diff --git a/src/lib/components/chat/UrlFetchModal.svelte b/src/lib/components/chat/UrlFetchModal.svelte
index 3dd4ca6c059..634984def5f 100644
--- a/src/lib/components/chat/UrlFetchModal.svelte
+++ b/src/lib/components/chat/UrlFetchModal.svelte
@@ -2,6 +2,7 @@
 	import Modal from "../Modal.svelte";
 	import { base } from "$app/paths";
 	import { tick } from "svelte";
+	import { pickSafeMime } from "$lib/utils/mime";
 
 	interface Props {
 		open?: boolean;
@@ -81,23 +82,36 @@
 				const txt = await res.text();
 				throw new Error(txt || `Failed to fetch (${res.status})`);
 			}
+			const forwardedType =
+				res.headers.get("x-forwarded-content-type");
 			const blob = await res.blob();
+			const mimeType = pickSafeMime(forwardedType, blob.type, trimmed);
 			// Optional client-side mime filter (same wildcard semantics as dropzone)
-			if (acceptMimeTypes.length > 0 && blob.type && !matchesAllowed(blob.type, acceptMimeTypes)) {
+			if (acceptMimeTypes.length > 0 && mimeType && !matchesAllowed(mimeType, acceptMimeTypes)) {
 				throw new Error("File type not allowed.");
 			}
 			const disp = res.headers.get("content-disposition");
-			let filename = "attachment";
-			const match = disp?.match(/filename[^;=\n]*=((['"]).*?\2|[^;\n]*)/);
-			if (match && match[1]) filename = match[1].replace(/['"]/g, "");
-			else {
+			const filename = (() => {
+				const filenameStar = disp?.match(/filename\*=UTF-8''([^;]+)/i)?.[1];
+				if (filenameStar) {
+					const cleaned = filenameStar.trim().replace(/['"]/g, "");
+					try {
+						return decodeURIComponent(cleaned);
+					} catch {
+						return cleaned;
+					}
+				}
+				const filenameMatch = disp?.match(/filename="?([^";]+)"?/i)?.[1];
+				if (filenameMatch) return filenameMatch.trim();
 				try {
 					const u = new URL(trimmed);
 					const last = u.pathname.split("/").pop() || "attachment";
-					filename = decodeURIComponent(last);
-				} catch {}
-			}
-			const file = new File([blob], filename, { type: blob.type || "application/octet-stream" });
+					return decodeURIComponent(last);
+				} catch {
+					return "attachment";
+				}
+			})();
+			const file = new File([blob], filename, { type: mimeType });
 			onfiles?.([file]);
 			close();
 		} catch (e) {
diff --git a/src/lib/utils/loadAttachmentsFromUrls.ts b/src/lib/utils/loadAttachmentsFromUrls.ts
index c56f2f64ed6..da6e11d41d1 100644
--- a/src/lib/utils/loadAttachmentsFromUrls.ts
+++ b/src/lib/utils/loadAttachmentsFromUrls.ts
@@ -1,4 +1,5 @@
 import { base } from "$app/paths";
+import { pickSafeMime } from "$lib/utils/mime";
 
 export interface AttachmentLoadResult {
 	files: File[];
@@ -31,10 +32,18 @@ function parseAttachmentUrls(searchParams: URLSearchParams): string[] {
 function extractFilename(url: string, contentDisposition?: string | null): string {
 	// Try to get filename from Content-Disposition header
 	if (contentDisposition) {
-		const match = contentDisposition.match(/filename[^;=\n]*=((['"]).*?\2|[^;\n]*)/);
-		if (match && match[1]) {
-			return match[1].replace(/['"]/g, "");
+		const filenameStar = contentDisposition.match(/filename\*=UTF-8''([^;]+)/i)?.[1];
+		if (filenameStar) {
+			const cleaned = filenameStar.trim().replace(/['"]/g, "");
+			try {
+				return decodeURIComponent(cleaned);
+			} catch {
+				return cleaned;
+			}
 		}
+
+		const match = contentDisposition.match(/filename[^;=\n]*=((['"]).*?\2|[^;\n]*)/);
+		if (match && match[1]) return match[1].replace(/['"]/g, "");
 	}
 
 	// Fallback: extract from URL
@@ -82,13 +91,16 @@ export async function loadAttachmentsFromUrls(
 					return;
 				}
 
+				const forwardedType =
+					response.headers.get("x-forwarded-content-type");
 				const blob = await response.blob();
+				const mimeType = pickSafeMime(forwardedType, blob.type, url);
 				const contentDisposition = response.headers.get("content-disposition");
 				const filename = extractFilename(url, contentDisposition);
 
 				// Create File object
 				const file = new File([blob], filename, {
-					type: blob.type || "application/octet-stream",
+					type: mimeType,
 				});
 
 				files.push(file);
diff --git a/src/lib/utils/mime.ts b/src/lib/utils/mime.ts
new file mode 100644
index 00000000000..0c4c3e4c61e
--- /dev/null
+++ b/src/lib/utils/mime.ts
@@ -0,0 +1,56 @@
+// Lightweight MIME helpers to avoid new dependencies.
+
+const EXTENSION_TO_MIME: Record<string, string> = {
+	png: "image/png",
+	jpg: "image/jpeg",
+	jpe: "image/jpeg",
+	jpeg: "image/jpeg",
+	gif: "image/gif",
+	webp: "image/webp",
+	svg: "image/svg+xml",
+	pdf: "application/pdf",
+	txt: "text/plain",
+	csv: "text/csv",
+	json: "application/json",
+	mp3: "audio/mpeg",
+	wav: "audio/wav",
+	ogg: "audio/ogg",
+	mp4: "video/mp4",
+	mov: "video/quicktime",
+	webm: "video/webm",
+	zip: "application/zip",
+	gz: "application/gzip",
+	tgz: "application/gzip",
+	tar: "application/x-tar",
+	html: "text/html",
+	htm: "text/html",
+	md: "text/markdown",
+};
+
+export function guessMimeFromUrl(url: string): string | undefined {
+	try {
+		const pathname = new URL(url).pathname;
+		const ext = pathname.split(".").pop()?.toLowerCase();
+		if (ext && EXTENSION_TO_MIME[ext]) return EXTENSION_TO_MIME[ext];
+	} catch {
+		/* ignore */
+	}
+	return undefined;
+}
+
+export function pickSafeMime(
+	forwardedType: string | null,
+	blobType: string | undefined,
+	url: string
+): string {
+	const inferred = guessMimeFromUrl(url);
+	if (forwardedType) return forwardedType;
+	if (
+		inferred &&
+		(!blobType || blobType === "application/octet-stream" || blobType.startsWith("text/plain"))
+	) {
+		return inferred;
+	}
+	if (blobType) return blobType;
+	return inferred || "application/octet-stream";
+}
diff --git a/src/routes/api/fetch-url/+server.ts b/src/routes/api/fetch-url/+server.ts
index 85cbe1d7c06..cfb83bb67e8 100644
--- a/src/routes/api/fetch-url/+server.ts
+++ b/src/routes/api/fetch-url/+server.ts
@@ -51,12 +51,14 @@ export async function GET({ url }) {
 		}
 
 		// Stream the response back
-		// Always return as text/plain to prevent any HTML/JS execution
-		const contentType = "text/plain; charset=utf-8";
+		const originalContentType = response.headers.get("content-type") || "application/octet-stream";
+		// Send as text/plain for safety; expose the original type via secondary header
+		const safeContentType = "text/plain; charset=utf-8";
 		const contentDisposition = response.headers.get("content-disposition");
 
 		const headers: HeadersInit = {
-			"Content-Type": contentType,
+			"Content-Type": safeContentType,
+			"X-Forwarded-Content-Type": originalContentType,
 			"Cache-Control": "public, max-age=3600",
 			...(contentDisposition ? { "Content-Disposition": contentDisposition } : {}),
 			...SECURITY_HEADERS,