diff --git a/app/Http/Controllers/Api/Client/Servers/FileController.php b/app/Http/Controllers/Api/Client/Servers/FileController.php
index a175f390f..9e705651b 100644
--- a/app/Http/Controllers/Api/Client/Servers/FileController.php
+++ b/app/Http/Controllers/Api/Client/Servers/FileController.php
@@ -6,6 +6,7 @@ use Carbon\CarbonImmutable;
 use Illuminate\Http\Response;
 use Pterodactyl\Models\Server;
 use Illuminate\Http\JsonResponse;
+use Illuminate\Support\Collection;
 use Pterodactyl\Services\Nodes\NodeJWTService;
 use Illuminate\Contracts\Routing\ResponseFactory;
 use Pterodactyl\Repositories\Wings\DaemonFileRepository;
@@ -70,7 +71,7 @@ class FileController extends ClientApiController
     {
         $contents = $this->fileRepository
             ->setServer($server)
-            ->getDirectory(urlencode(urldecode($request->get('directory') ?? '/')));
+            ->getDirectory($this->encode($request->get('directory') ?? '/'));
 
         return $this->fractal->collection($contents)
             ->transformWith($this->getTransformer(FileObjectTransformer::class))
@@ -91,7 +92,7 @@ class FileController extends ClientApiController
     {
         return new Response(
             $this->fileRepository->setServer($server)->getContent(
-                urlencode(urldecode($request->get('file'))), config('pterodactyl.files.max_edit_size')
+                $this->encode($request->get('file')), config('pterodactyl.files.max_edit_size')
             ),
             Response::HTTP_OK,
             ['Content-Type' => 'text/plain']
@@ -113,7 +114,7 @@ class FileController extends ClientApiController
         $token = $this->jwtService
             ->setExpiresAt(CarbonImmutable::now()->addMinutes(15))
             ->setClaims([
-                'file_path' => $request->get('file'),
+                'file_path' => rawurldecode($request->get('file')),
                 'server_uuid' => $server->uuid,
             ])
             ->handle($server->node, $request->user()->id . $server->uuid);
@@ -142,7 +143,7 @@ class FileController extends ClientApiController
     public function write(WriteFileContentRequest $request, Server $server): JsonResponse
     {
         $this->fileRepository->setServer($server)->putContent(
-            $request->get('file'),
+            $this->encode($request->get('file')),
             $request->getContent()
         );
 
@@ -261,4 +262,18 @@ class FileController extends ClientApiController
 
         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.
+     *
+     * @param string $path
+     * @return string
+     */
+    private function encode(string $path): string
+    {
+        return Collection::make(explode('/', rawurldecode($path)))->map(function ($value) {
+            return rawurlencode($value);
+        })->join('/');
+    }
 }
diff --git a/resources/scripts/api/server/files/getFileContents.ts b/resources/scripts/api/server/files/getFileContents.ts
index cec8788b5..da380362d 100644
--- a/resources/scripts/api/server/files/getFileContents.ts
+++ b/resources/scripts/api/server/files/getFileContents.ts
@@ -3,7 +3,7 @@ import http from '@/api/http';
 export default (server: string, file: string): Promise<string> => {
     return new Promise((resolve, reject) => {
         http.get(`/api/client/servers/${server}/files/contents`, {
-            params: { file: file.split('/').map(item => encodeURIComponent(item)).join('/') },
+            params: { file: encodeURI(decodeURI(file)) },
             transformResponse: res => res,
             responseType: 'text',
         })
diff --git a/resources/scripts/api/server/files/loadDirectory.ts b/resources/scripts/api/server/files/loadDirectory.ts
index 1bfd7877f..d29cc1605 100644
--- a/resources/scripts/api/server/files/loadDirectory.ts
+++ b/resources/scripts/api/server/files/loadDirectory.ts
@@ -17,7 +17,7 @@ export interface FileObject {
 
 export default async (uuid: string, directory?: string): Promise<FileObject[]> => {
     const { data } = await http.get(`/api/client/servers/${uuid}/files/list`, {
-        params: { directory: directory?.split('/').map(item => encodeURIComponent(item)).join('/') },
+        params: { directory: encodeURI(directory ?? '/') },
     });
 
     return (data.data || []).map(rawDataToFileObject);
diff --git a/resources/scripts/api/server/files/saveFileContents.ts b/resources/scripts/api/server/files/saveFileContents.ts
index b97e60a6b..7f6f44efc 100644
--- a/resources/scripts/api/server/files/saveFileContents.ts
+++ b/resources/scripts/api/server/files/saveFileContents.ts
@@ -2,7 +2,7 @@ import http from '@/api/http';
 
 export default async (uuid: string, file: string, content: string): Promise<void> => {
     await http.post(`/api/client/servers/${uuid}/files/write`, content, {
-        params: { file },
+        params: { file: encodeURI(decodeURI(file)) },
         headers: {
             'Content-Type': 'text/plain',
         },
diff --git a/resources/scripts/components/server/files/FileEditContainer.tsx b/resources/scripts/components/server/files/FileEditContainer.tsx
index 8305e04bd..4dd519f8d 100644
--- a/resources/scripts/components/server/files/FileEditContainer.tsx
+++ b/resources/scripts/components/server/files/FileEditContainer.tsx
@@ -61,7 +61,7 @@ export default () => {
         setLoading(true);
         clearFlashes('files:view');
         fetchFileContent()
-            .then(content => saveFileContents(uuid, encodeURIComponent(name || hash.replace(/^#/, '')), content))
+            .then(content => saveFileContents(uuid, name || hash.replace(/^#/, ''), content))
             .then(() => {
                 if (name) {
                     history.push(`/server/${id}/files/edit#/${name}`);
diff --git a/resources/scripts/components/server/files/FileManagerBreadcrumbs.tsx b/resources/scripts/components/server/files/FileManagerBreadcrumbs.tsx
index 968a651db..11b7abde7 100644
--- a/resources/scripts/components/server/files/FileManagerBreadcrumbs.tsx
+++ b/resources/scripts/components/server/files/FileManagerBreadcrumbs.tsx
@@ -33,10 +33,10 @@ export default ({ withinFileEditor, isNewFile }: Props) => {
         .filter(directory => !!directory)
         .map((directory, index, dirs) => {
             if (!withinFileEditor && index === dirs.length - 1) {
-                return { name: decodeURIComponent(encodeURIComponent(directory)) };
+                return { name: directory };
             }
 
-            return { name: decodeURIComponent(encodeURIComponent(directory)), path: `/${dirs.slice(0, index + 1).join('/')}` };
+            return { name: directory, path: `/${dirs.slice(0, index + 1).join('/')}` };
         });
 
     const onSelectAllClick = (e: React.ChangeEvent<HTMLInputElement>) => {
@@ -79,7 +79,7 @@ export default ({ withinFileEditor, isNewFile }: Props) => {
             }
             {file &&
             <React.Fragment>
-                <span css={tw`px-1 text-neutral-300`}>{decodeURIComponent(encodeURIComponent(file))}</span>
+                <span css={tw`px-1 text-neutral-300`}>{decodeURI(file)}</span>
             </React.Fragment>
             }
         </div>
diff --git a/resources/scripts/components/server/files/FileManagerContainer.tsx b/resources/scripts/components/server/files/FileManagerContainer.tsx
index 31985e940..6b274f969 100644
--- a/resources/scripts/components/server/files/FileManagerContainer.tsx
+++ b/resources/scripts/components/server/files/FileManagerContainer.tsx
@@ -36,7 +36,7 @@ export default () => {
     useEffect(() => {
         clearFlashes('files');
         setSelectedFiles([]);
-        setDirectory(hash.length > 0 ? hash : '/');
+        setDirectory(hash.length > 0 ? decodeURI(hash) : '/');
     }, [ hash ]);
 
     useEffect(() => {
diff --git a/resources/scripts/components/server/files/FileObjectRow.tsx b/resources/scripts/components/server/files/FileObjectRow.tsx
index 26c37ed21..f4ac06219 100644
--- a/resources/scripts/components/server/files/FileObjectRow.tsx
+++ b/resources/scripts/components/server/files/FileObjectRow.tsx
@@ -24,6 +24,8 @@ const Clickable: React.FC<{ file: FileObject }> = memo(({ file, children }) => {
     const history = useHistory();
     const match = useRouteMatch();
 
+    const destination = cleanDirectoryPath(`${directory}/${file.name}`).split('/').map(v => encodeURI(v)).join('/');
+
     const onRowClick = (e: React.MouseEvent<HTMLAnchorElement, MouseEvent>) => {
         // Don't rely on the onClick to work with the generated URL. Because of the way this
         // component re-renders you'll get redirected into a nested directory structure since
@@ -32,7 +34,7 @@ const Clickable: React.FC<{ file: FileObject }> = memo(({ file, children }) => {
         // Just trust me future me, leave this be.
         if (!file.isFile) {
             e.preventDefault();
-            history.push(`#${cleanDirectoryPath(`${directory}/${file.name}`)}`);
+            history.push(`#${destination}`);
         }
     };
 
@@ -43,7 +45,7 @@ const Clickable: React.FC<{ file: FileObject }> = memo(({ file, children }) => {
             </div>
             :
             <NavLink
-                to={`${match.url}/${file.isFile ? 'edit/' : ''}#${cleanDirectoryPath(`${directory}/${file.name}`)}`}
+                to={`${match.url}/${file.isFile ? 'edit/' : ''}#${destination}`}
                 css={tw`flex flex-1 text-neutral-300 no-underline p-3 overflow-hidden truncate`}
                 onClick={onRowClick}
             >
diff --git a/resources/scripts/components/server/files/NewDirectoryButton.tsx b/resources/scripts/components/server/files/NewDirectoryButton.tsx
index 0056cf688..dc91377bc 100644
--- a/resources/scripts/components/server/files/NewDirectoryButton.tsx
+++ b/resources/scripts/components/server/files/NewDirectoryButton.tsx
@@ -92,9 +92,7 @@ export default ({ className }: WithClassname) => {
                                 <span css={tw`text-neutral-200`}>This directory will be created as</span>
                                 &nbsp;/home/container/
                                 <span css={tw`text-cyan-200`}>
-                                    {decodeURIComponent(encodeURIComponent(
-                                        join(directory, values.directoryName).replace(/^(\.\.\/|\/)+/, ''),
-                                    ))}
+                                    {join(directory, values.directoryName).replace(/^(\.\.\/|\/)+/, '')}
                                 </span>
                             </p>
                             <div css={tw`flex justify-end`}>