diff --git a/flake.nix b/flake.nix
index 099ef5559cb1e..afe7a8246feba 100644
--- a/flake.nix
+++ b/flake.nix
@@ -97,7 +97,7 @@
             name = "coder-${osArch}";
             # Updated with ./scripts/update-flake.sh`.
             # This should be updated whenever go.mod changes!
-            vendorHash = "sha256-TRnB8wXSM8lJHAET+fMr6uKcqD0A4ilna1wPkgxn5/E=";
+            vendorHash = "sha256-/tj3Pit5h3zJbJS7A970hUB5dJT8VwOUcpLLIfBL96c=";
             proxyVendor = true;
             src = ./.;
             nativeBuildInputs = with pkgs; [ getopt openssl zstd ];
diff --git a/go.mod b/go.mod
index 9a53b87457d0f..bd90484747f96 100644
--- a/go.mod
+++ b/go.mod
@@ -42,7 +42,7 @@ 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 v1.1.1-0.20240522100209-5cd256cdcb39
+replace tailscale.com => github.com/coder/tailscale v1.1.1-0.20240528123714-e0fddea2bf02
 
 // This is replaced to include
 // 1. a fix for a data race: c.f. https://github.com/tailscale/wireguard-go/pull/25
diff --git a/go.sum b/go.sum
index ce61ee5166334..d8c3c4d9654ee 100644
--- a/go.sum
+++ b/go.sum
@@ -215,8 +215,8 @@ github.com/coder/serpent v0.7.0 h1:zGpD2GlF3lKIVkMjNGKbkip88qzd5r/TRcc30X/SrT0=
 github.com/coder/serpent v0.7.0/go.mod h1:REkJ5ZFHQUWFTPLExhXYZ1CaHFjxvGNRlLXLdsI08YA=
 github.com/coder/ssh v0.0.0-20231128192721-70855dedb788 h1:YoUSJ19E8AtuUFVYBpXuOD6a/zVP3rcxezNsoDseTUw=
 github.com/coder/ssh v0.0.0-20231128192721-70855dedb788/go.mod h1:aGQbuCLyhRLMzZF067xc84Lh7JDs1FKwCmF1Crl9dxQ=
-github.com/coder/tailscale v1.1.1-0.20240522100209-5cd256cdcb39 h1:v3x8FBqk45mbBybU1QrQy7CGiUpQDPBJT0C5g8bfGHE=
-github.com/coder/tailscale v1.1.1-0.20240522100209-5cd256cdcb39/go.mod h1:rp6BIJxCp127/hvvDWNkHC9MxAlKvQfoOtBr8s5sCqo=
+github.com/coder/tailscale v1.1.1-0.20240528123714-e0fddea2bf02 h1:nieqQqcg7Swa1NywfEi93yAagpj/LaszHsIt7wtq58M=
+github.com/coder/tailscale v1.1.1-0.20240528123714-e0fddea2bf02/go.mod h1:rp6BIJxCp127/hvvDWNkHC9MxAlKvQfoOtBr8s5sCqo=
 github.com/coder/terraform-provider-coder v0.22.0 h1:L72WFa9/6sc/nnXENPS8LpWi/2NBV+DRUW0WT//pEaU=
 github.com/coder/terraform-provider-coder v0.22.0/go.mod h1:wMun9UZ9HT2CzF6qPPBup1odzBpVUc0/xSFoXgdI3tk=
 github.com/coder/wgtunnel v0.1.13-0.20240522110300-ade90dfb2da0 h1:C2/eCr+r0a5Auuw3YOiSyLNHkdMtyCZHPFBx7syN4rk=