diff --git a/core/api.py b/core/api.py
index e1b3bbbd..61894aa5 100644
--- a/core/api.py
+++ b/core/api.py
@@ -4,20 +4,22 @@ import annotated_types
 from django.conf import settings
 from django.db.models import F
 from django.http import HttpResponse
-from ninja import Query
+from ninja import Query, UploadedFile
 from ninja_extra import ControllerBase, api_controller, paginate, route
 from ninja_extra.exceptions import PermissionDenied
 from ninja_extra.pagination import PageNumberPaginationExtra
 from ninja_extra.schemas import PaginatedResponseSchema
+from PIL import UnidentifiedImageError
 
 from club.models import Mailing
-from core.auth.api_permissions import CanAccessLookup, CanView
-from core.models import Group, SithFile, User
+from core.auth.api_permissions import CanAccessLookup, CanView, IsOldSubscriber
+from core.models import Group, QuickUploadImage, SithFile, User
 from core.schemas import (
     FamilyGodfatherSchema,
     GroupSchema,
     MarkdownSchema,
     SithFileSchema,
+    UploadedFileSchema,
     UserFamilySchema,
     UserFilterSchema,
     UserProfileSchema,
@@ -33,6 +35,25 @@ class MarkdownController(ControllerBase):
         return HttpResponse(markdown(body.text), content_type="text/html")
 
 
+@api_controller("/upload")
+class UploadController(ControllerBase):
+    @route.post("/image", response=UploadedFileSchema, permissions=[IsOldSubscriber])
+    def upload_image(self, file: UploadedFile):
+        if file.content_type.split("/")[0] != "image":
+            return self.create_response(
+                message=f"{file.name} isn't a file image", status_code=415
+            )
+
+        try:
+            image = QuickUploadImage.create_from_uploaded(file)
+        except UnidentifiedImageError:
+            return self.create_response(
+                message=f"{file.name} can't be processed", status_code=415
+            )
+
+        return image
+
+
 @api_controller("/mailings")
 class MailingListController(ControllerBase):
     @route.get("", response=str)
diff --git a/core/migrations/0045_quickuploadimage.py b/core/migrations/0045_quickuploadimage.py
new file mode 100644
index 00000000..876f3e89
--- /dev/null
+++ b/core/migrations/0045_quickuploadimage.py
@@ -0,0 +1,52 @@
+# Generated by Django 4.2.17 on 2025-02-28 10:51
+
+import django.db.models.deletion
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+    dependencies = [
+        ("contenttypes", "0002_remove_content_type_name"),
+        ("core", "0044_alter_userban_options"),
+    ]
+
+    operations = [
+        migrations.CreateModel(
+            name="QuickUploadImage",
+            fields=[
+                (
+                    "id",
+                    models.AutoField(
+                        auto_created=True,
+                        primary_key=True,
+                        serialize=False,
+                        verbose_name="ID",
+                    ),
+                ),
+                ("name", models.CharField(max_length=100)),
+                ("image", models.ImageField(upload_to="upload")),
+                ("content_type", models.CharField(max_length=50)),
+                (
+                    "related_model_id",
+                    models.PositiveIntegerField(blank=True, null=True),
+                ),
+                (
+                    "related_model_type",
+                    models.ForeignKey(
+                        blank=True,
+                        null=True,
+                        on_delete=django.db.models.deletion.CASCADE,
+                        to="contenttypes.contenttype",
+                    ),
+                ),
+            ],
+            options={
+                "indexes": [
+                    models.Index(
+                        fields=["related_model_type", "related_model_id"],
+                        name="core_quicku_related_23899b_idx",
+                    )
+                ],
+            },
+        ),
+    ]
diff --git a/core/models.py b/core/models.py
index 29c622fe..b8ee9064 100644
--- a/core/models.py
+++ b/core/models.py
@@ -17,7 +17,7 @@
 # details.
 #
 # You should have received a copy of the GNU General Public License along with
-# this program; if not, write to the Free Sofware Foundation, Inc., 59 Temple
+# this program; if not, write to the Free Software Foundation, Inc., 59 Temple
 # Place - Suite 330, Boston, MA 02111-1307, USA.
 #
 #
@@ -32,15 +32,19 @@ from datetime import timedelta
 from io import BytesIO
 from pathlib import Path
 from typing import TYPE_CHECKING, Optional, Self
+from uuid import uuid4
 
 from django.conf import settings
-from django.contrib.auth.models import AbstractUser, UserManager
+from django.contrib.auth.models import AbstractUser, ContentType, UserManager
 from django.contrib.auth.models import AnonymousUser as AuthAnonymousUser
 from django.contrib.auth.models import Group as AuthGroup
+from django.contrib.contenttypes.fields import GenericForeignKey
 from django.contrib.staticfiles.storage import staticfiles_storage
 from django.core import validators
 from django.core.cache import cache
 from django.core.exceptions import PermissionDenied, ValidationError
+from django.core.files import File
+from django.core.files.base import ContentFile
 from django.core.mail import send_mail
 from django.db import models, transaction
 from django.db.models import Exists, F, OuterRef, Q
@@ -54,6 +58,7 @@ from phonenumber_field.modelfields import PhoneNumberField
 from PIL import Image
 
 if TYPE_CHECKING:
+    from django.core.files.uploadedfile import UploadedFile
     from pydantic import NonNegativeInt
 
     from club.models import Club
@@ -1108,6 +1113,54 @@ class SithFile(models.Model):
         return reverse("core:download", kwargs={"file_id": self.id})
 
 
+class QuickUploadImage(models.Model):
+    """Images uploaded by user outside of the SithFile mechanism"""
+
+    IMAGE_NAME_SIZE = 100
+
+    name = models.CharField(max_length=IMAGE_NAME_SIZE, blank=False)
+    image = models.ImageField(upload_to="upload")
+    content_type = models.CharField(max_length=50, blank=False)
+
+    related_model = GenericForeignKey("related_model_type", "related_model_id")
+    related_model_id = models.PositiveIntegerField(null=True, blank=True)
+    related_model_type = models.ForeignKey(
+        ContentType, on_delete=models.CASCADE, null=True, blank=True
+    )
+
+    class Meta:
+        indexes = [models.Index(fields=["related_model_type", "related_model_id"])]
+
+    def __str__(self) -> str:
+        return f"{self.name}{Path(self.image.path).suffix}"
+
+    @classmethod
+    def create_from_uploaded(
+        cls, image: UploadedFile, related_model: models.Model | None = None
+    ) -> Self:
+        def convert_image(file: UploadedFile) -> ContentFile:
+            content = BytesIO()
+            Image.open(BytesIO(file.read())).save(
+                fp=content, format="webp", optimize=True
+            )
+            return ContentFile(content.getvalue())
+
+        name = Path(image.name).stem[: cls.IMAGE_NAME_SIZE - 1]
+        file = File(convert_image(image), name=f"{name}_{uuid4()}.webp")
+
+        return cls.objects.create(
+            name=name,
+            image=file,
+            content_type="image/webp",
+            related_model=related_model,
+        )
+
+    def can_be_viewed_by(self, user: User) -> bool:
+        if not self.related_model:
+            return True
+        return user.can_view(self.related_model)
+
+
 class LockError(Exception):
     """There was a lock error on the object."""
 
diff --git a/core/schemas.py b/core/schemas.py
index f4080c90..bf2ab234 100644
--- a/core/schemas.py
+++ b/core/schemas.py
@@ -10,7 +10,7 @@ from haystack.query import SearchQuerySet
 from ninja import FilterSchema, ModelSchema, Schema
 from pydantic import AliasChoices, Field
 
-from core.models import Group, SithFile, User
+from core.models import Group, QuickUploadImage, SithFile, User
 
 
 class SimpleUserSchema(ModelSchema):
@@ -47,6 +47,33 @@ class UserProfileSchema(ModelSchema):
         return reverse("core:download", kwargs={"file_id": obj.profile_pict_id})
 
 
+class UploadedFileSchema(ModelSchema):
+    class Meta:
+        model = QuickUploadImage
+        fields = ["id", "name", "content_type"]
+
+    width: int
+    height: int
+    size: int
+    href: str
+
+    @staticmethod
+    def resolve_width(obj: QuickUploadImage):
+        return obj.image.width
+
+    @staticmethod
+    def resolve_height(obj: QuickUploadImage):
+        return obj.image.height
+
+    @staticmethod
+    def resolve_size(obj: QuickUploadImage):
+        return obj.image.size
+
+    @staticmethod
+    def resolve_href(obj: QuickUploadImage) -> str:
+        return reverse("core:uploaded_image", kwargs={"image_id": obj.id})
+
+
 class SithFileSchema(ModelSchema):
     class Meta:
         model = SithFile
diff --git a/core/static/bundled/core/components/easymde-index.ts b/core/static/bundled/core/components/easymde-index.ts
index d99799a0..10ad06a5 100644
--- a/core/static/bundled/core/components/easymde-index.ts
+++ b/core/static/bundled/core/components/easymde-index.ts
@@ -6,13 +6,43 @@ import { inheritHtmlElement, registerComponent } from "#core:utils/web-component
 import type CodeMirror from "codemirror";
 // biome-ignore lint/style/useNamingConvention: This is how they called their namespace
 import EasyMDE from "easymde";
-import { markdownRenderMarkdown } from "#openapi";
+import { markdownRenderMarkdown, uploadUploadImage } from "#openapi";
 
 const loadEasyMde = (textarea: HTMLTextAreaElement) => {
-  new EasyMDE({
+  const easymde = new EasyMDE({
     element: textarea,
     spellChecker: false,
     autoDownloadFontAwesome: false,
+    uploadImage: true,
+    imagePathAbsolute: false,
+    imageUploadFunction: async (file, onSuccess, onError) => {
+      const response = await uploadUploadImage({
+        body: {
+          file: file,
+        },
+      });
+      if (response.response.status !== 200) {
+        onError(gettext("Invalid file"));
+        return;
+      }
+      onSuccess(response.data.href);
+      // Workaround function to add ! and image name to uploaded image
+      // Without this, you get [](url) instead of ![name](url)
+      let cursor = easymde.codemirror.getCursor();
+      easymde.codemirror.setSelection({ line: cursor.line, ch: cursor.ch - 1 });
+      easymde.codemirror.replaceSelection("!");
+
+      easymde.codemirror.setSelection({ line: cursor.line, ch: cursor.ch + 1 });
+      easymde.codemirror.replaceSelection(response.data.name);
+
+      // Move cursor at the end of the url and add a new line
+      cursor = easymde.codemirror.getCursor();
+      easymde.codemirror.setSelection({
+        line: cursor.line,
+        ch: cursor.ch + response.data.href.length + 3,
+      });
+      easymde.codemirror.replaceSelection("\n");
+    },
     previewRender: (plainText: string, preview: MarkdownInput) => {
       /* This is wrapped this way to allow time for Alpine to be loaded on the page */
       return Alpine.debounce((plainText: string, preview: MarkdownInput) => {
@@ -30,6 +60,14 @@ const loadEasyMde = (textarea: HTMLTextAreaElement) => {
       }, 300)(plainText, preview);
     },
     forceSync: true, // Avoid validation error on generic create view
+    imageTexts: {
+      sbInit: gettext("Attach files by drag and dropping or pasting from clipboard."),
+      sbOnDragEnter: gettext("Drop image to upload it."),
+      sbOnDrop: gettext("Uploading image #images_names# …"),
+      sbProgress: gettext("Uploading #file_name#: #progress#%"),
+      sbOnUploaded: gettext("Uploaded #image_name#"),
+      sizeUnits: gettext(" B, KB, MB"),
+    },
     toolbar: [
       {
         name: "heading-smaller",
@@ -120,6 +158,12 @@ const loadEasyMde = (textarea: HTMLTextAreaElement) => {
         className: "fa-regular fa-image",
         title: gettext("Insert image"),
       },
+      {
+        name: "upload-image",
+        action: EasyMDE.drawUploadedImage,
+        className: "fa-solid fa-file-arrow-up",
+        title: gettext("Upload image"),
+      },
       {
         name: "table",
         action: EasyMDE.drawTable,
diff --git a/core/urls.py b/core/urls.py
index 23fa9f11..08c9b9c5 100644
--- a/core/urls.py
+++ b/core/urls.py
@@ -30,6 +30,7 @@ from core.converters import (
     FourDigitYearConverter,
     TwoDigitMonthConverter,
 )
+from core.models import QuickUploadImage
 from core.views import (
     FileDeleteView,
     FileEditPropView,
@@ -213,6 +214,16 @@ urlpatterns = [
         "file/<int:file_id>/moderate/", FileModerateView.as_view(), name="file_moderate"
     ),
     path("file/<int:file_id>/download/", send_file, name="download"),
+    path(
+        "file/<int:image_id>/uploads/",
+        lambda request, image_id: send_file(
+            request=request,
+            file_id=image_id,
+            file_class=QuickUploadImage,
+            file_attr="image",
+        ),
+        name="uploaded_image",
+    ),
     # Page views
     path("page/", PageListView.as_view(), name="page_list"),
     path("page/create/", PageCreateView.as_view(), name="page_new"),
diff --git a/locale/fr/LC_MESSAGES/djangojs.po b/locale/fr/LC_MESSAGES/djangojs.po
index c222636a..ec7ebca1 100644
--- a/locale/fr/LC_MESSAGES/djangojs.po
+++ b/locale/fr/LC_MESSAGES/djangojs.po
@@ -7,7 +7,7 @@
 msgid ""
 msgstr ""
 "Report-Msgid-Bugs-To: \n"
-"POT-Creation-Date: 2025-02-25 16:10+0100\n"
+"POT-Creation-Date: 2025-02-27 00:27+0100\n"
 "PO-Revision-Date: 2024-09-17 11:54+0200\n"
 "Last-Translator: Sli <antoine@bartuccio.fr>\n"
 "Language-Team: AE info <ae.info@utbm.fr>\n"
@@ -34,6 +34,7 @@ msgid "Delete"
 msgstr "Supprimer"
 
 #: com/static/bundled/com/components/moderation-alert-index.ts
+#, javascript-format
 msgid ""
 "This event will take place every week for %s weeks. If you publish or delete "
 "this event, it will also be published (or deleted) for the following weeks."
@@ -54,6 +55,34 @@ msgstr "Vous devez taper %(number)s caractères de plus"
 msgid "No results found"
 msgstr "Aucun résultat trouvé"
 
+#: core/static/bundled/core/components/easymde-index.ts
+msgid "Invalid file"
+msgstr "Fichier invalide"
+
+#: core/static/bundled/core/components/easymde-index.ts
+msgid "Attach files by drag and dropping or pasting from clipboard."
+msgstr "Ajoutez des fichiez en glissant déposant ou collant depuis votre presse papier."
+
+#: core/static/bundled/core/components/easymde-index.ts
+msgid "Drop image to upload it."
+msgstr "Glissez une image pour la téléverser."
+
+#: core/static/bundled/core/components/easymde-index.ts
+msgid "Uploading image #images_names# …"
+msgstr "Téléversement de l'image #images_names# …"
+
+#: core/static/bundled/core/components/easymde-index.ts
+msgid "Uploading #file_name#: #progress#%"
+msgstr "Téléversement de #file_name#: #progress#%"
+
+#: core/static/bundled/core/components/easymde-index.ts
+msgid "Uploaded #image_name#"
+msgstr "#image_name# téléversé"
+
+#: core/static/bundled/core/components/easymde-index.ts
+msgid " B, KB, MB"
+msgstr " B, KB, MB"
+
 #: core/static/bundled/core/components/easymde-index.ts
 msgid "Heading"
 msgstr "Titre"
@@ -106,6 +135,10 @@ msgstr "Insérer lien"
 msgid "Insert image"
 msgstr "Insérer image"
 
+#: core/static/bundled/core/components/easymde-index.ts
+msgid "Upload image"
+msgstr "Téléverser une image"
+
 #: core/static/bundled/core/components/easymde-index.ts
 msgid "Insert table"
 msgstr "Insérer tableau"
diff --git a/package-lock.json b/package-lock.json
index d6d496e8..8386f161 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -27,7 +27,7 @@
         "cytoscape-cxtmenu": "^3.5.0",
         "cytoscape-klay": "^3.1.4",
         "d3-force-3d": "^3.0.5",
-        "easymde": "^2.18.0",
+        "easymde": "^2.19.0",
         "glob": "^11.0.0",
         "htmx.org": "^2.0.3",
         "jquery": "^3.7.1",
@@ -3663,14 +3663,14 @@
       "license": "MIT"
     },
     "node_modules/easymde": {
-      "version": "2.18.0",
-      "resolved": "https://registry.npmjs.org/easymde/-/easymde-2.18.0.tgz",
-      "integrity": "sha512-IxVVUxNWIoXLeqtBU4BLc+eS/ScYhT1Dcb6yF5Wchoj1iXAV+TIIDWx+NCaZhY7RcSHqDPKllbYq7nwGKILnoA==",
+      "version": "2.19.0",
+      "resolved": "https://registry.npmjs.org/easymde/-/easymde-2.19.0.tgz",
+      "integrity": "sha512-4F1aNImqse+9xIjLh9ttfpOVenecjFPxUmKbl1tGp72Z+OyIqLZPE/SgNyy88c/xU0mOy0WC3+tfbZDQ5PDWhg==",
       "license": "MIT",
       "dependencies": {
-        "@types/codemirror": "^5.60.4",
+        "@types/codemirror": "^5.60.10",
         "@types/marked": "^4.0.7",
-        "codemirror": "^5.63.1",
+        "codemirror": "^5.65.15",
         "codemirror-spell-checker": "1.1.2",
         "marked": "^4.1.0"
       }
diff --git a/package.json b/package.json
index 83b65145..5f09855c 100644
--- a/package.json
+++ b/package.json
@@ -54,7 +54,7 @@
     "cytoscape-cxtmenu": "^3.5.0",
     "cytoscape-klay": "^3.1.4",
     "d3-force-3d": "^3.0.5",
-    "easymde": "^2.18.0",
+    "easymde": "^2.19.0",
     "glob": "^11.0.0",
     "htmx.org": "^2.0.3",
     "jquery": "^3.7.1",