diff --git a/go.mod b/go.mod
index 9b29730c4e983..04e6b99e73293 100644
--- a/go.mod
+++ b/go.mod
@@ -33,7 +33,7 @@ replace github.com/dlclark/regexp2 => github.com/dlclark/regexp2 v1.7.0
 
 // There are a few minor changes we make to Tailscale that we're slowly upstreaming. Compare here:
 // https://github.com/tailscale/tailscale/compare/main...coder:tailscale:main
-replace tailscale.com => github.com/coder/tailscale v1.1.1-0.20230921183700-c821c9c9966d
+replace tailscale.com => github.com/coder/tailscale v1.1.1-0.20231030172646-324d125f1d8f
 
 // Fixes a race-condition in coder/wgtunnel.
 // Upstream PR: https://github.com/WireGuard/wireguard-go/pull/85
diff --git a/go.sum b/go.sum
index d15e6bebc2dc9..b1d3fbae25d2f 100644
--- a/go.sum
+++ b/go.sum
@@ -232,8 +232,8 @@ github.com/coder/retry v1.4.0 h1:g0fojHFxcdgM3sBULqgjFDxw1UIvaCqk4ngUDu0EWag=
 github.com/coder/retry v1.4.0/go.mod h1:blHMk9vs6LkoRT9ZHyuZo360cufXEhrxqvEzeMtRGoY=
 github.com/coder/ssh v0.0.0-20230621095435-9a7e23486f1c h1:TI7TzdFI0UvQmwgyQhtI1HeyYNRxAQpr8Tw/rjT8VSA=
 github.com/coder/ssh v0.0.0-20230621095435-9a7e23486f1c/go.mod h1:aGQbuCLyhRLMzZF067xc84Lh7JDs1FKwCmF1Crl9dxQ=
-github.com/coder/tailscale v1.1.1-0.20230921183700-c821c9c9966d h1:Y2nq36GM7lKzjrM2pi3BnjS4BNGDTJqkqhMMYAUl+YE=
-github.com/coder/tailscale v1.1.1-0.20230921183700-c821c9c9966d/go.mod h1:L8tPrwSi31RAMEMV8rjb0vYTGs7rXt8rAHbqY/p41j4=
+github.com/coder/tailscale v1.1.1-0.20231030172646-324d125f1d8f h1:M+UeuoMLQeduc1tXB4VuOAXBLHGrsl9YCo8MuGqbgD4=
+github.com/coder/tailscale v1.1.1-0.20231030172646-324d125f1d8f/go.mod h1:L8tPrwSi31RAMEMV8rjb0vYTGs7rXt8rAHbqY/p41j4=
 github.com/coder/terraform-provider-coder v0.12.2 h1:KsnJLHyTtELvV1Rzkm75iCQ7npXjL0KcoU3NTreagZU=
 github.com/coder/terraform-provider-coder v0.12.2/go.mod h1:+BHer8AX5Y0QqZS9viau+ZkDTaOCOE3ga1lx1QIJDrk=
 github.com/coder/wgtunnel v0.1.12 h1:j3v1Q7qyplrRyyNPm0DK50d3O3flboIErxBFhm4NCkA=