Fix .md attachment upload in student questions

Windows reports an empty or generic MIME type for .md files, so the
type-first check rejected them with "Разрешены только jpg, png, pdf, md"
even though the extension was allowed — a client hit this while sending
us a vault note.

Extension is now the primary gate; MIME is validated only when the
browser actually sent a meaningful one. Generic types fall back to a
type derived from the extension so the file is served correctly later.

Co-Authored-By: Claude Opus 5 (1M context) <noreply@anthropic.com>

src/app/api/student/question-upload/route.ts

@@ -4,10 +4,25 @@ import { auth } from "@/lib/auth";
 import { uploadFile } from "@/lib/s3";
 import { randomUUID } from "crypto";
 
+// Расширение — основной критерий: Windows не знает MIME-тип для .md и отдаёт
+// пустую строку или application/octet-stream, из-за чего заметки не прикреплялись.
+const ALLOWED_EXTS = new Set(["jpg", "jpeg", "png", "gif", "webp", "pdf", "md", "txt"]);
+
+// MIME проверяем дополнительно — но только когда браузер его вообще прислал
+// и это не обобщённый «просто файл».
 const ALLOWED_TYPES = new Set([
   "image/jpeg", "image/png", "image/gif", "image/webp",
   "application/pdf", "text/markdown", "text/x-markdown", "text/plain",
 ]);
+const GENERIC_TYPES = new Set(["", "application/octet-stream", "binary/octet-stream"]);
+
+// Для отдачи файла браузеру подставляем корректный тип, если своего не было
+const EXT_TO_TYPE: Record<string, string> = {
+  jpg: "image/jpeg", jpeg: "image/jpeg", png: "image/png",
+  gif: "image/gif", webp: "image/webp", pdf: "application/pdf",
+  md: "text/markdown", txt: "text/plain",
+};
+
 const MAX_BYTES = 10 * 1024 * 1024; // 10 MB
 
 export async function POST(req: NextRequest) {
@@ -22,22 +37,29 @@ export async function POST(req: NextRequest) {
     return NextResponse.json({ error: "Файл слишком большой (макс. 10 МБ)" }, { status: 413 });
   }
 
-  if (!ALLOWED_TYPES.has(file.type)) {
+  const ext = file.name.split(".").pop()?.toLowerCase() ?? "";
+  if (!ALLOWED_EXTS.has(ext)) {
     return NextResponse.json(
-      { error: "Разрешены только jpg, png, pdf, md" },
+      { error: "Разрешены только jpg, png, gif, webp, pdf, md, txt" },
       { status: 415 }
     );
   }
 
-  const ext = file.name.split(".").pop()?.toLowerCase() ?? "bin";
+  const declaredType = (file.type || "").toLowerCase();
-  const ALLOWED_EXTS = new Set(["jpg", "jpeg", "png", "gif", "webp", "pdf", "md", "txt"]);
+  if (!GENERIC_TYPES.has(declaredType) && !ALLOWED_TYPES.has(declaredType)) {
-  if (!ALLOWED_EXTS.has(ext)) {
+    return NextResponse.json(
-    return NextResponse.json({ error: "Недопустимое расширение файла" }, { status: 415 });
+      { error: "Разрешены только jpg, png, gif, webp, pdf, md, txt" },
+      { status: 415 }
+    );
   }
 
+  const contentType = GENERIC_TYPES.has(declaredType)
+    ? (EXT_TO_TYPE[ext] ?? "application/octet-stream")
+    : declaredType;
+
   const key = `questions/${session.user.id}/${randomUUID()}.${ext}`;
   const buffer = Buffer.from(await file.arrayBuffer());
-  const url = await uploadFile(key, buffer, file.type);
+  const url = await uploadFile(key, buffer, contentType);
 
   return NextResponse.json({ name: file.name, url, size: file.size });
 }