc-0.2.144 \
 		lock_api-0.4.9 \
 		memoffset-0.8.0 \
 		once_cell-1.17.2 \
-		openssl-0.10.54 \
+		openssl-0.10.60 \
 		openssl-macros-0.1.1 \
-		openssl-sys-0.9.88 \
+		openssl-sys-0.9.96 \
 		ouroboros-0.15.6 \
 		ouroboros_macro-0.15.6 \
 		parking_lot-0.12.1 \
 		parking_lot_core-0.9.7 \
 		pem-1.1.1 \
 		pkg-config-0.3.27 \
 		proc-macro-error-1.0.4 \
 		proc-macro-error-attr-1.0.4 \
 		proc-macro2-1.0.64 \
 		pyo3-0.18.3 \
 		pyo3-build-config-0.18.3 \
 		pyo3-ffi-0.18.3 \
 		pyo3-macros-0.18.3 \
 		pyo3-macros-backend-0.18.3 \
 		quote-1.0.28 \
 		redox_syscall-0.2.16 \
 		scopeguard-1.1.0 \
 		smallvec-1.10.0 \
 		syn-1.0.109 \
 		syn-2.0.18 \
 		target-lexicon-0.12.7 \
 		unicode-ident-1.0.9 \
 		unindent-0.1.11 \
 		vcpkg-0.2.15 \
 		version_check-0.9.4 \
 		windows-sys-0.45.0 \
 		windows-targets-0.42.2 \
 		windows_aarch64_gnullvm-0.42.2 \
 		windows_aarch64_msvc-0.42.2 \
 		windows_i686_gnu-0.42.2 \
 		windows_i686_msvc-0.42.2 \
 		windows_x86_64_gnu-0.42.2 \
 		windows_x86_64_gnullvm-0.42.2 \
 		windows_x86_64_msvc-0.42.2
diff --git a/security/py-cryptography/distinfo b/security/py-cryptography/distinfo
index ac7945f3dd77..6f18f589b11c 100644
--- a/security/py-cryptography/distinfo
+++ b/security/py-cryptography/distinfo
@@ -1,109 +1,111 @@
-TIMESTAMP = 1698341075
-SHA256 (cryptography-41.0.5.tar.gz) = 392cb88b597247177172e02da6b7a63deeff1937fa6fec3bbf902ebd75d97ec7
-SIZE (cryptography-41.0.5.tar.gz) = 630537
+TIMESTAMP = 1701363740
+SHA256 (cryptography-41.0.7.tar.gz) = 13f93ce9bea8016c253b34afc6bd6a75993e5c40672ed5405a9c832f0d4a00bc
+SIZE (cryptography-41.0.7.tar.gz) = 630892
 SHA256 (rust/crates/Inflector-0.11.4.crate) = fe438c63458706e03479442743baae6c88256498e6431708f6dfc520a26515d3
 SIZE (rust/crates/Inflector-0.11.4.crate) = 17438
 SHA256 (rust/crates/aliasable-0.1.3.crate) = 250f629c0161ad8107cf89319e990051fae62832fd343083bea452d93e2205fd
 SIZE (rust/crates/aliasable-0.1.3.crate) = 6169
 SHA256 (rust/crates/asn1-0.15.2.crate) = 28c19b9324de5b815b6487e0f8098312791b09de0dbf3d5c2db1fe2d95bab973
 SIZE (rust/crates/asn1-0.15.2.crate) = 34002
 SHA256 (rust/crates/asn1_derive-0.15.2.crate) = a045c3ccad89f244a86bd1e6cf1a7bf645296e7692698b056399b6efd4639407
 SIZE (rust/crates/asn1_derive-0.15.2.crate) = 6096
 SHA256 (rust/crates/autocfg-1.1.0.crate) = d468802bab17cbc0cc575e9b053f41e72aa36bfa6b7f55e3529ffa43161b97fa
 SIZE (rust/crates/autocfg-1.1.0.crate) = 13272
 SHA256 (rust/crates/base64-0.13.1.crate) = 9e1b586273c5702936fe7b7d6896644d8be71e6314cfe09d3167c95f712589e8
 SIZE (rust/crates/base64-0.13.1.crate) = 61002
 SHA256 (rust/crates/bitflags-1.3.2.crate) = bef38d45163c2f1dde094a7dfd33ccf595c92905c8f8f4fdc18d06fb1037718a
 SIZE (rust/crates/bitflags-1.3.2.crate) = 23021
+SHA256 (rust/crates/bitflags-2.4.1.crate) = 327762f6e5a765692301e5bb513e0d9fef63be86bbc14528052b1cd3e6f03e07
+SIZE (rust/crates/bitflags-2.4.1.crate) = 37043
 SHA256 (rust/crates/cc-1.0.79.crate) = 50d30906286121d95be3d479533b458f87493b30a4b5f79a607db8f5d11aa91f
 SIZE (rust/crates/cc-1.0.79.crate) = 62624
 SHA256 (rust/crates/cfg-if-1.0.0.crate) = baf1de4339761588bc0619e3cbc0120ee582ebb74b53b4efbf79117bd2da40fd
 SIZE (rust/crates/cfg-if-1.0.0.crate) = 7934
 SHA256 (rust/crates/foreign-types-0.3.2.crate) = f6f339eb8adc052cd2ca78910fda869aefa38d22d5cb648e6485e4d3fc06f3b1
 SIZE (rust/crates/foreign-types-0.3.2.crate) = 7504
 SHA256 (rust/crates/foreign-types-shared-0.1.1.crate) = 00b0228411908ca8685dba7fc2cdd70ec9990a6e753e89b6ac91a84c40fbaf4b
 SIZE (rust/crates/foreign-types-shared-0.1.1.crate) = 5672
 SHA256 (rust/crates/indoc-1.0.9.crate) = bfa799dd5ed20a7e349f3b4639aa80d74549c81716d9ec4f994c9b5815598306
 SIZE (rust/crates/indoc-1.0.9.crate) = 13475
 SHA256 (rust/crates/libc-0.2.144.crate) = 2b00cc1c228a6782d0f076e7b232802e0c5689d41bb5df366f2a6b6621cfdfe1
 SIZE (rust/crates/libc-0.2.144.crate) = 682092
 SHA256 (rust/crates/lock_api-0.4.9.crate) = 435011366fe56583b16cf956f9df0095b405b82d76425bc8981c0e22e60ec4df
 SIZE (rust/crates/lock_api-0.4.9.crate) = 25685
 SHA256 (rust/crates/memoffset-0.8.0.crate) = d61c719bcfbcf5d62b3a09efa6088de8c54bc0bfcd3ea7ae39fcc186108b8de1
 SIZE (rust/crates/memoffset-0.8.0.crate) = 8912
 SHA256 (rust/crates/once_cell-1.17.2.crate) = 9670a07f94779e00908f3e686eab508878ebb390ba6e604d3a284c00e8d0487b
 SIZE (rust/crates/once_cell-1.17.2.crate) = 33335
-SHA256 (rust/crates/openssl-0.10.54.crate) = 69b3f656a17a6cbc115b5c7a40c616947d213ba182135b014d6051b73ab6f019
-SIZE (rust/crates/openssl-0.10.54.crate) = 258266
+SHA256 (rust/crates/openssl-0.10.60.crate) = 79a4c6c3a2b158f7f8f2a2fc5a969fa3a068df6fc9dbb4a43845436e3af7c800
+SIZE (rust/crates/openssl-0.10.60.crate) = 265736
 SHA256 (rust/crates/openssl-macros-0.1.1.crate) = a948666b637a0f465e8564c73e89d4dde00d72d4d473cc972f390fc3dcee7d9c
 SIZE (rust/crates/openssl-macros-0.1.1.crate) = 5601
-SHA256 (rust/crates/openssl-sys-0.9.88.crate) = c2ce0f250f34a308dcfdbb351f511359857d4ed2134ba715a4eadd46e1ffd617
-SIZE (rust/crates/openssl-sys-0.9.88.crate) = 66011
+SHA256 (rust/crates/openssl-sys-0.9.96.crate) = 3812c071ba60da8b5677cc12bcb1d42989a65553772897a7e0355545a819838f
+SIZE (rust/crates/openssl-sys-0.9.96.crate) = 67743
 SHA256 (rust/crates/ouroboros-0.15.6.crate) = e1358bd1558bd2a083fed428ffeda486fbfb323e698cdda7794259d592ca72db
 SIZE (rust/crates/ouroboros-0.15.6.crate) = 11257
 SHA256 (rust/crates/ouroboros_macro-0.15.6.crate) = 5f7d21ccd03305a674437ee1248f3ab5d4b1db095cf1caf49f1713ddf61956b7
 SIZE (rust/crates/ouroboros_macro-0.15.6.crate) = 20751
 SHA256 (rust/crates/parking_lot-0.12.1.crate) = 3742b2c103b9f06bc9fff0a37ff4912935851bee6d36f3c02bcc755bcfec228f
 SIZE (rust/crates/parking_lot-0.12.1.crate) = 40967
 SHA256 (rust/crates/parking_lot_core-0.9.7.crate) = 9069cbb9f99e3a5083476ccb29ceb1de18b9118cafa53e90c9551235de2b9521
 SIZE (rust/crates/parking_lot_core-0.9.7.crate) = 32412
 SHA256 (rust/crates/pem-1.1.1.crate) = a8835c273a76a90455d7344889b0964598e3316e2a79ede8e36f16bdcf2228b8
 SIZE (rust/crates/pem-1.1.1.crate) = 11352
 SHA256 (rust/crates/pkg-config-0.3.27.crate) = 26072860ba924cbfa98ea39c8c19b4dd6a4a25423dbdf219c1eca91aa0cf6964
 SIZE (rust/crates/pkg-config-0.3.27.crate) = 18838
 SHA256 (rust/crates/proc-macro-error-1.0.4.crate) = da25490ff9892aab3fcf7c36f08cfb902dd3e71ca0f9f9517bea02a73a5ce38c
 SIZE (rust/crates/proc-macro-error-1.0.4.crate) = 25293
 SHA256 (rust/crates/proc-macro-error-attr-1.0.4.crate) = a1be40180e52ecc98ad80b184934baf3d0d29f979574e439af5a55274b35f869
 SIZE (rust/crates/proc-macro-error-attr-1.0.4.crate) = 7971
 SHA256 (rust/crates/proc-macro2-1.0.64.crate) = 78803b62cbf1f46fde80d7c0e803111524b9877184cfe7c3033659490ac7a7da
 SIZE (rust/crates/proc-macro2-1.0.64.crate) = 44848
 SHA256 (rust/crates/pyo3-0.18.3.crate) = e3b1ac5b3731ba34fdaa9785f8d74d17448cd18f30cf19e0c7e7b1fdb5272109
 SIZE (rust/crates/pyo3-0.18.3.crate) = 420236
 SHA256 (rust/crates/pyo3-build-config-0.18.3.crate) = 9cb946f5ac61bb61a5014924910d936ebd2b23b705f7a4a3c40b05c720b079a3
 SIZE (rust/crates/pyo3-build-config-0.18.3.crate) = 29137
 SHA256 (rust/crates/pyo3-ffi-0.18.3.crate) = fd4d7c5337821916ea2a1d21d1092e8443cf34879e53a0ac653fbb98f44ff65c
 SIZE (rust/crates/pyo3-ffi-0.18.3.crate) = 64474
 SHA256 (rust/crates/pyo3-macros-0.18.3.crate) = a9d39c55dab3fc5a4b25bbd1ac10a2da452c4aca13bb450f22818a002e29648d
 SIZE (rust/crates/pyo3-macros-0.18.3.crate) = 7175
 SHA256 (rust/crates/pyo3-macros-backend-0.18.3.crate) = 97daff08a4c48320587b5224cc98d609e3c27b6d437315bd40b605c98eeb5918
 SIZE (rust/crates/pyo3-macros-backend-0.18.3.crate) = 48922
 SHA256 (rust/crates/quote-1.0.28.crate) = 1b9ab9c7eadfd8df19006f1cf1a4aed13540ed5cbc047010ece5826e10825488
 SIZE (rust/crates/quote-1.0.28.crate) = 28382
 SHA256 (rust/crates/redox_syscall-0.2.16.crate) = fb5a58c1855b4b6819d59012155603f0b22ad30cad752600aadfcb695265519a
 SIZE (rust/crates/redox_syscall-0.2.16.crate) = 24012
 SHA256 (rust/crates/scopeguard-1.1.0.crate) = d29ab0c6d3fc0ee92fe66e2d99f700eab17a8d57d1c1d3b748380fb20baa78cd
 SIZE (rust/crates/scopeguard-1.1.0.crate) = 11470
 SHA256 (rust/crates/smallvec-1.10.0.crate) = a507befe795404456341dfab10cef66ead4c041f62b8b11bbb92bffe5d0953e0
 SIZE (rust/crates/smallvec-1.10.0.crate) = 31564
 SHA256 (rust/crates/syn-1.0.109.crate) = 72b64191b275b66ffe2469e8af2c1cfe3bafa67b529ead792a6d0160888b4237
 SIZE (rust/crates/syn-1.0.109.crate) = 237611
 SHA256 (rust/crates/syn-2.0.18.crate) = 32d41677bcbe24c20c52e7c70b0d8db04134c5d1066bf98662e2871ad200ea3e
 SIZE (rust/crates/syn-2.0.18.crate) = 240648
 SHA256 (rust/crates/target-lexicon-0.12.7.crate) = fd1ba337640d60c3e96bc6f0638a939b9c9a7f2c316a1598c279828b3d1dc8c5
 SIZE (rust/crates/target-lexicon-0.12.7.crate) = 24402
 SHA256 (rust/crates/unicode-ident-1.0.9.crate) = b15811caf2415fb889178633e7724bad2509101cde276048e013b9def5e51fa0
 SIZE (rust/crates/unicode-ident-1.0.9.crate) = 41978
 SHA256 (rust/crates/unindent-0.1.11.crate) = e1766d682d402817b5ac4490b3c3002d91dfa0d22812f341609f97b08757359c
 SIZE (rust/crates/unindent-0.1.11.crate) = 7700
 SHA256 (rust/crates/vcpkg-0.2.15.crate) = accd4ea62f7bb7a82fe23066fb0957d48ef677f6eeb8215f372f52e48bb32426
 SIZE (rust/crates/vcpkg-0.2.15.crate) = 228735
 SHA256 (rust/crates/version_check-0.9.4.crate) = 49874b5167b65d7193b8aba1567f5c7d93d001cafc34600cee003eda787e483f
 SIZE (rust/crates/version_check-0.9.4.crate) = 14895
 SHA256 (rust/crates/windows-sys-0.45.0.crate) = 75283be5efb2831d37ea142365f009c02ec203cd29a3ebecbc093d52315b66d0
 SIZE (rust/crates/windows-sys-0.45.0.crate) = 2568659
 SHA256 (rust/crates/windows-targets-0.42.2.crate) = 8e5180c00cd44c9b1c88adb3693291f1cd93605ded80c250a75d472756b4d071
 SIZE (rust/crates/windows-targets-0.42.2.crate) = 5492
 SHA256 (rust/crates/windows_aarch64_gnullvm-0.42.2.crate) = 597a5118570b68bc08d8d59125332c54f1ba9d9adeedeef5b99b02ba2b0698f8
 SIZE (rust/crates/windows_aarch64_gnullvm-0.42.2.crate) = 364071
 SHA256 (rust/crates/windows_aarch64_msvc-0.42.2.crate) = e08e8864a60f06ef0d0ff4ba04124db8b0fb3be5776a5cd47641e942e58c4d43
 SIZE (rust/crates/windows_aarch64_msvc-0.42.2.crate) = 666981
 SHA256 (rust/crates/windows_i686_gnu-0.42.2.crate) = c61d927d8da41da96a81f029489353e68739737d3beca43145c8afec9a31a84f
 SIZE (rust/crates/windows_i686_gnu-0.42.2.crate) = 736236
 SHA256 (rust/crates/windows_i686_msvc-0.42.2.crate) = 44d840b6ec649f480a41c8d80f9c65108b92d89345dd94027bfe06ac444d1060
 SIZE (rust/crates/windows_i686_msvc-0.42.2.crate) = 724951
 SHA256 (rust/crates/windows_x86_64_gnu-0.42.2.crate) = 8de912b8b8feb55c064867cf047dda097f92d51efad5b491dfb98f6bbb70cb36
 SIZE (rust/crates/windows_x86_64_gnu-0.42.2.crate) = 699373
 SHA256 (rust/crates/windows_x86_64_gnullvm-0.42.2.crate) = 26d41b46a36d453748aedef1486d5c7a85db22e56aff34643984ea85514e94a3
 SIZE (rust/crates/windows_x86_64_gnullvm-0.42.2.crate) = 364068
 SHA256 (rust/crates/windows_x86_64_msvc-0.42.2.crate) = 9aec5da331524158c6d1a4ac0ab1541149c0b9505fde06423b02f5ef0106b9f0
 SIZE (rust/crates/windows_x86_64_msvc-0.42.2.crate) = 666936