diff --git a/security/tailscale/Makefile b/security/tailscale/Makefile
index 705aeedab404..ff32684971d7 100644
--- a/security/tailscale/Makefile
+++ b/security/tailscale/Makefile
@@ -1,29 +1,29 @@
 PORTNAME=	tailscale
-PORTVERSION=	1.8.3
+PORTVERSION=	1.8.5
 DISTVERSIONPREFIX=	v
 CATEGORIES=	security
 
 MAINTAINER=	mikael@FreeBSD.org
 COMMENT=	Mesh VPN that makes it easy to connect your devices
 
 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.Long=${PORTVERSION} \
 		-X tailscale.com/version.Short=${PORTVERSION}"
 
 PLIST_FILES=	bin/tailscale  \
 		bin/tailscaled
 
 .include <bsd.port.mk>
diff --git a/security/tailscale/distinfo b/security/tailscale/distinfo
index b2ba30d51d20..373775578d53 100644
--- a/security/tailscale/distinfo
+++ b/security/tailscale/distinfo
@@ -1,5 +1,5 @@
-TIMESTAMP = 1620979249
-SHA256 (go/security_tailscale/tailscale-v1.8.3/v1.8.3.mod) = 95419a6ec25c6dab7daab9e7abef61349e18de3dd3118acbb1a6d4084d8ee9ca
-SIZE (go/security_tailscale/tailscale-v1.8.3/v1.8.3.mod) = 2133
-SHA256 (go/security_tailscale/tailscale-v1.8.3/v1.8.3.zip) = 7118b15e2ecbec8804241bf4617cc67e034929a5ed39f01207a63b28407a7fa6
-SIZE (go/security_tailscale/tailscale-v1.8.3/v1.8.3.zip) = 897287
+TIMESTAMP = 1622113145
+SHA256 (go/security_tailscale/tailscale-v1.8.5/v1.8.5.mod) = 95419a6ec25c6dab7daab9e7abef61349e18de3dd3118acbb1a6d4084d8ee9ca
+SIZE (go/security_tailscale/tailscale-v1.8.5/v1.8.5.mod) = 2133
+SHA256 (go/security_tailscale/tailscale-v1.8.5/v1.8.5.zip) = bed545490c0cade15253ad886d15b778306170b68b0c5f495345cd7a4b9848ca
+SIZE (go/security_tailscale/tailscale-v1.8.5/v1.8.5.zip) = 897507