diff --git a/go.mod b/go.mod
index fc7e53722e..e13cebfcf3 100644
--- a/go.mod
+++ b/go.mod
@@ -36,7 +36,7 @@ replace github.com/tcnksm/go-httpstat => github.com/coder/go-httpstat v0.0.0-202
 
 // 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 v1.1.1-0.20260519043957-6f014ff9434f
+replace tailscale.com => github.com/coder/tailscale v1.1.1-0.20260529105257-b7c5fc6e6399
 
 // 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 3c08d31834..e639f168f3 100644
--- a/go.sum
+++ b/go.sum
@@ -350,8 +350,8 @@ github.com/coder/serpent v0.15.0 h1:jobR7DnPsxzEMD0cRiailwlY+4v6HAPS/8emIgBpaIU=
 github.com/coder/serpent v0.15.0/go.mod h1:7OIvFBYMd+OqarMy5einBl8AtRr8LliopVU7pyrwucY=
 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 v1.1.1-0.20260519043957-6f014ff9434f h1:gYivllu5CHhvRr4SM93zSQDj9cG2V+Pc0URTFy3fF/Y=
-github.com/coder/tailscale v1.1.1-0.20260519043957-6f014ff9434f/go.mod h1:WTWP5ZNODDXHwWlQ1Jc2MFhqxu93pUs7lIy28Fd5a5E=
+github.com/coder/tailscale v1.1.1-0.20260529105257-b7c5fc6e6399 h1:4IhFSmu0DSfWrvmHCb8aXDjWqSEYoIDA1L7Ar82Dm84=
+github.com/coder/tailscale v1.1.1-0.20260529105257-b7c5fc6e6399/go.mod h1:IatCC3hlq/ncu6DjZ+GJ/hNjSf5TmO+Xtc6B20k0q/c=
 github.com/coder/terraform-config-inspect v0.0.0-20250107175719-6d06d90c630e h1:JNLPDi2P73laR1oAclY6jWzAbucf70ASAvf5mh2cME0=
 github.com/coder/terraform-config-inspect v0.0.0-20250107175719-6d06d90c630e/go.mod h1:Gz/z9Hbn+4KSp8A2FBtNszfLSdT2Tn/uAKGuVqqWmDI=
 github.com/coder/terraform-provider-coder/v2 v2.18.0 h1:b60ixwf7pVPuiL0GkHZf+1mVj94/HZhCNpsfjAK34mI=