diff --git a/go.mod b/go.mod
index d84905c703..d8b7385222 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 v1.1.1-0.20250410041146-e62bfe0e9301
+replace tailscale.com => github.com/coder/tailscale v1.1.1-0.20250422090654-5090e715905e
 
 // 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 26b0fb5faa..313e0724a6 100644
--- a/go.sum
+++ b/go.sum
@@ -919,8 +919,8 @@ github.com/coder/serpent v0.10.0 h1:ofVk9FJXSek+SmL3yVE3GoArP83M+1tX+H7S4t8BSuM=
 github.com/coder/serpent v0.10.0/go.mod h1:cZFW6/fP+kE9nd/oRkEHJpG6sXCtQ+AX7WMMEHv0Y3Q=
 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 v1.1.1-0.20250410041146-e62bfe0e9301 h1:RMo8EZAMYnM9+HtCBDvXbcgCf0t8Roo1ZLiy8fVuooQ=
-github.com/coder/tailscale v1.1.1-0.20250410041146-e62bfe0e9301/go.mod h1:1ggFFdHTRjPRu9Yc1yA7nVHBYB50w9Ce7VIXNqcW6Ko=
+github.com/coder/tailscale v1.1.1-0.20250422090654-5090e715905e h1:nope/SZfoLB9MCOB9wdCE6gW5+8l3PhFrDC5IWPL8bk=
+github.com/coder/tailscale v1.1.1-0.20250422090654-5090e715905e/go.mod h1:1ggFFdHTRjPRu9Yc1yA7nVHBYB50w9Ce7VIXNqcW6Ko=
 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 v2.4.0-pre1 h1:jdpJAMk5EtkOmQFs9+hFC8eRxiEdrTrzwAzepiIejto=
diff --git a/tailnet/test/integration/integration_test.go b/tailnet/test/integration/integration_test.go
index f248747d10..b2cfa90067 100644
--- a/tailnet/test/integration/integration_test.go
+++ b/tailnet/test/integration/integration_test.go
@@ -12,6 +12,7 @@ import (
 	"net/http"
 	"net/url"
 	"os"
+	"os/exec"
 	"os/signal"
 	"path/filepath"
 	"runtime"
@@ -156,6 +157,14 @@ func TestIntegration(t *testing.T) {
 			// isolated NetNS.
 			t.Parallel()
 
+			// Fail early if NGINX is not installed in tests that require it.
+			if _, ok := topo.Server.(integration.NGINXServerOptions); ok {
+				_, err := exec.LookPath("nginx")
+				if err != nil {
+					t.Fatalf("could not find nginx in PATH: %v", err)
+				}
+			}
+
 			log := testutil.Logger(t)
 			networking := topo.SetupNetworking(t, log)