diff --git a/.jules/sentinel.md b/.jules/sentinel.md
index 08e5bfbd..7f07c72c 100644
--- a/.jules/sentinel.md
+++ b/.jules/sentinel.md
@@ -1,9 +1,4 @@
-## 2025-02-18 - Custom Regex Sanitization Risks
-**Vulnerability:** The codebase used a custom regex-based implementation (`lib/security/sanitize-html.ts`) for HTML sanitization, which is fragile and prone to XSS bypasses (e.g. unquoted attributes).
-**Learning:** Developers often underestimate the complexity of HTML parsing. Relying on custom regex creates a false sense of security.
-**Prevention:** Always use established, battle-tested libraries like `isomorphic-dompurify` for HTML sanitization. Ensure `jsdom` is added as a production dependency for `isomorphic-dompurify` to work correctly in SSR environments.
-
-## 2025-03-08 - Unsafe SVG Rendering via dangerouslySetInnerHTML
-**Vulnerability:** User-controlled SVG strings (`avatar.svg_data`) were being injected directly into the DOM using `dangerouslySetInnerHTML`. An attacker could inject an SVG containing embedded malicious `<script>` tags or `onload` event handlers, leading to Stored Cross-Site Scripting (XSS).
-**Learning:** Rendering raw SVGs inline is inherently dangerous. SVGs are essentially XML documents capable of embedding JavaScript.
-**Prevention:** When you need to display user-provided SVGs and you don't need to manipulate their internal paths via CSS/JS, do not use `dangerouslySetInnerHTML`. Instead, render the SVG securely by encoding it as a data URI (`data:image/svg+xml;charset=utf-8,${encodeURIComponent(svgData)}`) and using it as the `src` attribute of a standard `<img>` tag. This forces the browser to treat the SVG strictly as an image, entirely disabling any embedded script execution.
\ No newline at end of file
+## 2024-05-20 - Unvalidated File Types on Presigned URLs
+**Vulnerability:** The presigned URL generation endpoint (`app/api/upload/presigned/route.ts`) checks file size manually, but bypasses the central `validateFile` function. It does not validate `fileName` extensions against `DANGEROUS_EXTENSIONS` or `fileType` against allowed mime types. This can allow users to request signed URLs to upload arbitrary and dangerous file types (like `.exe` or `.html`) directly to the storage bucket, bypassing client-side checks.
+**Learning:** Even when delegating the actual upload to a third-party service via presigned URLs, the endpoint generating the URL must still perform strict validation on the proposed file metadata (name and type), as attackers can trivially bypass client-side checks to request a signature for a malicious payload.
+**Prevention:** Always use centralized validation utilities (like `validateFile` from `lib/constants/upload.ts`) on all file upload paths, whether handling the stream directly or issuing a presigned URL.
diff --git a/app/api/upload/presigned/route.ts b/app/api/upload/presigned/route.ts
index e9307f2c..98ece6dc 100644
--- a/app/api/upload/presigned/route.ts
+++ b/app/api/upload/presigned/route.ts
@@ -2,6 +2,11 @@ import { NextRequest, NextResponse } from "next/server";
 import { b2 } from "@/lib/backblaze";
 import { requireUploadAccess } from "@/lib/security/upload-access";
 import { safeServerError } from "@/lib/security/route-guards";
+import {
+  validateFile,
+  ALLOWED_GENERAL_TYPES,
+  MAX_GENERAL_SIZE,
+} from "@/lib/constants/upload";
 
 export async function POST(request: NextRequest) {
   try {
@@ -32,9 +37,16 @@ export async function POST(request: NextRequest) {
       return NextResponse.json({ error: "Valid fileSize is required" }, { status: 400 });
     }
 
-    const MAX_FILE_SIZE = 40 * 1024 * 1024;
-    if (fileSize > MAX_FILE_SIZE) {
-      return NextResponse.json({ error: "File too large" }, { status: 400 });
+    const validation = validateFile(
+      fileName,
+      fileSize,
+      fileType,
+      ALLOWED_GENERAL_TYPES,
+      MAX_GENERAL_SIZE
+    );
+
+    if (!validation.valid) {
+      return NextResponse.json({ error: validation.error }, { status: 400 });
     }
 
     const presignedData = await b2.getPresignedUploadUrl(