diff --git a/src/lib/components/inputs/CheckBox.svelte b/src/lib/components/inputs/CheckBox.svelte
new file mode 100644
index 0000000..813a7e0
--- /dev/null
+++ b/src/lib/components/inputs/CheckBox.svelte
@@ -0,0 +1,23 @@
+<script lang="ts">
+  import type { Snippet } from "svelte";
+
+  import IconCheckCircle from "~icons/material-symbols/check-circle";
+  import IconCheckCircleOutline from "~icons/material-symbols/check-circle-outline";
+
+  interface Props {
+    children: Snippet;
+    checked?: boolean;
+  }
+
+  let { children, checked = $bindable(false) }: Props = $props();
+</script>
+
+<label class="flex items-center justify-center gap-x-1">
+  <input bind:checked type="checkbox" class="hidden" />
+  {@render children?.()}
+  {#if checked}
+    <IconCheckCircle class="text-primary-600" />
+  {:else}
+    <IconCheckCircleOutline class="text-gray-300" />
+  {/if}
+</label>
diff --git a/src/lib/components/inputs/index.ts b/src/lib/components/inputs/index.ts
index c2c534d..47cb929 100644
--- a/src/lib/components/inputs/index.ts
+++ b/src/lib/components/inputs/index.ts
@@ -1 +1,2 @@
+export { default as CheckBox } from "./CheckBox.svelte";
 export { default as TextInput } from "./TextInput.svelte";
diff --git a/src/lib/modules/filesystem.ts b/src/lib/modules/filesystem.ts
index f098456..0e786ce 100644
--- a/src/lib/modules/filesystem.ts
+++ b/src/lib/modules/filesystem.ts
@@ -66,7 +66,7 @@ export type CategoryInfo =
       dataKeyVersion?: Date;
       name: string;
       subCategoryIds: number[];
-      files: number[];
+      files: { id: number; isRecursive: boolean }[];
     };
 
 const directoryInfoStore = new Map<DirectoryId, Writable<DirectoryInfo | null>>();
@@ -256,7 +256,7 @@ const fetchCategoryInfoFromServer = async (
     const { dataKey } = await unwrapDataKey(metadata!.dek, masterKey);
     const name = await decryptString(metadata!.name, metadata!.nameIv, dataKey);
 
-    res = await callGetApi(`/api/category/${id}/file/list`);
+    res = await callGetApi(`/api/category/${id}/file/list?recursive=true`);
     if (!res.ok) {
       throw new Error("Failed to fetch category files");
     }
@@ -269,7 +269,7 @@ const fetchCategoryInfoFromServer = async (
       dataKeyVersion: new Date(metadata!.dekVersion),
       name,
       subCategoryIds: subCategories,
-      files,
+      files: files.map(({ file, isRecursive }) => ({ id: file, isRecursive })),
     });
   }
 };
diff --git a/src/lib/organisms/Category/Category.svelte b/src/lib/organisms/Category/Category.svelte
index d70a6d3..563293d 100644
--- a/src/lib/organisms/Category/Category.svelte
+++ b/src/lib/organisms/Category/Category.svelte
@@ -1,5 +1,6 @@
 <script lang="ts">
   import type { Writable } from "svelte/store";
+  import { CheckBox } from "$lib/components/inputs";
   import { getFileInfo, type FileInfo, type CategoryInfo } from "$lib/modules/filesystem";
   import type { SelectedCategory } from "$lib/molecules/Categories";
   import SubCategories from "$lib/molecules/SubCategories.svelte";
@@ -16,6 +17,7 @@
     onSubCategoryClick: (subCategory: SelectedCategory) => void;
     onSubCategoryCreateClick: () => void;
     onSubCategoryMenuClick: (subCategory: SelectedCategory) => void;
+    isFileRecursive: boolean;
   }
 
   let {
@@ -25,12 +27,16 @@
     onSubCategoryClick,
     onSubCategoryCreateClick,
     onSubCategoryMenuClick,
+    isFileRecursive = $bindable(),
   }: Props = $props();
 
   let files: Writable<FileInfo | null>[] = $state([]);
 
   $effect(() => {
-    files = info.files?.map((id) => getFileInfo(id, $masterKeyStore?.get(1)?.key!)) ?? [];
+    files =
+      info.files
+        ?.filter(({ isRecursive }) => isFileRecursive || !isRecursive)
+        .map(({ id }) => getFileInfo(id, $masterKeyStore?.get(1)?.key!)) ?? [];
 
     // TODO: Sorting
   });
@@ -51,7 +57,12 @@
   </div>
   {#if info.id !== "root"}
     <div class="space-y-4 bg-white p-4">
-      <p class="text-lg font-bold text-gray-800">파일</p>
+      <div class="flex items-center justify-between">
+        <p class="text-lg font-bold text-gray-800">파일</p>
+        <CheckBox bind:checked={isFileRecursive}>
+          <p class="font-medium">하위 카테고리의 파일</p>
+        </CheckBox>
+      </div>
       <div class="space-y-1">
         {#key info}
           {#each files as file}
diff --git a/src/lib/server/db/file.ts b/src/lib/server/db/file.ts
index 46c8d66..e108e29 100644
--- a/src/lib/server/db/file.ts
+++ b/src/lib/server/db/file.ts
@@ -1,3 +1,4 @@
+import { sql } from "kysely";
 import pg from "pg";
 import { IntegrityError } from "./error";
 import db from "./kysely";
@@ -290,34 +291,37 @@ export const getAllFilesByParent = async (userId: number, parentId: DirectoryId)
   );
 };
 
-export const getAllFilesByCategory = async (userId: number, categoryId: number) => {
+export const getAllFilesByCategory = async (
+  userId: number,
+  categoryId: number,
+  recursive: boolean,
+) => {
   const files = await db
-    .selectFrom("file")
-    .innerJoin("file_category", "file.id", "file_category.file_id")
-    .selectAll("file")
-    .where("user_id", "=", userId)
-    .where("category_id", "=", categoryId)
+    .withRecursive("cte", (db) =>
+      db
+        .selectFrom("file")
+        .innerJoin("file_category", "file.id", "file_category.file_id")
+        .selectAll("file_category")
+        .select(sql<number>`0`.as("depth"))
+        .where("user_id", "=", userId)
+        .where("category_id", "=", categoryId)
+        .$if(recursive, (qb) =>
+          qb.unionAll((db) =>
+            db
+              .selectFrom("file")
+              .innerJoin("file_category", "file.id", "file_category.file_id")
+              .innerJoin("category", "file_category.category_id", "category.id")
+              .innerJoin("cte", "category.parent_id", "cte.category_id")
+              .selectAll("file_category")
+              .select(sql<number>`cte.depth + 1`.as("depth"))
+              .where("file.user_id", "=", userId),
+          ),
+        ),
+    )
+    .selectFrom("cte")
+    .select(["file_id", "depth"])
     .execute();
-  return files.map(
-    (file) =>
-      ({
-        id: file.id,
-        parentId: file.parent_id ?? "root",
-        userId: file.user_id,
-        path: file.path,
-        mekVersion: file.master_encryption_key_version,
-        encDek: file.encrypted_data_encryption_key,
-        dekVersion: file.data_encryption_key_version,
-        hskVersion: file.hmac_secret_key_version,
-        contentHmac: file.content_hmac,
-        contentType: file.content_type,
-        encContentIv: file.encrypted_content_iv,
-        encContentHash: file.encrypted_content_hash,
-        encName: file.encrypted_name,
-        encCreatedAt: file.encrypted_created_at,
-        encLastModifiedAt: file.encrypted_last_modified_at,
-      }) satisfies File,
-  );
+  return files.map(({ file_id, depth }) => ({ id: file_id, isRecursive: depth > 0 }));
 };
 
 export const getAllFileIdsByContentHmac = async (
diff --git a/src/lib/server/schemas/category.ts b/src/lib/server/schemas/category.ts
index 026ce3a..a11d525 100644
--- a/src/lib/server/schemas/category.ts
+++ b/src/lib/server/schemas/category.ts
@@ -23,7 +23,12 @@ export const categoryFileAddRequest = z.object({
 export type CategoryFileAddRequest = z.infer<typeof categoryFileAddRequest>;
 
 export const categoryFileListResponse = z.object({
-  files: z.number().int().positive().array(),
+  files: z.array(
+    z.object({
+      file: z.number().int().positive(),
+      isRecursive: z.boolean(),
+    }),
+  ),
 });
 export type CategoryFileListResponse = z.infer<typeof categoryFileListResponse>;
 
diff --git a/src/lib/server/services/category.ts b/src/lib/server/services/category.ts
index 229bea7..0d03696 100644
--- a/src/lib/server/services/category.ts
+++ b/src/lib/server/services/category.ts
@@ -66,14 +66,14 @@ export const addCategoryFile = async (userId: number, categoryId: number, fileId
   }
 };
 
-export const getCategoryFiles = async (userId: number, categoryId: number) => {
+export const getCategoryFiles = async (userId: number, categoryId: number, recursive: boolean) => {
   const category = await getCategory(userId, categoryId);
   if (!category) {
     error(404, "Invalid category id");
   }
 
-  const files = await getAllFilesByCategory(userId, categoryId);
-  return { files: files.map(({ id }) => id) };
+  const files = await getAllFilesByCategory(userId, categoryId, recursive);
+  return { files };
 };
 
 export const removeCategoryFile = async (userId: number, categoryId: number, fileId: number) => {
diff --git a/src/routes/(main)/category/[[id]]/+page.svelte b/src/routes/(main)/category/[[id]]/+page.svelte
index 163b890..d83ded2 100644
--- a/src/routes/(main)/category/[[id]]/+page.svelte
+++ b/src/routes/(main)/category/[[id]]/+page.svelte
@@ -22,6 +22,8 @@
   let info: Writable<CategoryInfo | null> | undefined = $state();
   let selectedSubCategory: SelectedCategory | undefined = $state();
 
+  let isFileRecursive = $state(false);
+
   let isCreateCategoryModalOpen = $state(false);
   let isSubCategoryMenuBottomSheetOpen = $state(false);
   let isRenameCategoryModalOpen = $state(false);
@@ -49,6 +51,7 @@
   <div class="flex-grow bg-gray-100 pb-[5.5em]">
     {#if $info}
       <Category
+        bind:isFileRecursive
         info={$info}
         onFileClick={({ id }) => goto(`/file/${id}`)}
         onFileRemoveClick={({ id }) => {
diff --git a/src/routes/api/category/[id]/file/list/+server.ts b/src/routes/api/category/[id]/file/list/+server.ts
index e2aa7af..db55ba5 100644
--- a/src/routes/api/category/[id]/file/list/+server.ts
+++ b/src/routes/api/category/[id]/file/list/+server.ts
@@ -5,13 +5,23 @@ import { categoryFileListResponse, type CategoryFileListResponse } from "$lib/se
 import { getCategoryFiles } from "$lib/server/services/category";
 import type { RequestHandler } from "./$types";
 
-export const GET: RequestHandler = async ({ locals, params }) => {
+export const GET: RequestHandler = async ({ locals, url, params }) => {
   const { userId } = await authorize(locals, "activeClient");
 
-  const zodRes = z.object({ id: z.coerce.number().int().positive() }).safeParse(params);
-  if (!zodRes.success) error(400, "Invalid path parameters");
-  const { id } = zodRes.data;
+  const paramsZodRes = z.object({ id: z.coerce.number().int().positive() }).safeParse(params);
+  if (!paramsZodRes.success) error(400, "Invalid path parameters");
+  const { id } = paramsZodRes.data;
 
-  const { files } = await getCategoryFiles(userId, id);
-  return json(categoryFileListResponse.parse({ files }) as CategoryFileListResponse);
+  const queryZodRes = z
+    .object({ recursive: z.coerce.boolean().nullable() })
+    .safeParse({ recursive: url.searchParams.get("recursive") });
+  if (!queryZodRes.success) error(400, "Invalid query parameters");
+  const { recursive } = queryZodRes.data;
+
+  const { files } = await getCategoryFiles(userId, id, recursive ?? false);
+  return json(
+    categoryFileListResponse.parse({
+      files: files.map(({ id, isRecursive }) => ({ file: id, isRecursive })),
+    }) as CategoryFileListResponse,
+  );
 };