diff --git a/SECURITY.md b/SECURITY.md
index 358a5c2..9f5e525 100644
--- a/SECURITY.md
+++ b/SECURITY.md
@@ -4,7 +4,7 @@
 
 | Version | Supported          |
 | ------- | ------------------ |
-| 3.4.4   | :white_check_mark: |
+| 3.4.8   | :white_check_mark: |
 | < 3     | :x:                |
 | < 2     | :x:                |
 
diff --git a/package.json b/package.json
index 06bc351..7c81942 100644
--- a/package.json
+++ b/package.json
@@ -42,6 +42,7 @@
     "fflate": "^0.7.3",
     "find-my-way": "^6.3.0",
     "minio": "^7.0.28",
+    "ms": "canary",
     "multer": "^1.4.5-lts.1",
     "next": "^12.1.6",
     "prisma": "^4.1.0",
diff --git a/src/components/File.tsx b/src/components/File.tsx
index f49dcda..f0e36ed 100644
--- a/src/components/File.tsx
+++ b/src/components/File.tsx
@@ -1,4 +1,4 @@
-import { Button, Card, Group, Modal, Stack, Text, Title, useMantineTheme } from '@mantine/core';
+import { Button, Card, Group, Modal, Stack, Text, Title, Tooltip, useMantineTheme } from '@mantine/core';
 import { useClipboard } from '@mantine/hooks';
 import { showNotification } from '@mantine/notifications';
 import useFetch from 'hooks/useFetch';
@@ -8,8 +8,18 @@ import { CalendarIcon, ClockIcon, CopyIcon, CrossIcon, DeleteIcon, FileIcon, Has
 import MutedText from './MutedText';
 import { relativeTime } from 'lib/clientUtils';
 
-export function FileMeta({ Icon, title, subtitle }) {
-  return (
+export function FileMeta({ Icon, title, subtitle, ...other }) {
+  return other.tooltip ? (
+    <Group>
+      <Icon size={24} />
+      <Tooltip label={other.tooltip}>
+        <Stack spacing={1}>
+          <Text>{title}</Text>
+          <MutedText size='md'>{subtitle}</MutedText>
+        </Stack>
+      </Tooltip>
+    </Group>
+  ) : (
     <Group>
       <Icon size={24} />
       <Stack spacing={1}>
@@ -88,7 +98,12 @@ export default function File({ image, updateImages }) {
             <FileMeta Icon={FileIcon} title='Name' subtitle={image.file} />
             <FileMeta Icon={ImageIcon} title='Type' subtitle={image.mimetype} />
             <FileMeta Icon={CalendarIcon} title='Uploaded at' subtitle={new Date(image.created_at).toLocaleString()} />
-            {image.expires_at && <FileMeta Icon={ClockIcon} title='Expires' subtitle={relativeTime(new Date(image.expires_at))} />}
+            {image.expires_at && <FileMeta
+              Icon={ClockIcon}
+              title='Expires'
+              subtitle={relativeTime(new Date(image.expires_at))}
+              tooltip={new Date(image.expires_at).toLocaleString()}
+            />}
             <FileMeta Icon={HashIcon} title='ID' subtitle={image.id} />
           </Stack>
         </Stack>
diff --git a/src/components/pages/Upload.tsx b/src/components/pages/Upload.tsx
index 49198c2..6417a3a 100644
--- a/src/components/pages/Upload.tsx
+++ b/src/components/pages/Upload.tsx
@@ -140,7 +140,7 @@ export default function Upload() {
 
     req.open('POST', '/api/upload');
     req.setRequestHeader('Authorization', user.token);
-    expires !== 'never' && req.setRequestHeader('Expires-At', expires_at.toISOString());
+    expires !== 'never' && req.setRequestHeader('Expires-At', 'date=' + expires_at.toISOString());
 
     req.send(body);
   };
diff --git a/src/lib/clientUtils.ts b/src/lib/clientUtils.ts
index e1b09dc..17851a2 100644
--- a/src/lib/clientUtils.ts
+++ b/src/lib/clientUtils.ts
@@ -1,4 +1,5 @@
-import type { Image, User } from '@prisma/client';
+import type { Image, ImageFormat, User } from '@prisma/client';
+import ms, { StringValue } from 'ms';
 
 export function parse(str: string, image: Image, user: User) {
   if (!str) return null;
@@ -50,3 +51,35 @@ export function relativeTime(to: Date, from: Date = new Date()) {
   }
 }
 
+export function humanTime(string: StringValue | string): Date {
+  try {
+    const mil = ms(string as StringValue);
+    if (typeof mil !== 'number') return null; 
+    if (isNaN(mil)) return null;
+    if (!mil) return null;
+  
+    return new Date(Date.now() + mil);
+  } catch (_) {
+    return null;
+  }
+}
+
+export function parseExpiry(header: string): Date | null {
+  if (!header) return null;
+  header = header.toLowerCase();
+
+  if (header.startsWith('date=')) {
+    const date = new Date(header.substring(5));
+
+    if (!date.getTime()) return null;
+    if (date.getTime() < Date.now()) return null;
+    return date;
+  }
+
+  const human = humanTime(header);
+
+  if (!human) return null;
+  if (human.getTime() < Date.now()) return null;
+
+  return human;
+}
\ No newline at end of file
diff --git a/src/pages/api/upload.ts b/src/pages/api/upload.ts
index f7ea556..ad68298 100644
--- a/src/pages/api/upload.ts
+++ b/src/pages/api/upload.ts
@@ -9,6 +9,8 @@ import { format as formatDate } from 'fecha';
 import datasource from 'lib/datasource';
 import { randomUUID } from 'crypto';
 import sharp from 'sharp';
+import { humanTime, parseExpiry } from 'lib/clientUtils';
+import { StringValue } from 'ms';
 
 const uploader = multer();
 
@@ -42,21 +44,27 @@ async function handler(req: NextApiReq, res: NextApiRes) {
   await run(uploader.array('file'))(req, res);
 
   if (!req.files) return res.error('no files');
-
   if (req.files && req.files.length === 0) return res.error('no files');
 
+  const response: { files: string[], expires_at?: Date } = { files: [] };
+
   const expires_at = req.headers['expires-at'] as string;
-  const expiry = expires_at ? new Date(expires_at) : null;
-  if (expiry) {
-    if (!expiry.getTime()) return res.bad('invalid date');
-    if (expiry.getTime() < Date.now()) return res.bad('date is in the past');
+  let expiry: Date;
+
+  if (expires_at) {
+    expiry = parseExpiry(expires_at);
+    if (!expiry) return res.error('invalid date');
+    else {
+      response.expires_at = expiry;
+    }
   }
 
   const rawFormat = ((req.headers.format || '') as string).toUpperCase() || 'RANDOM';
   const format: ImageFormat = Object.keys(ImageFormat).includes(rawFormat) && ImageFormat[rawFormat];
+
   const imageCompressionPercent = req.headers['image-compression-percent'] ? Number(req.headers['image-compression-percent']) : null;
 
-  const files = [];
+
   for (let i = 0; i !== req.files.length; ++i) {
     const file = req.files[i];
     if (file.size > zconfig.uploader[user.administrator ? 'admin_limit' : 'user_limit']) return res.error(`file[${i}] size too big`);
@@ -78,6 +86,9 @@ async function handler(req: NextApiReq, res: NextApiRes) {
       case ImageFormat.NAME:
         fileName = file.originalname.split('.')[0];
         break;
+      default:
+        fileName = randomChars(zconfig.uploader.length);
+        break;
     }
 
     let password = null;
@@ -90,7 +101,7 @@ async function handler(req: NextApiReq, res: NextApiRes) {
     const image = await prisma.image.create({
       data: {
         file: `${fileName}.${compressionUsed ? 'jpg' : ext}`,
-        mimetype: req.headers.uploadtext ? 'text/plain' : file.mimetype,
+        mimetype: req.headers.uploadtext ? 'text/plain' : (compressionUsed ? 'image/jpeg' : file.mimetype),
         userId: user.id,
         embed: !!req.headers.embed,
         format,
@@ -112,9 +123,9 @@ async function handler(req: NextApiReq, res: NextApiRes) {
     Logger.get('image').info(`User ${user.username} (${user.id}) uploaded an image ${image.file} (${image.id})`);
     if (user.domains.length) {
       const domain = user.domains[Math.floor(Math.random() * user.domains.length)];
-      files.push(`${domain}${zconfig.uploader.route === '/' ? '' : zconfig.uploader.route}/${invis ? invis.invis : image.file}`);
+      response.files.push(`${domain}${zconfig.uploader.route === '/' ? '' : zconfig.uploader.route}/${invis ? invis.invis : image.file}`);
     } else {
-      files.push(`${zconfig.core.https ? 'https' : 'http'}://${req.headers.host}${zconfig.uploader.route === '/' ? '' : zconfig.uploader.route}/${invis ? invis.invis : image.file}`);
+      response.files.push(`${zconfig.core.https ? 'https' : 'http'}://${req.headers.host}${zconfig.uploader.route === '/' ? '' : zconfig.uploader.route}/${invis ? invis.invis : image.file}`);
     }
   }
 
@@ -140,7 +151,7 @@ async function handler(req: NextApiReq, res: NextApiRes) {
     }
   }
 
-  return res.json({ files });
+  return res.json(response);
 }
 
 function run(middleware: any) {
diff --git a/src/pages/api/user/recent.ts b/src/pages/api/user/recent.ts
index cc42f00..fd0f7d8 100644
--- a/src/pages/api/user/recent.ts
+++ b/src/pages/api/user/recent.ts
@@ -19,6 +19,7 @@ async function handler(req: NextApiReq, res: NextApiRes) {
     },
     select: {
       created_at: true,
+      expires_at: true,
       file: true,
       mimetype: true,
       id: true,
diff --git a/yarn.lock b/yarn.lock
index 4062406..25ad837 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -6009,6 +6009,13 @@ __metadata:
   languageName: node
   linkType: hard
 
+"ms@npm:canary":
+  version: 3.0.0-canary.1
+  resolution: "ms@npm:3.0.0-canary.1"
+  checksum: 5ec76c0932cf83ac3e7f70f1a4c0d4db4dbc91de6ea5f7d336c67b48f513c8cb4c0fce3a07e3d84ee931dbdc9a48f33ed1c485e834279fff8906d385e86684ae
+  languageName: node
+  linkType: hard
+
 "mssql@npm:8.1.2":
   version: 8.1.2
   resolution: "mssql@npm:8.1.2"
@@ -8896,6 +8903,7 @@ __metadata:
     fflate: ^0.7.3
     find-my-way: ^6.3.0
     minio: ^7.0.28
+    ms: canary
     multer: ^1.4.5-lts.1
     next: ^12.1.6
     npm-run-all: ^4.1.5