diff --git a/security/tailscale/Makefile b/security/tailscale/Makefile
index 15ba604bf372..ff885556ac38 100644
--- a/security/tailscale/Makefile
+++ b/security/tailscale/Makefile
@@ -1,30 +1,30 @@
 PORTNAME=	tailscale
-PORTVERSION=	1.64.2
+PORTVERSION=	1.66.0
 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 477f54f7cec5..f9bb6d1606ed 100644
--- a/security/tailscale/distinfo
+++ b/security/tailscale/distinfo
@@ -1,5 +1,5 @@
-TIMESTAMP = 1713379891
-SHA256 (go/security_tailscale/tailscale-v1.64.2/v1.64.2.mod) = 792c3444d2e75cc08c11dfce429b6ce8abb9b5d87714753b7e7be9d8ea6388d2
-SIZE (go/security_tailscale/tailscale-v1.64.2/v1.64.2.mod) = 18985
-SHA256 (go/security_tailscale/tailscale-v1.64.2/v1.64.2.zip) = 1b9efdb4614b8753631f2e1767481cd6e4b98db6d4f0cba3007e6dd64ed0ec0a
-SIZE (go/security_tailscale/tailscale-v1.64.2/v1.64.2.zip) = 3237477
+TIMESTAMP = 1715203457
+SHA256 (go/security_tailscale/tailscale-v1.66.0/v1.66.0.mod) = 65b4bde2a734982377e407e3edd36afe7707685d727e3e14b9a1e94a528fb24e
+SIZE (go/security_tailscale/tailscale-v1.66.0/v1.66.0.mod) = 18961
+SHA256 (go/security_tailscale/tailscale-v1.66.0/v1.66.0.zip) = b4444fccf7f88273c9f9d4cedf7dc2c6fd9d17a5ea233d62af0330d5c1716118
+SIZE (go/security_tailscale/tailscale-v1.66.0/v1.66.0.zip) = 3389358