diff --git a/app/Http/Controllers/Server/FileController.php b/app/Http/Controllers/Server/FileController.php
index f19e5f477..23bba17ee 100644
--- a/app/Http/Controllers/Server/FileController.php
+++ b/app/Http/Controllers/Server/FileController.php
@@ -39,18 +39,6 @@ class FileController extends Controller
         $this->authorize('list-files', $server);
 
         $requestDirectory = '/' . trim(urldecode($request->route()->parameter('directory', '/')), '/');
-        $directory = [
-            'header' => $requestDirectory !== '/' ? $requestDirectory : '',
-            'first' => $requestDirectory !== '/',
-        ];
-
-        $goBack = explode('/', trim($requestDirectory, '/'));
-        if (! empty(array_filter($goBack)) && count($goBack) >= 2) {
-            array_pop($goBack);
-            $directory['show'] = true;
-            $directory['link'] = '/' . implode('/', $goBack);
-            $directory['link_show'] = implode('/', $goBack) . '/';
-        }
 
         try {
             $contents = $this->fileRepository->setServer($server)->setToken(
@@ -63,7 +51,7 @@ class FileController extends Controller
         return JsonResponse::create([
             'contents' => $contents,
             'editable' => config('pterodactyl.files.editable'),
-            'current_directory' => $directory,
+            'current_directory' => $requestDirectory,
         ]);
     }
 }
diff --git a/resources/assets/scripts/components/server/subpages/FileManager.vue b/resources/assets/scripts/components/server/subpages/FileManager.vue
index 9c39101bb..1b1f62cdf 100644
--- a/resources/assets/scripts/components/server/subpages/FileManager.vue
+++ b/resources/assets/scripts/components/server/subpages/FileManager.vue
@@ -1,5 +1,17 @@
 <template>
     <div>
+        <div class="filemanager-breadcrumbs">
+            /<span class="px-1">home</span><!--
+            -->/<router-link :to="{ name: 'server-files' }" class="px-1">container</router-link><!--
+            --><span v-for="crumb in breadcrumbs" class="inline-block">
+                <span v-if="crumb.path">
+                    /<router-link :to="{ name: 'server-files', params: { path: crumb.path } }" class="px-1">{{crumb.directoryName}}</router-link>
+                </span>
+                <span v-else>
+                    /<span class="px-1 font-semibold">{{crumb.directoryName}}</span>
+                </span>
+            </span>
+        </div>
         <div v-if="loading">
             <div class="spinner spinner-xl blue"></div>
         </div>
@@ -14,28 +26,40 @@
                 <div class="flex-1 text-right">Modified</div>
                 <div class="flex-none w-1/6">Actions</div>
             </div>
-            <div class="row clickable" v-for="directory in directories" v-on:click="currentDirectory = directory.name">
-                <div class="flex-none icon"><folder-icon/></div>
-                <div class="flex-1">{{directory.name}}</div>
-                <div class="flex-1 text-right text-grey-dark"></div>
-                <div class="flex-1 text-right text-grey-dark">{{formatDate(directory.modified)}}</div>
-                <div class="flex-none w-1/6"></div>
+            <div v-if="!directories.length && !files.length">
+                <p class="text-grey text-sm text-center p-6 pb-4">This directory is empty.</p>
             </div>
-            <div class="row" v-for="file in files" :class="{ clickable: canEdit(file) }">
-                <div class="flex-none icon">
-                    <file-text-icon v-if="!file.symlink"/>
-                    <link2-icon v-else/>
+            <div v-else>
+                <router-link class="row clickable"
+                             v-for="directory in directories"
+                             :to="{ name: 'server-files', params: { path: getClickablePath(directory.name).replace(/^\//, '') }}"
+                             :key="directory.name + directory.modified"
+                >
+                    <div class="flex-none icon">
+                        <folder-icon/>
+                    </div>
+                    <div class="flex-1">{{directory.name}}</div>
+                    <div class="flex-1 text-right text-grey-dark"></div>
+                    <div class="flex-1 text-right text-grey-dark">{{formatDate(directory.modified)}}</div>
+                    <div class="flex-none w-1/6"></div>
+                </router-link>
+                <div class="row" v-for="file in files" :class="{ clickable: canEdit(file) }">
+                    <div class="flex-none icon">
+                        <file-text-icon v-if="!file.symlink"/>
+                        <link2-icon v-else/>
+                    </div>
+                    <div class="flex-1">{{file.name}}</div>
+                    <div class="flex-1 text-right text-grey-dark">{{readableSize(file.size)}}</div>
+                    <div class="flex-1 text-right text-grey-dark">{{formatDate(file.modified)}}</div>
+                    <div class="flex-none w-1/6"></div>
                 </div>
-                <div class="flex-1">{{file.name}}</div>
-                <div class="flex-1 text-right text-grey-dark">{{readableSize(file.size)}}</div>
-                <div class="flex-1 text-right text-grey-dark">{{formatDate(file.modified)}}</div>
-                <div class="flex-none w-1/6"></div>
             </div>
         </div>
     </div>
 </template>
 
 <script>
+    import _ from 'lodash';
     import filter from 'lodash/filter';
     import isObject from 'lodash/isObject';
     import format from 'date-fns/format';
@@ -44,14 +68,43 @@
 
     export default {
         name: 'file-manager-page',
-        components: { FileTextIcon, FolderIcon, Link2Icon },
+        components: {FileTextIcon, FolderIcon, Link2Icon},
 
         computed: {
             ...mapState('server', ['server', 'credentials']),
             ...mapState('socket', ['connected']),
+
+            /**
+             * Configure the breadcrumbs that display on the filemanager based on the directory that the
+             * user is currently in.
+             */
+            breadcrumbs: function () {
+                const directories = this.currentDirectory.replace(/^\/|\/$/, '').split('/');
+                if (directories.length < 1 || !directories[0]) {
+                    return [];
+                }
+
+                return _.map(directories, function (value, key) {
+                    if (key === directories.length - 1) {
+                        return {directoryName: value};
+                    }
+
+                    return {
+                        directoryName: value,
+                        path: directories.slice(0, key + 1).join('/'),
+                    };
+                });
+            }
         },
 
         watch: {
+            /**
+             * When the route changes reload the directory.
+             */
+            '$route': function (to) {
+                this.currentDirectory = to.params.path || '/';
+            },
+
             /**
              * Watch the current directory setting and when it changes update the file listing.
              */
@@ -72,7 +125,7 @@
 
         data: function () {
             return {
-                currentDirectory: '/',
+                currentDirectory: this.$route.params.path || '/',
                 loading: true,
                 errorMessage: null,
 
@@ -95,7 +148,7 @@
 
                 window.axios.get(this.route('server.files', {
                     server: this.$route.params.id,
-                    directory: this.currentDirectory,
+                    directory: encodeURI(this.currentDirectory.replace(/^\/|\/$/, '')),
                 }))
                     .then((response) => {
                         this.files = filter(response.data.contents, function (o) {
@@ -110,7 +163,12 @@
                         this.errorMessage = null;
                     })
                     .catch(err => {
-                        console.error({ err });
+                        console.error({err});
+                        if (err.response.status === 404) {
+                            this.errorMessage = 'The directory you requested could not be located on the server.';
+                            return;
+                        }
+
                         if (err.response.data && isObject(err.response.data.errors)) {
                             err.response.data.errors.forEach(error => {
                                 this.errorMessage = error.detail;
@@ -132,6 +190,15 @@
                 return this.editableFiles.indexOf(file.mime) >= 0;
             },
 
+            /**
+             * Return a formatted directory path that is used to switch to a nested directory.
+             *
+             * @return {String}
+             */
+            getClickablePath (directory) {
+                return `${this.currentDirectory.replace(/\/$/, '')}/${directory}`;
+            },
+
             /**
              * Return the human readable filesize for a given number of bytes. This
              * uses 1024 as the base, so the response is denoted accordingly.
@@ -152,7 +219,7 @@
                     u++;
                 } while (Math.abs(bytes) >= 1024 && u < units.length - 1);
 
-                return `${bytes.toFixed(1)} ${units[u]}`
+                return `${bytes.toFixed(1)} ${units[u]}`;
             },
 
             /**
diff --git a/resources/assets/scripts/router.js b/resources/assets/scripts/router.js
index a3b542522..e4136663f 100644
--- a/resources/assets/scripts/router.js
+++ b/resources/assets/scripts/router.js
@@ -41,7 +41,7 @@ const routes = [
     { path: '/server/:id', component: Server,
         children: [
             { name: 'server', path: '', component: ConsolePage },
-            { name: 'server-files', path: 'files', component: FileManagerPage },
+            { name: 'server-files', path: 'files/:path(.*)?', component: FileManagerPage },
             { name: 'server-subusers', path: 'subusers', component: ServerSubusers },
             { name: 'server-schedules', path: 'schedules', component: ServerSchedules },
             { name: 'server-databases', path: 'databases', component: ServerDatabases },
diff --git a/resources/assets/styles/components/filemanager.css b/resources/assets/styles/components/filemanager.css
index faf0c4159..6dc54c13c 100644
--- a/resources/assets/styles/components/filemanager.css
+++ b/resources/assets/styles/components/filemanager.css
@@ -1,5 +1,5 @@
 .filemanager {
-  & > .header {
+  & .header {
     @apply .flex .text-sm .pb-4 .font-bold .border-b .border-grey-light .mb-3;
 
     & > div {
@@ -7,15 +7,15 @@
     }
   }
 
-  & > .row {
-    @apply .flex .text-sm .py-3 .text-sm .border .border-transparent;
+  & .row {
+    @apply .flex .text-sm .py-3 .text-sm .border .border-transparent .text-black;
 
     & > div {
       @apply .pr-4;
     }
 
     &.clickable {
-      @apply .rounded .cursor-pointer;
+      @apply .rounded .cursor-pointer .no-underline;
 
       &:hover {
         @apply .bg-grey-lightest .border-blue-light .text-blue-dark;
@@ -30,3 +30,15 @@
     }
   }
 }
+
+.filemanager-breadcrumbs {
+  @apply .px-4 .py-3 .mb-6 .rounded .border .bg-grey-lightest .text-grey-darker;
+
+  & a {
+    @apply .no-underline .text-blue-light;
+
+    &:hover {
+      @apply .text-blue-dark;
+    }
+  }
+}