diff --git a/apps/nextjs/src/app/[locale]/boards/[name]/settings/_background.tsx b/apps/nextjs/src/app/[locale]/boards/[name]/settings/_background.tsx
index 71a0450da..7b105fe9c 100644
--- a/apps/nextjs/src/app/[locale]/boards/[name]/settings/_background.tsx
+++ b/apps/nextjs/src/app/[locale]/boards/[name]/settings/_background.tsx
@@ -120,11 +120,14 @@ export const BackgroundSettingsContent = ({ board }: Props) => {
               />
               {session?.user.permissions.includes("media-upload") && (
                 <UploadMedia
-                  onSuccess={({ url }) =>
+                  onSuccess={(medias) => {
+                    const first = medias.at(0);
+                    if (!first) return;
+
                     startTransition(() => {
-                      form.setFieldValue("backgroundImageUrl", url);
-                    })
-                  }
+                      form.setFieldValue("backgroundImageUrl", first.url);
+                    });
+                  }}
                 >
                   {({ onClick, loading }) => (
                     <ActionIcon onClick={onClick} loading={loading} mt={24} size={36} variant="default">
diff --git a/apps/nextjs/src/app/[locale]/manage/medias/_actions/upload-media.tsx b/apps/nextjs/src/app/[locale]/manage/medias/_actions/upload-media.tsx
index ced023c56..377c2edf6 100644
--- a/apps/nextjs/src/app/[locale]/manage/medias/_actions/upload-media.tsx
+++ b/apps/nextjs/src/app/[locale]/manage/medias/_actions/upload-media.tsx
@@ -14,7 +14,7 @@ export const UploadMediaButton = () => {
   };
 
   return (
-    <UploadMedia onSettled={onSettledAsync}>
+    <UploadMedia onSettled={onSettledAsync} multiple>
       {({ onClick, loading }) => (
         <Button onClick={onClick} loading={loading} rightSection={<IconUpload size={16} stroke={1.5} />}>
           {t("media.action.upload.label")}
diff --git a/packages/api/src/router/medias/media-router.ts b/packages/api/src/router/medias/media-router.ts
index ee7cfe3c4..a3f958ff5 100644
--- a/packages/api/src/router/medias/media-router.ts
+++ b/packages/api/src/router/medias/media-router.ts
@@ -55,34 +55,47 @@ export const mediaRouter = createTRPCRouter({
     .requiresPermission("media-upload")
     .input(mediaUploadSchema)
     .mutation(async ({ ctx, input }) => {
-      const content = Buffer.from(await input.file.arrayBuffer());
-      const id = createId();
-      const media = {
-        id,
-        creatorId: ctx.session.user.id,
-        content,
-        size: input.file.size,
-        contentType: input.file.type,
-        name: input.file.name,
-      } satisfies InferInsertModel<typeof medias>;
-      await ctx.db.insert(medias).values(media);
+      const files = await Promise.all(
+        input.files.map(async (file) => ({
+          id: createId(),
+          meta: file,
+          content: Buffer.from(await file.arrayBuffer()),
+        })),
+      );
+      const insertMedias = files.map(
+        (file): InferInsertModel<typeof medias> => ({
+          id: file.id,
+          creatorId: ctx.session.user.id,
+          content: file.content,
+          size: file.meta.size,
+          contentType: file.meta.type,
+          name: file.meta.name,
+        }),
+      );
+      await ctx.db.insert(medias).values(insertMedias);
 
       const localIconRepository = await ctx.db.query.iconRepositories.findFirst({
         where: eq(iconRepositories.slug, LOCAL_ICON_REPOSITORY_SLUG),
       });
 
-      if (!localIconRepository) return id;
+      const ids = files.map((file) => file.id);
+      if (!localIconRepository) return ids;
 
-      const icon = mapMediaToIcon(media);
-      await ctx.db.insert(icons).values({
-        id: createId(),
-        checksum: icon.checksum,
-        name: icon.fileNameWithExtension,
-        url: icon.imageUrl,
-        iconRepositoryId: localIconRepository.id,
-      });
+      await ctx.db.insert(icons).values(
+        insertMedias.map((media) => {
+          const icon = mapMediaToIcon(media);
 
-      return id;
+          return {
+            id: createId(),
+            checksum: icon.checksum,
+            name: icon.fileNameWithExtension,
+            url: icon.imageUrl,
+            iconRepositoryId: localIconRepository.id,
+          };
+        }),
+      );
+
+      return ids;
     }),
   deleteMedia: protectedProcedure.input(byIdSchema).mutation(async ({ ctx, input }) => {
     const dbMedia = await ctx.db.query.medias.findFirst({
diff --git a/packages/forms-collection/src/icon-picker/icon-picker.tsx b/packages/forms-collection/src/icon-picker/icon-picker.tsx
index aa18248d7..1fdf3ee96 100644
--- a/packages/forms-collection/src/icon-picker/icon-picker.tsx
+++ b/packages/forms-collection/src/icon-picker/icon-picker.tsx
@@ -165,11 +165,14 @@ export const IconPicker = ({
           />
           {session?.user.permissions.includes("media-upload") && (
             <UploadMedia
-              onSuccess={({ url }) => {
+              onSuccess={(medias) => {
+                const first = medias.at(0);
+                if (!first) return;
+
                 startTransition(() => {
-                  setValue(url);
-                  setPreviewUrl(url);
-                  setSearch(url);
+                  setValue(first.url);
+                  setPreviewUrl(first.url);
+                  setSearch(first.url);
                 });
               }}
             >
diff --git a/packages/forms-collection/src/upload-media/upload-media.tsx b/packages/forms-collection/src/upload-media/upload-media.tsx
index 2d48e9004..1a0779259 100644
--- a/packages/forms-collection/src/upload-media/upload-media.tsx
+++ b/packages/forms-collection/src/upload-media/upload-media.tsx
@@ -9,27 +9,31 @@ import { supportedMediaUploadFormats } from "@homarr/validation/media";
 
 interface UploadMediaProps {
   children: (props: { onClick: () => void; loading: boolean }) => JSX.Element;
+  multiple?: boolean;
   onSettled?: () => MaybePromise<void>;
-  onSuccess?: (media: { id: string; url: string }) => MaybePromise<void>;
+  onSuccess?: (media: { id: string; url: string }[]) => MaybePromise<void>;
 }
 
-export const UploadMedia = ({ children, onSettled, onSuccess }: UploadMediaProps) => {
+export const UploadMedia = ({ children, onSettled, onSuccess, multiple = false }: UploadMediaProps) => {
   const t = useI18n();
   const { mutateAsync, isPending } = clientApi.media.uploadMedia.useMutation();
 
-  const handleFileUploadAsync = async (file: File | null) => {
-    if (!file) return;
+  const handleFileUploadAsync = async (files: File[] | File | null) => {
+    if (!files || (Array.isArray(files) && files.length === 0)) return;
+    const filesArray: File[] = Array.isArray(files) ? files : [files];
     const formData = new FormData();
-    formData.append("file", file);
+    filesArray.forEach((file) => formData.append("files", file));
     await mutateAsync(formData, {
-      async onSuccess(mediaId) {
+      async onSuccess(mediaIds) {
         showSuccessNotification({
           message: t("media.action.upload.notification.success.message"),
         });
-        await onSuccess?.({
-          id: mediaId,
-          url: `/api/user-medias/${mediaId}`,
-        });
+        await onSuccess?.(
+          mediaIds.map((id) => ({
+            id,
+            url: `/api/user-medias/${id}`,
+          })),
+        );
       },
       onError() {
         showErrorNotification({
@@ -43,7 +47,7 @@ export const UploadMedia = ({ children, onSettled, onSuccess }: UploadMediaProps
   };
 
   return (
-    <FileButton onChange={handleFileUploadAsync} accept={supportedMediaUploadFormats.join(",")}>
+    <FileButton onChange={handleFileUploadAsync} accept={supportedMediaUploadFormats.join(",")} multiple={multiple}>
       {({ onClick }) => children({ onClick, loading: isPending })}
     </FileButton>
   );
diff --git a/packages/validation/src/media.ts b/packages/validation/src/media.ts
index cece4a19f..4d4fbc982 100644
--- a/packages/validation/src/media.ts
+++ b/packages/validation/src/media.ts
@@ -1,3 +1,4 @@
+import z from "zod";
 import { zfd } from "zod-form-data";
 
 import { createCustomErrorParams } from "./form/i18n";
@@ -5,30 +6,34 @@ import { createCustomErrorParams } from "./form/i18n";
 export const supportedMediaUploadFormats = ["image/png", "image/jpeg", "image/webp", "image/gif", "image/svg+xml"];
 
 export const mediaUploadSchema = zfd.formData({
-  file: zfd.file().check((context) => {
-    if (!supportedMediaUploadFormats.includes(context.value.type)) {
-      context.issues.push({
-        code: "custom",
-        params: createCustomErrorParams({
-          key: "invalidFileType",
-          params: { expected: `one of ${supportedMediaUploadFormats.join(", ")}` },
-        }),
-        input: context.value.type,
-      });
-      return;
-    }
+  files: zfd.repeatable(
+    z.array(
+      zfd.file().check((context) => {
+        if (!supportedMediaUploadFormats.includes(context.value.type)) {
+          context.issues.push({
+            code: "custom",
+            params: createCustomErrorParams({
+              key: "invalidFileType",
+              params: { expected: `one of ${supportedMediaUploadFormats.join(", ")}` },
+            }),
+            input: context.value.type,
+          });
+          return;
+        }
 
-    if (context.value.size > 1024 * 1024 * 32) {
-      // Don't forget to update the limit in nginx.conf (client_max_body_size)
-      context.issues.push({
-        code: "custom",
-        params: createCustomErrorParams({
-          key: "fileTooLarge",
-          params: { maxSize: "32 MB" },
-        }),
-        input: context.value.size,
-      });
-      return;
-    }
-  }),
+        if (context.value.size > 1024 * 1024 * 32) {
+          // Don't forget to update the limit in nginx.conf (client_max_body_size)
+          context.issues.push({
+            code: "custom",
+            params: createCustomErrorParams({
+              key: "fileTooLarge",
+              params: { maxSize: "32 MB" },
+            }),
+            input: context.value.size,
+          });
+          return;
+        }
+      }),
+    ),
+  ),
 });