diff --git a/app/Http/Controllers/Api/Client/Servers/FileController.php b/app/Http/Controllers/Api/Client/Servers/FileController.php
index 9e705651b..0e3a62f2e 100644
--- a/app/Http/Controllers/Api/Client/Servers/FileController.php
+++ b/app/Http/Controllers/Api/Client/Servers/FileController.php
@@ -16,6 +16,7 @@ use Pterodactyl\Http\Requests\Api\Client\Servers\Files\CopyFileRequest;
 use Pterodactyl\Http\Requests\Api\Client\Servers\Files\ListFilesRequest;
 use Pterodactyl\Http\Requests\Api\Client\Servers\Files\DeleteFileRequest;
 use Pterodactyl\Http\Requests\Api\Client\Servers\Files\RenameFileRequest;
+use Pterodactyl\Http\Requests\Api\Client\Servers\Files\ChmodFilesRequest;
 use Pterodactyl\Http\Requests\Api\Client\Servers\Files\CreateFolderRequest;
 use Pterodactyl\Http\Requests\Api\Client\Servers\Files\CompressFilesRequest;
 use Pterodactyl\Http\Requests\Api\Client\Servers\Files\DecompressFilesRequest;
@@ -263,6 +264,25 @@ class FileController extends ClientApiController
         return new JsonResponse([], Response::HTTP_NO_CONTENT);
     }
 
+    /**
+     * Updates file permissions for file(s) in the given root directory.
+     *
+     * @param \Pterodactyl\Http\Requests\Api\Client\Servers\Files\ChmodFilesRequest $request
+     * @param \Pterodactyl\Models\Server $server
+     * @return \Illuminate\Http\JsonResponse
+     *
+     * @throws \Pterodactyl\Exceptions\Http\Connection\DaemonConnectionException
+     */
+    public function chmod(ChmodFilesRequest $request, Server $server): JsonResponse
+    {
+        $this->fileRepository->setServer($server)
+            ->chmodFiles(
+                $request->input('root'), $request->input('files')
+            );
+
+        return new JsonResponse([], Response::HTTP_NO_CONTENT);
+    }
+
     /**
      * Encodes a given file name & path in a format that should work for a good majority
      * of file names without too much confusing logic.
diff --git a/app/Http/Requests/Api/Client/Servers/Files/ChmodFilesRequest.php b/app/Http/Requests/Api/Client/Servers/Files/ChmodFilesRequest.php
new file mode 100644
index 000000000..158a0a7fd
--- /dev/null
+++ b/app/Http/Requests/Api/Client/Servers/Files/ChmodFilesRequest.php
@@ -0,0 +1,31 @@
+<?php
+
+namespace Pterodactyl\Http\Requests\Api\Client\Servers\Files;
+
+use Pterodactyl\Models\Permission;
+use Pterodactyl\Contracts\Http\ClientPermissionsRequest;
+use Pterodactyl\Http\Requests\Api\Client\ClientApiRequest;
+
+class ChmodFilesRequest extends ClientApiRequest implements ClientPermissionsRequest
+{
+    /**
+     * @return string
+     */
+    public function permission(): string
+    {
+        return Permission::ACTION_FILE_UPDATE;
+    }
+
+    /**
+     * @return array
+     */
+    public function rules(): array
+    {
+        return [
+            'root' => 'required|nullable|string',
+            'files' => 'required|array',
+            'files.*.file' => 'required|string',
+            'files.*.mode' => 'required|numeric',
+        ];
+    }
+}
diff --git a/app/Repositories/Wings/DaemonFileRepository.php b/app/Repositories/Wings/DaemonFileRepository.php
index 1ae424585..c36a8abb0 100644
--- a/app/Repositories/Wings/DaemonFileRepository.php
+++ b/app/Repositories/Wings/DaemonFileRepository.php
@@ -269,4 +269,32 @@ class DaemonFileRepository extends DaemonRepository
             throw new DaemonConnectionException($exception);
         }
     }
+
+    /**
+     * Chmods the given files.
+     *
+     * @param string|null $root
+     * @param array $files
+     * @return \Psr\Http\Message\ResponseInterface
+     *
+     * @throws \Pterodactyl\Exceptions\Http\Connection\DaemonConnectionException
+     */
+    public function chmodFiles(?string $root, array $files): ResponseInterface
+    {
+        Assert::isInstanceOf($this->server, Server::class);
+
+        try {
+            return $this->getHttpClient()->post(
+                sprintf('/api/servers/%s/files/chmod', $this->server->uuid),
+                [
+                    'json' => [
+                        'root' => $root ?? '/',
+                        'files' => $files,
+                    ],
+                ]
+            );
+        } catch (TransferException $exception) {
+            throw new DaemonConnectionException($exception);
+        }
+    }
 }
diff --git a/app/Transformers/Daemon/FileObjectTransformer.php b/app/Transformers/Daemon/FileObjectTransformer.php
index 84fcaf2d4..f19d9028c 100644
--- a/app/Transformers/Daemon/FileObjectTransformer.php
+++ b/app/Transformers/Daemon/FileObjectTransformer.php
@@ -25,6 +25,7 @@ class FileObjectTransformer extends BaseDaemonTransformer
         return [
             'name' => Arr::get($item, 'name'),
             'mode' => Arr::get($item, 'mode'),
+            'mode_bits' => Arr::get($item, 'mode_bits'),
             'size' => Arr::get($item, 'size'),
             'is_file' => Arr::get($item, 'file', true),
             'is_symlink' => Arr::get($item, 'symlink', false),
diff --git a/resources/scripts/api/server/files/chmodFiles.ts b/resources/scripts/api/server/files/chmodFiles.ts
new file mode 100644
index 000000000..8bafd6d6e
--- /dev/null
+++ b/resources/scripts/api/server/files/chmodFiles.ts
@@ -0,0 +1,14 @@
+import http from '@/api/http';
+
+interface Data {
+    file: string;
+    mode: string;
+}
+
+export default (uuid: string, directory: string, files: Data[]): Promise<void> => {
+    return new Promise((resolve, reject) => {
+        http.post(`/api/client/servers/${uuid}/files/chmod`, { root: directory, files })
+            .then(() => resolve())
+            .catch(reject);
+    });
+};
diff --git a/resources/scripts/api/server/files/loadDirectory.ts b/resources/scripts/api/server/files/loadDirectory.ts
index d29cc1605..52bf8853e 100644
--- a/resources/scripts/api/server/files/loadDirectory.ts
+++ b/resources/scripts/api/server/files/loadDirectory.ts
@@ -5,6 +5,7 @@ export interface FileObject {
     key: string;
     name: string;
     mode: string;
+    modeBits: string,
     size: number;
     isFile: boolean;
     isSymlink: boolean;
diff --git a/resources/scripts/api/transformers.ts b/resources/scripts/api/transformers.ts
index f17787e03..e08c00076 100644
--- a/resources/scripts/api/transformers.ts
+++ b/resources/scripts/api/transformers.ts
@@ -16,6 +16,7 @@ export const rawDataToFileObject = (data: FractalResponseData): FileObject => ({
     key: `${data.attributes.is_file ? 'file' : 'dir'}_${data.attributes.name}`,
     name: data.attributes.name,
     mode: data.attributes.mode,
+    modeBits: data.attributes.mode_bits,
     size: Number(data.attributes.size),
     isFile: data.attributes.is_file,
     isSymlink: data.attributes.is_symlink,
diff --git a/resources/scripts/components/server/files/ChmodFileModal.tsx b/resources/scripts/components/server/files/ChmodFileModal.tsx
new file mode 100644
index 000000000..a7997469b
--- /dev/null
+++ b/resources/scripts/components/server/files/ChmodFileModal.tsx
@@ -0,0 +1,75 @@
+import { fileBitsToString } from '@/helpers';
+import useFileManagerSwr from '@/plugins/useFileManagerSwr';
+import React from 'react';
+import Modal, { RequiredModalProps } from '@/components/elements/Modal';
+import { Form, Formik, FormikHelpers } from 'formik';
+import Field from '@/components/elements/Field';
+import chmodFiles from '@/api/server/files/chmodFiles';
+import { ServerContext } from '@/state/server';
+import tw from 'twin.macro';
+import Button from '@/components/elements/Button';
+import useFlash from '@/plugins/useFlash';
+
+interface FormikValues {
+    mode: string;
+}
+
+interface File {
+    file: string,
+    mode: string,
+}
+
+type OwnProps = RequiredModalProps & { files: File[] };
+
+const ChmodFileModal = ({ files, ...props }: OwnProps) => {
+    const uuid = ServerContext.useStoreState(state => state.server.data!.uuid);
+    const { mutate } = useFileManagerSwr();
+    const { clearFlashes, clearAndAddHttpError } = useFlash();
+    const directory = ServerContext.useStoreState(state => state.files.directory);
+    const setSelectedFiles = ServerContext.useStoreActions(actions => actions.files.setSelectedFiles);
+
+    const submit = ({ mode }: FormikValues, { setSubmitting }: FormikHelpers<FormikValues>) => {
+        clearFlashes('files');
+
+        mutate(data => data.map(f => f.name === files[0].file ? { ...f, mode: fileBitsToString(mode, !f.isFile), modeBits: mode } : f), false);
+
+        const data = files.map(f => ({ file: f.file, mode: mode }));
+
+        chmodFiles(uuid, directory, data)
+            .then((): Promise<any> => files.length > 0 ? mutate() : Promise.resolve())
+            .then(() => setSelectedFiles([]))
+            .catch(error => {
+                mutate();
+                setSubmitting(false);
+                clearAndAddHttpError({ key: 'files', error });
+            })
+            .then(() => props.onDismissed());
+    };
+
+    return (
+        <Formik onSubmit={submit} initialValues={{ mode: files.length > 1 ? '' : (files[0].mode || '') }}>
+            {({ isSubmitting }) => (
+                <Modal {...props} dismissable={!isSubmitting} showSpinnerOverlay={isSubmitting}>
+                    <Form css={tw`m-0`}>
+                        <div css={tw`flex flex-wrap items-end`}>
+                            <div css={tw`w-full sm:flex-1 sm:mr-4`}>
+                                <Field
+                                    type={'string'}
+                                    id={'file_mode'}
+                                    name={'mode'}
+                                    label={'File Mode'}
+                                    autoFocus
+                                />
+                            </div>
+                            <div css={tw`w-full sm:w-auto mt-4 sm:mt-0`}>
+                                <Button css={tw`w-full`}>Update</Button>
+                            </div>
+                        </div>
+                    </Form>
+                </Modal>
+            )}
+        </Formik>
+    );
+};
+
+export default ChmodFileModal;
diff --git a/resources/scripts/components/server/files/FileDropdownMenu.tsx b/resources/scripts/components/server/files/FileDropdownMenu.tsx
index 48d53eeb2..603ed80ea 100644
--- a/resources/scripts/components/server/files/FileDropdownMenu.tsx
+++ b/resources/scripts/components/server/files/FileDropdownMenu.tsx
@@ -5,6 +5,7 @@ import {
     faCopy,
     faEllipsisH,
     faFileArchive,
+    faFileCode,
     faFileDownload,
     faLevelUpAlt,
     faPencilAlt,
@@ -30,8 +31,9 @@ import compressFiles from '@/api/server/files/compressFiles';
 import decompressFiles from '@/api/server/files/decompressFiles';
 import isEqual from 'react-fast-compare';
 import ConfirmationModal from '@/components/elements/ConfirmationModal';
+import ChmodFileModal from '@/components/server/files/ChmodFileModal';
 
-type ModalType = 'rename' | 'move';
+type ModalType = 'rename' | 'move' | 'chmod';
 
 const StyledRow = styled.div<{ $danger?: boolean }>`
     ${tw`p-2 flex items-center rounded`};
@@ -140,14 +142,23 @@ const FileDropdownMenu = ({ file }: { file: FileObject }) => {
                 renderToggle={onClick => (
                     <div css={tw`p-3 hover:text-white`} onClick={onClick}>
                         <FontAwesomeIcon icon={faEllipsisH}/>
-                        {!!modal &&
-                        <RenameFileModal
-                            visible
-                            appear
-                            files={[ file.name ]}
-                            useMoveTerminology={modal === 'move'}
-                            onDismissed={() => setModal(null)}
-                        />
+                        {modal ?
+                            modal === 'chmod' ?
+                                <ChmodFileModal
+                                    visible
+                                    appear
+                                    files={[ { file: file.name, mode: file.modeBits } ]}
+                                    onDismissed={() => setModal(null)}
+                                />
+                                :
+                                <RenameFileModal
+                                    visible
+                                    appear
+                                    files={[ file.name ]}
+                                    useMoveTerminology={modal === 'move'}
+                                    onDismissed={() => setModal(null)}
+                                />
+                            : null
                         }
                         <SpinnerOverlay visible={showSpinner} fixed size={'large'}/>
                     </div>
@@ -156,6 +167,7 @@ const FileDropdownMenu = ({ file }: { file: FileObject }) => {
                 <Can action={'file.update'}>
                     <Row onClick={() => setModal('rename')} icon={faPencilAlt} title={'Rename'}/>
                     <Row onClick={() => setModal('move')} icon={faLevelUpAlt} title={'Move'}/>
+                    <Row onClick={() => setModal('chmod')} icon={faFileCode} title={'Permissions'}/>
                 </Can>
                 {file.isFile &&
                 <Can action={'file.create'}>
diff --git a/resources/scripts/components/server/files/FileObjectRow.tsx b/resources/scripts/components/server/files/FileObjectRow.tsx
index fccef1ec6..89a080759 100644
--- a/resources/scripts/components/server/files/FileObjectRow.tsx
+++ b/resources/scripts/components/server/files/FileObjectRow.tsx
@@ -64,7 +64,11 @@ const FileObjectRow = ({ file }: { file: FileObject }) => (
     >
         <SelectFileCheckbox name={file.name}/>
         <Clickable file={file}>
-            <div css={tw`flex-none self-center text-neutral-400 mr-4 text-lg pl-3 ml-6`}>
+            <div css={tw`w-24 ml-6 pl-3 hidden md:block`}>
+                {file.mode}
+            </div>
+
+            <div css={tw`flex-none self-center text-neutral-400 ml-6 md:ml-0 mr-4 text-lg pl-3`}>
                 {file.isFile ?
                     <FontAwesomeIcon icon={file.isSymlink ? faFileImport : file.isArchiveType() ? faFileArchive : faFileAlt}/>
                     :
diff --git a/resources/scripts/components/server/files/NewDirectoryButton.tsx b/resources/scripts/components/server/files/NewDirectoryButton.tsx
index dc91377bc..56b58e17e 100644
--- a/resources/scripts/components/server/files/NewDirectoryButton.tsx
+++ b/resources/scripts/components/server/files/NewDirectoryButton.tsx
@@ -25,7 +25,8 @@ const schema = object().shape({
 const generateDirectoryData = (name: string): FileObject => ({
     key: `dir_${name.split('/', 1)[0] ?? name}`,
     name: name.replace(/^(\/*)/, '').split('/', 1)[0] ?? name,
-    mode: '0644',
+    mode: 'drwxr-xr-x',
+    modeBits: '0755',
     size: 0,
     isFile: false,
     isSymlink: false,
diff --git a/resources/scripts/helpers.ts b/resources/scripts/helpers.ts
index 84358193b..fdeef7ecd 100644
--- a/resources/scripts/helpers.ts
+++ b/resources/scripts/helpers.ts
@@ -20,3 +20,33 @@ export const randomInt = (low: number, high: number) => Math.floor(Math.random()
 export const cleanDirectoryPath = (path: string) => path.replace(/(^#\/*)|(\/(\/*))|(^$)/g, '/');
 
 export const capitalize = (s: string) => s.charAt(0).toUpperCase() + s.slice(1).toLowerCase();
+
+export function fileBitsToString (mode: string, directory: boolean): string {
+    const m = parseInt(mode, 8);
+
+    let buf = '';
+    'dalTLDpSugct?'.split('').forEach((c, i) => {
+        if ((m & (1 << (32 - 1 - i))) !== 0) {
+            buf = buf + c;
+        }
+    });
+
+    if (buf.length === 0) {
+        // If the file is directory, make sure it has the directory flag.
+        if (directory) {
+            buf = 'd';
+        } else {
+            buf = '-';
+        }
+    }
+
+    'rwxrwxrwx'.split('').forEach((c, i) => {
+        if ((m & (1 << (9 - 1 - i))) !== 0) {
+            buf = buf + c;
+        } else {
+            buf = buf + '-';
+        }
+    });
+
+    return buf;
+}
diff --git a/routes/api-client.php b/routes/api-client.php
index 170828be1..35a2938dd 100644
--- a/routes/api-client.php
+++ b/routes/api-client.php
@@ -64,6 +64,7 @@ Route::group(['prefix' => '/servers/{server}', 'middleware' => [AuthenticateServ
         Route::post('/decompress', 'Servers\FileController@decompress');
         Route::post('/delete', 'Servers\FileController@delete');
         Route::post('/create-folder', 'Servers\FileController@create');
+        Route::post('/chmod', 'Servers\FileController@chmod');
         Route::get('/upload', 'Servers\FileUploadController');
     });