diff --git a/security/tailscale/Makefile b/security/tailscale/Makefile
index 36b03566a665..2c93e630aa6a 100644
--- a/security/tailscale/Makefile
+++ b/security/tailscale/Makefile
@@ -1,30 +1,30 @@
 PORTNAME=	tailscale
-PORTVERSION=	1.98.10
+PORTVERSION=	1.102.1
 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=		cpe go:1.26+,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 29e66330de58..d189fe62d799 100644
--- a/security/tailscale/distinfo
+++ b/security/tailscale/distinfo
@@ -1,5 +1,5 @@
-TIMESTAMP = 1785426009
-SHA256 (go/security_tailscale/tailscale-v1.98.10/v1.98.10.mod) = 9e279724ca54b2c4fca9540e371a421ae31165e030cbd512e6b1dcddf252c7f4
-SIZE (go/security_tailscale/tailscale-v1.98.10/v1.98.10.mod) = 25725
-SHA256 (go/security_tailscale/tailscale-v1.98.10/v1.98.10.zip) = c717d6a05c788ae2558d15dc73a0985c932fecb204687cd72e76efbbaa81de1f
-SIZE (go/security_tailscale/tailscale-v1.98.10/v1.98.10.zip) = 6221056
+TIMESTAMP = 1785875722
+SHA256 (go/security_tailscale/tailscale-v1.102.1/v1.102.1.mod) = 8bda32792d06d8df55fdb8187c00263112f2444bf75f83ffe3600c85871233fc
+SIZE (go/security_tailscale/tailscale-v1.102.1/v1.102.1.mod) = 26754
+SHA256 (go/security_tailscale/tailscale-v1.102.1/v1.102.1.zip) = 7350f6001cbb42f9707faba94068cbd07af519853fac50f7eee6df86ac11cbd8
+SIZE (go/security_tailscale/tailscale-v1.102.1/v1.102.1.zip) = 6876210