diff --git a/security/tailscale/Makefile b/security/tailscale/Makefile
index b603c1eb0d53..4f3b1c4c8bd3 100644
--- a/security/tailscale/Makefile
+++ b/security/tailscale/Makefile
@@ -1,30 +1,30 @@
 PORTNAME=	tailscale
-PORTVERSION=	1.66.3
+PORTVERSION=	1.66.4
 DISTVERSIONPREFIX=	v
 CATEGORIES=	security net-vpn
 
 MAINTAINER=	ashish@FreeBSD.org
 COMMENT=	Mesh VPN that makes it easy to connect your devices
 WWW=		https://tailscale.com/
 
 LICENSE=	BSD3CLAUSE
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 RUN_DEPENDS=	ca_root_nss>0:security/ca_root_nss
 
 USES=		go:1.22,modules
 
 GO_MODULE=	github.com/tailscale/tailscale
 
 USE_RC_SUBR=	tailscaled
 
 GO_TARGET=	./cmd/tailscale \
 		./cmd/tailscaled
 GO_BUILDFLAGS=	-tags xversion -ldflags "\
 		-X tailscale.com/version.longStamp=${PORTVERSION} \
 		-X tailscale.com/version.shortStamp=${PORTVERSION}"
 
 PLIST_FILES=	bin/tailscale  \
 		bin/tailscaled
 
 .include <bsd.port.mk>
diff --git a/security/tailscale/distinfo b/security/tailscale/distinfo
index 4b36e3b1c399..71ff93be2e6c 100644
--- a/security/tailscale/distinfo
+++ b/security/tailscale/distinfo
@@ -1,5 +1,5 @@
-TIMESTAMP = 1715722488
-SHA256 (go/security_tailscale/tailscale-v1.66.3/v1.66.3.mod) = 65b4bde2a734982377e407e3edd36afe7707685d727e3e14b9a1e94a528fb24e
-SIZE (go/security_tailscale/tailscale-v1.66.3/v1.66.3.mod) = 18961
-SHA256 (go/security_tailscale/tailscale-v1.66.3/v1.66.3.zip) = 09985e6f02b3117b14b29968d43df10b41945a6dc6e9359af50426b02a1eb1ae
-SIZE (go/security_tailscale/tailscale-v1.66.3/v1.66.3.zip) = 3392837
+TIMESTAMP = 1716254809
+SHA256 (go/security_tailscale/tailscale-v1.66.4/v1.66.4.mod) = 65b4bde2a734982377e407e3edd36afe7707685d727e3e14b9a1e94a528fb24e
+SIZE (go/security_tailscale/tailscale-v1.66.4/v1.66.4.mod) = 18961
+SHA256 (go/security_tailscale/tailscale-v1.66.4/v1.66.4.zip) = 70daac33cddaf103966ad14f82f4040be7cf62bcc47ead634d68a53a70ec6881
+SIZE (go/security_tailscale/tailscale-v1.66.4/v1.66.4.zip) = 3391722