diff --git a/prisma/migrations/20220728183855_expiring_images/migration.sql b/prisma/migrations/20220728183855_expiring_images/migration.sql
new file mode 100644
index 0000000..b30e87c
--- /dev/null
+++ b/prisma/migrations/20220728183855_expiring_images/migration.sql
@@ -0,0 +1,2 @@
+-- AlterTable
+ALTER TABLE "Image" ADD COLUMN     "expires_at" TIMESTAMP(3);
diff --git a/prisma/schema.prisma b/prisma/schema.prisma
index adacefd..abd4950 100644
--- a/prisma/schema.prisma
+++ b/prisma/schema.prisma
@@ -36,6 +36,7 @@ model Image {
   file       String
   mimetype   String          @default("image/png")
   created_at DateTime        @default(now())
+  expires_at DateTime?
   views      Int             @default(0)
   favorite   Boolean         @default(false)
   embed      Boolean         @default(false)
diff --git a/src/components/File.tsx b/src/components/File.tsx
index 8712fdd..f49dcda 100644
--- a/src/components/File.tsx
+++ b/src/components/File.tsx
@@ -4,8 +4,9 @@ import { showNotification } from '@mantine/notifications';
 import useFetch from 'hooks/useFetch';
 import { useState } from 'react';
 import Type from './Type';
-import { CalendarIcon, CopyIcon, CrossIcon, DeleteIcon, FileIcon, HashIcon, ImageIcon, StarIcon } from './icons';
+import { CalendarIcon, ClockIcon, CopyIcon, CrossIcon, DeleteIcon, FileIcon, HashIcon, ImageIcon, StarIcon } from './icons';
 import MutedText from './MutedText';
+import { relativeTime } from 'lib/clientUtils';
 
 export function FileMeta({ Icon, title, subtitle }) {
   return (
@@ -22,7 +23,6 @@ export function FileMeta({ Icon, title, subtitle }) {
 export default function File({ image, updateImages }) {
   const [open, setOpen] = useState(false);
   const clipboard = useClipboard();
-  const theme = useMantineTheme();
 
   const handleDelete = async () => {
     const res = await useFetch('/api/user/files', 'DELETE', { id: image.id });
@@ -88,6 +88,7 @@ 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))} />}
             <FileMeta Icon={HashIcon} title='ID' subtitle={image.id} />
           </Stack>
         </Stack>
diff --git a/src/components/icons/ClockIcon.tsx b/src/components/icons/ClockIcon.tsx
new file mode 100644
index 0000000..e55f7a2
--- /dev/null
+++ b/src/components/icons/ClockIcon.tsx
@@ -0,0 +1,5 @@
+import { Clock } from 'react-feather';
+
+export default function ClockIcon({ ...props }) {
+  return <Clock size={15} {...props} />;
+}
\ No newline at end of file
diff --git a/src/components/icons/index.tsx b/src/components/icons/index.tsx
index d9530ad..45d17a4 100644
--- a/src/components/icons/index.tsx
+++ b/src/components/icons/index.tsx
@@ -22,6 +22,7 @@ import PlayIcon from './PlayIcon';
 import CalendarIcon from './CalendarIcon';
 import HashIcon from './HashIcon';
 import TagIcon from './TagIcon';
+import ClockIcon from './ClockIcon';
 
 export {
   ActivityIcon,
@@ -48,4 +49,5 @@ export {
   CalendarIcon,
   HashIcon,
   TagIcon,
+  ClockIcon,
 };
\ No newline at end of file
diff --git a/src/components/pages/Upload.tsx b/src/components/pages/Upload.tsx
index 0fef926..0422a1a 100644
--- a/src/components/pages/Upload.tsx
+++ b/src/components/pages/Upload.tsx
@@ -1,13 +1,44 @@
-import { Button, Collapse, Group, Progress, Title } from '@mantine/core';
+import { Button, Collapse, Group, Progress, Select, Title } from '@mantine/core';
 import { randomId, useClipboard } from '@mantine/hooks';
 import { showNotification, updateNotification } from '@mantine/notifications';
 import Dropzone from 'components/dropzone/Dropzone';
 import FileDropzone from 'components/dropzone/DropzoneFile';
-import { CrossIcon, UploadIcon } from 'components/icons';
+import { ClockIcon, CrossIcon, UploadIcon } from 'components/icons';
 import Link from 'components/Link';
 import { useStoreSelector } from 'lib/redux/store';
 import { useEffect, useState } from 'react';
 
+const expires = [
+  '5min',
+  '10min',
+  '15min',
+  '30min',
+  '1h',
+  '2h',
+  '3h',
+  '4h',
+  '5h',
+  '6h',
+  '8h',
+  '12h',
+  '1d',
+  '3d',
+  '5d',
+  '7d',
+  '1w',
+  '1.5w',
+  '2w',
+  '3w',
+  '1m',
+  '1.5m',
+  '2m',
+  '3m',
+  '6m',
+  '8m',
+  '1y',
+  'never',
+];
+
 export default function Upload() {
   const clipboard = useClipboard();
   const user = useStoreSelector(state => state.user);
@@ -15,6 +46,7 @@ export default function Upload() {
   const [files, setFiles] = useState([]);
   const [progress, setProgress] = useState(0);
   const [loading, setLoading] = useState(false);
+  const [expires, setExpires] = useState('never');
 
   useEffect(() => {
     window.addEventListener('paste', (e: ClipboardEvent) => {
@@ -29,6 +61,36 @@ export default function Upload() {
   });
 
   const handleUpload = async () => {
+    const expires_at = expires === 'never' ? null : new Date({
+      '5min': Date.now() + 5 * 60 * 1000,
+      '10min': Date.now() + 10 * 60 * 1000,
+      '15min': Date.now() + 15 * 60 * 1000,
+      '30min': Date.now() + 30 * 60 * 1000,
+      '1h': Date.now() + 60 * 60 * 1000,
+      '2h': Date.now() + 2 * 60 * 60 * 1000,
+      '3h': Date.now() + 3 * 60 * 60 * 1000,
+      '4h': Date.now() + 4 * 60 * 60 * 1000,
+      '5h': Date.now() + 5 * 60 * 60 * 1000,
+      '6h': Date.now() + 6 * 60 * 60 * 1000,
+      '8h': Date.now() + 8 * 60 * 60 * 1000,
+      '12h': Date.now() + 12 * 60 * 60 * 1000,
+      '1d': Date.now() + 24 * 60 * 60 * 1000,
+      '3d': Date.now() + 3 * 24 * 60 * 60 * 1000,
+      '5d': Date.now() + 5 * 24 * 60 * 60 * 1000,
+      '7d': Date.now() + 7 * 24 * 60 * 60 * 1000,
+      '1w': Date.now() + 7 * 24 * 60 * 60 * 1000,
+      '1.5w': Date.now() + 1.5 * 7 * 24 * 60 * 60 * 1000,
+      '2w': Date.now() + 2 * 7 * 24 * 60 * 60 * 1000,
+      '3w': Date.now() + 3 * 7 * 24 * 60 * 60 * 1000,
+      '1m': Date.now() + 30 * 24 * 60 * 60 * 1000,
+      '1.5m': Date.now() + 1.5 * 30 * 24 * 60 * 60 * 1000,
+      '2m': Date.now() + 2 * 30 * 24 * 60 * 60 * 1000,
+      '3m': Date.now() + 3 * 30 * 24 * 60 * 60 * 1000,
+      '6m': Date.now() + 6 * 30 * 24 * 60 * 60 * 1000,
+      '8m': Date.now() + 8 * 30 * 24 * 60 * 60 * 1000,
+      '1y': Date.now() + 365 * 24 * 60 * 60 * 1000,
+    }[expires]);
+
     setProgress(0);
     setLoading(true);
     const body = new FormData();
@@ -78,6 +140,7 @@ export default function Upload() {
 
     req.open('POST', '/api/upload');
     req.setRequestHeader('Authorization', user.token);
+    req.setRequestHeader('Expires-At', expires_at.toISOString());
     req.send(body);
   };
 
@@ -95,8 +158,43 @@ export default function Upload() {
         {progress !== 0 && <Progress mt='md' value={progress} animate />}
       </Collapse>
 
-      <Group position='right'>
-        <Button leftIcon={<UploadIcon />} mt={12} onClick={handleUpload} disabled={files.length === 0 ? true : false}>Upload</Button>
+      <Group position='right' mt='md'>
+        <Select
+          value={expires}
+          onChange={(e) => setExpires(e)}
+          icon={<ClockIcon size={14} />}
+          data={[
+            { value: 'never', label: 'Never' },
+            { value: '5min', label: '5 minutes' },
+            { value: '10min', label: '10 minutes' },
+            { value: '15min', label: '15 minutes' },
+            { value: '30min', label: '30 minutes' },
+            { value: '1h', label: '1 hour' },
+            { value: '2h', label: '2 hours' },
+            { value: '3h', label: '3 hours' },
+            { value: '4h', label: '4 hours' },
+            { value: '5h', label: '5 hours' },
+            { value: '6h', label: '6 hours' },
+            { value: '8h', label: '8 hours' },
+            { value: '12h', label: '12 hours' },
+            { value: '1d', label: '1 day' },
+            { value: '3d', label: '3 days' },
+            { value: '5d', label: '5 days' },
+            { value: '7d', label: '7 days' },
+            { value: '1w', label: '1 week' },
+            { value: '1.5w', label: '1.5 weeks' },
+            { value: '2w', label: '2 weeks' },
+            { value: '3w', label: '3 weeks' },
+            { value: '1m', label: '1 month' },
+            { value: '1.5m', label: '1.5 months' },
+            { value: '2m', label: '2 months' },
+            { value: '3m', label: '3 months' },
+            { value: '6m', label: '6 months' },
+            { value: '8m', label: '8 months' },
+            { value: '1y', label: '1 year' },
+          ]}
+        />
+        <Button leftIcon={<UploadIcon />} onClick={handleUpload} disabled={files.length === 0 ? true : false}>Upload</Button>
       </Group>
     </>
   );
diff --git a/src/lib/clientUtils.ts b/src/lib/clientUtils.ts
index 581c555..e1b09dc 100644
--- a/src/lib/clientUtils.ts
+++ b/src/lib/clientUtils.ts
@@ -27,4 +27,26 @@ export function bytesToRead(bytes: number) {
   }
 
   return `${bytes.toFixed(1)} ${units[num]}`;
-}
\ No newline at end of file
+}
+
+export const units = {
+  year: 365 * 24 * 60 * 60 * 1000,
+  month: 30 * 24 * 60 * 60 * 1000,
+  day: 24 * 60 * 60 * 1000,
+  hour: 60 * 60 * 1000,
+  minute: 60 * 1000,
+  second: 1000,
+};
+
+export function relativeTime(to: Date, from: Date = new Date()) {
+  const time = new Date(to.getTime() - from.getTime());
+  
+  const rtf = new Intl.RelativeTimeFormat('en', { style: 'long' });
+
+  for (const unit in units) {
+    if (time > units[unit]) {
+      return rtf.format(Math.floor(Math.round(time.getTime() / units[unit])), unit as Intl.RelativeTimeFormatUnit || 'second');
+    }
+  }
+}
+
diff --git a/src/pages/api/upload.ts b/src/pages/api/upload.ts
index c5e5dd8..8482c54 100644
--- a/src/pages/api/upload.ts
+++ b/src/pages/api/upload.ts
@@ -44,6 +44,13 @@ async function handler(req: NextApiReq, res: NextApiRes) {
 
   if (req.files && req.files.length === 0) return res.error('no 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');
+  }
+
   const rawFormat = ((req.headers.format || '') as string).toUpperCase() || 'RANDOM';
   const format: ImageFormat = Object.keys(ImageFormat).includes(rawFormat) && ImageFormat[rawFormat];
   const files = [];
@@ -84,6 +91,7 @@ async function handler(req: NextApiReq, res: NextApiRes) {
         embed: !!req.headers.embed,
         format,
         password,
+        expires_at: expiry,
       },
     });
 
diff --git a/src/pages/api/user/files.ts b/src/pages/api/user/files.ts
index 810915d..19693b0 100644
--- a/src/pages/api/user/files.ts
+++ b/src/pages/api/user/files.ts
@@ -69,6 +69,7 @@ async function handler(req: NextApiReq, res: NextApiRes) {
       },
       select: {
         created_at: true,
+        expires_at: true,
         file: true,
         mimetype: true,
         id: true,
diff --git a/src/server/index.ts b/src/server/index.ts
index 4c3aa3f..711daef 100644
--- a/src/server/index.ts
+++ b/src/server/index.ts
@@ -143,6 +143,14 @@ async function rawFileDb(
   prisma: PrismaClient,
   image: Image,
 ) {
+  if (image.expires_at && image.expires_at < new Date()) {
+    Logger.get('server').info(`${image.file} expired`);
+    await datasource.delete(image.file);
+    await prisma.image.delete({ where: { id: image.id } });
+
+    return nextServer.render404(req, res as ServerResponse);
+  }
+
   const data = await datasource.get(image.file);
   if (!data) return nextServer.render404(req, res as ServerResponse);
 
@@ -169,6 +177,13 @@ async function fileDb(
   handle: RequestHandler,
   image: Image,
 ) {
+  if (image.expires_at && image.expires_at < new Date()) {
+    await datasource.delete(image.file);
+    await prisma.image.delete({ where: { id: image.id } });
+    
+    return nextServer.render404(req, res as ServerResponse);
+  }
+
   const ext = image.file.split('.').pop();
   if (Object.keys(exts).includes(ext)) return handle(req, res as ServerResponse);