diff --git a/security/tailscale/Makefile b/security/tailscale/Makefile
index 16435721b1c2..205f5e75023c 100644
--- a/security/tailscale/Makefile
+++ b/security/tailscale/Makefile
@@ -1,30 +1,30 @@
 PORTNAME=	tailscale
-PORTVERSION=	1.44.0
+PORTVERSION=	1.44.2
 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: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 7a4a5c441ab0..c9836f140a26 100644
--- a/security/tailscale/distinfo
+++ b/security/tailscale/distinfo
@@ -1,5 +1,5 @@
-TIMESTAMP = 1687429532
-SHA256 (go/security_tailscale/tailscale-v1.44.0/v1.44.0.mod) = f55ae95d7089ff3d5a8b2da3fb6392835dd9d80efedb35d605d25d96e280af5c
-SIZE (go/security_tailscale/tailscale-v1.44.0/v1.44.0.mod) = 17964
-SHA256 (go/security_tailscale/tailscale-v1.44.0/v1.44.0.zip) = 17f31b97fd01e57e1959848a11fa6fe5ba7fd4561e7f5b5d94dc1d7af8feb9d2
-SIZE (go/security_tailscale/tailscale-v1.44.0/v1.44.0.zip) = 2317609
+TIMESTAMP = 1689751989
+SHA256 (go/security_tailscale/tailscale-v1.44.2/v1.44.2.mod) = f55ae95d7089ff3d5a8b2da3fb6392835dd9d80efedb35d605d25d96e280af5c
+SIZE (go/security_tailscale/tailscale-v1.44.2/v1.44.2.mod) = 17964
+SHA256 (go/security_tailscale/tailscale-v1.44.2/v1.44.2.zip) = 937cb7b08978228cb56b58155eea5a65ed935edda7e78f2509879abd64eb7619
+SIZE (go/security_tailscale/tailscale-v1.44.2/v1.44.2.zip) = 2317574