diff --git a/go.mod b/go.mod
index 486d3c5391..847ee6e02f 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 v1.1.1-0.20230829194950-a67722fa7a82
+replace tailscale.com => github.com/coder/tailscale v1.1.1-0.20230921183700-c821c9c9966d
 
 // This is replaced to include a fix that causes a deadlock when closing the
 // wireguard network.
diff --git a/go.sum b/go.sum
index 77fab37952..ebc1042872 100644
--- a/go.sum
+++ b/go.sum
@@ -227,8 +227,8 @@ 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 v1.1.1-0.20230829194950-a67722fa7a82 h1:kscNsmYro53j6uPNTU3KYDLGFLu1N42qI28eZ6vuUVY=
-github.com/coder/tailscale v1.1.1-0.20230829194950-a67722fa7a82/go.mod h1:L8tPrwSi31RAMEMV8rjb0vYTGs7rXt8rAHbqY/p41j4=
+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/terraform-provider-coder v0.11.1 h1:1sXcHfQrX8XhmLbtKxBED2lZ5jk3/ezBtaw6uVhpJZ4=
 github.com/coder/terraform-provider-coder v0.11.1/go.mod h1:UIfU3bYNeSzJJvHyJ30tEKjD6Z9utloI+HUM/7n94CY=
 github.com/coder/wgtunnel v0.1.12 h1:j3v1Q7qyplrRyyNPm0DK50d3O3flboIErxBFhm4NCkA=