diff --git a/security/sslproxy/Makefile b/security/sslproxy/Makefile
index 6124041d86af..10e13bff8c7a 100644
--- a/security/sslproxy/Makefile
+++ b/security/sslproxy/Makefile
@@ -1,33 +1,33 @@
 PORTNAME=	sslproxy
 DISTVERSIONPREFIX=	v
-DISTVERSION=	0.9.8
+DISTVERSION=	0.9.9
 PORTEPOCH=	1
 CATEGORIES=	security
 
 MAINTAINER=	bofh@FreeBSD.org
 COMMENT=	Transparent and scalable SSL/TLS interception
 WWW=		https://github.com/sonertari/SSLproxy
 
 LICENSE=	BSD2CLAUSE
 
 LIB_DEPENDS=	libevent.so:devel/libevent \
 		libnet.so:net/libnet
 
 USES=		gmake pkgconfig sqlite ssl uidfix
 USE_GITHUB=	yes
 GH_ACCOUNT=	sonertari
 GH_PROJECT=	SSLproxy
 
 MAKEFILE=	GNUmakefile
 MAKE_ENV=	INSTALLUID=${UID} INSTALLGID=${GID}
 
 PLIST_FILES=	bin/sslproxy share/man/man1/sslproxy.1.gz \
 		share/man/man5/sslproxy.conf.5.gz \
 		"@sample etc/sslproxy.conf.sample"
 
 post-patch:
 	@${REINPLACE_CMD} -e \
 		's|^EXAMPLESDIR.*|EXAMPLESDIR?=	etc|g' \
 			${WRKSRC}/Mk/main.mk
 
 .include <bsd.port.mk>
diff --git a/security/sslproxy/distinfo b/security/sslproxy/distinfo
index 8454a5af8d27..2ff774ee6415 100644
--- a/security/sslproxy/distinfo
+++ b/security/sslproxy/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1746776448
-SHA256 (sonertari-SSLproxy-v0.9.8_GH0.tar.gz) = 48241797622bc86a8cb9b6ea3cdddae0fff77e83e48576b9df4677fcff109b8f
-SIZE (sonertari-SSLproxy-v0.9.8_GH0.tar.gz) = 2146651
+TIMESTAMP = 1763139527
+SHA256 (sonertari-SSLproxy-v0.9.9_GH0.tar.gz) = 1374ebd7c379c0250ea9540800d4a95d22a846b4bf5e211b5833d69ffb3b61ae
+SIZE (sonertari-SSLproxy-v0.9.9_GH0.tar.gz) = 2151271
diff --git a/security/sslproxy/files/patch-Mk_main.mk b/security/sslproxy/files/patch-Mk_main.mk
index 70b4b18cbc84..2ec376d84f9d 100644
--- a/security/sslproxy/files/patch-Mk_main.mk
+++ b/security/sslproxy/files/patch-Mk_main.mk
@@ -1,51 +1,60 @@
---- Mk/main.mk.orig	2022-12-26 01:44:45 UTC
+--- Mk/main.mk.orig	2025-11-09 10:48:19 UTC
 +++ Mk/main.mk
-@@ -302,11 +302,13 @@ endif
+@@ -198,7 +198,7 @@ MANDIR?=	share/man
+ 
+ PREFIX?=	/usr/local
+ MANDIR?=	share/man
+-EXAMPLESDIR?=	share/examples
++EXAMPLESDIR?=	etc
+ 
+ INSTALLUID?=	0
+ INSTALLGID?=	0
+@@ -299,11 +299,13 @@ endif
  		&& echo sqlite3)
  endif
  endif
 +PKGS:=		$(PKGS)
  TPKGS:=		
  ifndef CHECK_BASE
  TPKGS+=		$(shell $(PKGCONFIG) $(PCFLAGS) --exists check \
  		&& echo check)
  endif
 +TPKGS:=		$(TPKGS)
  
  # Function: Generate list of base paths to search when locating packages
  # $1 packagename
-@@ -422,18 +424,24 @@ ifneq (,$(strip $(PKGS)))
+@@ -428,18 +430,24 @@ ifneq (,$(strip $(PKGS)))
  endif
  
  ifneq (,$(strip $(PKGS)))
 -PKG_CFLAGS+=	$(shell $(PKGCONFIG) $(PCFLAGS) --cflags-only-other $(PKGS))
 -PKG_CPPFLAGS+=	$(shell $(PKGCONFIG) $(PCFLAGS) --cflags-only-I $(PKGS))
 -PKG_LDFLAGS+=	$(shell $(PKGCONFIG) $(PCFLAGS) --libs-only-L \
 -		--libs-only-other $(PKGS))
 -PKG_LIBS+=	$(shell $(PKGCONFIG) $(PCFLAGS) --libs-only-l $(PKGS))
 +PKGS_CFLAGS!=	$(PKGCONFIG) $(PCFLAGS) --cflags-only-other $(PKGS)
 +PKG_CFLAGS+=	$(PKGS_CFLAGS)
 +PKGS_CPPFLAGS!=	$(PKGCONFIG) $(PCFLAGS) --cflags-only-I $(PKGS)
 +PKG_CPPFLAGS+=	$(PKGS_CPPFLAGS)
 +PKGS_LDFLAGS!=	$(PKGCONFIG) $(PCFLAGS) --libs-only-L --libs-only-other $(PKGS)
 +PKG_LDFLAGS+=	$(PKGS_LDFLAGS)
 +PKGS_LIBS!=	$(PKGCONFIG) $(PCFLAGS) --libs-only-l $(PKGS)
 +PKG_LIBS+=	$(PKGS_LIBS)
  endif
  ifneq (,$(strip $(TPKGS)))
 -TPKG_CFLAGS+=	$(shell $(PKGCONFIG) $(PCFLAGS) --cflags-only-other $(TPKGS))
 -TPKG_CPPFLAGS+=	$(shell $(PKGCONFIG) $(PCFLAGS) --cflags-only-I $(TPKGS))
 -TPKG_LDFLAGS+=	$(shell $(PKGCONFIG) $(PCFLAGS) --libs-only-L \
 -		--libs-only-other $(TPKGS))
 -TPKG_LIBS+=	$(shell $(PKGCONFIG) $(PCFLAGS) --libs-only-l $(TPKGS))
 +TPKGS_CFLAGS!=	$(PKGCONFIG) $(PCFLAGS) --cflags-only-other $(TPKGS)
 +TPKG_CFLAGS+=	$(TPKGS_CFLAGS)
 +TPKGS_CPPFLAGS!=$(PKGCONFIG) $(PCFLAGS) --cflags-only-I $(TPKGS)
 +TPKG_CPPFLAGS+=$(TPKGS_CPPFLAGS)
 +TPKGS_LDFLAGS!=	$(PKGCONFIG) $(PCFLAGS) --libs-only-L --libs-only-other $(TPKGS)
 +TPKG_LDFLAGS+=	$(TPKGS_LDFLAGS)
 +TPKGS_LIBS!=	$(PKGCONFIG) $(PCFLAGS) --libs-only-l $(TPKGS)
 +TPKG_LIBS+=	$(TPKGS_LIBS)
  endif
  
  CPPDEFS+=	-D_GNU_SOURCE \
diff --git a/security/sslproxy/files/patch-src_filter.c b/security/sslproxy/files/patch-src_filter.c
new file mode 100644
index 000000000000..ccf5bff6277a
--- /dev/null
+++ b/security/sslproxy/files/patch-src_filter.c
@@ -0,0 +1,39 @@
+--- src/filter.c.orig	2025-11-14 18:16:45 UTC
++++ src/filter.c
+@@ -1150,12 +1150,12 @@ filter_ip_btree_str(kbtree_t(ip) *btree)
+ 	i->ip = *p; \
+ 	append_list(&ip, i, filter_ip_list_t); \
+ } while (0)
+-	
++
+ 	filter_ip_list_t *ip = NULL;
+ 	__kb_traverse(filter_ip_p_t, btree, build_ip_list);
+ 
+ 	char *s = filter_ip_list_str(ip);
+-	
++
+ 	free_list(ip, filter_ip_list_t);
+ 	return s;
+ }
+@@ -1363,7 +1363,7 @@ filter_desc_acm_str(ACMachine(char) *acm)
+ 	ACM_foreach_keyword(acm, build_desc_list_acm);
+ 
+ 	char *s = filter_desc_list_str(desc_list_acm);
+-	
++
+ 	free_list(desc_list_acm, filter_desc_list_t);
+ 	desc_list_acm = NULL;
+ 	return s;
+@@ -1701,10 +1701,12 @@ err:
+ 			free(rule->sni);
+ 		if (rule->cn)
+ 			free(rule->cn);
++#ifndef WITHOUT_USERAUTH
+ 		if (rule->user)
+ 			free(rule->user);
+ 		if (rule->desc)
+ 			free(rule->desc);
++#endif /* !WITHOUT_USERAUTH */
+ 		if (rule->ip)
+ 			free(rule->ip);
+ 		free(rule);