diff --git a/security/sslscan/Makefile b/security/sslscan/Makefile
index 18733a257fa6..c3a93286e713 100644
--- a/security/sslscan/Makefile
+++ b/security/sslscan/Makefile
@@ -1,35 +1,35 @@
 PORTNAME=	sslscan
-DISTVERSION=	2.0.16
+DISTVERSION=	2.1.3
 CATEGORIES=	security
 MASTER_SITES=	https://www.openssl.org/source/:openssl \
 		ftp://ftp.cert.dfn.de/pub/tools/net/openssl/source/:openssl
 DISTFILES=	openssl-${OPENSSL_VERSION}.tar.gz:openssl
 
 MAINTAINER=	gavin@FreeBSD.org
 COMMENT=	Fast SSL port scanner
 WWW=		https://github.com/rbsec/sslscan/
 
 LICENSE=	GPLv3
 
 USES=		gmake perl5
 USE_PERL5=	build
 USE_GITHUB=	yes
 GH_ACCOUNT=	rbsec
-OPENSSL_VERSION=	3.1.0
+OPENSSL_VERSION=	3.2.1
 
 ALL_TARGET=	static
 
 .include <bsd.port.options.mk>
 
 .if ${ARCH} == powerpc64
 MAKE_ENV+=	OSSL_TARGET=BSD-ppc64
 .elif ${ARCH} == powerpc64le
 MAKE_ENV+=        OSSL_TARGET=BSD-ppc64le
 .elif ${ARCH} == riscv64
 MAKE_ENV+=        OSSL_TARGET=BSD-riscv64
 .endif
 
 post-patch:
 	$(LN) -sf "${WRKDIR}/openssl-${OPENSSL_VERSION}" "${WRKSRC}/openssl"
 
 .include <bsd.port.mk>
diff --git a/security/sslscan/distinfo b/security/sslscan/distinfo
index 5cc7753c42a2..dbcfa5fa418a 100644
--- a/security/sslscan/distinfo
+++ b/security/sslscan/distinfo
@@ -1,5 +1,5 @@
-TIMESTAMP = 1683839135
-SHA256 (openssl-3.1.0.tar.gz) = aaa925ad9828745c4cad9d9efeb273deca820f2cdcf2c3ac7d7c1212b7c497b4
-SIZE (openssl-3.1.0.tar.gz) = 15525381
-SHA256 (rbsec-sslscan-2.0.16_GH0.tar.gz) = eae49b9c2023f9c9adeb10c50a6ee3ddf5da7aae20f6a6c59251e7a84aa44131
-SIZE (rbsec-sslscan-2.0.16_GH0.tar.gz) = 113523
+TIMESTAMP = 1707630173
+SHA256 (openssl-3.2.1.tar.gz) = 83c7329fe52c850677d75e5d0b0ca245309b97e8ecbcfdc1dfdc4ab9fac35b39
+SIZE (openssl-3.2.1.tar.gz) = 17733249
+SHA256 (rbsec-sslscan-2.1.3_GH0.tar.gz) = 6beec9345635b41fa2c1bbc5f0854f10014e4b2b4179e9e9a3bda6bdb9e1aa41
+SIZE (rbsec-sslscan-2.1.3_GH0.tar.gz) = 113917
diff --git a/security/sslscan/files/patch-Makefile b/security/sslscan/files/patch-Makefile
index bba98af1b52f..8319713a5c77 100644
--- a/security/sslscan/files/patch-Makefile
+++ b/security/sslscan/files/patch-Makefile
@@ -1,112 +1,114 @@
---- Makefile.orig	2023-04-08 21:36:58 UTC
-+++ Makefile
+--- Makefile.orig	2023-11-14 21:36:52.000000000 +0000
++++ Makefile	2023-11-20 13:57:16.349229000 +0000
 @@ -1,12 +1,7 @@
  # set gcc as default if CC is not set
  
 -GIT_VERSION = $(shell git describe --tags --always --dirty=-wip)
 +VERSION = $(shell grep -E -o -m 1 "[0-9]+\.[0-9]+\.[0-9]+" Changelog)
  
 -# Ugly hack to get version if git isn't installed
 -ifeq ($(GIT_VERSION),)
 -  GIT_VERSION = $(shell grep -E -o -m 1 "[0-9]+\.[0-9]+\.[0-9]+" Changelog)
 -endif
 -
  # Detect OS
  OS := $(shell uname)
  ARCH := $(shell uname -m)
-@@ -26,11 +21,11 @@ endif
+@@ -26,11 +21,11 @@
  
  SRCS      = sslscan.c
  BINDIR    = $(PREFIX)/bin
 -MANDIR    = $(PREFIX)/share/man
 +MANDIR    = $(PREFIX)/man
  MAN1DIR   = $(MANDIR)/man1
  
  WARNINGS  = -Wall -Wformat=2 -Wformat-security -Wno-deprecated-declarations
 -DEFINES   = -DVERSION=\"$(GIT_VERSION)\"
 +DEFINES   = -DVERSION=\"$(VERSION)\"
  
  # for dynamic linking
  LIBS      = -lssl -lcrypto
-@@ -58,36 +53,12 @@ endif
+@@ -58,38 +53,12 @@
  CFLAGS += -std=gnu11
  
  # for static linking
 -ifeq ($(STATIC_BUILD), TRUE)
  PWD          = $(shell pwd)/openssl
  LDFLAGS      += -L${PWD}/
  CFLAGS       += -I${PWD}/include/ -I${PWD}/
 -ifeq ($(OS), Darwin)
 -LIBS	     = ./openssl/libssl.a ./openssl/libcrypto.a -lz -lpthread
 -else
  LIBS         = -lssl -lcrypto -lz -lpthread
 -endif
 -ifneq ($(OS), FreeBSD)
 -	LIBS += -ldl
 -endif
 -ifeq ($(OS), SunOS)
 -	LIBS += -lsocket -lnsl
 -endif
 -GIT_VERSION  := $(GIT_VERSION)-static
 -else
 -# for dynamic linking
 -LDFLAGS   += -L/usr/local/lib -L/usr/local/ssl/lib -L/usr/local/opt/openssl/lib -L/opt/local/lib
 -CFLAGS    += -I/usr/local/include -I/usr/local/ssl/include -I/usr/local/ssl/include/openssl -I/usr/local/opt/openssl/include -I/opt/local/include -I/opt/local/include/openssl
 -endif
 +VERSION  := $(VERSION)-static
  
 -# Find the number of processors on the system (used in -j option in building OpenSSL).
 -# Uses /usr/bin/nproc if available, otherwise defaults to 1.
 -NUM_PROCS = 1
 -ifneq (,$(wildcard /usr/bin/nproc))
 -	NUM_PROCS = `/usr/bin/nproc --all`
 -endif
--
+-ifeq ($(OS), Darwin)
+-	NUM_PROCS = `sysctl -n hw.ncpu`
+-endif
 -
  .PHONY: all sslscan clean install uninstall static opensslpull
  
  all: sslscan
-@@ -114,6 +85,9 @@ ifeq ($(OS), Darwin)
+@@ -116,6 +85,9 @@
  	install sslscan $(DESTDIR)$(BINDIR)/sslscan;
  	install -d $(DESTDIR)$(MAN1DIR)/;
  	install sslscan.1 $(DESTDIR)$(MAN1DIR)/sslscan.1;
 +else ifeq ($(OS), FreeBSD)
 +	install -s -m 755 sslscan $(DESTDIR)$(BINDIR)
 +	install -m 644 sslscan.1 $(DESTDIR)$(MAN1DIR)
  else
  	install -D sslscan $(DESTDIR)$(BINDIR)/sslscan;
  	install -D sslscan.1 $(DESTDIR)$(MAN1DIR)/sslscan.1;
-@@ -126,11 +100,7 @@ uninstall:
+@@ -128,11 +100,7 @@
  .openssl.is.fresh: opensslpull
  	true
  opensslpull:
 -	if [ -d openssl -a -d openssl/.git ]; then \
--		cd ./openssl && git checkout OpenSSL_1_1_1-stable && git pull | grep -q "Already up-to-date." && [ -e ../.openssl.is.fresh ] || touch ../.openssl.is.fresh ; \
+-		cd ./openssl && git checkout `git ls-remote https://github.com/openssl/openssl | grep -Eo '(openssl-3\.0\.[0-9]+)' | sort --version-sort | tail -n 1` && git pull | grep -q "Already up-to-date." && [ -e ../.openssl.is.fresh ] || touch ../.openssl.is.fresh ; \
 -	else \
--		git clone --depth 1 -b OpenSSL_1_1_1-stable https://github.com/openssl/openssl ./openssl && cd ./openssl && touch ../.openssl.is.fresh ; \
+-	git clone --depth 1 -b `git ls-remote https://github.com/openssl/openssl | grep -Eo '(openssl-3\.0\.[0-9]+)' | sort -V | tail -n 1` https://github.com/openssl/openssl ./openssl && cd ./openssl && touch ../.openssl.is.fresh ; \
 -	fi
 +	true
  
  # Need to build OpenSSL differently on OSX
  ifeq ($(OS), Darwin)
-@@ -144,16 +114,15 @@ openssl/Makefile: .openssl.is.fresh
+@@ -146,16 +114,15 @@
  # Any other *NIX platform
  else
  openssl/Makefile: .openssl.is.fresh
 -	cd ./openssl; ./config -v -fstack-protector-all -D_FORTIFY_SOURCE=2 -fPIC no-shared enable-weak-ssl-ciphers zlib
 +	cd ./openssl; ./config -v -fstack-protector-all -D_FORTIFY_SOURCE=2 -fPIC no-shared enable-weak-ssl-ciphers zlib $(OSSL_TARGET)
  endif
  
  openssl/libcrypto.a: openssl/Makefile
 -	$(MAKE) -j $(NUM_PROCS) -C openssl depend
--	$(MAKE) -j $(NUM_PROCS) -C openssl all
+-	$(MAKE) -j $(NUM_PROCS) -C openssl build_libs
 -#	$(MAKE) -j $(NUM_PROCS) -C openssl test # Disabled because this takes 45+ minutes for OpenSSL v1.1.1.
 +	$(MAKE) -C openssl depend
-+	$(MAKE) -C openssl build_sw
++	$(MAKE) -C openssl build_libs
  
  static: openssl/libcrypto.a
 -	$(MAKE) -j $(NUM_PROCS) sslscan STATIC_BUILD=TRUE
 +	$(MAKE) sslscan STATIC_BUILD=TRUE
  
  docker:
  	docker build -t sslscan:sslscan .