diff --git a/security/tailscale/Makefile b/security/tailscale/Makefile
index 4c2ad5c7fdd7..ae0634faa7d6 100644
--- a/security/tailscale/Makefile
+++ b/security/tailscale/Makefile
@@ -1,30 +1,30 @@
 PORTNAME=	tailscale
-PORTVERSION=	1.56.1
+PORTVERSION=	1.58.0
 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:1.21,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 533e0b5b2e4f..b5738e3683a7 100644
--- a/security/tailscale/distinfo
+++ b/security/tailscale/distinfo
@@ -1,5 +1,5 @@
-TIMESTAMP = 1702760101
-SHA256 (go/security_tailscale/tailscale-v1.56.1/v1.56.1.mod) = c95f6d68a334462301d00375a445bce7e7b67c4028c83ceae0ba1c6e725f7584
-SIZE (go/security_tailscale/tailscale-v1.56.1/v1.56.1.mod) = 18699
-SHA256 (go/security_tailscale/tailscale-v1.56.1/v1.56.1.zip) = 327c0f7e0796ca483e44aae3e6f48ba7b7f680489b5cfee2f56516c13a9d9da1
-SIZE (go/security_tailscale/tailscale-v1.56.1/v1.56.1.zip) = 2981340
+TIMESTAMP = 1705616886
+SHA256 (go/security_tailscale/tailscale-v1.58.0/v1.58.0.mod) = da0c715d863dd50609914de1a7dd3339a341b64c21e5d594418be55c44e7d297
+SIZE (go/security_tailscale/tailscale-v1.58.0/v1.58.0.mod) = 18802
+SHA256 (go/security_tailscale/tailscale-v1.58.0/v1.58.0.zip) = 6eebed3e58865427e0e2086911d32446066e48cd2003fa234d7163888912784b
+SIZE (go/security_tailscale/tailscale-v1.58.0/v1.58.0.zip) = 3048752