diff --git a/security/libressl-devel/Makefile b/security/libressl-devel/Makefile
index f1dc45b4f09f..d283eb990452 100644
--- a/security/libressl-devel/Makefile
+++ b/security/libressl-devel/Makefile
@@ -1,65 +1,65 @@
 # Created by: Bernard Spil <brnrd@FreeBSD.org>
 
 PORTNAME=	libressl
-PORTVERSION=	3.5.1
+PORTVERSION=	3.5.2
 CATEGORIES=	security devel
 MASTER_SITES=	OPENBSD/LibreSSL
 PKGNAMESUFFIX=	-devel
 
 MAINTAINER=	brnrd@FreeBSD.org
 COMMENT=	Free version of the SSL/TLS protocol forked from OpenSSL
 
 LICENSE=	BSD4CLAUSE
 LICENSE_FILE=	${WRKSRC}/COPYING
 
 FLAVORS=	default libtls
 FLAVOR?=	${FLAVORS:[1]}
 libtls_DESCR=	pkg-descr-libtls
 libtls_PKGNAMESUFFIX=	-devel-libtls
 libtls_PLIST=	pkg-plist-libtls
 
 CPE_VENDOR=	openbsd
 
 OPTIONS_DEFINE=	LIBTLS MAN3 NC
 OPTIONS_DEFAULT=	MAN3 NC
 LIBTLS_DESC=	Only install libtls (no libcrypto/libssl)
 MAN3_DESC=	Install API manpages (section 3)
 NC_DESC=	Install TLS-enabled netcat
 
 CONFLICTS_INSTALL=		libressl \
 				libretls
 default_CONFLICTS_INSTALL=	openssl
 
 .if ${FLAVOR:U} == default
 OPTIONS_EXCLUDE=	LIBTLS
 .elif ${FLAVOR:U} == libtls
 OPTIONS_SLAVE=		LIBTLS
 OPTIONS_EXCLUDE=	MAN3
 .endif
 
 LIBTLS_CONFIGURE_ENABLE=	libtls-only
 NC_CONFIGURE_ENABLE=		nc
 
 GNU_CONFIGURE=	yes
 USES=		cpe libtool pathfix pkgconfig
 USE_LDCONFIG=	yes
 OPTIONS_SUB=	yes
 CFLAGS+=	-fpic -DPIC -Wl,-rpath,${PREFIX}/lib -Wl,--as-needed
 LDFLAGS+=	-pthread
 
 INSTALL_TARGET=	install-strip
 TEST_TARGET=	check
 
 post-patch-MAN3-off:
 	${REINPLACE_CMD} -e '/^install-man:/s/install-man3//' \
 		-e '/$$(MAKE) $$(AM_MAKEFLAGS) install-data-hook/d' \
 		${WRKSRC}/man/Makefile.in
 
 post-install:
 	${RM} -r ${STAGEDIR}/${PREFIX}/etc/ssl/cert.pem
 
 post-stage-MAN3-on:
 	(cd ${STAGEDIR}${MANPREFIX}; ${FIND} man/man3 -not -type d | \
 		${SED} 's/$$/.gz/' >> ${TMPPLIST})
 
 .include <bsd.port.mk>
diff --git a/security/libressl-devel/distinfo b/security/libressl-devel/distinfo
index 593f051d0443..9674527c80bd 100644
--- a/security/libressl-devel/distinfo
+++ b/security/libressl-devel/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1647457483
-SHA256 (libressl-3.5.1.tar.gz) = a7d0026f67622275ec8f8239ded422a653d5ccc84df55dea2acd406017185608
-SIZE (libressl-3.5.1.tar.gz) = 4030718
+TIMESTAMP = 1650811506
+SHA256 (libressl-3.5.2.tar.gz) = 56feab8e21c3fa6549f8b7d7511658b8e98518162838a795314732654adf3e5f
+SIZE (libressl-3.5.2.tar.gz) = 4039407
diff --git a/security/libressl-devel/pkg-plist b/security/libressl-devel/pkg-plist
index 55b7886f76da..df28628fbba7 100644
--- a/security/libressl-devel/pkg-plist
+++ b/security/libressl-devel/pkg-plist
@@ -1,104 +1,104 @@
 %%NC%%bin/nc
 bin/ocspcheck
 bin/openssl
 etc/ssl/openssl.cnf
 etc/ssl/x509v3.cnf
 include/openssl/aes.h
 include/openssl/asn1.h
 include/openssl/asn1t.h
 include/openssl/bio.h
 include/openssl/blowfish.h
 include/openssl/bn.h
 include/openssl/buffer.h
 include/openssl/camellia.h
 include/openssl/cast.h
 include/openssl/chacha.h
 include/openssl/cmac.h
 include/openssl/cms.h
 include/openssl/comp.h
 include/openssl/conf.h
 include/openssl/conf_api.h
 include/openssl/crypto.h
 include/openssl/ct.h
 include/openssl/cterr.h
 include/openssl/curve25519.h
 include/openssl/des.h
 include/openssl/dh.h
 include/openssl/dsa.h
 include/openssl/dso.h
 include/openssl/dtls1.h
 include/openssl/ec.h
 include/openssl/ecdh.h
 include/openssl/ecdsa.h
 include/openssl/engine.h
 include/openssl/err.h
 include/openssl/evp.h
 include/openssl/gost.h
 include/openssl/hkdf.h
 include/openssl/hmac.h
 include/openssl/idea.h
 include/openssl/lhash.h
 include/openssl/md4.h
 include/openssl/md5.h
 include/openssl/modes.h
 include/openssl/obj_mac.h
 include/openssl/objects.h
 include/openssl/ocsp.h
 include/openssl/opensslconf.h
 include/openssl/opensslfeatures.h
 include/openssl/opensslv.h
 include/openssl/ossl_typ.h
 include/openssl/pem.h
 include/openssl/pem2.h
 include/openssl/pkcs12.h
 include/openssl/pkcs7.h
 include/openssl/poly1305.h
 include/openssl/rand.h
 include/openssl/rc2.h
 include/openssl/rc4.h
 include/openssl/ripemd.h
 include/openssl/rsa.h
 include/openssl/safestack.h
 include/openssl/sha.h
 include/openssl/sm3.h
 include/openssl/sm4.h
 include/openssl/srtp.h
 include/openssl/ssl.h
 include/openssl/ssl2.h
 include/openssl/ssl23.h
 include/openssl/ssl3.h
 include/openssl/stack.h
 include/openssl/tls1.h
 include/openssl/ts.h
 include/openssl/txt_db.h
 include/openssl/ui.h
 include/openssl/ui_compat.h
 include/openssl/whrlpool.h
 include/openssl/x509.h
 include/openssl/x509_verify.h
 include/openssl/x509_vfy.h
 include/openssl/x509v3.h
 include/tls.h
 lib/libcrypto.a
 lib/libcrypto.so
 lib/libcrypto.so.49
 lib/libcrypto.so.49.0.0
 lib/libssl.a
 lib/libssl.so
 lib/libssl.so.52
 lib/libssl.so.52.0.0
 lib/libtls.a
 lib/libtls.so
-lib/libtls.so.24
-lib/libtls.so.24.0.1
+lib/libtls.so.25
+lib/libtls.so.25.0.0
 libdata/pkgconfig/libcrypto.pc
 libdata/pkgconfig/libssl.pc
 libdata/pkgconfig/libtls.pc
 libdata/pkgconfig/openssl.pc
 %%NC%%man/man1/nc.1.gz
 man/man1/openssl.1.gz
 man/man5/openssl.cnf.5.gz
 man/man5/x509v3.cnf.5.gz
 man/man8/ocspcheck.8.gz
 @dir etc/ssl/certs
 @dir include/openssl