diff --git a/packages/app/src/attachments/utils.test.ts b/packages/app/src/attachments/utils.test.ts
index 270b8860d..6c50ce17c 100644
--- a/packages/app/src/attachments/utils.test.ts
+++ b/packages/app/src/attachments/utils.test.ts
@@ -1,5 +1,12 @@
 import { describe, expect, it } from "vitest";
-import { createImageSourceCacheKey, parseDataUrl, parseImageDataUrl, pathToFileUri } from "./utils";
+import {
+  createImageSourceCacheKey,
+  fileUriToPath,
+  localFileSourceToPath,
+  parseDataUrl,
+  parseImageDataUrl,
+  pathToFileUri,
+} from "./utils";
 
 describe("pathToFileUri", () => {
   it("converts POSIX absolute paths to file URIs", () => {
@@ -23,6 +30,24 @@ describe("pathToFileUri", () => {
   });
 });
 
+describe("fileUriToPath", () => {
+  it("converts Windows drive-letter file URIs back to paths", () => {
+    expect(fileUriToPath("file:///C:/Users/file.txt")).toBe("C:/Users/file.txt");
+  });
+});
+
+describe("localFileSourceToPath", () => {
+  it("decodes markdown-encoded Windows drive-letter paths", () => {
+    expect(localFileSourceToPath("C:%5CUsers%5Cfile.txt")).toBe("C:/Users/file.txt");
+  });
+
+  it("preserves literal percent sequences in plain local paths", () => {
+    expect(localFileSourceToPath("/tmp/image%20with%20literal%20percent.png")).toBe(
+      "/tmp/image%20with%20literal%20percent.png",
+    );
+  });
+});
+
 describe("parseDataUrl", () => {
   it("accepts base64 data URLs with media-type parameters", () => {
     expect(parseDataUrl("data:image/png;charset=utf-8;name=preview;base64,AAECAw==")).toEqual({
diff --git a/packages/app/src/attachments/utils.ts b/packages/app/src/attachments/utils.ts
index 713d21ca2..e1422a7f4 100644
--- a/packages/app/src/attachments/utils.ts
+++ b/packages/app/src/attachments/utils.ts
@@ -139,11 +139,41 @@ export function pathToFileUri(path: string): string {
   return `file:///${path.replace(/\\/g, "/")}`;
 }
 
+function decodeFilePathSource(source: string): string {
+  try {
+    return decodeURIComponent(source);
+  } catch {
+    return source;
+  }
+}
+
+function normalizeWindowsDrivePath(path: string): string {
+  if (!/^[A-Za-z]:[\\/]/.test(path)) {
+    return path;
+  }
+  return path.replace(/\\/g, "/");
+}
+
+function isMarkdownEncodedWindowsDrivePath(source: string): boolean {
+  return /^[A-Za-z]:(?:%5[Cc]|%2[Ff])/.test(source);
+}
+
 export function fileUriToPath(uri: string): string {
   if (!uri.startsWith("file://")) {
     return uri;
   }
-  return decodeURIComponent(uri.replace(/^file:\/\//, ""));
+  const decodedPath = decodeFilePathSource(uri.replace(/^file:\/\//, ""));
+  return normalizeWindowsDrivePath(decodedPath.replace(/^\/([A-Za-z]:[\\/])/, "$1"));
+}
+
+export function localFileSourceToPath(source: string): string {
+  let path = source;
+  if (source.startsWith("file://")) {
+    path = fileUriToPath(source);
+  } else if (isMarkdownEncodedWindowsDrivePath(source)) {
+    path = decodeFilePathSource(source);
+  }
+  return normalizeWindowsDrivePath(path);
 }
 
 export function getFileExtensionFromName(fileName: string | null | undefined): string {
diff --git a/packages/app/src/utils/assistant-image-source.test.ts b/packages/app/src/utils/assistant-image-source.test.ts
index 2c2183ec8..9dda97e9a 100644
--- a/packages/app/src/utils/assistant-image-source.test.ts
+++ b/packages/app/src/utils/assistant-image-source.test.ts
@@ -79,6 +79,19 @@ describe("resolveAssistantImageSource", () => {
     });
   });
 
+  it("normalizes markdown-encoded Windows paths into file RPC requests", () => {
+    expect(
+      resolveAssistantImageSource({
+        source: "C:%5CUsers%5Chanse%5CAppData%5CLocal%5CTemp%5Cpaseo-attachments%5Cimage.png",
+        workspaceRoot: "C:/Users/hanse/eatingkat",
+      }),
+    ).toEqual({
+      kind: "file_rpc",
+      cwd: "C:/",
+      path: "C:/Users/hanse/AppData/Local/Temp/paseo-attachments/image.png",
+    });
+  });
+
   it("falls back to the drive root for Windows absolute paths", () => {
     expect(
       resolveAssistantImageSource({
diff --git a/packages/app/src/utils/assistant-image-source.ts b/packages/app/src/utils/assistant-image-source.ts
index d3cd01b73..3e67dd26e 100644
--- a/packages/app/src/utils/assistant-image-source.ts
+++ b/packages/app/src/utils/assistant-image-source.ts
@@ -1,4 +1,4 @@
-import { fileUriToPath } from "@/attachments/utils";
+import { localFileSourceToPath } from "@/attachments/utils";
 import { resolveFilePreviewReadTarget } from "@/file-explorer/preview-target";
 
 export type AssistantImageSourceResolution =
@@ -18,13 +18,8 @@ export function resolveAssistantImageSource(input: {
     return { kind: "direct", uri: source };
   }
 
-  const sourcePath = source.startsWith("file://") ? fileUriToPath(source) : source;
-  if (!sourcePath) {
-    return null;
-  }
-
   const readTarget = resolveFilePreviewReadTarget({
-    path: sourcePath,
+    path: localFileSourceToPath(source),
     workspaceRoot: input.workspaceRoot,
   });
   if (!readTarget) {
diff --git a/packages/server/src/server/agent/providers/claude/agent.image-rendering.test.ts b/packages/server/src/server/agent/providers/claude/agent.image-rendering.test.ts
index 194b51e5c..444019cfb 100644
--- a/packages/server/src/server/agent/providers/claude/agent.image-rendering.test.ts
+++ b/packages/server/src/server/agent/providers/claude/agent.image-rendering.test.ts
@@ -1,4 +1,5 @@
 import { existsSync, rmSync } from "node:fs";
+import { fileURLToPath } from "node:url";
 import type { SDKMessage } from "@anthropic-ai/claude-agent-sdk";
 import { describe, expect, test } from "vitest";
 
@@ -146,7 +147,8 @@ function markdownImageSource(markdown: string): string {
     throw new Error(`Expected markdown image, got: ${markdown}`);
   }
   // Reverse escapeMarkdownImageSource: "\\" -> "\" and "\)" -> ")" (Windows paths are escaped).
-  return match[1].replace(/\\(.)/g, "$1");
+  const source = match[1].replace(/\\(.)/g, "$1");
+  return source.startsWith("file://") ? fileURLToPath(source) : source;
 }
 
 describe("Claude tool_result image rendering", () => {
diff --git a/packages/server/src/server/agent/providers/codex-app-server-agent.test.ts b/packages/server/src/server/agent/providers/codex-app-server-agent.test.ts
index f7472ef28..3a82f7410 100644
--- a/packages/server/src/server/agent/providers/codex-app-server-agent.test.ts
+++ b/packages/server/src/server/agent/providers/codex-app-server-agent.test.ts
@@ -6,6 +6,7 @@ import { mkdtemp } from "node:fs/promises";
 import { tmpdir } from "node:os";
 import path from "node:path";
 import { PassThrough } from "node:stream";
+import { fileURLToPath } from "node:url";
 
 import type {
   AgentLaunchContext,
@@ -111,7 +112,8 @@ function markdownImageSource(markdown: string): string {
   if (!match) {
     throw new Error(`Expected markdown image, got: ${markdown}`);
   }
-  return match[1].replace(/\\\)/g, ")");
+  const source = match[1].replace(/\\\)/g, ")");
+  return source.startsWith("file://") ? fileURLToPath(source) : source;
 }
 
 function emitCodexUserMessage(
diff --git a/packages/server/src/server/agent/providers/provider-image-output.test.ts b/packages/server/src/server/agent/providers/provider-image-output.test.ts
index 8f5410cb1..71d28e1d4 100644
--- a/packages/server/src/server/agent/providers/provider-image-output.test.ts
+++ b/packages/server/src/server/agent/providers/provider-image-output.test.ts
@@ -1,9 +1,20 @@
 import { describe, expect, test } from "vitest";
 
-import { isProviderImageMarkdown } from "./provider-image-output.js";
+import {
+  isProviderImageMarkdown,
+  renderProviderImageOutputAsAssistantMarkdown,
+} from "./provider-image-output.js";
 
 const HASH = "a".repeat(64);
 
+function renderImageMarkdown(path: string): string {
+  const item = renderProviderImageOutputAsAssistantMarkdown({ path });
+  if (!item || item.type !== "assistant_message") {
+    throw new Error("Expected provider image output to render as assistant markdown.");
+  }
+  return item.text;
+}
+
 describe("isProviderImageMarkdown", () => {
   test("matches the markdown emitted for a materialized attachment", () => {
     expect(isProviderImageMarkdown(`![Image](/tmp/paseo-attachments/${HASH}.png)`)).toBe(true);
@@ -18,6 +29,17 @@ describe("isProviderImageMarkdown", () => {
     ).toBe(true);
   });
 
+  test("emits Windows file paths as file URIs", () => {
+    const markdown = renderImageMarkdown(
+      `C:\\Users\\me\\AppData\\Local\\Temp\\paseo-attachments\\${HASH}.png`,
+    );
+
+    expect(markdown).toBe(
+      `![Image](file:///C:/Users/me/AppData/Local/Temp/paseo-attachments/${HASH}.png)`,
+    );
+    expect(isProviderImageMarkdown(markdown)).toBe(true);
+  });
+
   test("rejects user-authored markdown that is not a materialized attachment", () => {
     // No content hash — a hand-written path, not something the writer produced.
     expect(isProviderImageMarkdown("![diagram](./paseo-attachments/notes.png)")).toBe(false);
diff --git a/packages/server/src/server/agent/providers/provider-image-output.ts b/packages/server/src/server/agent/providers/provider-image-output.ts
index 0a4a154f7..d02c58185 100644
--- a/packages/server/src/server/agent/providers/provider-image-output.ts
+++ b/packages/server/src/server/agent/providers/provider-image-output.ts
@@ -66,11 +66,10 @@ export function materializeProviderImage(image: {
   return { path: filePath };
 }
 
-// Recognizes the markdown renderProviderImageOutputAsAssistantMarkdown emits for a materialized
-// provider image: its source is a content-hashed file in the attachments dir. Matching the full
-// <hash>.<ext> shape (not just a leading "![") keeps user-authored text from being mistaken for a
-// provider image when it reaches the history-replay filter. The separator class allows one-or-more
-// because on Windows the path uses "\\" and escapeMarkdownImageSource doubles each backslash.
+// Recognizes markdown rendered for a materialized provider image: its source is a content-hashed
+// file in the attachments dir. Matching the full <hash>.<ext> shape (not just a leading "![")
+// keeps user-authored text from being mistaken for a provider image during history replay. The
+// separator still accepts old doubled-backslash Windows history; new Windows output uses file URIs.
 const PROVIDER_IMAGE_MARKDOWN = new RegExp(
   `^!\\[[^\\]]*\\]\\([^)]*${PROVIDER_IMAGE_ATTACHMENT_DIR}[/\\\\]+[0-9a-f]{64}\\.[a-z0-9]+\\)`,
 );
@@ -96,8 +95,15 @@ function escapeMarkdownImageAlt(value: string): string {
   return value.replace(/\\/g, "\\\\").replace(/\]/g, "\\]");
 }
 
+function markdownImageSource(value: string): string {
+  if (/^[A-Za-z]:[\\/]/.test(value)) {
+    return `file:///${value.replace(/\\/g, "/")}`;
+  }
+  return value;
+}
+
 function escapeMarkdownImageSource(value: string): string {
-  return value.replace(/\\/g, "\\\\").replace(/\)/g, "\\)");
+  return markdownImageSource(value).replace(/\\/g, "\\\\").replace(/\)/g, "\\)");
 }
 
 export function renderProviderImageOutputAsAssistantMarkdown(