diff --git a/CHANGELOG.md b/CHANGELOG.md
index 520cb109b0..88f3981473 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -13,6 +13,7 @@
 - Enhance: ウィジェットの表示設定をプレビューを見ながら行えるように
 - Enhance: ウィジェットの設定項目のラベルの多言語対応
 - Fix: ドライブクリーナーでファイルを削除しても画面に反映されない問題を修正 #16061
+- Fix: ドライブのソートが「登録日（昇順）」の場合に正しく動作しない問題を修正
 
 ### Server
 - Enhance: OAuthのクライアント情報取得（Client Information Discovery）において、IndieWeb Living Standard 11 July 2024で定義されているJSONドキュメント形式に対応しました
diff --git a/packages/frontend/src/components/MkDrive.vue b/packages/frontend/src/components/MkDrive.vue
index 314a776c54..71ffb252df 100644
--- a/packages/frontend/src/components/MkDrive.vue
+++ b/packages/frontend/src/components/MkDrive.vue
@@ -133,12 +133,12 @@ SPDX-License-Identifier: AGPL-3.0-only
 			</TransitionGroup>
 
 			<MkButton
-				v-show="filesPaginator.canFetchOlder.value"
-				v-appear="shouldEnableInfiniteScroll ? filesPaginator.fetchOlder : null"
+				v-show="canFetchFiles"
+				v-appear="shouldEnableInfiniteScroll ? fetchMoreFiles : null"
 				:class="$style.loadMore"
 				primary
 				rounded
-				@click="filesPaginator.fetchOlder()"
+				@click="fetchMoreFiles"
 			>{{ i18n.ts.loadMore }}</MkButton>
 
 			<div v-if="filesPaginator.items.value.length == 0 && foldersPaginator.items.value.length == 0 && !fetching" :class="$style.empty">
@@ -238,10 +238,9 @@ const filesPaginator = markRaw(new Paginator('drive/files', {
 	params: () => ({ // 自動でリロードしたくないためcomputedParamsは使わない
 		folderId: folder.value ? folder.value.id : null,
 		type: props.type,
-		sort: sortModeSelect.value,
+		sort: ['-createdAt', '+createdAt'].includes(sortModeSelect.value) ? null : sortModeSelect.value,
 	}),
 }));
-
 const foldersPaginator = markRaw(new Paginator('drive/folders', {
 	limit: 30,
 	canFetchDetection: 'limit',
@@ -250,6 +249,16 @@ const foldersPaginator = markRaw(new Paginator('drive/folders', {
 	}),
 }));
 
+const canFetchFiles = computed(() => !fetching.value && (filesPaginator.order.value === 'oldest' ? filesPaginator.canFetchNewer.value : filesPaginator.canFetchOlder.value));
+
+async function fetchMoreFiles() {
+	if (filesPaginator.order.value === 'oldest') {
+		filesPaginator.fetchNewer();
+	} else {
+		filesPaginator.fetchOlder();
+	}
+}
+
 const filesTimeline = makeDateGroupedTimelineComputedRef(filesPaginator.items, 'month');
 const shouldBeGroupedByDate = computed(() => ['+createdAt', '-createdAt'].includes(sortModeSelect.value));
 
@@ -260,10 +269,10 @@ watch(sortModeSelect, () => {
 
 async function initialize() {
 	fetching.value = true;
-	await Promise.all([
-		foldersPaginator.init(),
-		filesPaginator.init(),
-	]);
+	await foldersPaginator.reload();
+	filesPaginator.initialDirection = sortModeSelect.value === '-createdAt' ? 'newer' : 'older';
+	filesPaginator.order.value = sortModeSelect.value === '-createdAt' ? 'oldest' : 'newest';
+	await filesPaginator.reload();
 	fetching.value = false;
 }