diff --git a/src/core/task/Task.ts b/src/core/task/Task.ts
index 3a83edc7e6..b571c180da 100644
--- a/src/core/task/Task.ts
+++ b/src/core/task/Task.ts
@@ -872,7 +872,21 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 			throw new Error("Current ask promise was ignored")
 		}
 
-		const result = { response: this.askResponse!, text: this.askResponseText, images: this.askResponseImages }
+		let result: { response: ClineAskResponse; text?: string; images?: string[] } = {
+			response: this.askResponse!,
+			text: this.askResponseText,
+			images: this.askResponseImages,
+		}
+		// Normalize any image refs to base64 data URLs before handing back to callers
+		if (Array.isArray(result.images) && result.images.length > 0) {
+			try {
+				const { normalizeImageRefsToDataUrls } = await import("../../integrations/misc/imageDataUrl")
+				const normalized = await normalizeImageRefsToDataUrls(result.images)
+				result.images = normalized
+			} catch (e) {
+				console.error("[Task#ask] Failed to normalize image refs:", e)
+			}
+		}
 		this.askResponse = undefined
 		this.askResponseText = undefined
 		this.askResponseImages = undefined
@@ -1070,6 +1084,16 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 			throw new Error(`[RooCode#say] task ${this.taskId}.${this.instanceId} aborted`)
 		}
 
+		// Ensure any image refs are normalized to base64 data URLs before persisting or sending to APIs
+		if (Array.isArray(images) && images.length > 0) {
+			try {
+				const { normalizeImageRefsToDataUrls } = await import("../../integrations/misc/imageDataUrl")
+				images = await normalizeImageRefsToDataUrls(images)
+			} catch (e) {
+				console.error("[Task#say] Failed to normalize image refs:", e)
+			}
+		}
+
 		if (partial !== undefined) {
 			const lastMessage = this.clineMessages.at(-1)
 
diff --git a/src/integrations/misc/imageDataUrl.ts b/src/integrations/misc/imageDataUrl.ts
index 9aaccc461a..bd8f14c14b 100644
--- a/src/integrations/misc/imageDataUrl.ts
+++ b/src/integrations/misc/imageDataUrl.ts
@@ -38,6 +38,24 @@ export async function normalizeImageRefsToDataUrls(imageRefs: string[]): Promise
  * Converts a webview URI to a file system path
  */
 function webviewUriToFilePath(webviewUri: string): string {
+	// Handle VS Code CDN-style webview URLs:
+	// Example: https://file+.vscode-resource.vscode-cdn.net/file/<absolute_path_to_image>
+	if (webviewUri.startsWith("https://")) {
+		try {
+			const u = new URL(webviewUri)
+			if (u.host === "vscode-cdn.net" || u.host.endsWith(".vscode-cdn.net")) {
+				// Path is like /file/<abs-path> - strip the /file/ prefix
+				let p = u.pathname || ""
+				if (p.startsWith("/file/")) {
+					p = p.slice("/file/".length)
+				}
+				return path.normalize(decodeURIComponent(p))
+			}
+		} catch {
+			// fall through if not a valid URL or not the expected host
+		}
+	}
+
 	// Handle vscode-resource URIs like:
 	// vscode-resource://vscode-webview/path/to/file
 	if (webviewUri.includes("vscode-resource://")) {