diff -udprN /usr/ports/security/wolfssl/distinfo ./distinfo
--- /usr/ports/security/wolfssl/distinfo	2017-12-25 11:47:17.901959000 +0000
+++ ./distinfo	2019-12-04 01:19:10.549807000 +0000
@@ -1,3 +1,3 @@
-TIMESTAMP = 1514202234
-SHA256 (wolfssl-3.13.0.zip) = 196a3256a9044ecb89504ce77850342c82e676e7f2cad77f5584be3516b6060e
-SIZE (wolfssl-3.13.0.zip) = 3969070
+TIMESTAMP = 1575422350
+SHA256 (wolfssl-4.2.0.zip) = 7aa4c8b9ac7eed76f0275abb13b4bd59a2e749211242cc6e364c3cdc9f3d959d
+SIZE (wolfssl-4.2.0.zip) = 7181171
diff -udprN /usr/ports/security/wolfssl/Makefile ./Makefile
--- /usr/ports/security/wolfssl/Makefile	2019-11-04 21:21:03.729751000 +0000
+++ ./Makefile	2019-12-04 01:18:47.493358000 +0000
@@ -1,32 +1,35 @@
 # $FreeBSD: head/security/wolfssl/Makefile 516744 2019-11-04 21:21:03Z rene $
 
 PORTNAME=	wolfssl
-PORTVERSION=	3.13.0
+PORTVERSION=	4.2.0
 CATEGORIES=	security devel
 MASTER_SITES=	https://www.wolfssl.com/
 
-MAINTAINER=	ports@FreeBSD.org
+MAINTAINER=	johans@FreeBSD.org
 COMMENT=	Embedded SSL C-Library
 
 LICENSE=	GPLv2
 
-BROKEN_mips=		fails to package: pkg-static: Unable to access file libwolfssl.so.3: No such file or directory
-BROKEN_mips64=		fails to package: pkg-static: Unable to access file libwolfssl.so.3: No such file or directory
+BROKEN_mips=	fails to package: pkg-static: Unable to access file libwolfssl.so.3: No such file or directory
+BROKEN_mips64=	fails to package: pkg-static: Unable to access file libwolfssl.so.3: No such file or directory
 
 BUILD_DEPENDS=	bash:shells/bash
 
 USES=		libtool zip
+USE_LDCONFIG=	yes
+
 GNU_CONFIGURE=	yes
 CONFIGURE_SHELL=bash
 CONFIGURE_ARGS=	--disable-dependency-tracking \
 		--enable-shared --enable-static \
 		--enable-dtls --enable-opensslextra --enable-ipv6 \
 		--enable-dsa --enable-dh --enable-ecc --enable-sni \
-		--enable-ripemd --enable-sha512 --enable-opensslcoexist
-
-USE_LDCONFIG=	yes
+		--enable-ripemd --enable-sha512 --enable-opensslcoexist\
+		--enable-tls13 --enable-tls13-draft18\
+		--enable-tls13-draft22 --enable-tls13-draft23\
+		--enable-tls13-draft26 --enable-tls13-draft28\
+		--enable-ssh --enable-keygen
 PORTDOCS=	*
-
 OPTIONS_DEFINE=	DOCS
 
 post-configure:
diff -udprN /usr/ports/security/wolfssl/pkg-plist ./pkg-plist
--- /usr/ports/security/wolfssl/pkg-plist	2017-12-25 11:47:17.901959000 +0000
+++ ./pkg-plist	2019-12-04 01:33:27.400538000 +0000
@@ -99,6 +99,7 @@ include/wolfssl/openssl/aes.h
 include/wolfssl/openssl/asn1.h
 include/wolfssl/openssl/bio.h
 include/wolfssl/openssl/bn.h
+include/wolfssl/openssl/buffer.h
 include/wolfssl/openssl/conf.h
 include/wolfssl/openssl/crypto.h
 include/wolfssl/openssl/des.h
@@ -116,13 +117,16 @@ include/wolfssl/openssl/hmac.h
 include/wolfssl/openssl/lhash.h
 include/wolfssl/openssl/md4.h
 include/wolfssl/openssl/md5.h
+include/wolfssl/openssl/objects.h
 include/wolfssl/openssl/ocsp.h
 include/wolfssl/openssl/opensslconf.h
 include/wolfssl/openssl/opensslv.h
 include/wolfssl/openssl/ossl_typ.h
 include/wolfssl/openssl/pem.h
+include/wolfssl/openssl/pkcs7.h
 include/wolfssl/openssl/pkcs12.h
 include/wolfssl/openssl/rand.h
+include/wolfssl/openssl/rc4.h
 include/wolfssl/openssl/ripemd.h
 include/wolfssl/openssl/rsa.h
 include/wolfssl/openssl/sha.h
@@ -130,6 +134,7 @@ include/wolfssl/openssl/ssl.h
 include/wolfssl/openssl/ssl23.h
 include/wolfssl/openssl/stack.h
 include/wolfssl/openssl/ui.h
+include/wolfssl/openssl/x509_vfy.h
 include/wolfssl/openssl/x509.h
 include/wolfssl/openssl/x509v3.h
 include/wolfssl/options.h
@@ -152,6 +157,7 @@ include/wolfssl/wolfcrypt/cmac.h
 include/wolfssl/wolfcrypt/coding.h
 include/wolfssl/wolfcrypt/compress.h
 include/wolfssl/wolfcrypt/cpuid.h
+include/wolfssl/wolfcrypt/cryptocb.h
 include/wolfssl/wolfcrypt/curve25519.h
 include/wolfssl/wolfcrypt/des3.h
 include/wolfssl/wolfcrypt/dh.h
@@ -201,6 +207,6 @@ include/wolfssl/wolfcrypt/wolfmath.h
 include/wolfssl/wolfio.h
 lib/libwolfssl.a
 lib/libwolfssl.so
-lib/libwolfssl.so.15
-lib/libwolfssl.so.15.0.0
+lib/libwolfssl.so.23
+lib/libwolfssl.so.23.0.0
 libdata/pkgconfig/wolfssl.pc