diff --git a/app/Entities/Entity.php b/app/Entities/Entity.php
index 14328386c..ed3040929 100644
--- a/app/Entities/Entity.php
+++ b/app/Entities/Entity.php
@@ -287,6 +287,22 @@ class Entity extends Ownable
         return $path;
     }
 
+    /**
+     * Get the parent entity if existing.
+     * This is the "static" parent and does not include dynamic
+     * relations such as shelves to books.
+     */
+    public function getParent(): ?Entity
+    {
+        if ($this->isA('page')) {
+            return $this->chapter_id ? $this->chapter()->withTrashed()->first() : $this->book->withTrashed()->first();
+        }
+        if ($this->isA('chapter')) {
+            return $this->book->withTrashed()->first();
+        }
+        return null;
+    }
+
     /**
      * Rebuild the permissions for this entity.
      */
diff --git a/app/Entities/Managers/TrashCan.php b/app/Entities/Managers/TrashCan.php
index aedf4d7af..f99c62801 100644
--- a/app/Entities/Managers/TrashCan.php
+++ b/app/Entities/Managers/TrashCan.php
@@ -180,24 +180,91 @@ class TrashCan
 
     /**
      * Destroy all items that have pending deletions.
+     * @throws Exception
      */
     public function destroyFromAllDeletions(): int
     {
         $deletions = Deletion::all();
         $deleteCount = 0;
         foreach ($deletions as $deletion) {
-            // For each one we load in the relation since it may have already
-            // been deleted as part of another deletion in this loop.
-            $entity = $deletion->deletable()->first();
-            if ($entity) {
-                $count = $this->destroyEntity($deletion->deletable);
-                $deleteCount += $count;
-            }
-            $deletion->delete();
+            $deleteCount += $this->destroyFromDeletion($deletion);
         }
         return $deleteCount;
     }
 
+    /**
+     * Destroy an element from the given deletion model.
+     * @throws Exception
+     */
+    public function destroyFromDeletion(Deletion $deletion): int
+    {
+        // We directly load the deletable element here just to ensure it still
+        // exists in the event it has already been destroyed during this request.
+        $entity = $deletion->deletable()->first();
+        $count = 0;
+        if ($entity) {
+            $count = $this->destroyEntity($deletion->deletable);
+        }
+        $deletion->delete();
+        return $count;
+    }
+
+    /**
+     * Restore the content within the given deletion.
+     * @throws Exception
+     */
+    public function restoreFromDeletion(Deletion $deletion): int
+    {
+        $shouldRestore = true;
+        $restoreCount = 0;
+        $parent = $deletion->deletable->getParent();
+
+        if ($parent && $parent->trashed()) {
+            $shouldRestore = false;
+        }
+
+        if ($shouldRestore) {
+            $restoreCount = $this->restoreEntity($deletion->deletable);
+        }
+
+        $deletion->delete();
+        return $restoreCount;
+    }
+
+    /**
+     * Restore an entity so it is essentially un-deleted.
+     * Deletions on restored child elements will be removed during this restoration.
+     */
+    protected function restoreEntity(Entity $entity): int
+    {
+        $count = 1;
+        $entity->restore();
+
+        if ($entity->isA('chapter') || $entity->isA('book')) {
+            foreach ($entity->pages()->withTrashed()->withCount('deletions')->get() as $page) {
+                if ($page->deletions_count > 0) {
+                    $page->deletions()->delete();
+                }
+
+                $page->restore();
+                $count++;
+            }
+        }
+
+        if ($entity->isA('book')) {
+            foreach ($entity->chapters()->withTrashed()->withCount('deletions')->get() as $chapter) {
+                if ($chapter->deletions_count === 0) {
+                    $chapter->deletions()->delete();
+                }
+
+                $chapter->restore();
+                $count++;
+            }
+        }
+
+        return $count;
+    }
+
     /**
      * Destroy the given entity.
      */
diff --git a/app/Entities/Page.php b/app/Entities/Page.php
index 32ba2981d..8ad05e7aa 100644
--- a/app/Entities/Page.php
+++ b/app/Entities/Page.php
@@ -49,14 +49,6 @@ class Page extends BookChild
         return $array;
     }
 
-    /**
-     * Get the parent item
-     */
-    public function parent(): Entity
-    {
-        return $this->chapter_id ? $this->chapter : $this->book;
-    }
-
     /**
      * Get the chapter that this page is in, If applicable.
      * @return BelongsTo
diff --git a/app/Entities/Repos/PageRepo.php b/app/Entities/Repos/PageRepo.php
index 87839192b..3b9b1f34c 100644
--- a/app/Entities/Repos/PageRepo.php
+++ b/app/Entities/Repos/PageRepo.php
@@ -321,7 +321,7 @@ class PageRepo
      */
     public function copy(Page $page, string $parentIdentifier = null, string $newName = null): Page
     {
-        $parent = $parentIdentifier ? $this->findParentByIdentifier($parentIdentifier) : $page->parent();
+        $parent = $parentIdentifier ? $this->findParentByIdentifier($parentIdentifier) : $page->getParent();
         if ($parent === null) {
             throw new MoveOperationException('Book or chapter to move page into not found');
         }
@@ -440,8 +440,9 @@ class PageRepo
      */
     protected function getNewPriority(Page $page): int
     {
-        if ($page->parent() instanceof Chapter) {
-            $lastPage = $page->parent()->pages('desc')->first();
+        $parent = $page->getParent();
+        if ($parent instanceof Chapter) {
+            $lastPage = $parent->pages('desc')->first();
             return $lastPage ? $lastPage->priority + 1 : 0;
         }
 
diff --git a/app/Http/Controllers/PageController.php b/app/Http/Controllers/PageController.php
index 57d70fb32..ee998996f 100644
--- a/app/Http/Controllers/PageController.php
+++ b/app/Http/Controllers/PageController.php
@@ -78,7 +78,7 @@ class PageController extends Controller
     public function editDraft(string $bookSlug, int $pageId)
     {
         $draft = $this->pageRepo->getById($pageId);
-        $this->checkOwnablePermission('page-create', $draft->parent());
+        $this->checkOwnablePermission('page-create', $draft->getParent());
         $this->setPageTitle(trans('entities.pages_edit_draft'));
 
         $draftsEnabled = $this->isSignedIn();
@@ -104,7 +104,7 @@ class PageController extends Controller
             'name' => 'required|string|max:255'
         ]);
         $draftPage = $this->pageRepo->getById($pageId);
-        $this->checkOwnablePermission('page-create', $draftPage->parent());
+        $this->checkOwnablePermission('page-create', $draftPage->getParent());
 
         $page = $this->pageRepo->publishDraft($draftPage, $request->all());
         Activity::add($page, 'page_create', $draftPage->book->id);
diff --git a/app/Http/Controllers/RecycleBinController.php b/app/Http/Controllers/RecycleBinController.php
index 3cbc99df3..64459da23 100644
--- a/app/Http/Controllers/RecycleBinController.php
+++ b/app/Http/Controllers/RecycleBinController.php
@@ -2,36 +2,103 @@
 
 use BookStack\Entities\Deletion;
 use BookStack\Entities\Managers\TrashCan;
-use Illuminate\Http\Request;
 
 class RecycleBinController extends Controller
 {
+
+    protected $recycleBinBaseUrl = '/settings/recycle-bin';
+
+    /**
+     * On each request to a method of this controller check permissions
+     * using a middleware closure.
+     */
+    public function __construct()
+    {
+        // TODO - Check this is enforced.
+        $this->middleware(function ($request, $next) {
+            $this->checkPermission('settings-manage');
+            $this->checkPermission('restrictions-manage-all');
+            return $next($request);
+        });
+        parent::__construct();
+    }
+
+
     /**
      * Show the top-level listing for the recycle bin.
      */
     public function index()
     {
-        $this->checkPermission('settings-manage');
-        $this->checkPermission('restrictions-manage-all');
-
         $deletions = Deletion::query()->with(['deletable', 'deleter'])->paginate(10);
 
-        return view('settings.recycle-bin', [
+        return view('settings.recycle-bin.index', [
             'deletions' => $deletions,
         ]);
     }
 
+    /**
+     * Show the page to confirm a restore of the deletion of the given id.
+     */
+    public function showRestore(string $id)
+    {
+        /** @var Deletion $deletion */
+        $deletion = Deletion::query()->findOrFail($id);
+
+        return view('settings.recycle-bin.restore', [
+            'deletion' => $deletion,
+        ]);
+    }
+
+    /**
+     * Restore the element attached to the given deletion.
+     * @throws \Exception
+     */
+    public function restore(string $id)
+    {
+        /** @var Deletion $deletion */
+        $deletion = Deletion::query()->findOrFail($id);
+        $restoreCount = (new TrashCan())->restoreFromDeletion($deletion);
+
+        $this->showSuccessNotification(trans('settings.recycle_bin_restore_notification', ['count' => $restoreCount]));
+        return redirect($this->recycleBinBaseUrl);
+    }
+
+    /**
+     * Show the page to confirm a Permanent deletion of the element attached to the deletion of the given id.
+     */
+    public function showDestroy(string $id)
+    {
+        /** @var Deletion $deletion */
+        $deletion = Deletion::query()->findOrFail($id);
+
+        return view('settings.recycle-bin.destroy', [
+            'deletion' => $deletion,
+        ]);
+    }
+
+    /**
+     * Permanently delete the content associated with the given deletion.
+     * @throws \Exception
+     */
+    public function destroy(string $id)
+    {
+        /** @var Deletion $deletion */
+        $deletion = Deletion::query()->findOrFail($id);
+        $deleteCount = (new TrashCan())->destroyFromDeletion($deletion);
+
+        $this->showSuccessNotification(trans('settings.recycle_bin_destroy_notification', ['count' => $deleteCount]));
+        return redirect($this->recycleBinBaseUrl);
+    }
+
     /**
      * Empty out the recycle bin.
+     * @throws \Exception
      */
     public function empty()
     {
-        $this->checkPermission('settings-manage');
-        $this->checkPermission('restrictions-manage-all');
-
         $deleteCount = (new TrashCan())->destroyFromAllDeletions();
 
-        $this->showSuccessNotification(trans('settings.recycle_bin_empty_notification', ['count' => $deleteCount]));
-        return redirect('/settings/recycle-bin');
+        $this->showSuccessNotification(trans('settings.recycle_bin_destroy_notification', ['count' => $deleteCount]));
+        return redirect($this->recycleBinBaseUrl);
     }
 }
diff --git a/resources/lang/en/settings.php b/resources/lang/en/settings.php
index 6de6c2f1a..b9d91e18c 100755
--- a/resources/lang/en/settings.php
+++ b/resources/lang/en/settings.php
@@ -89,10 +89,18 @@ return [
     'recycle_bin_deleted_item' => 'Deleted Item',
     'recycle_bin_deleted_by' => 'Deleted By',
     'recycle_bin_deleted_at' => 'Deletion Time',
+    'recycle_bin_permanently_delete' => 'Permanently Delete',
+    'recycle_bin_restore' => 'Restore',
     'recycle_bin_contents_empty' => 'The recycle bin is currently empty',
     'recycle_bin_empty' => 'Empty Recycle Bin',
     'recycle_bin_empty_confirm' => 'This will permanently destroy all items in the recycle bin including content contained within each item. Are you sure you want to empty the recycle bin?',
-    'recycle_bin_empty_notification' => 'Deleted :count total items from the recycle bin.',
+    'recycle_bin_destroy_confirm' => 'This action will permanently delete this item, along with any child elements listed below, from the system and you will not be able to restore this content. Are you sure you want to permanently delete this item?',
+    'recycle_bin_destroy_list' => 'Items to be Destroyed',
+    'recycle_bin_restore_list' => 'Items to be Restored',
+    'recycle_bin_restore_confirm' => 'This action will restore the deleted item, including any child elements, to their original location. If the original location has since been deleted, and is now in the recycle bin, the parent item will also need to be restored.',
+    'recycle_bin_restore_deleted_parent' => 'The parent of this item has also been deleted. These will remain deleted until that parent is also restored.',
+    'recycle_bin_destroy_notification' => 'Deleted :count total items from the recycle bin.',
+    'recycle_bin_restore_notification' => 'Restored :count total items from the recycle bin.',
 
     // Audit Log
     'audit' => 'Audit Log',
diff --git a/resources/sass/_layout.scss b/resources/sass/_layout.scss
index 519cb27ad..c4e412f0e 100644
--- a/resources/sass/_layout.scss
+++ b/resources/sass/_layout.scss
@@ -150,22 +150,25 @@ body.flexbox {
 .justify-flex-end {
   justify-content: flex-end;
 }
+.justify-center {
+  justify-content: center;
+}
 
 
 /**
  * Display and float utilities
  */
 .block {
-  display: block;
+  display: block !important;
   position: relative;
 }
 
 .inline {
-  display: inline;
+  display: inline !important;
 }
 
 .block.inline {
-  display: inline-block;
+  display: inline-block !important;
 }
 
 .hidden {
diff --git a/resources/views/partials/entity-display-item.blade.php b/resources/views/partials/entity-display-item.blade.php
new file mode 100644
index 000000000..d6633edbe
--- /dev/null
+++ b/resources/views/partials/entity-display-item.blade.php
@@ -0,0 +1,7 @@
+<?php $type = $entity->getType(); ?>
+<div class="{{$type}} {{$type === 'page' && $entity->draft ? 'draft' : ''}} {{$classes ?? ''}} entity-list-item no-hover">
+    <span role="presentation" class="icon text-{{$type}} {{$type === 'page' && $entity->draft ? 'draft' : ''}}">@icon($type)</span>
+    <div class="content">
+        <div class="entity-list-item-name break-text">{{ $entity->name }}</div>
+    </div>
+</div>
\ No newline at end of file
diff --git a/resources/views/settings/recycle-bin/deletable-entity-list.blade.php b/resources/views/settings/recycle-bin/deletable-entity-list.blade.php
new file mode 100644
index 000000000..07ad94f8e
--- /dev/null
+++ b/resources/views/settings/recycle-bin/deletable-entity-list.blade.php
@@ -0,0 +1,11 @@
+@include('partials.entity-display-item', ['entity' => $entity])
+@if($entity->isA('book'))
+    @foreach($entity->chapters()->withTrashed()->get() as $chapter)
+        @include('partials.entity-display-item', ['entity' => $chapter])
+    @endforeach
+@endif
+@if($entity->isA('book') || $entity->isA('chapter'))
+    @foreach($entity->pages()->withTrashed()->get() as $page)
+        @include('partials.entity-display-item', ['entity' => $page])
+    @endforeach
+@endif
\ No newline at end of file
diff --git a/resources/views/settings/recycle-bin/destroy.blade.php b/resources/views/settings/recycle-bin/destroy.blade.php
new file mode 100644
index 000000000..2cc11dabf
--- /dev/null
+++ b/resources/views/settings/recycle-bin/destroy.blade.php
@@ -0,0 +1,31 @@
+@extends('simple-layout')
+
+@section('body')
+    <div class="container small">
+
+        <div class="grid left-focus v-center no-row-gap">
+            <div class="py-m">
+                @include('settings.navbar', ['selected' => 'maintenance'])
+            </div>
+        </div>
+
+        <div class="card content-wrap auto-height">
+            <h2 class="list-heading">{{ trans('settings.recycle_bin_permanently_delete') }}</h2>
+            <p class="text-muted">{{ trans('settings.recycle_bin_destroy_confirm') }}</p>
+            <form action="{{ url('/settings/recycle-bin/' . $deletion->id) }}" method="post">
+                {!! method_field('DELETE') !!}
+                {!! csrf_field() !!}
+                <a href="{{ url('/settings/recycle-bin') }}" class="button outline">{{ trans('common.cancel') }}</a>
+                <button type="submit" class="button">{{ trans('common.delete_confirm') }}</button>
+            </form>
+
+            @if($deletion->deletable instanceof \BookStack\Entities\Entity)
+                <hr class="mt-m">
+                <h5>{{ trans('settings.recycle_bin_destroy_list') }}</h5>
+                @include('settings.recycle-bin.deletable-entity-list', ['entity' => $deletion->deletable])
+            @endif
+
+        </div>
+
+    </div>
+@stop
diff --git a/resources/views/settings/recycle-bin.blade.php b/resources/views/settings/recycle-bin/index.blade.php
similarity index 76%
rename from resources/views/settings/recycle-bin.blade.php
rename to resources/views/settings/recycle-bin/index.blade.php
index 145eb5d3c..6a61ff9fa 100644
--- a/resources/views/settings/recycle-bin.blade.php
+++ b/resources/views/settings/recycle-bin/index.blade.php
@@ -44,10 +44,11 @@
                     <th>{{ trans('settings.recycle_bin_deleted_item') }}</th>
                     <th>{{ trans('settings.recycle_bin_deleted_by') }}</th>
                     <th>{{ trans('settings.recycle_bin_deleted_at') }}</th>
+                    <th></th>
                 </tr>
                 @if(count($deletions) === 0)
                     <tr>
-                        <td colspan="3">
+                        <td colspan="4">
                             <p class="text-muted"><em>{{ trans('settings.recycle_bin_contents_empty') }}</em></p>
                         </td>
                     </tr>
@@ -55,12 +56,15 @@
                 @foreach($deletions as $deletion)
                 <tr>
                     <td>
-                        <div class="table-entity-item mb-m">
+                        <div class="table-entity-item">
                             <span role="presentation" class="icon text-{{$deletion->deletable->getType()}}">@icon($deletion->deletable->getType())</span>
                             <div class="text-{{ $deletion->deletable->getType() }}">
                                 {{ $deletion->deletable->name }}
                             </div>
                         </div>
+                        @if($deletion->deletable instanceof \BookStack\Entities\Book || $deletion->deletable instanceof \BookStack\Entities\Chapter)
+                            <div class="mb-m"></div>
+                        @endif
                         @if($deletion->deletable instanceof \BookStack\Entities\Book)
                             <div class="pl-xl block inline">
                                 <div class="text-chapter">
@@ -77,7 +81,16 @@
                         @endif
                     </td>
                     <td>@include('partials.table-user', ['user' => $deletion->deleter, 'user_id' => $deletion->deleted_by])</td>
-                    <td>{{ $deletion->created_at }}</td>
+                    <td width="200">{{ $deletion->created_at }}</td>
+                    <td width="150" class="text-right">
+                        <div component="dropdown" class="dropdown-container">
+                            <button type="button" refs="dropdown@toggle" class="button outline">{{ trans('common.actions') }}</button>
+                            <ul refs="dropdown@menu" class="dropdown-menu">
+                                <li><a class="block" href="{{ url('/settings/recycle-bin/'.$deletion->id.'/restore') }}">{{ trans('settings.recycle_bin_restore') }}</a></li>
+                                <li><a class="block" href="{{ url('/settings/recycle-bin/'.$deletion->id.'/destroy') }}">{{ trans('settings.recycle_bin_permanently_delete') }}</a></li>
+                            </ul>
+                        </div>
+                    </td>
                 </tr>
                 @endforeach
             </table>
diff --git a/resources/views/settings/recycle-bin/restore.blade.php b/resources/views/settings/recycle-bin/restore.blade.php
new file mode 100644
index 000000000..79ccf1b7d
--- /dev/null
+++ b/resources/views/settings/recycle-bin/restore.blade.php
@@ -0,0 +1,33 @@
+@extends('simple-layout')
+
+@section('body')
+    <div class="container small">
+
+        <div class="grid left-focus v-center no-row-gap">
+            <div class="py-m">
+                @include('settings.navbar', ['selected' => 'maintenance'])
+            </div>
+        </div>
+
+        <div class="card content-wrap auto-height">
+            <h2 class="list-heading">{{ trans('settings.recycle_bin_restore') }}</h2>
+            <p class="text-muted">{{ trans('settings.recycle_bin_restore_confirm') }}</p>
+            <form action="{{ url('/settings/recycle-bin/' . $deletion->id . '/restore') }}" method="post">
+                {!! csrf_field() !!}
+                <a href="{{ url('/settings/recycle-bin') }}" class="button outline">{{ trans('common.cancel') }}</a>
+                <button type="submit" class="button">{{ trans('settings.recycle_bin_restore') }}</button>
+            </form>
+
+            @if($deletion->deletable instanceof \BookStack\Entities\Entity)
+                <hr class="mt-m">
+                <h5>{{ trans('settings.recycle_bin_restore_list') }}</h5>
+                @if($deletion->deletable->getParent() && $deletion->deletable->getParent()->trashed())
+                    <p class="text-neg">{{ trans('settings.recycle_bin_restore_deleted_parent') }}</p>
+                @endif
+                @include('settings.recycle-bin.deletable-entity-list', ['entity' => $deletion->deletable])
+            @endif
+
+        </div>
+
+    </div>
+@stop
diff --git a/routes/web.php b/routes/web.php
index 20f6639a5..b87355105 100644
--- a/routes/web.php
+++ b/routes/web.php
@@ -169,6 +169,10 @@ Route::group(['middleware' => 'auth'], function () {
         // Recycle Bin
         Route::get('/recycle-bin', 'RecycleBinController@index');
         Route::post('/recycle-bin/empty', 'RecycleBinController@empty');
+        Route::get('/recycle-bin/{id}/destroy', 'RecycleBinController@showDestroy');
+        Route::delete('/recycle-bin/{id}', 'RecycleBinController@destroy');
+        Route::get('/recycle-bin/{id}/restore', 'RecycleBinController@showRestore');
+        Route::post('/recycle-bin/{id}/restore', 'RecycleBinController@restore');
 
         // Audit Log
         Route::get('/audit', 'AuditLogController@index');