diff --git a/apps/web/lib/url-guard.test.ts b/apps/web/lib/url-guard.test.ts
index 8d3fda4..afe4e73 100644
--- a/apps/web/lib/url-guard.test.ts
+++ b/apps/web/lib/url-guard.test.ts
@@ -1,5 +1,15 @@
 import { describe, it, expect } from "vitest";
-import { validateExternalUrl, domainOf } from "./url-guard";
+import { ipv4FromMappedIPv6, validateExternalUrl, domainOf } from "./url-guard";
+
+describe("ipv4FromMappedIPv6", () => {
+  it("converts dotted-quad IPv4-mapped IPv6 literals", () => {
+    expect(ipv4FromMappedIPv6("::ffff:192.168.1.1")).toBe("192.168.1.1");
+    expect(ipv4FromMappedIPv6("::ffff:0:169.254.169.254")).toBe("169.254.169.254");
+  });
+  it("rejects dotted-quad octets outside the IPv4 range", () => {
+    expect(ipv4FromMappedIPv6("::ffff:256.0.0.1")).toBe(null);
+  });
+});
 
 describe("validateExternalUrl (SSRF guard)", () => {
   it("allows public https URLs", () => {
@@ -8,6 +18,11 @@ describe("validateExternalUrl (SSRF guard)", () => {
   it("blocks localhost", () => {
     expect(validateExternalUrl("http://localhost/x").ok).toBe(false);
   });
+  it("blocks internal hostnames with DNS root dots", () => {
+    expect(validateExternalUrl("http://localhost./x").ok).toBe(false);
+    expect(validateExternalUrl("http://app.localhost./x").ok).toBe(false);
+    expect(validateExternalUrl("http://metadata.google.internal./x").ok).toBe(false);
+  });
   it("blocks private 10.x", () => {
     expect(validateExternalUrl("http://10.0.0.5/x").ok).toBe(false);
   });
diff --git a/apps/web/lib/url-guard.ts b/apps/web/lib/url-guard.ts
index 7490554..de1d318 100644
--- a/apps/web/lib/url-guard.ts
+++ b/apps/web/lib/url-guard.ts
@@ -2,7 +2,14 @@
  * Basic SSRF guard for user-provided media URLs. Blocks non-http(s) schemes and
  * obvious private / internal hosts. DNS-rebinding is out of scope for the MVP.
  */
-function ipv4FromMappedIPv6(host: string): string | null {
+export function ipv4FromMappedIPv6(host: string): string | null {
+  const dotted = host.match(/^::ffff:(?:0:)?(\d{1,3})\.(\d{1,3})\.(\d{1,3})\.(\d{1,3})$/i);
+  if (dotted) {
+    const octets = dotted.slice(1).map(Number);
+    if (octets.some((octet) => octet > 255)) return null;
+    return octets.join(".");
+  }
+
   const match = host.match(/^::ffff:(?:0:)?([0-9a-f]{1,4}):([0-9a-f]{1,4})$/i);
   if (!match) return null;
   const high = Number.parseInt(match[1]!, 16);
@@ -15,6 +22,7 @@ function isBlockedHost(host: string): boolean {
   const ipv4 = ipv4FromMappedIPv6(host) ?? host;
   return (
     ipv4 === "localhost" ||
+    ipv4.endsWith(".localhost") ||
     ipv4 === "0.0.0.0" ||
     ipv4 === "::1" ||
     ipv4 === "::" ||
@@ -42,7 +50,7 @@ export function validateExternalUrl(raw: string): { ok: true; url: URL } | { ok:
   if (url.protocol !== "http:" && url.protocol !== "https:") {
     return { ok: false, error: "Only http and https URLs are allowed." };
   }
-  const host = url.hostname.toLowerCase().replace(/^\[(.*)\]$/, "$1");
+  const host = url.hostname.toLowerCase().replace(/^\[(.*)\]$/, "$1").replace(/\.+$/, "");
   if (isBlockedHost(host)) {
     return { ok: false, error: "That host is not allowed." };
   }