diff --git a/.run/PostHog.run.xml b/.run/PostHog.run.xml
index 3f9cfc21a8e..7f4cfc9c346 100644
--- a/.run/PostHog.run.xml
+++ b/.run/PostHog.run.xml
@@ -4,14 +4,14 @@
     <option name="INTERPRETER_OPTIONS" value="" />
     <option name="PARENT_ENVS" value="true" />
     <envs>
-      <env name="PYTHONUNBUFFERED" value="1" />
-      <env name="DJANGO_SETTINGS_MODULE" value="posthog.settings" />
-      <env name="DEBUG" value="1" />
       <env name="CLICKHOUSE_SECURE" value="False" />
-      <env name="KAFKA_URL" value="kafka://localhost" />
       <env name="DATABASE_URL" value="postgres://posthog:posthog@localhost:5432/posthog" />
-      <env name="SKIP_SERVICE_VERSION_REQUIREMENTS" value="1" />
+      <env name="DEBUG" value="1" />
+      <env name="DJANGO_SETTINGS_MODULE" value="posthog.settings" />
+      <env name="KAFKA_URL" value="kafka://localhost" />
       <env name="PRINT_SQL" value="1" />
+      <env name="PYTHONUNBUFFERED" value="1" />
+      <env name="SKIP_SERVICE_VERSION_REQUIREMENTS" value="1" />
     </envs>
     <option name="SDK_HOME" value="$PROJECT_DIR$/env/bin/python" />
     <option name="WORKING_DIRECTORY" value="" />
@@ -29,4 +29,4 @@
     <option name="customRunCommand" value="" />
     <method v="2" />
   </configuration>
-</component>
+</component>
\ No newline at end of file
diff --git a/frontend/src/lib/api.ts b/frontend/src/lib/api.ts
index 46c0cac95cd..40700f04db4 100644
--- a/frontend/src/lib/api.ts
+++ b/frontend/src/lib/api.ts
@@ -25,6 +25,7 @@ import {
     SubscriptionType,
     TeamType,
     UserType,
+    MediaUploadResponse,
 } from '~/types'
 import { getCurrentOrganizationId, getCurrentTeamId } from './utils/logics'
 import { CheckboxValueType } from 'antd/lib/checkbox/Group'
@@ -328,6 +329,10 @@ class ApiRequest {
         return this.integrations(teamId).addPathComponent(id).addPathComponent('channels')
     }
 
+    public media(teamId?: TeamType['id']): ApiRequest {
+        return this.projectsDetail(teamId).addPathComponent('uploaded_media')
+    }
+
     // Request finalization
 
     public async get(options?: { signal?: AbortSignal }): Promise<any> {
@@ -819,6 +824,12 @@ const api = {
         },
     },
 
+    media: {
+        async upload(data: FormData): Promise<MediaUploadResponse> {
+            return await new ApiRequest().media().create({ data })
+        },
+    },
+
     async get(url: string, signal?: AbortSignal): Promise<any> {
         const res = await api.getRaw(url, signal)
         return await getJSONOrThrow(res)
diff --git a/frontend/src/lib/components/Cards/TextCard/TextCard.scss b/frontend/src/lib/components/Cards/TextCard/TextCard.scss
index df54d48b22e..db2e0a859d7 100644
--- a/frontend/src/lib/components/Cards/TextCard/TextCard.scss
+++ b/frontend/src/lib/components/Cards/TextCard/TextCard.scss
@@ -49,4 +49,8 @@
     p {
         margin-bottom: 0;
     }
+
+    img {
+        max-width: 100%;
+    }
 }
diff --git a/frontend/src/lib/components/LemonTextArea/LemonTextArea.scss b/frontend/src/lib/components/LemonTextArea/LemonTextArea.scss
index aa4a991d7da..01999d56871 100644
--- a/frontend/src/lib/components/LemonTextArea/LemonTextArea.scss
+++ b/frontend/src/lib/components/LemonTextArea/LemonTextArea.scss
@@ -36,3 +36,9 @@
         border: 1px solid var(--danger);
     }
 }
+
+.LemonTextMarkdown {
+    &.FileDropTarget {
+        border: 3px dashed var(--primary);
+    }
+}
diff --git a/frontend/src/lib/components/LemonTextArea/LemonTextArea.tsx b/frontend/src/lib/components/LemonTextArea/LemonTextArea.tsx
index 8a041df36ea..8c52a46135b 100644
--- a/frontend/src/lib/components/LemonTextArea/LemonTextArea.tsx
+++ b/frontend/src/lib/components/LemonTextArea/LemonTextArea.tsx
@@ -1,10 +1,18 @@
 import './LemonTextArea.scss'
-import React, { useRef } from 'react'
+import React, { createRef, useEffect, useRef, useState } from 'react'
 import clsx from 'clsx'
 import TextareaAutosize from 'react-textarea-autosize'
 import { Tabs } from 'antd'
-import { IconMarkdown } from 'lib/components/icons'
+import { IconMarkdown, IconTools, IconUploadFile } from 'lib/components/icons'
 import { TextCardBody } from 'lib/components/Cards/TextCard/TextCard'
+import { Spinner } from 'lib/components/Spinner/Spinner'
+import api from 'lib/api'
+import { lemonToast } from 'lib/components/lemonToast'
+import { useValues } from 'kea'
+import { preflightLogic } from 'scenes/PreflightCheck/preflightLogic'
+import posthog from 'posthog-js'
+import { Link } from 'lib/components/Link'
+import { Tooltip } from 'lib/components/Tooltip'
 
 export interface LemonTextAreaProps
     extends Pick<
@@ -48,9 +56,7 @@ export const LemonTextArea = React.forwardRef<HTMLTextAreaElement, LemonTextArea
 
                 onKeyDown?.(e)
             }}
-            onChange={(event) => {
-                onChange?.(event.currentTarget.value ?? '')
-            }}
+            onChange={(event) => onChange?.(event.currentTarget.value ?? '')}
             {...textProps}
         />
     )
@@ -63,13 +69,121 @@ interface LemonTextMarkdownProps {
 }
 
 export function LemonTextMarkdown({ value, onChange, ...editAreaProps }: LemonTextMarkdownProps): JSX.Element {
+    const { objectStorageAvailable } = useValues(preflightLogic)
+
+    // dragCounter and drag are used to track whether the user is dragging a file over the textarea
+    // without drag counter the textarea highlight would flicker when the user drags a file over it
+    let dragCounter = 0
+    const [drag, setDrag] = useState(false)
+
+    const [isUploading, setIsUploading] = useState(false)
+
+    const dropRef = createRef<HTMLDivElement>()
+
+    const handleDrag = (e: DragEvent): void => {
+        e.preventDefault()
+        e.stopPropagation()
+    }
+
+    const handleDragIn = (e: DragEvent): void => {
+        e.preventDefault()
+        e.stopPropagation()
+        dragCounter++
+        if (e.dataTransfer?.items && e.dataTransfer.items.length > 0) {
+            setDrag(true)
+        }
+    }
+
+    const handleDragOut = (e: DragEvent): void => {
+        e.preventDefault()
+        e.stopPropagation()
+        dragCounter--
+        if (dragCounter === 0) {
+            setDrag(false)
+        }
+    }
+
+    const handleDrop = async (e: DragEvent): Promise<void> => {
+        e.preventDefault()
+        e.stopPropagation()
+        setDrag(false)
+        if (e.dataTransfer?.files && e.dataTransfer.files.length > 0) {
+            try {
+                setIsUploading(true)
+                const formData = new FormData()
+                formData.append('image', e.dataTransfer.files[0])
+                const media = await api.media.upload(formData)
+                onChange(value + `\n\n![${media.name}](${media.image_location})`)
+                posthog.capture('markdown image uploaded', { name: media.name })
+            } catch (error) {
+                const errorDetail = (error as any).detail || 'unknown error'
+                posthog.capture('markdown image upload failed', { error: errorDetail })
+                lemonToast.error(`Error uploading image: ${errorDetail}`)
+            } finally {
+                setIsUploading(false)
+            }
+            e.dataTransfer.clearData()
+            dragCounter = 0
+        }
+    }
+
+    useEffect(() => {
+        const div = dropRef.current
+        if (!div || !objectStorageAvailable) {
+            return
+        } else {
+            div.addEventListener('dragenter', handleDragIn)
+            div.addEventListener('dragleave', handleDragOut)
+            div.addEventListener('dragover', handleDrag)
+            div.addEventListener('drop', handleDrop)
+            return () => {
+                div?.removeEventListener('dragenter', handleDragIn)
+                div?.removeEventListener('dragleave', handleDragOut)
+                div?.removeEventListener('dragover', handleDrag)
+                div?.removeEventListener('drop', handleDrop)
+            }
+        }
+    }, [value, objectStorageAvailable])
+
     return (
         <Tabs>
             <Tabs.TabPane tab="Write" key="write-card" destroyInactiveTabPane={true}>
-                <LemonTextArea {...editAreaProps} autoFocus value={value} onChange={(newValue) => onChange(newValue)} />
-                <div className="text-muted inline-flex items-center space-x-1">
-                    <IconMarkdown className={'text-2xl'} />
-                    <span>Markdown formatting support</span>
+                <div
+                    ref={dropRef}
+                    className={clsx('LemonTextMarkdown flex flex-col p-2 space-y-1 rounded', drag && 'FileDropTarget')}
+                >
+                    <LemonTextArea {...editAreaProps} autoFocus value={value} onChange={onChange} />
+                    <div className="text-muted inline-flex items-center space-x-1">
+                        <IconMarkdown className={'text-2xl'} />
+                        <span>Markdown formatting support</span>
+                    </div>
+                    {objectStorageAvailable ? (
+                        <div className="text-muted inline-flex items-center space-x-1">
+                            <IconUploadFile className={'text-2xl mr-1'} />
+                            <span>Attach images by dragging and dropping them</span>
+                        </div>
+                    ) : (
+                        <div className="text-muted inline-flex items-center space-x-1">
+                            <Tooltip title={'Enable object storage to add images by dragging and dropping.'}>
+                                <IconTools className={'text-xl mr-1'} />
+                            </Tooltip>
+                            <span>
+                                Add external images using{' '}
+                                <Link to={'https://www.markdownguide.org/basic-syntax/#images-1'}>
+                                    {' '}
+                                    Markdown image links
+                                </Link>
+                                .
+                            </span>
+                        </div>
+                    )}
+
+                    {isUploading && (
+                        <div className="text-muted inline-flex items-center space-x-1">
+                            <Spinner />
+                            uploading image...
+                        </div>
+                    )}
                 </div>
             </Tabs.TabPane>
             <Tabs.TabPane tab="Preview" key={'preview-card'}>
diff --git a/frontend/src/scenes/PreflightCheck/preflightLogic.tsx b/frontend/src/scenes/PreflightCheck/preflightLogic.tsx
index 2400d1becad..ee879aedfc5 100644
--- a/frontend/src/scenes/PreflightCheck/preflightLogic.tsx
+++ b/frontend/src/scenes/PreflightCheck/preflightLogic.tsx
@@ -198,6 +198,10 @@ export const preflightLogic = kea<preflightLogicType>([
             (preflight): boolean =>
                 Boolean(preflight && Object.values(preflight.available_social_auth_providers).filter((i) => i).length),
         ],
+        objectStorageAvailable: [
+            (s) => [s.preflight],
+            (preflight): boolean => Boolean(preflight && preflight.object_storage),
+        ],
         realm: [
             (s) => [s.preflight],
             (preflight): Realm | null => {
diff --git a/frontend/src/types.ts b/frontend/src/types.ts
index df39053efc9..145d2ac16eb 100644
--- a/frontend/src/types.ts
+++ b/frontend/src/types.ts
@@ -2101,3 +2101,9 @@ export enum FeatureFlagReleaseType {
     ReleaseToggle = 'Release toggle',
     Variants = 'Multiple variants',
 }
+
+export interface MediaUploadResponse {
+    id: string
+    image_location: string
+    name: string
+}
diff --git a/latest_migrations.manifest b/latest_migrations.manifest
index 38c27b11b60..c993e98b403 100644
--- a/latest_migrations.manifest
+++ b/latest_migrations.manifest
@@ -3,7 +3,7 @@ auth: 0012_alter_user_first_name_max_length
 axes: 0006_remove_accesslog_trusted
 contenttypes: 0002_remove_content_type_name
 ee: 0013_silence_deprecated_tags_warnings
-posthog: 0269_soft_delete_tiles
+posthog: 0270_add_uploaded_media
 rest_hooks: 0002_swappable_hook_model
 sessions: 0001_initial
 social_django: 0010_uid_db_index
diff --git a/posthog/api/__init__.py b/posthog/api/__init__.py
index e660fa3e661..922bf038799 100644
--- a/posthog/api/__init__.py
+++ b/posthog/api/__init__.py
@@ -31,6 +31,7 @@ from . import (
     sharing,
     site_app,
     team,
+    uploaded_media,
     user,
 )
 
@@ -105,6 +106,7 @@ projects_router.register(
     r"property_definitions", property_definition.PropertyDefinitionViewSet, "project_property_definitions", ["team_id"]
 )
 
+projects_router.register(r"uploaded_media", uploaded_media.MediaViewSet, "project_media", ["team_id"])
 
 # General endpoints (shared across CH & PG)
 router.register(r"login", authentication.LoginViewSet)
diff --git a/posthog/api/dashboard.py b/posthog/api/dashboard.py
index 66fece5f224..479fc3b5ad8 100644
--- a/posthog/api/dashboard.py
+++ b/posthog/api/dashboard.py
@@ -6,11 +6,12 @@ from django.db.models import Prefetch, Q, QuerySet
 from django.shortcuts import get_object_or_404
 from django.utils.timezone import now
 from drf_spectacular.utils import extend_schema
-from rest_framework import exceptions, response, serializers, viewsets
+from rest_framework import exceptions, serializers, viewsets
 from rest_framework.decorators import action
 from rest_framework.exceptions import PermissionDenied
 from rest_framework.permissions import SAFE_METHODS, BasePermission, IsAuthenticated
 from rest_framework.request import Request
+from rest_framework.response import Response
 
 from posthog.api.forbid_destroy_model import ForbidDestroyModel
 from posthog.api.insight import InsightSerializer, InsightViewSet
@@ -360,17 +361,17 @@ class DashboardsViewSet(TaggedItemViewSetMixin, StructuredViewSetMixin, ForbidDe
 
         return queryset
 
-    def retrieve(self, request: Request, *args: Any, **kwargs: Any) -> response.Response:
+    def retrieve(self, request: Request, *args: Any, **kwargs: Any) -> Response:
         pk = kwargs["pk"]
         queryset = self.get_queryset()
         dashboard = get_object_or_404(queryset, pk=pk)
         dashboard.last_accessed_at = now()
         dashboard.save(update_fields=["last_accessed_at"])
         serializer = DashboardSerializer(dashboard, context={"view": self, "request": request})
-        return response.Response(serializer.data)
+        return Response(serializer.data)
 
     @action(methods=["PATCH"], detail=True)
-    def move_tile(self, request: Request, *args: Any, **kwargs: Any) -> response.Response:
+    def move_tile(self, request: Request, *args: Any, **kwargs: Any) -> Response:
         # TODO could things be rearranged so this is  PATCH call on a resource and not a custom endpoint?
         tile = request.data["tile"]
         from_dashboard = kwargs["pk"]
@@ -383,7 +384,7 @@ class DashboardsViewSet(TaggedItemViewSetMixin, StructuredViewSetMixin, ForbidDe
         serializer = DashboardSerializer(
             Dashboard.objects.get(id=from_dashboard), context={"view": self, "request": request}
         )
-        return response.Response(serializer.data)
+        return Response(serializer.data)
 
 
 class LegacyDashboardsViewSet(DashboardsViewSet):
diff --git a/posthog/api/test/test_uploaded_media.py b/posthog/api/test/test_uploaded_media.py
new file mode 100644
index 00000000000..6b9549fb5dc
--- /dev/null
+++ b/posthog/api/test/test_uploaded_media.py
@@ -0,0 +1,98 @@
+import os
+import re
+import shutil
+import tempfile
+
+from boto3 import resource
+from botocore.config import Config
+from django.core.files.uploadedfile import SimpleUploadedFile
+from django.test import override_settings
+from rest_framework import status
+
+from posthog.models import UploadedMedia
+from posthog.settings import (
+    OBJECT_STORAGE_ACCESS_KEY_ID,
+    OBJECT_STORAGE_BUCKET,
+    OBJECT_STORAGE_ENDPOINT,
+    OBJECT_STORAGE_SECRET_ACCESS_KEY,
+)
+from posthog.storage import object_storage
+from posthog.test.base import APIBaseTest
+
+MEDIA_ROOT = tempfile.mkdtemp()
+
+TEST_BUCKET = "Test-Uploads"
+
+
+def get_path_to(fixture_file: str) -> str:
+    file_dir = os.path.dirname(__file__)
+    return os.path.join(file_dir, "fixtures", fixture_file)
+
+
+@override_settings(MEDIA_ROOT=MEDIA_ROOT)
+class TestMediaAPI(APIBaseTest):
+    @classmethod
+    def tearDownClass(cls):
+        shutil.rmtree(MEDIA_ROOT, ignore_errors=True)  # delete the temp dir
+        # delete s3 files
+        s3 = resource(
+            "s3",
+            endpoint_url=OBJECT_STORAGE_ENDPOINT,
+            aws_access_key_id=OBJECT_STORAGE_ACCESS_KEY_ID,
+            aws_secret_access_key=OBJECT_STORAGE_SECRET_ACCESS_KEY,
+            config=Config(signature_version="s3v4"),
+            region_name="us-east-1",
+        )
+        bucket = s3.Bucket(OBJECT_STORAGE_BUCKET)
+        bucket.objects.filter(Prefix=TEST_BUCKET).delete()
+
+        super().tearDownClass()
+
+    def test_can_upload_and_retrieve_a_file(self) -> None:
+        with self.settings(OBJECT_STORAGE_ENABLED=True, OBJECT_STORAGE_MEDIA_UPLOADS_FOLDER=TEST_BUCKET):
+            fake_file = SimpleUploadedFile(name="test_image.jpg", content=b"a fake image", content_type="image/jpeg")
+            response = self.client.post(
+                f"/api/projects/{self.team.id}/uploaded_media", {"image": fake_file}, format="multipart"
+            )
+            self.assertEqual(response.status_code, status.HTTP_201_CREATED, response.json())
+            assert response.json()["name"] == "test_image.jpg"
+            media_location = response.json()["image_location"]
+            assert re.match(r"^http://localhost:8000/uploaded_media/.*/test_image.jpg", media_location) is not None
+
+            upload = UploadedMedia.objects.get(id=response.json()["id"])
+
+            content = object_storage.read_bytes(upload.media_location)
+            assert content == b"a fake image"
+
+            self.client.logout()
+            response = self.client.get(media_location)
+
+            assert response.status_code == status.HTTP_200_OK
+            assert response.headers["Content-Type"] == "image/jpeg"
+
+    def test_rejects_non_image_file_type(self) -> None:
+        fake_file = SimpleUploadedFile(name="test_image.jpg", content=b"a fake image", content_type="text/csv")
+        response = self.client.post(
+            f"/api/projects/{self.team.id}/uploaded_media", {"image": fake_file}, format="multipart"
+        )
+        self.assertEqual(response.status_code, status.HTTP_415_UNSUPPORTED_MEDIA_TYPE, response.json())
+
+    def test_rejects_too_large_file_type(self) -> None:
+        four_megabytes_plus_a_little = b"1" * (4 * 1024 * 1024 + 1)
+        fake_big_file = SimpleUploadedFile(
+            name="test_image.jpg", content=four_megabytes_plus_a_little, content_type="image/jpeg"
+        )
+        response = self.client.post(
+            f"/api/projects/{self.team.id}/uploaded_media", {"image": fake_big_file}, format="multipart"
+        )
+        self.assertEqual(response.status_code, status.HTTP_400_BAD_REQUEST, response.json())
+        self.assertEqual(response.json()["detail"], "Uploaded media must be less than 4MB")
+
+    def test_rejects_upload_when_object_storage_is_unavailable(self) -> None:
+        with override_settings(OBJECT_STORAGE_ENABLED=False):
+            fake_big_file = SimpleUploadedFile(name="test_image.jpg", content=b"", content_type="image/jpeg")
+            response = self.client.post(
+                f"/api/projects/{self.team.id}/uploaded_media", {"image": fake_big_file}, format="multipart"
+            )
+            self.assertEqual(response.status_code, status.HTTP_400_BAD_REQUEST, response.json())
+            self.assertEqual(response.json()["detail"], "Object storage must be available to allow media uploads.")
diff --git a/posthog/api/uploaded_media.py b/posthog/api/uploaded_media.py
new file mode 100644
index 00000000000..0323d12290c
--- /dev/null
+++ b/posthog/api/uploaded_media.py
@@ -0,0 +1,101 @@
+from typing import Dict
+
+from django.http import HttpResponse
+from django.views.decorators.csrf import csrf_exempt
+from drf_spectacular.utils import extend_schema
+from rest_framework import status, viewsets
+from rest_framework.exceptions import APIException, NotFound, UnsupportedMediaType, ValidationError
+from rest_framework.parsers import FormParser, MultiPartParser
+from rest_framework.permissions import IsAuthenticatedOrReadOnly
+from rest_framework.response import Response
+
+from posthog.api.routing import StructuredViewSetMixin
+from posthog.internal_metrics import incr
+from posthog.models import UploadedMedia
+from posthog.models.uploaded_media import ObjectStorageUnavailable
+from posthog.permissions import ProjectMembershipNecessaryPermissions, TeamMemberAccessPermission
+from posthog.storage import object_storage
+
+FOUR_MEGABYTES = 4 * 1024 * 1024
+
+
+@csrf_exempt
+def download(request, *args, **kwargs) -> HttpResponse:
+    """
+    Images are immutable, so we can cache them forever
+    They are served unauthenticated as they might be presented on shared dashboards
+    """
+    instance: UploadedMedia = UploadedMedia.objects.get(pk=kwargs["image_uuid"])
+
+    if not instance or not instance.file_name == kwargs["file_name"]:
+        raise NotFound("Image not found")
+
+    file_bytes = object_storage.read_bytes(instance.media_location)
+
+    incr("uploaded_media.served", tags={"team_id": instance.team_id, "uuid": kwargs["image_uuid"]})
+
+    return HttpResponse(
+        file_bytes,
+        content_type=instance.content_type,
+        headers={"Cache-Control": "public, max-age=315360000, immutable"},
+    )
+
+
+class MediaViewSet(StructuredViewSetMixin, viewsets.GenericViewSet):
+    queryset = UploadedMedia.objects.all()
+    parser_classes = (MultiPartParser, FormParser)
+    permission_classes = [
+        IsAuthenticatedOrReadOnly,
+        ProjectMembershipNecessaryPermissions,
+        TeamMemberAccessPermission,
+    ]
+
+    @extend_schema(
+        description="""
+    When object storage is available this API allows upload of media which can be used, for example, in text cards on dashboards.
+
+    Uploaded media must have a content type beginning with 'image/' and be less than 4MB.
+    """
+    )
+    def create(self, request, *args, **kwargs) -> Response:
+        try:
+            file = request.data["image"]
+
+            if file.size > FOUR_MEGABYTES:
+                raise ValidationError(code="file_too_large", detail="Uploaded media must be less than 4MB")
+
+            if file.content_type.startswith("image/"):
+                uploaded_media = UploadedMedia.save_content(
+                    team=self.team,
+                    created_by=request.user,
+                    file_name=file.name,
+                    content_type=file.content_type,
+                    content=file.file,
+                )
+                if uploaded_media is None:
+                    raise APIException("Could not save media")
+                headers = self.get_success_headers(uploaded_media.get_absolute_url())
+                incr("uploaded_media.uploaded", tags={"team_id": self.team.pk, "content_type": file.content_type})
+                return Response(
+                    {
+                        "id": uploaded_media.id,
+                        "image_location": uploaded_media.get_absolute_url(),
+                        "name": uploaded_media.file_name,
+                    },
+                    status=status.HTTP_201_CREATED,
+                    headers=headers,
+                )
+            else:
+                raise UnsupportedMediaType(file.content_type)
+        except KeyError:
+            raise ValidationError(code="no-image-provided", detail="An image file must be provided")
+        except ObjectStorageUnavailable:
+            raise ValidationError(
+                code="object_storage_required", detail="Object storage must be available to allow media uploads."
+            )
+
+    def get_success_headers(self, location: str) -> Dict:
+        try:
+            return {"Location": location}
+        except (TypeError, KeyError):
+            return {}
diff --git a/posthog/migrations/0270_add_uploaded_media.py b/posthog/migrations/0270_add_uploaded_media.py
new file mode 100644
index 00000000000..eac6c04e6c5
--- /dev/null
+++ b/posthog/migrations/0270_add_uploaded_media.py
@@ -0,0 +1,42 @@
+# Generated by Django 3.2.15 on 2022-10-13 10:24
+
+import django.db.models.deletion
+from django.conf import settings
+from django.db import migrations, models
+
+import posthog.models.utils
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ("posthog", "0269_soft_delete_tiles"),
+    ]
+
+    operations = [
+        migrations.CreateModel(
+            name="UploadedMedia",
+            fields=[
+                (
+                    "id",
+                    models.UUIDField(
+                        default=posthog.models.utils.UUIDT, editable=False, primary_key=True, serialize=False
+                    ),
+                ),
+                ("created_at", models.DateTimeField(auto_now_add=True)),
+                ("media_location", models.TextField(blank=True, max_length=1000, null=True)),
+                ("content_type", models.TextField(blank=True, max_length=100, null=True)),
+                ("file_name", models.TextField(blank=True, max_length=1000, null=True)),
+                (
+                    "created_by",
+                    models.ForeignKey(
+                        blank=True, null=True, on_delete=django.db.models.deletion.SET_NULL, to=settings.AUTH_USER_MODEL
+                    ),
+                ),
+                ("team", models.ForeignKey(on_delete=django.db.models.deletion.CASCADE, to="posthog.team")),
+            ],
+            options={
+                "abstract": False,
+            },
+        ),
+    ]
diff --git a/posthog/models/__init__.py b/posthog/models/__init__.py
index cf1a5071b31..7fb66853485 100644
--- a/posthog/models/__init__.py
+++ b/posthog/models/__init__.py
@@ -39,6 +39,7 @@ from .subscription import Subscription
 from .tag import Tag
 from .tagged_item import TaggedItem
 from .team import Team
+from .uploaded_media import UploadedMedia
 from .user import User, UserManager
 
 __all__ = [
@@ -97,6 +98,7 @@ __all__ = [
     "TaggedItem",
     "Team",
     "Text",
+    "UploadedMedia",
     "User",
     "UserManager",
     "UserPromptSequenceState",
diff --git a/posthog/models/uploaded_media.py b/posthog/models/uploaded_media.py
new file mode 100644
index 00000000000..91d3987417b
--- /dev/null
+++ b/posthog/models/uploaded_media.py
@@ -0,0 +1,71 @@
+from typing import List, Optional
+
+import structlog
+from django.conf import settings
+from django.db import models
+from sentry_sdk import capture_exception
+
+from posthog.models.team import Team
+from posthog.models.user import User
+from posthog.models.utils import UUIDModel
+from posthog.storage import object_storage
+from posthog.storage.object_storage import ObjectStorageError
+from posthog.utils import absolute_uri
+
+logger = structlog.get_logger(__name__)
+
+
+class ObjectStorageUnavailable(Exception):
+    pass
+
+
+class UploadedMedia(UUIDModel):
+    team: models.ForeignKey = models.ForeignKey("Team", on_delete=models.CASCADE)
+    created_at: models.DateTimeField = models.DateTimeField(auto_now_add=True, blank=True)
+    created_by: models.ForeignKey = models.ForeignKey("User", on_delete=models.SET_NULL, null=True, blank=True)
+
+    # path in object storage or some other location identifier for the asset
+    # 1000 characters would hold a 20 UUID forward slash separated path with space to spare
+    media_location: models.TextField = models.TextField(null=True, blank=True, max_length=1000)
+    content_type: models.TextField = models.TextField(null=True, blank=True, max_length=100)
+    file_name: models.TextField = models.TextField(null=True, blank=True, max_length=1000)
+
+    def get_absolute_url(self) -> str:
+        return absolute_uri(f"/uploaded_media/{self.id}/{self.file_name}")
+
+    @classmethod
+    def save_content(
+        cls, team: Team, created_by: User, file_name: str, content_type: str, content: bytes
+    ) -> Optional["UploadedMedia"]:
+        try:
+            media = UploadedMedia.objects.create(
+                team=team, created_by=created_by, file_name=file_name, content_type=content_type
+            )
+            if settings.OBJECT_STORAGE_ENABLED:
+                save_content_to_object_storage(media, content)
+            else:
+                logger.error(
+                    "uploaded_media.upload_attempted_without_object_storage_configured",
+                    file_name=file_name,
+                    team=team.pk,
+                )
+                raise ObjectStorageUnavailable()
+            return media
+        except ObjectStorageError as ose:
+            capture_exception(ose)
+            logger.error(
+                "uploaded_media.object-storage-error", file_name=file_name, team=team.pk, exception=ose, exc_info=True
+            )
+            return None
+
+
+def save_content_to_object_storage(uploaded_media: UploadedMedia, content: bytes) -> None:
+    path_parts: List[str] = [
+        settings.OBJECT_STORAGE_MEDIA_UPLOADS_FOLDER,
+        f"team-{uploaded_media.team.pk}",
+        f"media-{uploaded_media.pk}",
+    ]
+    object_path = f'/{"/".join(path_parts)}'
+    object_storage.write(object_path, content)
+    uploaded_media.media_location = object_path
+    uploaded_media.save(update_fields=["media_location"])
diff --git a/posthog/settings/object_storage.py b/posthog/settings/object_storage.py
index abdac8aa83b..b18917a98b1 100644
--- a/posthog/settings/object_storage.py
+++ b/posthog/settings/object_storage.py
@@ -23,3 +23,4 @@ OBJECT_STORAGE_ENABLED = get_from_env("OBJECT_STORAGE_ENABLED", True if DEBUG el
 OBJECT_STORAGE_BUCKET = os.getenv("OBJECT_STORAGE_BUCKET", "posthog")
 OBJECT_STORAGE_SESSION_RECORDING_FOLDER = os.getenv("OBJECT_STORAGE_SESSION_RECORDING_FOLDER", "session_recordings")
 OBJECT_STORAGE_EXPORTS_FOLDER = os.getenv("OBJECT_STORAGE_EXPORTS_FOLDER", "exports")
+OBJECT_STORAGE_MEDIA_UPLOADS_FOLDER = os.getenv("OBJECT_STORAGE_MEDIA_UPLOADS_FOLDER", "media_uploads")
diff --git a/posthog/settings/web.py b/posthog/settings/web.py
index 19b1f25a7a2..f5b1f2d57bf 100644
--- a/posthog/settings/web.py
+++ b/posthog/settings/web.py
@@ -250,6 +250,8 @@ GZIP_RESPONSE_ALLOW_LIST = get_list(
                 "^/?api/projects/\\d+/session_recordings/?$",
                 "^/?api/projects/\\d+/exports/\\d+/content/?$",
                 "^/?api/projects/\\d+/activity_log/important_changes/?$",
+                "^/?api/projects/\\d+/uploaded_media/?$",
+                "^/uploaded_media/.*$",
             ]
         ),
     )
diff --git a/posthog/urls.py b/posthog/urls.py
index 90bab23a54d..46558204341 100644
--- a/posthog/urls.py
+++ b/posthog/urls.py
@@ -23,6 +23,7 @@ from posthog.api import (
     signup,
     site_app,
     unsubscribe,
+    uploaded_media,
     user,
 )
 from posthog.api.decide import hostname_in_allowed_url_list
@@ -153,6 +154,7 @@ urlpatterns = [
         "login/<str:backend>/", authentication.sso_login, name="social_begin"
     ),  # overrides from `social_django.urls` to validate proper license
     path("", include("social_django.urls", namespace="social")),
+    path("uploaded_media/<str:image_uuid>/<str:file_name>", uploaded_media.download),
 ]
 
 if settings.DEBUG: