diff --git a/src/media/parse.test.ts b/src/media/parse.test.ts
index de60ca357..95a088f22 100644
--- a/src/media/parse.test.ts
+++ b/src/media/parse.test.ts
@@ -27,6 +27,27 @@ describe("splitMediaFromOutput", () => {
     expect(result.text).toBe("");
   });
 
+  it("normalizes Windows file URLs", () => {
+    const result = splitMediaFromOutput("MEDIA:file:///C:/Users/pete/My%20File.png");
+    const expected =
+      process.platform === "win32" ? "C:\\Users\\pete\\My File.png" : "C:/Users/pete/My File.png";
+    expect(result.mediaUrls).toEqual([expected]);
+    expect(result.text).toBe("");
+  });
+
+  it("accepts Windows drive letter paths", () => {
+    const result = splitMediaFromOutput("MEDIA:C:/Users/pete/My File.png");
+    expect(result.mediaUrls).toEqual(["C:/Users/pete/My File.png"]);
+    expect(result.text).toBe("");
+  });
+
+  it("accepts Windows drive letter paths with backslashes", () => {
+    const filePath = "C:\\Users\\pete\\My File.png";
+    const result = splitMediaFromOutput(`MEDIA:${filePath}`);
+    expect(result.mediaUrls).toEqual([filePath]);
+    expect(result.text).toBe("");
+  });
+
   it("keeps audio_as_voice detection stable across calls", () => {
     const input = "Hello [[audio_as_voice]]";
     const first = splitMediaFromOutput(input);
diff --git a/src/media/parse.ts b/src/media/parse.ts
index de0c6a5bc..b421f67fa 100644
--- a/src/media/parse.ts
+++ b/src/media/parse.ts
@@ -1,5 +1,7 @@
 // Shared helpers for parsing MEDIA tokens from command/stdout text.
 
+import { fileURLToPath } from "node:url";
+
 import { parseFenceSpans } from "../markdown/fences.js";
 import { parseAudioTag } from "./audio-tags.js";
 
@@ -7,7 +9,15 @@ import { parseAudioTag } from "./audio-tags.js";
 export const MEDIA_TOKEN_RE = /\bMEDIA:\s*`?([^\n]+)`?/gi;
 
 export function normalizeMediaSource(src: string) {
-  return src.startsWith("file://") ? src.replace("file://", "") : src;
+  if (!src.startsWith("file://")) return src;
+  try {
+    const filePath = fileURLToPath(src);
+    // Normalize drive-letter paths that appear as `/C:/...` on non-Windows platforms.
+    return filePath.replace(/^\/([a-zA-Z]:[\\/])/, "$1");
+  } catch {
+    // Best-effort fallback for malformed file URLs.
+    return src.replace("file://", "");
+  }
 }
 
 function cleanCandidate(raw: string) {
@@ -19,6 +29,8 @@ function isValidMedia(candidate: string, opts?: { allowSpaces?: boolean }) {
   if (candidate.length > 4096) return false;
   if (!opts?.allowSpaces && /\s/.test(candidate)) return false;
   if (/^https?:\/\//i.test(candidate)) return true;
+  if (/^[a-zA-Z]:[\\/]/.test(candidate)) return true;
+  if (candidate.startsWith("\\\\")) return true;
   if (candidate.startsWith("/")) return true;
   if (candidate.startsWith("./")) return true;
   if (candidate.startsWith("../")) return true;
@@ -118,6 +130,7 @@ export function splitMediaFromOutput(raw: string): {
         trimmedPayload.startsWith("./") ||
         trimmedPayload.startsWith("../") ||
         trimmedPayload.startsWith("~") ||
+        /^[a-zA-Z]:[\\/]/.test(trimmedPayload) ||
         trimmedPayload.startsWith("file://");
       if (
         !unwrapped &&