diff --git a/app/Auth/Permissions/PermissionService.php b/app/Auth/Permissions/PermissionService.php
index 7e710edaf..a5ab4ea9a 100644
--- a/app/Auth/Permissions/PermissionService.php
+++ b/app/Auth/Permissions/PermissionService.php
@@ -732,18 +732,21 @@ class PermissionService
     }
 
     /**
-     * Filters pages that are a direct relation to another item.
+     * Add conditions to a query to filter the selection to related entities
+     * where permissions are granted.
+     * @param $entityType
      * @param $query
      * @param $tableName
      * @param $entityIdColumn
      * @return mixed
      */
-    public function filterRelatedPages($query, $tableName, $entityIdColumn)
+    public function filterRelatedEntity($entityType, $query, $tableName, $entityIdColumn)
     {
         $this->currentAction = 'view';
         $tableDetails = ['tableName' => $tableName, 'entityIdColumn' => $entityIdColumn];
 
-        $pageMorphClass = $this->entityProvider->page->getMorphClass();
+        $pageMorphClass = $this->entityProvider->get($entityType)->getMorphClass();
+
         $q = $query->where(function ($query) use ($tableDetails, $pageMorphClass) {
             $query->where(function ($query) use (&$tableDetails, $pageMorphClass) {
                 $query->whereExists(function ($permissionQuery) use (&$tableDetails, $pageMorphClass) {
@@ -761,7 +764,9 @@ class PermissionService
                 });
             })->orWhere($tableDetails['entityIdColumn'], '=', 0);
         });
+
         $this->clean();
+
         return $q;
     }
 
diff --git a/app/Auth/User.php b/app/Auth/User.php
index 05e77e13d..12f022b06 100644
--- a/app/Auth/User.php
+++ b/app/Auth/User.php
@@ -24,7 +24,7 @@ class User extends Model implements AuthenticatableContract, CanResetPasswordCon
      * The attributes that are mass assignable.
      * @var array
      */
-    protected $fillable = ['name', 'email', 'image_id'];
+    protected $fillable = ['name', 'email'];
 
     /**
      * The attributes excluded from the model's JSON form.
diff --git a/app/Auth/UserRepo.php b/app/Auth/UserRepo.php
index 1a73d0072..94ebb27ab 100644
--- a/app/Auth/UserRepo.php
+++ b/app/Auth/UserRepo.php
@@ -198,7 +198,7 @@ class UserRepo
         $user->delete();
         
         // Delete user profile images
-        $profileImages = $images = Image::where('type', '=', 'user')->where('created_by', '=', $user->id)->get();
+        $profileImages = Image::where('type', '=', 'user')->where('uploaded_to', '=', $user->id)->get();
         foreach ($profileImages as $image) {
             Images::destroy($image);
         }
diff --git a/app/Entities/Repos/EntityRepo.php b/app/Entities/Repos/EntityRepo.php
index 88ca1bca6..1cff46da1 100644
--- a/app/Entities/Repos/EntityRepo.php
+++ b/app/Entities/Repos/EntityRepo.php
@@ -762,7 +762,7 @@ class EntityRepo
      */
     public function searchForImage($imageString)
     {
-        $pages = $this->entityQuery('page')->where('html', 'like', '%' . $imageString . '%')->get();
+        $pages = $this->entityQuery('page')->where('html', 'like', '%' . $imageString . '%')->get(['id', 'name', 'slug', 'book_id']);
         foreach ($pages as $page) {
             $page->url = $page->getUrl();
             $page->html = '';
diff --git a/app/Http/Controllers/BookController.php b/app/Http/Controllers/BookController.php
index 24e0d784d..7c8ad5c2f 100644
--- a/app/Http/Controllers/BookController.php
+++ b/app/Http/Controllers/BookController.php
@@ -6,6 +6,7 @@ use BookStack\Entities\Book;
 use BookStack\Entities\EntityContextManager;
 use BookStack\Entities\Repos\EntityRepo;
 use BookStack\Entities\ExportService;
+use BookStack\Uploads\ImageRepo;
 use Illuminate\Http\Request;
 use Illuminate\Http\Response;
 use Views;
@@ -17,6 +18,7 @@ class BookController extends Controller
     protected $userRepo;
     protected $exportService;
     protected $entityContextManager;
+    protected $imageRepo;
 
     /**
      * BookController constructor.
@@ -24,17 +26,20 @@ class BookController extends Controller
      * @param UserRepo $userRepo
      * @param ExportService $exportService
      * @param EntityContextManager $entityContextManager
+     * @param ImageRepo $imageRepo
      */
     public function __construct(
         EntityRepo $entityRepo,
         UserRepo $userRepo,
         ExportService $exportService,
-        EntityContextManager $entityContextManager
+        EntityContextManager $entityContextManager,
+        ImageRepo $imageRepo
     ) {
         $this->entityRepo = $entityRepo;
         $this->userRepo = $userRepo;
         $this->exportService = $exportService;
         $this->entityContextManager = $entityContextManager;
+        $this->imageRepo = $imageRepo;
         parent::__construct();
     }
 
@@ -101,13 +106,15 @@ class BookController extends Controller
      * @param string $shelfSlug
      * @return Response
      * @throws \BookStack\Exceptions\NotFoundException
+     * @throws \BookStack\Exceptions\ImageUploadException
      */
     public function store(Request $request, string $shelfSlug = null)
     {
         $this->checkPermission('book-create-all');
         $this->validate($request, [
             'name' => 'required|string|max:255',
-            'description' => 'string|max:1000'
+            'description' => 'string|max:1000',
+            'image' => $this->imageRepo->getImageValidationRules(),
         ]);
 
         $bookshelf = null;
@@ -117,6 +124,7 @@ class BookController extends Controller
         }
 
         $book = $this->entityRepo->createFromInput('book', $request->all());
+        $this->bookUpdateActions($book, $request);
         Activity::add($book, 'book_create', $book->id);
 
         if ($bookshelf) {
@@ -170,20 +178,27 @@ class BookController extends Controller
 
     /**
      * Update the specified book in storage.
-     * @param  Request $request
+     * @param Request $request
      * @param          $slug
      * @return Response
+     * @throws \BookStack\Exceptions\ImageUploadException
+     * @throws \BookStack\Exceptions\NotFoundException
      */
-    public function update(Request $request, $slug)
+    public function update(Request $request, string $slug)
     {
         $book = $this->entityRepo->getBySlug('book', $slug);
         $this->checkOwnablePermission('book-update', $book);
         $this->validate($request, [
             'name' => 'required|string|max:255',
-            'description' => 'string|max:1000'
+            'description' => 'string|max:1000',
+            'image' => $this->imageRepo->getImageValidationRules(),
         ]);
+
          $book = $this->entityRepo->updateFromInput('book', $book, $request->all());
+         $this->bookUpdateActions($book, $request);
+
          Activity::add($book, 'book_update', $book->id);
+
          return redirect($book->getUrl());
     }
 
@@ -311,7 +326,12 @@ class BookController extends Controller
         $book = $this->entityRepo->getBySlug('book', $bookSlug);
         $this->checkOwnablePermission('book-delete', $book);
         Activity::addMessage('book_delete', 0, $book->name);
+
+        if ($book->cover) {
+            $this->imageRepo->destroyImage($book->cover);
+        }
         $this->entityRepo->destroyBook($book);
+
         return redirect('/books');
     }
 
@@ -383,4 +403,28 @@ class BookController extends Controller
         $textContent = $this->exportService->bookToPlainText($book);
         return $this->downloadResponse($textContent, $bookSlug . '.txt');
     }
+
+    /**
+     * Common actions to run on book update.
+     * Handles updating the cover image.
+     * @param Book $book
+     * @param Request $request
+     * @throws \BookStack\Exceptions\ImageUploadException
+     */
+    protected function bookUpdateActions(Book $book, Request $request)
+    {
+        // Update the cover image if in request
+        if ($request->has('image')) {
+            $newImage = $request->file('image');
+            $image = $this->imageRepo->saveNew($newImage, 'cover_book', $book->id, 512, 512, true);
+            $book->image_id = $image->id;
+            $book->save();
+        }
+
+        if ($request->has('image_reset')) {
+            $this->imageRepo->destroyImage($book->cover);
+            $book->image_id = 0;
+            $book->save();
+        }
+    }
 }
diff --git a/app/Http/Controllers/BookshelfController.php b/app/Http/Controllers/BookshelfController.php
index b86bc2e38..dba2503ef 100644
--- a/app/Http/Controllers/BookshelfController.php
+++ b/app/Http/Controllers/BookshelfController.php
@@ -5,6 +5,7 @@ use BookStack\Auth\UserRepo;
 use BookStack\Entities\Bookshelf;
 use BookStack\Entities\EntityContextManager;
 use BookStack\Entities\Repos\EntityRepo;
+use BookStack\Uploads\ImageRepo;
 use Illuminate\Http\Request;
 use Illuminate\Http\Response;
 use Views;
@@ -15,18 +16,21 @@ class BookshelfController extends Controller
     protected $entityRepo;
     protected $userRepo;
     protected $entityContextManager;
+    protected $imageRepo;
 
     /**
      * BookController constructor.
      * @param EntityRepo $entityRepo
      * @param UserRepo $userRepo
      * @param EntityContextManager $entityContextManager
+     * @param ImageRepo $imageRepo
      */
-    public function __construct(EntityRepo $entityRepo, UserRepo $userRepo, EntityContextManager $entityContextManager)
+    public function __construct(EntityRepo $entityRepo, UserRepo $userRepo, EntityContextManager $entityContextManager, ImageRepo $imageRepo)
     {
         $this->entityRepo = $entityRepo;
         $this->userRepo = $userRepo;
         $this->entityContextManager = $entityContextManager;
+        $this->imageRepo = $imageRepo;
         parent::__construct();
     }
 
@@ -82,8 +86,9 @@ class BookshelfController extends Controller
 
     /**
      * Store a newly created bookshelf in storage.
-     * @param  Request $request
+     * @param Request $request
      * @return Response
+     * @throws \BookStack\Exceptions\ImageUploadException
      */
     public function store(Request $request)
     {
@@ -91,13 +96,14 @@ class BookshelfController extends Controller
         $this->validate($request, [
             'name' => 'required|string|max:255',
             'description' => 'string|max:1000',
+            'image' => $this->imageRepo->getImageValidationRules(),
         ]);
 
-        $bookshelf = $this->entityRepo->createFromInput('bookshelf', $request->all());
-        $this->entityRepo->updateShelfBooks($bookshelf, $request->get('books', ''));
-        Activity::add($bookshelf, 'bookshelf_create');
+        $shelf = $this->entityRepo->createFromInput('bookshelf', $request->all());
+        $this->shelfUpdateActions($shelf, $request);
 
-        return redirect($bookshelf->getUrl());
+        Activity::add($shelf, 'bookshelf_create');
+        return redirect($shelf->getUrl());
     }
 
 
@@ -109,19 +115,19 @@ class BookshelfController extends Controller
      */
     public function show(string $slug)
     {
-        /** @var Bookshelf $bookshelf */
-        $bookshelf = $this->entityRepo->getBySlug('bookshelf', $slug);
-        $this->checkOwnablePermission('book-view', $bookshelf);
+        /** @var Bookshelf $shelf */
+        $shelf = $this->entityRepo->getBySlug('bookshelf', $slug);
+        $this->checkOwnablePermission('book-view', $shelf);
 
-        $books = $this->entityRepo->getBookshelfChildren($bookshelf);
-        Views::add($bookshelf);
-        $this->entityContextManager->setShelfContext($bookshelf->id);
+        $books = $this->entityRepo->getBookshelfChildren($shelf);
+        Views::add($shelf);
+        $this->entityContextManager->setShelfContext($shelf->id);
 
-        $this->setPageTitle($bookshelf->getShortName());
+        $this->setPageTitle($shelf->getShortName());
         return view('shelves.show', [
-            'shelf' => $bookshelf,
+            'shelf' => $shelf,
             'books' => $books,
-            'activity' => Activity::entityActivity($bookshelf, 20, 1)
+            'activity' => Activity::entityActivity($shelf, 20, 1)
         ]);
     }
 
@@ -133,19 +139,19 @@ class BookshelfController extends Controller
      */
     public function edit(string $slug)
     {
-        $bookshelf = $this->entityRepo->getBySlug('bookshelf', $slug); /** @var $bookshelf Bookshelf */
-        $this->checkOwnablePermission('bookshelf-update', $bookshelf);
+        $shelf = $this->entityRepo->getBySlug('bookshelf', $slug); /** @var $shelf Bookshelf */
+        $this->checkOwnablePermission('bookshelf-update', $shelf);
 
-        $shelfBooks = $this->entityRepo->getBookshelfChildren($bookshelf);
+        $shelfBooks = $this->entityRepo->getBookshelfChildren($shelf);
         $shelfBookIds = $shelfBooks->pluck('id');
         $books = $this->entityRepo->getAll('book', false, 'update');
         $books = $books->filter(function ($book) use ($shelfBookIds) {
              return !$shelfBookIds->contains($book->id);
         });
 
-        $this->setPageTitle(trans('entities.shelves_edit_named', ['name' => $bookshelf->getShortName()]));
+        $this->setPageTitle(trans('entities.shelves_edit_named', ['name' => $shelf->getShortName()]));
         return view('shelves.edit', [
-            'shelf' => $bookshelf,
+            'shelf' => $shelf,
             'books' => $books,
             'shelfBooks' => $shelfBooks,
         ]);
@@ -154,10 +160,11 @@ class BookshelfController extends Controller
 
     /**
      * Update the specified bookshelf in storage.
-     * @param  Request $request
+     * @param Request $request
      * @param string $slug
      * @return Response
      * @throws \BookStack\Exceptions\NotFoundException
+     * @throws \BookStack\Exceptions\ImageUploadException
      */
     public function update(Request $request, string $slug)
     {
@@ -166,10 +173,12 @@ class BookshelfController extends Controller
         $this->validate($request, [
             'name' => 'required|string|max:255',
             'description' => 'string|max:1000',
+            'image' => $this->imageRepo->getImageValidationRules(),
         ]);
 
          $shelf = $this->entityRepo->updateFromInput('bookshelf', $shelf, $request->all());
-         $this->entityRepo->updateShelfBooks($shelf, $request->get('books', ''));
+         $this->shelfUpdateActions($shelf, $request);
+
          Activity::add($shelf, 'bookshelf_update');
 
          return redirect($shelf->getUrl());
@@ -184,11 +193,11 @@ class BookshelfController extends Controller
      */
     public function showDelete(string $slug)
     {
-        $bookshelf = $this->entityRepo->getBySlug('bookshelf', $slug); /** @var $bookshelf Bookshelf */
-        $this->checkOwnablePermission('bookshelf-delete', $bookshelf);
+        $shelf = $this->entityRepo->getBySlug('bookshelf', $slug); /** @var $shelf Bookshelf */
+        $this->checkOwnablePermission('bookshelf-delete', $shelf);
 
-        $this->setPageTitle(trans('entities.shelves_delete_named', ['name' => $bookshelf->getShortName()]));
-        return view('shelves.delete', ['shelf' => $bookshelf]);
+        $this->setPageTitle(trans('entities.shelves_delete_named', ['name' => $shelf->getShortName()]));
+        return view('shelves.delete', ['shelf' => $shelf]);
     }
 
     /**
@@ -200,10 +209,15 @@ class BookshelfController extends Controller
      */
     public function destroy(string $slug)
     {
-        $bookshelf = $this->entityRepo->getBySlug('bookshelf', $slug); /** @var $bookshelf Bookshelf */
-        $this->checkOwnablePermission('bookshelf-delete', $bookshelf);
-        Activity::addMessage('bookshelf_delete', 0, $bookshelf->name);
-        $this->entityRepo->destroyBookshelf($bookshelf);
+        $shelf = $this->entityRepo->getBySlug('bookshelf', $slug); /** @var $shelf Bookshelf */
+        $this->checkOwnablePermission('bookshelf-delete', $shelf);
+        Activity::addMessage('bookshelf_delete', 0, $shelf->name);
+
+        if ($shelf->cover) {
+            $this->imageRepo->destroyImage($shelf->cover);
+        }
+        $this->entityRepo->destroyBookshelf($shelf);
+
         return redirect('/shelves');
     }
 
@@ -215,12 +229,12 @@ class BookshelfController extends Controller
      */
     public function showPermissions(string $slug)
     {
-        $bookshelf = $this->entityRepo->getBySlug('bookshelf', $slug);
-        $this->checkOwnablePermission('restrictions-manage', $bookshelf);
+        $shelf = $this->entityRepo->getBySlug('bookshelf', $slug);
+        $this->checkOwnablePermission('restrictions-manage', $shelf);
 
         $roles = $this->userRepo->getRestrictableRoles();
         return view('shelves.permissions', [
-            'shelf' => $bookshelf,
+            'shelf' => $shelf,
             'roles' => $roles
         ]);
     }
@@ -235,12 +249,12 @@ class BookshelfController extends Controller
      */
     public function permissions(string $slug, Request $request)
     {
-        $bookshelf = $this->entityRepo->getBySlug('bookshelf', $slug);
-        $this->checkOwnablePermission('restrictions-manage', $bookshelf);
+        $shelf = $this->entityRepo->getBySlug('bookshelf', $slug);
+        $this->checkOwnablePermission('restrictions-manage', $shelf);
 
-        $this->entityRepo->updateEntityPermissionsFromRequest($request, $bookshelf);
+        $this->entityRepo->updateEntityPermissionsFromRequest($request, $shelf);
         session()->flash('success', trans('entities.shelves_permissions_updated'));
-        return redirect($bookshelf->getUrl());
+        return redirect($shelf->getUrl());
     }
 
     /**
@@ -251,11 +265,37 @@ class BookshelfController extends Controller
      */
     public function copyPermissions(string $slug)
     {
-        $bookshelf = $this->entityRepo->getBySlug('bookshelf', $slug);
-        $this->checkOwnablePermission('restrictions-manage', $bookshelf);
+        $shelf = $this->entityRepo->getBySlug('bookshelf', $slug);
+        $this->checkOwnablePermission('restrictions-manage', $shelf);
 
-        $updateCount = $this->entityRepo->copyBookshelfPermissions($bookshelf);
+        $updateCount = $this->entityRepo->copyBookshelfPermissions($shelf);
         session()->flash('success', trans('entities.shelves_copy_permission_success', ['count' => $updateCount]));
-        return redirect($bookshelf->getUrl());
+        return redirect($shelf->getUrl());
+    }
+
+    /**
+     * Common actions to run on bookshelf update.
+     * @param Bookshelf $shelf
+     * @param Request $request
+     * @throws \BookStack\Exceptions\ImageUploadException
+     */
+    protected function shelfUpdateActions(Bookshelf $shelf, Request $request)
+    {
+        // Update the books that the shelf references
+        $this->entityRepo->updateShelfBooks($shelf, $request->get('books', ''));
+
+        // Update the cover image if in request
+        if ($request->has('image')) {
+            $newImage = $request->file('image');
+            $image = $this->imageRepo->saveNew($newImage, 'cover_shelf', $shelf->id, 512, 512, true);
+            $shelf->image_id = $image->id;
+            $shelf->save();
+        }
+
+        if ($request->has('image_reset')) {
+            $this->imageRepo->destroyImage($shelf->cover);
+            $shelf->image_id = 0;
+            $shelf->save();
+        }
     }
 }
diff --git a/app/Http/Controllers/ImageController.php b/app/Http/Controllers/ImageController.php
deleted file mode 100644
index 4d6f759b3..000000000
--- a/app/Http/Controllers/ImageController.php
+++ /dev/null
@@ -1,246 +0,0 @@
-<?php namespace BookStack\Http\Controllers;
-
-use BookStack\Entities\Repos\EntityRepo;
-use BookStack\Exceptions\ImageUploadException;
-use BookStack\Repos\PageRepo;
-use BookStack\Uploads\Image;
-use BookStack\Uploads\ImageRepo;
-use Illuminate\Filesystem\Filesystem as File;
-use Illuminate\Http\Request;
-
-class ImageController extends Controller
-{
-    protected $image;
-    protected $file;
-    protected $imageRepo;
-
-    /**
-     * ImageController constructor.
-     * @param Image $image
-     * @param File $file
-     * @param ImageRepo $imageRepo
-     */
-    public function __construct(Image $image, File $file, ImageRepo $imageRepo)
-    {
-        $this->image = $image;
-        $this->file = $file;
-        $this->imageRepo = $imageRepo;
-        parent::__construct();
-    }
-
-    /**
-     * Provide an image file from storage.
-     * @param string $path
-     * @return mixed
-     */
-    public function showImage(string $path)
-    {
-        $path = storage_path('uploads/images/' . $path);
-        if (!file_exists($path)) {
-            abort(404);
-        }
-
-        return response()->file($path);
-    }
-
-    /**
-     * Get all images for a specific type, Paginated
-     * @param string $type
-     * @param int $page
-     * @return \Illuminate\Http\JsonResponse
-     */
-    public function getAllByType($type, $page = 0)
-    {
-        $imgData = $this->imageRepo->getPaginatedByType($type, $page);
-        return response()->json($imgData);
-    }
-
-    /**
-     * Search through images within a particular type.
-     * @param $type
-     * @param int $page
-     * @param Request $request
-     * @return mixed
-     */
-    public function searchByType(Request $request, $type, $page = 0)
-    {
-        $this->validate($request, [
-            'term' => 'required|string'
-        ]);
-
-        $searchTerm = $request->get('term');
-        $imgData = $this->imageRepo->searchPaginatedByType($type, $searchTerm, $page, 24);
-        return response()->json($imgData);
-    }
-
-    /**
-     * Get all images for a user.
-     * @param int $page
-     * @return \Illuminate\Http\JsonResponse
-     */
-    public function getAllForUserType($page = 0)
-    {
-        $imgData = $this->imageRepo->getPaginatedByType('user', $page, 24, $this->currentUser->id);
-        return response()->json($imgData);
-    }
-
-    /**
-     * Get gallery images with a specific filter such as book or page
-     * @param $filter
-     * @param int $page
-     * @param Request $request
-     * @return \Illuminate\Contracts\Routing\ResponseFactory|\Illuminate\Http\JsonResponse|\Symfony\Component\HttpFoundation\Response
-     */
-    public function getGalleryFiltered(Request $request, $filter, $page = 0)
-    {
-        $this->validate($request, [
-            'page_id' => 'required|integer'
-        ]);
-
-        $validFilters = collect(['page', 'book']);
-        if (!$validFilters->contains($filter)) {
-            return response('Invalid filter', 500);
-        }
-
-        $pageId = $request->get('page_id');
-        $imgData = $this->imageRepo->getGalleryFiltered(strtolower($filter), $pageId, $page, 24);
-
-        return response()->json($imgData);
-    }
-
-    /**
-     * Handles image uploads for use on pages.
-     * @param string $type
-     * @param Request $request
-     * @return \Illuminate\Http\JsonResponse
-     * @throws \Exception
-     */
-    public function uploadByType($type, Request $request)
-    {
-        $this->checkPermission('image-create-all');
-        $this->validate($request, [
-            'file' => 'image_extension|no_double_extension|mimes:jpeg,png,gif,bmp,webp,tiff'
-        ]);
-
-        if (!$this->imageRepo->isValidType($type)) {
-            return $this->jsonError(trans('errors.image_upload_type_error'));
-        }
-
-        $imageUpload = $request->file('file');
-
-        try {
-            $uploadedTo = $request->get('uploaded_to', 0);
-            $image = $this->imageRepo->saveNew($imageUpload, $type, $uploadedTo);
-        } catch (ImageUploadException $e) {
-            return response($e->getMessage(), 500);
-        }
-
-        return response()->json($image);
-    }
-
-    /**
-     * Upload a drawing to the system.
-     * @param Request $request
-     * @return \Illuminate\Contracts\Routing\ResponseFactory|\Illuminate\Http\JsonResponse|\Symfony\Component\HttpFoundation\Response
-     */
-    public function uploadDrawing(Request $request)
-    {
-        $this->validate($request, [
-            'image' => 'required|string',
-            'uploaded_to' => 'required|integer'
-        ]);
-        $this->checkPermission('image-create-all');
-        $imageBase64Data = $request->get('image');
-
-        try {
-            $uploadedTo = $request->get('uploaded_to', 0);
-            $image = $this->imageRepo->saveDrawing($imageBase64Data, $uploadedTo);
-        } catch (ImageUploadException $e) {
-            return response($e->getMessage(), 500);
-        }
-
-        return response()->json($image);
-    }
-
-    /**
-     * Get the content of an image based64 encoded.
-     * @param $id
-     * @return \Illuminate\Http\JsonResponse|mixed
-     */
-    public function getBase64Image($id)
-    {
-        $image = $this->imageRepo->getById($id);
-        $imageData = $this->imageRepo->getImageData($image);
-        if ($imageData === null) {
-            return $this->jsonError("Image data could not be found");
-        }
-        return response()->json([
-            'content' => base64_encode($imageData)
-        ]);
-    }
-
-    /**
-     * Generate a sized thumbnail for an image.
-     * @param $id
-     * @param $width
-     * @param $height
-     * @param $crop
-     * @return \Illuminate\Http\JsonResponse
-     * @throws ImageUploadException
-     * @throws \Exception
-     */
-    public function getThumbnail($id, $width, $height, $crop)
-    {
-        $this->checkPermission('image-create-all');
-        $image = $this->imageRepo->getById($id);
-        $thumbnailUrl = $this->imageRepo->getThumbnail($image, $width, $height, $crop == 'false');
-        return response()->json(['url' => $thumbnailUrl]);
-    }
-
-    /**
-     * Update image details
-     * @param integer $imageId
-     * @param Request $request
-     * @return \Illuminate\Http\JsonResponse
-     * @throws ImageUploadException
-     * @throws \Exception
-     */
-    public function update($imageId, Request $request)
-    {
-        $this->validate($request, [
-            'name' => 'required|min:2|string'
-        ]);
-        $image = $this->imageRepo->getById($imageId);
-        $this->checkOwnablePermission('image-update', $image);
-        $image = $this->imageRepo->updateImageDetails($image, $request->all());
-        return response()->json($image);
-    }
-
-    /**
-     * Show the usage of an image on pages.
-     * @param \BookStack\Entities\Repos\EntityRepo $entityRepo
-     * @param $id
-     * @return \Illuminate\Http\JsonResponse
-     */
-    public function usage(EntityRepo $entityRepo, $id)
-    {
-        $image = $this->imageRepo->getById($id);
-        $pageSearch = $entityRepo->searchForImage($image->url);
-        return response()->json($pageSearch);
-    }
-
-    /**
-     * Deletes an image and all thumbnail/image files
-     * @param int $id
-     * @return \Illuminate\Http\JsonResponse
-     * @throws \Exception
-     */
-    public function destroy($id)
-    {
-        $image = $this->imageRepo->getById($id);
-        $this->checkOwnablePermission('image-delete', $image);
-
-        $this->imageRepo->destroyImage($image);
-        return response()->json(trans('components.images_deleted'));
-    }
-}
diff --git a/app/Http/Controllers/Images/DrawioImageController.php b/app/Http/Controllers/Images/DrawioImageController.php
new file mode 100644
index 000000000..2deb64d96
--- /dev/null
+++ b/app/Http/Controllers/Images/DrawioImageController.php
@@ -0,0 +1,89 @@
+<?php
+
+namespace BookStack\Http\Controllers\Images;
+
+use BookStack\Exceptions\ImageUploadException;
+use BookStack\Uploads\ImageRepo;
+use Illuminate\Http\Request;
+use BookStack\Http\Controllers\Controller;
+
+class DrawioImageController extends Controller
+{
+    protected $imageRepo;
+
+    /**
+     * DrawioImageController constructor.
+     * @param ImageRepo $imageRepo
+     */
+    public function __construct(ImageRepo $imageRepo)
+    {
+        $this->imageRepo = $imageRepo;
+        parent::__construct();
+    }
+
+    /**
+     * Get a list of gallery images, in a list.
+     * Can be paged and filtered by entity.
+     * @param Request $request
+     * @return \Illuminate\Http\JsonResponse
+     */
+    public function list(Request $request)
+    {
+        $page = $request->get('page', 1);
+        $searchTerm = $request->get('search', null);
+        $uploadedToFilter = $request->get('uploaded_to', null);
+        $parentTypeFilter = $request->get('filter_type', null);
+
+        $imgData = $this->imageRepo->getEntityFiltered('drawio', $parentTypeFilter, $page, 24, $uploadedToFilter, $searchTerm);
+        return response()->json($imgData);
+    }
+
+    /**
+     * Store a new gallery image in the system.
+     * @param Request $request
+     * @return Illuminate\Http\JsonResponse
+     * @throws \Exception
+     */
+    public function create(Request $request)
+    {
+        $this->validate($request, [
+            'image' => 'required|string',
+            'uploaded_to' => 'required|integer'
+        ]);
+
+        $this->checkPermission('image-create-all');
+        $imageBase64Data = $request->get('image');
+
+        try {
+            $uploadedTo = $request->get('uploaded_to', 0);
+            $image = $this->imageRepo->saveDrawing($imageBase64Data, $uploadedTo);
+        } catch (ImageUploadException $e) {
+            return response($e->getMessage(), 500);
+        }
+
+        return response()->json($image);
+    }
+
+    /**
+     * Get the content of an image based64 encoded.
+     * @param $id
+     * @return \Illuminate\Http\JsonResponse|mixed
+     */
+    public function getAsBase64($id)
+    {
+        $image = $this->imageRepo->getById($id);
+        $page = $image->getPage();
+        if ($image === null || $image->type !== 'drawio' || !userCan('page-view', $page)) {
+            return $this->jsonError("Image data could not be found");
+        }
+
+        $imageData = $this->imageRepo->getImageData($image);
+        if ($imageData === null) {
+            return $this->jsonError("Image data could not be found");
+        }
+        return response()->json([
+            'content' => base64_encode($imageData)
+        ]);
+    }
+
+}
diff --git a/app/Http/Controllers/Images/GalleryImageController.php b/app/Http/Controllers/Images/GalleryImageController.php
new file mode 100644
index 000000000..35087463b
--- /dev/null
+++ b/app/Http/Controllers/Images/GalleryImageController.php
@@ -0,0 +1,65 @@
+<?php
+
+namespace BookStack\Http\Controllers\Images;
+
+use BookStack\Exceptions\ImageUploadException;
+use BookStack\Uploads\ImageRepo;
+use Illuminate\Http\Request;
+use BookStack\Http\Controllers\Controller;
+
+class GalleryImageController extends Controller
+{
+    protected $imageRepo;
+
+    /**
+     * GalleryImageController constructor.
+     * @param ImageRepo $imageRepo
+     */
+    public function __construct(ImageRepo $imageRepo)
+    {
+        $this->imageRepo = $imageRepo;
+        parent::__construct();
+    }
+
+    /**
+     * Get a list of gallery images, in a list.
+     * Can be paged and filtered by entity.
+     * @param Request $request
+     * @return \Illuminate\Http\JsonResponse
+     */
+    public function list(Request $request)
+    {
+        $page = $request->get('page', 1);
+        $searchTerm = $request->get('search', null);
+        $uploadedToFilter = $request->get('uploaded_to', null);
+        $parentTypeFilter = $request->get('filter_type', null);
+
+        $imgData = $this->imageRepo->getEntityFiltered('gallery', $parentTypeFilter, $page, 24, $uploadedToFilter, $searchTerm);
+        return response()->json($imgData);
+    }
+
+    /**
+     * Store a new gallery image in the system.
+     * @param Request $request
+     * @return Illuminate\Http\JsonResponse
+     * @throws \Exception
+     */
+    public function create(Request $request)
+    {
+        $this->checkPermission('image-create-all');
+        $this->validate($request, [
+            'file' => $this->imageRepo->getImageValidationRules()
+        ]);
+
+        try {
+            $imageUpload = $request->file('file');
+            $uploadedTo = $request->get('uploaded_to', 0);
+            $image = $this->imageRepo->saveNew($imageUpload, 'gallery', $uploadedTo);
+        } catch (ImageUploadException $e) {
+            return response($e->getMessage(), 500);
+        }
+
+        return response()->json($image);
+    }
+
+}
diff --git a/app/Http/Controllers/Images/ImageController.php b/app/Http/Controllers/Images/ImageController.php
new file mode 100644
index 000000000..024003f87
--- /dev/null
+++ b/app/Http/Controllers/Images/ImageController.php
@@ -0,0 +1,115 @@
+<?php namespace BookStack\Http\Controllers\Images;
+
+use BookStack\Entities\Repos\EntityRepo;
+use BookStack\Exceptions\ImageUploadException;
+use BookStack\Http\Controllers\Controller;
+use BookStack\Repos\PageRepo;
+use BookStack\Uploads\Image;
+use BookStack\Uploads\ImageRepo;
+use Illuminate\Filesystem\Filesystem as File;
+use Illuminate\Http\Request;
+
+class ImageController extends Controller
+{
+    protected $image;
+    protected $file;
+    protected $imageRepo;
+
+    /**
+     * ImageController constructor.
+     * @param Image $image
+     * @param File $file
+     * @param ImageRepo $imageRepo
+     */
+    public function __construct(Image $image, File $file, ImageRepo $imageRepo)
+    {
+        $this->image = $image;
+        $this->file = $file;
+        $this->imageRepo = $imageRepo;
+        parent::__construct();
+    }
+
+    /**
+     * Provide an image file from storage.
+     * @param string $path
+     * @return mixed
+     */
+    public function showImage(string $path)
+    {
+        $path = storage_path('uploads/images/' . $path);
+        if (!file_exists($path)) {
+            abort(404);
+        }
+
+        return response()->file($path);
+    }
+
+
+    /**
+     * Update image details
+     * @param integer $id
+     * @param Request $request
+     * @return \Illuminate\Http\JsonResponse
+     * @throws ImageUploadException
+     * @throws \Exception
+     */
+    public function update($id, Request $request)
+    {
+        $this->validate($request, [
+            'name' => 'required|min:2|string'
+        ]);
+
+        $image = $this->imageRepo->getById($id);
+        $this->checkImagePermission($image);
+        $this->checkOwnablePermission('image-update', $image);
+
+        $image = $this->imageRepo->updateImageDetails($image, $request->all());
+        return response()->json($image);
+    }
+
+    /**
+     * Show the usage of an image on pages.
+     * @param \BookStack\Entities\Repos\EntityRepo $entityRepo
+     * @param $id
+     * @return \Illuminate\Http\JsonResponse
+     */
+    public function usage(EntityRepo $entityRepo, $id)
+    {
+        $image = $this->imageRepo->getById($id);
+        $this->checkImagePermission($image);
+        $pageSearch = $entityRepo->searchForImage($image->url);
+        return response()->json($pageSearch);
+    }
+
+    /**
+     * Deletes an image and all thumbnail/image files
+     * @param int $id
+     * @return \Illuminate\Http\JsonResponse
+     * @throws \Exception
+     */
+    public function destroy($id)
+    {
+        $image = $this->imageRepo->getById($id);
+        $this->checkOwnablePermission('image-delete', $image);
+        $this->checkImagePermission($image);
+
+        $this->imageRepo->destroyImage($image);
+        return response()->json(trans('components.images_deleted'));
+    }
+
+    /**
+     * Check related page permission and ensure type is drawio or gallery.
+     * @param Image $image
+     */
+    protected function checkImagePermission(Image $image)
+    {
+        if ($image->type !== 'drawio' && $image->type !== 'gallery') {
+            $this->showPermissionError();
+        }
+
+        $relatedPage = $image->getPage();
+        if ($relatedPage) {
+            $this->checkOwnablePermission('page-view', $relatedPage);
+        }
+    }
+}
diff --git a/app/Http/Controllers/SettingController.php b/app/Http/Controllers/SettingController.php
index 159e19a2b..650833c7f 100644
--- a/app/Http/Controllers/SettingController.php
+++ b/app/Http/Controllers/SettingController.php
@@ -1,6 +1,7 @@
 <?php namespace BookStack\Http\Controllers;
 
 use BookStack\Auth\User;
+use BookStack\Uploads\ImageRepo;
 use BookStack\Uploads\ImageService;
 use Illuminate\Http\Request;
 use Illuminate\Http\Response;
@@ -8,6 +9,19 @@ use Setting;
 
 class SettingController extends Controller
 {
+    protected $imageRepo;
+
+    /**
+     * SettingController constructor.
+     * @param $imageRepo
+     */
+    public function __construct(ImageRepo $imageRepo)
+    {
+        $this->imageRepo = $imageRepo;
+        parent::__construct();
+    }
+
+
     /**
      * Display a listing of the settings.
      * @return Response
@@ -35,6 +49,9 @@ class SettingController extends Controller
     {
         $this->preventAccessForDemoUsers();
         $this->checkPermission('settings-manage');
+        $this->validate($request, [
+            'app_logo' => $this->imageRepo->getImageValidationRules(),
+        ]);
 
         // Cycles through posted settings and update them
         foreach ($request->all() as $name => $value) {
@@ -42,7 +59,21 @@ class SettingController extends Controller
                 continue;
             }
             $key = str_replace('setting-', '', trim($name));
-            Setting::put($key, $value);
+            setting()->put($key, $value);
+        }
+
+        // Update logo image if set
+        if ($request->has('app_logo')) {
+            $logoFile = $request->file('app_logo');
+            $this->imageRepo->destroyByType('system');
+            $image = $this->imageRepo->saveNew($logoFile, 'system', 0, null, 86);
+            setting()->put('app-logo', $image->url);
+        }
+
+        // Clear logo image if requested
+        if ($request->get('app_logo_reset', null)) {
+            $this->imageRepo->destroyByType('system');
+            setting()->remove('app-logo');
         }
 
         session()->flash('success', trans('settings.settings_save_success'));
diff --git a/app/Http/Controllers/UserController.php b/app/Http/Controllers/UserController.php
index 1bb5d46cd..1367f631b 100644
--- a/app/Http/Controllers/UserController.php
+++ b/app/Http/Controllers/UserController.php
@@ -4,6 +4,7 @@ use BookStack\Auth\Access\SocialAuthService;
 use BookStack\Auth\User;
 use BookStack\Auth\UserRepo;
 use BookStack\Exceptions\UserUpdateException;
+use BookStack\Uploads\ImageRepo;
 use Illuminate\Http\Request;
 use Illuminate\Http\Response;
 
@@ -12,16 +13,19 @@ class UserController extends Controller
 
     protected $user;
     protected $userRepo;
+    protected $imageRepo;
 
     /**
      * UserController constructor.
-     * @param User     $user
+     * @param User $user
      * @param UserRepo $userRepo
+     * @param ImageRepo $imageRepo
      */
-    public function __construct(User $user, UserRepo $userRepo)
+    public function __construct(User $user, UserRepo $userRepo, ImageRepo $imageRepo)
     {
         $this->user = $user;
         $this->userRepo = $userRepo;
+        $this->imageRepo = $imageRepo;
         parent::__construct();
     }
 
@@ -107,9 +111,7 @@ class UserController extends Controller
      */
     public function edit($id, SocialAuthService $socialAuthService)
     {
-        $this->checkPermissionOr('users-manage', function () use ($id) {
-            return $this->currentUser->id == $id;
-        });
+        $this->checkPermissionOrCurrentUser('users-manage', $id);
 
         $user = $this->user->findOrFail($id);
 
@@ -123,24 +125,24 @@ class UserController extends Controller
 
     /**
      * Update the specified user in storage.
-     * @param  Request $request
-     * @param  int $id
+     * @param Request $request
+     * @param int $id
      * @return Response
      * @throws UserUpdateException
+     * @throws \BookStack\Exceptions\ImageUploadException
      */
     public function update(Request $request, $id)
     {
         $this->preventAccessForDemoUsers();
-        $this->checkPermissionOr('users-manage', function () use ($id) {
-            return $this->currentUser->id == $id;
-        });
+        $this->checkPermissionOrCurrentUser('users-manage', $id);
 
         $this->validate($request, [
             'name'             => 'min:2',
             'email'            => 'min:2|email|unique:users,email,' . $id,
             'password'         => 'min:5|required_with:password_confirm',
             'password-confirm' => 'same:password|required_with:password',
-            'setting'          => 'array'
+            'setting'          => 'array',
+            'profile_image'    => $this->imageRepo->getImageValidationRules(),
         ]);
 
         $user = $this->userRepo->getById($id);
@@ -170,10 +172,23 @@ class UserController extends Controller
             }
         }
 
+        // Save profile image if in request
+        if ($request->has('profile_image')) {
+            $imageUpload = $request->file('profile_image');
+            $this->imageRepo->destroyImage($user->avatar);
+            $image = $this->imageRepo->saveNew($imageUpload, 'user', $user->id);
+            $user->image_id = $image->id;
+        }
+
+        // Delete the profile image if set to
+        if ($request->has('profile_image_reset')) {
+            $this->imageRepo->destroyImage($user->avatar);
+        }
+
         $user->save();
         session()->flash('success', trans('settings.users_edit_success'));
 
-        $redirectUrl = userCan('users-manage') ? '/settings/users' : '/settings/users/' . $user->id;
+        $redirectUrl = userCan('users-manage') ? '/settings/users' : ('/settings/users/' . $user->id);
         return redirect($redirectUrl);
     }
 
@@ -184,9 +199,7 @@ class UserController extends Controller
      */
     public function delete($id)
     {
-        $this->checkPermissionOr('users-manage', function () use ($id) {
-            return $this->currentUser->id == $id;
-        });
+        $this->checkPermissionOrCurrentUser('users-manage', $id);
 
         $user = $this->userRepo->getById($id);
         $this->setPageTitle(trans('settings.users_delete_named', ['userName' => $user->name]));
@@ -202,9 +215,7 @@ class UserController extends Controller
     public function destroy($id)
     {
         $this->preventAccessForDemoUsers();
-        $this->checkPermissionOr('users-manage', function () use ($id) {
-            return $this->currentUser->id == $id;
-        });
+        $this->checkPermissionOrCurrentUser('users-manage', $id);
 
         $user = $this->userRepo->getById($id);
 
diff --git a/app/Uploads/Image.php b/app/Uploads/Image.php
index df6d9fb0d..6fa5db2a5 100644
--- a/app/Uploads/Image.php
+++ b/app/Uploads/Image.php
@@ -1,5 +1,6 @@
 <?php namespace BookStack\Uploads;
 
+use BookStack\Entities\Page;
 use BookStack\Ownable;
 use Images;
 
@@ -20,4 +21,14 @@ class Image extends Ownable
     {
         return Images::getThumbnail($this, $width, $height, $keepRatio);
     }
+
+    /**
+     * Get the page this image has been uploaded to.
+     * Only applicable to gallery or drawio image types.
+     * @return Page|null
+     */
+    public function getPage()
+    {
+        return $this->belongsTo(Page::class, 'uploaded_to')->first();
+    }
 }
diff --git a/app/Uploads/ImageRepo.php b/app/Uploads/ImageRepo.php
index 0ef8cad48..16d1bb3d1 100644
--- a/app/Uploads/ImageRepo.php
+++ b/app/Uploads/ImageRepo.php
@@ -2,6 +2,7 @@
 
 use BookStack\Auth\Permissions\PermissionService;
 use BookStack\Entities\Page;
+use Illuminate\Database\Eloquent\Builder;
 use Symfony\Component\HttpFoundation\File\UploadedFile;
 
 class ImageRepo
@@ -19,7 +20,12 @@ class ImageRepo
      * @param \BookStack\Auth\Permissions\PermissionService $permissionService
      * @param \BookStack\Entities\Page $page
      */
-    public function __construct(Image $image, ImageService $imageService, PermissionService $permissionService, Page $page)
+    public function __construct(
+        Image $image,
+        ImageService $imageService,
+        PermissionService $permissionService,
+        Page $page
+    )
     {
         $this->image = $image;
         $this->imageService = $imageService;
@@ -31,7 +37,7 @@ class ImageRepo
     /**
      * Get an image with the given id.
      * @param $id
-     * @return mixed
+     * @return Image
      */
     public function getById($id)
     {
@@ -44,95 +50,115 @@ class ImageRepo
      * @param $query
      * @param int $page
      * @param int $pageSize
+     * @param bool $filterOnPage
      * @return array
      */
-    private function returnPaginated($query, $page = 0, $pageSize = 24)
+    private function returnPaginated($query, $page = 1, $pageSize = 24)
     {
-        $images = $this->restrictionService->filterRelatedPages($query, 'images', 'uploaded_to');
-        $images = $images->orderBy('created_at', 'desc')->skip($pageSize * $page)->take($pageSize + 1)->get();
+        $images = $query->orderBy('created_at', 'desc')->skip($pageSize * ($page - 1))->take($pageSize + 1)->get();
         $hasMore = count($images) > $pageSize;
 
-        $returnImages = $images->take(24);
+        $returnImages = $images->take($pageSize);
         $returnImages->each(function ($image) {
             $this->loadThumbs($image);
         });
 
         return [
             'images'  => $returnImages,
-            'hasMore' => $hasMore
+            'has_more' => $hasMore
         ];
     }
 
     /**
-     * Gets a load images paginated, filtered by image type.
+     * Fetch a list of images in a paginated format, filtered by image type.
+     * Can be filtered by uploaded to and also by name.
      * @param string $type
      * @param int $page
      * @param int $pageSize
-     * @param bool|int $userFilter
+     * @param int $uploadedTo
+     * @param string|null $search
+     * @param callable|null $whereClause
      * @return array
      */
-    public function getPaginatedByType($type, $page = 0, $pageSize = 24, $userFilter = false)
+    public function getPaginatedByType(
+        string $type,
+        int $page = 0,
+        int $pageSize = 24,
+        int $uploadedTo = null,
+        string $search = null,
+        callable $whereClause = null
+    )
     {
-        $images = $this->image->where('type', '=', strtolower($type));
+        $imageQuery = $this->image->newQuery()->where('type', '=', strtolower($type));
 
-        if ($userFilter !== false) {
-            $images = $images->where('created_by', '=', $userFilter);
+        if ($uploadedTo !== null) {
+            $imageQuery = $imageQuery->where('uploaded_to', '=', $uploadedTo);
         }
 
-        return $this->returnPaginated($images, $page, $pageSize);
+        if ($search !== null) {
+            $imageQuery = $imageQuery->where('name', 'LIKE', '%' . $search . '%');
+        }
+
+        // Filter by page access
+        $imageQuery = $this->restrictionService->filterRelatedEntity('page', $imageQuery, 'images', 'uploaded_to');
+
+        if ($whereClause !== null) {
+            $imageQuery = $imageQuery->where($whereClause);
+        }
+
+        return $this->returnPaginated($imageQuery, $page, $pageSize);
     }
 
     /**
-     * Search for images by query, of a particular type.
+     * Get paginated gallery images within a specific page or book.
      * @param string $type
+     * @param string $filterType
      * @param int $page
      * @param int $pageSize
-     * @param string $searchTerm
+     * @param int|null $uploadedTo
+     * @param string|null $search
      * @return array
      */
-    public function searchPaginatedByType($type, $searchTerm, $page = 0, $pageSize = 24)
+    public function getEntityFiltered(
+        string $type,
+        string $filterType = null,
+        int $page = 0,
+        int $pageSize = 24,
+        int $uploadedTo = null,
+        string $search = null
+    )
     {
-        $images = $this->image->where('type', '=', strtolower($type))->where('name', 'LIKE', '%' . $searchTerm . '%');
-        return $this->returnPaginated($images, $page, $pageSize);
-    }
+        $contextPage = $this->page->findOrFail($uploadedTo);
+        $parentFilter = null;
 
-    /**
-     * Get gallery images with a particular filter criteria such as
-     * being within the current book or page.
-     * @param $filter
-     * @param $pageId
-     * @param int $pageNum
-     * @param int $pageSize
-     * @return array
-     */
-    public function getGalleryFiltered($filter, $pageId, $pageNum = 0, $pageSize = 24)
-    {
-        $images = $this->image->where('type', '=', 'gallery');
-
-        $page = $this->page->findOrFail($pageId);
-
-        if ($filter === 'page') {
-            $images = $images->where('uploaded_to', '=', $page->id);
-        } elseif ($filter === 'book') {
-            $validPageIds = $page->book->pages->pluck('id')->toArray();
-            $images = $images->whereIn('uploaded_to', $validPageIds);
+        if ($filterType === 'book' || $filterType === 'page') {
+            $parentFilter = function(Builder $query) use ($filterType, $contextPage) {
+                if ($filterType === 'page') {
+                    $query->where('uploaded_to', '=', $contextPage->id);
+                } elseif ($filterType === 'book') {
+                    $validPageIds = $contextPage->book->pages()->get(['id'])->pluck('id')->toArray();
+                    $query->whereIn('uploaded_to', $validPageIds);
+                }
+            };
         }
 
-        return $this->returnPaginated($images, $pageNum, $pageSize);
+        return $this->getPaginatedByType($type, $page, $pageSize, null, $search, $parentFilter);
     }
 
     /**
      * Save a new image into storage and return the new image.
      * @param UploadedFile $uploadFile
-     * @param  string $type
+     * @param string $type
      * @param int $uploadedTo
+     * @param int|null $resizeWidth
+     * @param int|null $resizeHeight
+     * @param bool $keepRatio
      * @return Image
      * @throws \BookStack\Exceptions\ImageUploadException
-     * @throws \Exception
      */
-    public function saveNew(UploadedFile $uploadFile, $type, $uploadedTo = 0)
+    public function saveNew(UploadedFile $uploadFile, $type, $uploadedTo = 0, int $resizeWidth = null, int $resizeHeight = null, bool $keepRatio = true)
     {
-        $image = $this->imageService->saveNewFromUpload($uploadFile, $type, $uploadedTo);
+        $image = $this->imageService->saveNewFromUpload($uploadFile, $type, $uploadedTo, $resizeWidth, $resizeHeight, $keepRatio);
         $this->loadThumbs($image);
         return $image;
     }
@@ -175,12 +201,27 @@ class ImageRepo
      * @return bool
      * @throws \Exception
      */
-    public function destroyImage(Image $image)
+    public function destroyImage(Image $image = null)
     {
-        $this->imageService->destroy($image);
+        if ($image) {
+            $this->imageService->destroy($image);
+        }
         return true;
     }
 
+    /**
+     * Destroy all images of a certain type.
+     * @param string $imageType
+     * @throws \Exception
+     */
+    public function destroyByType(string $imageType)
+    {
+        $images = $this->image->where('type', '=', $imageType)->get();
+        foreach ($images as $image) {
+            $this->destroyImage($image);
+        }
+    }
+
 
     /**
      * Load thumbnails onto an image object.
@@ -191,8 +232,8 @@ class ImageRepo
     protected function loadThumbs(Image $image)
     {
         $image->thumbs = [
-            'gallery' => $this->getThumbnail($image, 150, 150),
-            'display' => $this->getThumbnail($image, 840, 0, true)
+            'gallery' => $this->getThumbnail($image, 150, 150, false),
+            'display' => $this->getThumbnail($image, 840, null, true)
         ];
     }
 
@@ -208,7 +249,7 @@ class ImageRepo
      * @throws \BookStack\Exceptions\ImageUploadException
      * @throws \Exception
      */
-    public function getThumbnail(Image $image, $width = 220, $height = 220, $keepRatio = false)
+    protected function getThumbnail(Image $image, $width = 220, $height = 220, $keepRatio = false)
     {
         try {
             return $this->imageService->getThumbnail($image, $width, $height, $keepRatio);
@@ -232,13 +273,11 @@ class ImageRepo
     }
 
     /**
-     * Check if the provided image type is valid.
-     * @param $type
-     * @return bool
+     * Get the validation rules for image files.
+     * @return string
      */
-    public function isValidType($type)
+    public function getImageValidationRules()
     {
-        $validTypes = ['gallery', 'cover', 'system', 'user'];
-        return in_array($type, $validTypes);
+        return 'image_extension|no_double_extension|mimes:jpeg,png,gif,bmp,webp,tiff';
     }
 }
diff --git a/app/Uploads/ImageService.php b/app/Uploads/ImageService.php
index 1dd8b713d..eaf787c9c 100644
--- a/app/Uploads/ImageService.php
+++ b/app/Uploads/ImageService.php
@@ -9,6 +9,7 @@ use Illuminate\Contracts\Cache\Repository as Cache;
 use Illuminate\Contracts\Filesystem\Factory as FileSystem;
 use Intervention\Image\Exception\NotSupportedException;
 use Intervention\Image\ImageManager;
+use phpDocumentor\Reflection\Types\Integer;
 use Symfony\Component\HttpFoundation\File\UploadedFile;
 
 class ImageService extends UploadService
@@ -57,15 +58,30 @@ class ImageService extends UploadService
     /**
      * Saves a new image from an upload.
      * @param UploadedFile $uploadedFile
-     * @param  string $type
+     * @param string $type
      * @param int $uploadedTo
+     * @param int|null $resizeWidth
+     * @param int|null $resizeHeight
+     * @param bool $keepRatio
      * @return mixed
      * @throws ImageUploadException
      */
-    public function saveNewFromUpload(UploadedFile $uploadedFile, $type, $uploadedTo = 0)
+    public function saveNewFromUpload(
+        UploadedFile $uploadedFile,
+        string $type,
+        int $uploadedTo = 0,
+        int $resizeWidth = null,
+        int $resizeHeight = null,
+        bool $keepRatio = true
+    )
     {
         $imageName = $uploadedFile->getClientOriginalName();
         $imageData = file_get_contents($uploadedFile->getRealPath());
+
+        if ($resizeWidth !== null || $resizeHeight !== null) {
+            $imageData = $this->resizeImage($imageData, $resizeWidth, $resizeHeight, $keepRatio);
+        }
+
         return $this->saveNew($imageName, $imageData, $type, $uploadedTo);
     }
 
@@ -122,7 +138,7 @@ class ImageService extends UploadService
         $secureUploads = setting('app-secure-images');
         $imageName = str_replace(' ', '-', $imageName);
 
-        $imagePath = '/uploads/images/' . $type . '/' . Date('Y-m-M') . '/';
+        $imagePath = '/uploads/images/' . $type . '/' . Date('Y-m') . '/';
 
         while ($storage->exists($imagePath . $imageName)) {
             $imageName = str_random(3) . $imageName;
@@ -201,8 +217,28 @@ class ImageService extends UploadService
             return $this->getPublicUrl($thumbFilePath);
         }
 
+        $thumbData = $this->resizeImage($storage->get($imagePath), $width, $height, $keepRatio);
+
+        $storage->put($thumbFilePath, $thumbData);
+        $storage->setVisibility($thumbFilePath, 'public');
+        $this->cache->put('images-' . $image->id . '-' . $thumbFilePath, $thumbFilePath, 60 * 72);
+
+        return $this->getPublicUrl($thumbFilePath);
+    }
+
+    /**
+     * Resize image data.
+     * @param string $imageData
+     * @param int $width
+     * @param int $height
+     * @param bool $keepRatio
+     * @return string
+     * @throws ImageUploadException
+     */
+    protected function resizeImage(string $imageData, $width = 220, $height = null, bool $keepRatio = true)
+    {
         try {
-            $thumb = $this->imageTool->make($storage->get($imagePath));
+            $thumb = $this->imageTool->make($imageData);
         } catch (Exception $e) {
             if ($e instanceof \ErrorException || $e instanceof NotSupportedException) {
                 throw new ImageUploadException(trans('errors.cannot_create_thumbs'));
@@ -211,20 +247,14 @@ class ImageService extends UploadService
         }
 
         if ($keepRatio) {
-            $thumb->resize($width, null, function ($constraint) {
+            $thumb->resize($width, $height, function ($constraint) {
                 $constraint->aspectRatio();
                 $constraint->upsize();
             });
         } else {
             $thumb->fit($width, $height);
         }
-
-        $thumbData = (string)$thumb->encode();
-        $storage->put($thumbFilePath, $thumbData);
-        $storage->setVisibility($thumbFilePath, 'public');
-        $this->cache->put('images-' . $image->id . '-' . $thumbFilePath, $thumbFilePath, 60 * 72);
-
-        return $this->getPublicUrl($thumbFilePath);
+        return (string)$thumb->encode();
     }
 
     /**
@@ -306,6 +336,7 @@ class ImageService extends UploadService
         $image = $this->saveNewFromUrl($userAvatarUrl, 'user', $imageName);
         $image->created_by = $user->id;
         $image->updated_by = $user->id;
+        $image->uploaded_to = $user->id;
         $image->save();
 
         return $image;
diff --git a/resources/assets/js/components/image-picker.js b/resources/assets/js/components/image-picker.js
index 7cbed4509..7455fa622 100644
--- a/resources/assets/js/components/image-picker.js
+++ b/resources/assets/js/components/image-picker.js
@@ -4,54 +4,50 @@ class ImagePicker {
     constructor(elem) {
         this.elem = elem;
         this.imageElem = elem.querySelector('img');
-        this.input = elem.querySelector('input');
+        this.imageInput = elem.querySelector('input[type=file]');
+        this.resetInput = elem.querySelector('input[data-reset-input]');
+        this.removeInput = elem.querySelector('input[data-remove-input]');
 
-        this.isUsingIds = elem.getAttribute('data-current-id') !== '';
-        this.isResizing = elem.getAttribute('data-resize-height') && elem.getAttribute('data-resize-width');
-        this.isResizeCropping = elem.getAttribute('data-resize-crop') !== '';
+        this.defaultImage = elem.getAttribute('data-default-image');
 
-        let selectButton = elem.querySelector('button[data-action="show-image-manager"]');
-        selectButton.addEventListener('click', this.selectImage.bind(this));
-
-        let resetButton = elem.querySelector('button[data-action="reset-image"]');
+        const resetButton = elem.querySelector('button[data-action="reset-image"]');
         resetButton.addEventListener('click', this.reset.bind(this));
 
-        let removeButton = elem.querySelector('button[data-action="remove-image"]');
+        const removeButton = elem.querySelector('button[data-action="remove-image"]');
         if (removeButton) {
             removeButton.addEventListener('click', this.removeImage.bind(this));
         }
+
+        this.imageInput.addEventListener('change', this.fileInputChange.bind(this));
     }
 
-    selectImage() {
-        window.ImageManager.show(image => {
-            if (!this.isResizing) {
-                this.setImage(image);
-                return;
-            }
+    fileInputChange() {
+        this.resetInput.setAttribute('disabled', 'disabled');
+        if (this.removeInput) {
+            this.removeInput.setAttribute('disabled', 'disabled');
+        }
 
-            let requestString = '/images/thumb/' + image.id + '/' + this.elem.getAttribute('data-resize-width') + '/' + this.elem.getAttribute('data-resize-height') + '/' + (this.isResizeCropping ? 'true' : 'false');
-
-            window.$http.get(window.baseUrl(requestString)).then(resp => {
-                image.url = resp.data.url;
-                this.setImage(image);
-            });
-        });
+        for (let file of this.imageInput.files) {
+            this.imageElem.src = window.URL.createObjectURL(file);
+        }
+        this.imageElem.classList.remove('none');
     }
 
     reset() {
-        this.setImage({id: 0, url: this.elem.getAttribute('data-default-image')});
-    }
-
-    setImage(image) {
-        this.imageElem.src = image.url;
-        this.input.value = this.isUsingIds ? image.id : image.url;
+        this.imageInput.value = '';
+        this.imageElem.src = this.defaultImage;
+        this.resetInput.removeAttribute('disabled');
+        if (this.removeInput) {
+            this.removeInput.setAttribute('disabled', 'disabled');
+        }
         this.imageElem.classList.remove('none');
     }
 
     removeImage() {
-        this.imageElem.src = this.elem.getAttribute('data-default-image');
+        this.imageInput.value = '';
         this.imageElem.classList.add('none');
-        this.input.value = 'none';
+        this.removeInput.removeAttribute('disabled');
+        this.resetInput.setAttribute('disabled', 'disabled');
     }
 
 }
diff --git a/resources/assets/js/components/markdown-editor.js b/resources/assets/js/components/markdown-editor.js
index 55cf67813..b099a7ca9 100644
--- a/resources/assets/js/components/markdown-editor.js
+++ b/resources/assets/js/components/markdown-editor.js
@@ -394,9 +394,7 @@ class MarkdownEditor {
         const drawingId = imgContainer.getAttribute('drawio-diagram');
 
         DrawIO.show(() => {
-            return window.$http.get(window.baseUrl(`/images/base64/${drawingId}`)).then(resp => {
-                return `data:image/png;base64,${resp.data.content}`;
-            });
+            return DrawIO.load(drawingId);
         }, (pngData) => {
 
             let data = {
diff --git a/resources/assets/js/components/wysiwyg-editor.js b/resources/assets/js/components/wysiwyg-editor.js
index ce5cfbf4e..b894c3fa6 100644
--- a/resources/assets/js/components/wysiwyg-editor.js
+++ b/resources/assets/js/components/wysiwyg-editor.js
@@ -257,39 +257,38 @@ function drawIoPlugin() {
         DrawIO.show(drawingInit, updateContent);
     }
 
-    function updateContent(pngData) {
-        let id = "image-" + Math.random().toString(16).slice(2);
-        let loadingImage = window.baseUrl('/loading.gif');
-        let data = {
-            image: pngData,
-            uploaded_to: Number(document.getElementById('page-editor').getAttribute('page-id'))
-        };
+    async function updateContent(pngData) {
+        const id = "image-" + Math.random().toString(16).slice(2);
+        const loadingImage = window.baseUrl('/loading.gif');
+        const pageId = Number(document.getElementById('page-editor').getAttribute('page-id'));
 
         // Handle updating an existing image
         if (currentNode) {
             DrawIO.close();
             let imgElem = currentNode.querySelector('img');
-            window.$http.post(window.baseUrl(`/images/drawing/upload`), data).then(resp => {
-                pageEditor.dom.setAttrib(imgElem, 'src', resp.data.url);
-                pageEditor.dom.setAttrib(currentNode, 'drawio-diagram', resp.data.id);
-            }).catch(err => {
+            try {
+                const img = await DrawIO.upload(pngData, pageId);
+                pageEditor.dom.setAttrib(imgElem, 'src', img.url);
+                pageEditor.dom.setAttrib(currentNode, 'drawio-diagram', img.id);
+            } catch (err) {
                 window.$events.emit('error', trans('errors.image_upload_error'));
                 console.log(err);
-            });
+            }
             return;
         }
 
-        setTimeout(() => {
+        setTimeout(async () => {
             pageEditor.insertContent(`<div drawio-diagram contenteditable="false"><img src="${loadingImage}" id="${id}"></div>`);
             DrawIO.close();
-            window.$http.post(window.baseUrl('/images/drawing/upload'), data).then(resp => {
-                pageEditor.dom.setAttrib(id, 'src', resp.data.url);
-                pageEditor.dom.get(id).parentNode.setAttribute('drawio-diagram', resp.data.id);
-            }).catch(err => {
+            try {
+                const img = await DrawIO.upload(pngData, pageId);
+                pageEditor.dom.setAttrib(id, 'src', img.url);
+                pageEditor.dom.get(id).parentNode.setAttribute('drawio-diagram', img.id);
+            } catch (err) {
                 pageEditor.dom.remove(id);
                 window.$events.emit('error', trans('errors.image_upload_error'));
                 console.log(err);
-            });
+            }
         }, 5);
     }
 
@@ -300,9 +299,7 @@ function drawIoPlugin() {
         }
 
         let drawingId = currentNode.getAttribute('drawio-diagram');
-        return window.$http.get(window.baseUrl(`/images/base64/${drawingId}`)).then(resp => {
-            return `data:image/png;base64,${resp.data.content}`;
-        });
+        return DrawIO.load(drawingId);
     }
 
     window.tinymce.PluginManager.add('drawio', function(editor, url) {
diff --git a/resources/assets/js/services/drawio.js b/resources/assets/js/services/drawio.js
index b4fcfd59f..a570737d1 100644
--- a/resources/assets/js/services/drawio.js
+++ b/resources/assets/js/services/drawio.js
@@ -66,4 +66,23 @@ function drawPostMessage(data) {
     iFrame.contentWindow.postMessage(JSON.stringify(data), '*');
 }
 
-export default {show, close};
\ No newline at end of file
+async function upload(imageData, pageUploadedToId) {
+    let data = {
+        image: imageData,
+        uploaded_to: pageUploadedToId,
+    };
+    const resp = await window.$http.post(window.baseUrl(`/images/drawio`), data);
+    return resp.data;
+}
+
+/**
+ * Load an existing image, by fetching it as Base64 from the system.
+ * @param drawingId
+ * @returns {Promise<string>}
+ */
+async function load(drawingId) {
+    const resp = await window.$http.get(window.baseUrl(`/images/drawio/base64/${drawingId}`));
+    return `data:image/png;base64,${resp.data.content}`;
+}
+
+export default {show, close, upload, load};
\ No newline at end of file
diff --git a/resources/assets/js/vues/image-manager.js b/resources/assets/js/vues/image-manager.js
index 6bfc2662d..dd1d9d17a 100644
--- a/resources/assets/js/vues/image-manager.js
+++ b/resources/assets/js/vues/image-manager.js
@@ -1,7 +1,7 @@
 import * as Dates from "../services/dates";
 import dropzone from "./components/dropzone";
 
-let page = 0;
+let page = 1;
 let previousClickTime = 0;
 let previousClickImage = 0;
 let dataLoaded = false;
@@ -20,7 +20,7 @@ const data = {
     selectedImage: false,
     dependantPages: false,
     showing: false,
-    view: 'all',
+    filter: null,
     hasMore: false,
     searching: false,
     searchTerm: '',
@@ -56,32 +56,37 @@ const methods = {
         this.$el.children[0].components.overlay.hide();
     },
 
-    fetchData() {
-        let url = baseUrl + page;
-        let query = {};
-        if (this.uploadedTo !== false) query.page_id = this.uploadedTo;
-        if (this.searching) query.term = this.searchTerm;
+    async fetchData() {
+        let query = {
+            page,
+            search: this.searching ? this.searchTerm : null,
+            uploaded_to: this.uploadedTo || null,
+            filter_type: this.filter,
+        };
 
-        this.$http.get(url, {params: query}).then(response => {
-            this.images = this.images.concat(response.data.images);
-            this.hasMore = response.data.hasMore;
-            page++;
-        });
+        const {data} = await this.$http.get(baseUrl, {params: query});
+        this.images = this.images.concat(data.images);
+        this.hasMore = data.has_more;
+        page++;
     },
 
-    setView(viewName) {
-        this.view = viewName;
+    setFilterType(filterType) {
+        this.filter = filterType;
         this.resetState();
         this.fetchData();
     },
 
     resetState() {
         this.cancelSearch();
+        this.resetListView();
+        this.deleteConfirm = false;
+        baseUrl = window.baseUrl(`/images/${this.imageType}`);
+    },
+
+    resetListView() {
         this.images = [];
         this.hasMore = false;
-        this.deleteConfirm = false;
-        page = 0;
-        baseUrl = window.baseUrl(`/images/${this.imageType}/${this.view}/`);
+        page = 1;
     },
 
     searchImages() {
@@ -94,10 +99,7 @@ const methods = {
         }
 
         this.searching = true;
-        this.images = [];
-        this.hasMore = false;
-        page = 0;
-        baseUrl = window.baseUrl(`/images/${this.imageType}/search/`);
+        this.resetListView();
         this.fetchData();
     },
 
@@ -110,10 +112,10 @@ const methods = {
     },
 
     imageSelect(image) {
-        let dblClickTime = 300;
-        let currentTime = Date.now();
-        let timeDiff = currentTime - previousClickTime;
-        let isDblClick = timeDiff < dblClickTime && image.id === previousClickImage;
+        const dblClickTime = 300;
+        const currentTime = Date.now();
+        const timeDiff = currentTime - previousClickTime;
+        const isDblClick = timeDiff < dblClickTime && image.id === previousClickImage;
 
         if (isDblClick) {
             this.callbackAndHide(image);
@@ -132,11 +134,11 @@ const methods = {
         this.hide();
     },
 
-    saveImageDetails() {
-        let url = window.baseUrl(`/images/update/${this.selectedImage.id}`);
-        this.$http.put(url, this.selectedImage).then(response => {
-            this.$events.emit('success', trans('components.image_update_success'));
-        }).catch(error => {
+    async saveImageDetails() {
+        let url = window.baseUrl(`/images/${this.selectedImage.id}`);
+        try {
+            await this.$http.put(url, this.selectedImage)
+        } catch (error) {
             if (error.response.status === 422) {
                 let errors = error.response.data;
                 let message = '';
@@ -145,27 +147,29 @@ const methods = {
                 });
                 this.$events.emit('error', message);
             }
-        });
+        }
     },
 
-    deleteImage() {
+    async deleteImage() {
 
         if (!this.deleteConfirm) {
-            let url = window.baseUrl(`/images/usage/${this.selectedImage.id}`);
-            this.$http.get(url).then(resp => {
-                this.dependantPages = resp.data;
-            }).catch(console.error).then(() => {
-                this.deleteConfirm = true;
-            });
+            const url = window.baseUrl(`/images/usage/${this.selectedImage.id}`);
+            try {
+                const {data} = await this.$http.get(url);
+                this.dependantPages = data;
+            } catch (error) {
+                console.error(error);
+            }
+            this.deleteConfirm = true;
             return;
         }
-        let url = window.baseUrl(`/images/${this.selectedImage.id}`);
-        this.$http.delete(url).then(resp => {
-            this.images.splice(this.images.indexOf(this.selectedImage), 1);
-            this.selectedImage = false;
-            this.$events.emit('success', trans('components.image_delete_success'));
-            this.deleteConfirm = false;
-        });
+
+        const url = window.baseUrl(`/images/${this.selectedImage.id}`);
+        await this.$http.delete(url);
+        this.images.splice(this.images.indexOf(this.selectedImage), 1);
+        this.selectedImage = false;
+        this.$events.emit('success', trans('components.image_delete_success'));
+        this.deleteConfirm = false;
     },
 
     getDate(stringDate) {
@@ -180,7 +184,7 @@ const methods = {
 
 const computed = {
     uploadUrl() {
-        return window.baseUrl(`/images/${this.imageType}/upload`);
+        return window.baseUrl(`/images/${this.imageType}`);
     }
 };
 
@@ -188,7 +192,7 @@ function mounted() {
     window.ImageManager = this;
     this.imageType = this.$el.getAttribute('image-type');
     this.uploadedTo = this.$el.getAttribute('uploaded-to');
-    baseUrl = window.baseUrl('/images/' + this.imageType + '/all/')
+    baseUrl = window.baseUrl('/images/' + this.imageType)
 }
 
 export default {
diff --git a/resources/assets/sass/_forms.scss b/resources/assets/sass/_forms.scss
index f40c92a19..48f4a902e 100644
--- a/resources/assets/sass/_forms.scss
+++ b/resources/assets/sass/_forms.scss
@@ -251,7 +251,7 @@ input[type=date] {
 }
 
 .form-group {
-  .text-pos, .text-neg {
+  div.text-pos, div.text-neg, p.text-post, p.text-neg {
     padding: $-xs 0;
   }
 }
diff --git a/resources/assets/sass/_layout.scss b/resources/assets/sass/_layout.scss
index 137048935..9bb4e1c70 100644
--- a/resources/assets/sass/_layout.scss
+++ b/resources/assets/sass/_layout.scss
@@ -140,6 +140,10 @@ body.flexbox {
   display: inline-block;
 }
 
+.hidden {
+  display: none;
+}
+
 .float {
   float: left;
   &.right {
diff --git a/resources/lang/en/validation.php b/resources/lang/en/validation.php
index 9baeb9f30..210980ac2 100644
--- a/resources/lang/en/validation.php
+++ b/resources/lang/en/validation.php
@@ -71,6 +71,7 @@ return [
     'timezone'             => 'The :attribute must be a valid zone.',
     'unique'               => 'The :attribute has already been taken.',
     'url'                  => 'The :attribute format is invalid.',
+    'uploaded'             => 'The file could not be uploaded. The server may not accept files of this size.',
 
     // Custom validation lines
     'custom' => [
diff --git a/resources/views/books/create.blade.php b/resources/views/books/create.blade.php
index 882ce556a..40b781441 100644
--- a/resources/views/books/create.blade.php
+++ b/resources/views/books/create.blade.php
@@ -33,5 +33,4 @@
         </div>
     </div>
 
-    @include('components.image-manager', ['imageType' => 'cover'])
 @stop
\ No newline at end of file
diff --git a/resources/views/books/edit.blade.php b/resources/views/books/edit.blade.php
index f048b543b..2e51ed6e9 100644
--- a/resources/views/books/edit.blade.php
+++ b/resources/views/books/edit.blade.php
@@ -16,12 +16,10 @@
 
         <div class="content-wrap card">
             <h1 class="list-heading">{{ trans('entities.books_edit') }}</h1>
-            <form action="{{ $book->getUrl() }}" method="POST">
+            <form action="{{ $book->getUrl() }}" method="POST" enctype="multipart/form-data">
                 <input type="hidden" name="_method" value="PUT">
                 @include('books.form', ['model' => $book])
             </form>
         </div>
     </div>
-
-    @include('components.image-manager', ['imageType' => 'cover'])
 @stop
\ No newline at end of file
diff --git a/resources/views/books/form.blade.php b/resources/views/books/form.blade.php
index ebbc279fd..4edec240a 100644
--- a/resources/views/books/form.blade.php
+++ b/resources/views/books/form.blade.php
@@ -18,13 +18,9 @@
         <p class="small">{{ trans('common.cover_image_description') }}</p>
 
         @include('components.image-picker', [
-            'resizeHeight' => '512',
-            'resizeWidth' => '512',
-            'showRemove' => false,
             'defaultImage' => baseUrl('/book_default_cover.png'),
-            'currentImage' => isset($model) ? $model->getBookCover() : baseUrl('/book_default_cover.png') ,
-            'currentId' => isset($model) && $model->image_id ? $model->image_id : 0,
-            'name' => 'image_id',
+            'currentImage' => (isset($model) && $model->cover) ? $model->getBookCover() : baseUrl('/book_default_cover.png') ,
+            'name' => 'image',
             'imageClass' => 'cover'
         ])
     </div>
diff --git a/resources/views/components/image-manager.blade.php b/resources/views/components/image-manager.blade.php
index df577b545..7c9084ad1 100644
--- a/resources/views/components/image-manager.blade.php
+++ b/resources/views/components/image-manager.blade.php
@@ -10,12 +10,12 @@
             <div class="flex-fill image-manager-body">
 
                 <div class="image-manager-content">
-                    <div v-if="imageType === 'gallery'" class="image-manager-header primary-background-light nav-tabs grid third">
-                        <div class="tab-item" title="{{ trans('components.image_all_title') }}" :class="{selected: (view=='all')}" @click="setView('all')">@icon('images') {{ trans('components.image_all') }}</div>
-                        <div class="tab-item" title="{{ trans('components.image_book_title') }}" :class="{selected: (view=='book')}" @click="setView('book')">@icon('book', ['class' => 'text-book svg-icon']) {{ trans('entities.book') }}</div>
-                        <div class="tab-item" title="{{ trans('components.image_page_title') }}" :class="{selected: (view=='page')}" @click="setView('page')">@icon('page', ['class' => 'text-page svg-icon']) {{ trans('entities.page') }}</div>
+                    <div v-if="imageType === 'gallery' || imageType === 'drawio'" class="image-manager-header primary-background-light nav-tabs grid third">
+                        <div class="tab-item" title="{{ trans('components.image_all_title') }}" :class="{selected: !filter}" @click="setFilterType(null)">@icon('images') {{ trans('components.image_all') }}</div>
+                        <div class="tab-item" title="{{ trans('components.image_book_title') }}" :class="{selected: (filter=='book')}" @click="setFilterType('book')">@icon('book', ['class' => 'text-book svg-icon']) {{ trans('entities.book') }}</div>
+                        <div class="tab-item" title="{{ trans('components.image_page_title') }}" :class="{selected: (filter=='page')}" @click="setFilterType('page')">@icon('page', ['class' => 'text-page svg-icon']) {{ trans('entities.page') }}</div>
                     </div>
-                    <div v-show="view === 'all'" >
+                    <div>
                         <form @submit.prevent="searchImages" class="contained-search-box">
                             <input placeholder="{{ trans('components.image_search_hint') }}" v-model="searchTerm">
                             <button :class="{active: searching}" title="{{ trans('common.search_clear') }}" type="button" @click="cancelSearch()" class="text-button cancel">@icon('close')</button>
@@ -63,7 +63,7 @@
                                     <button type="button" class="button icon outline" @click="deleteImage">@icon('delete')</button>
 
                                 </div>
-                                <button class="button anim fadeIn float right" v-show="selectedImage" @click="callbackAndHide(selectedImage)">
+                                <button class="button primary anim fadeIn float right" v-show="selectedImage" @click="callbackAndHide(selectedImage)">
                                     {{ trans('components.image_select_image') }}
                                 </button>
                                 <div class="clearfix"></div>
diff --git a/resources/views/components/image-picker.blade.php b/resources/views/components/image-picker.blade.php
index e7c74c786..73885aeb4 100644
--- a/resources/views/components/image-picker.blade.php
+++ b/resources/views/components/image-picker.blade.php
@@ -1,20 +1,32 @@
-<div class="image-picker" image-picker="{{$name}}" data-default-image="{{ $defaultImage }}" data-resize-height="{{ $resizeHeight }}" data-resize-width="{{ $resizeWidth }}" data-current-id="{{ $currentId ?? '' }}" data-resize-crop="{{ $resizeCrop ?? '' }}">
+<div class="image-picker @if($errors->has($name)) has-error @endif"
+     image-picker="{{$name}}"
+     data-default-image="{{ $defaultImage }}">
 
     <div class="grid half">
         <div class="text-center">
             <img @if($currentImage && $currentImage !== 'none') src="{{$currentImage}}" @else src="{{$defaultImage}}" @endif  class="{{$imageClass}} @if($currentImage=== 'none') none @endif" alt="{{ trans('components.image_preview') }}">
         </div>
         <div class="text-center">
-            <button class="button outline small" type="button" data-action="show-image-manager">{{ trans('components.image_select_image') }}</button>
+
+            <label for="{{ $name }}" class="button outline">{{ trans('components.image_select_image') }}</label>
+            <input type="file" class="hidden" accept="image/*" name="{{ $name }}" id="{{ $name }}">
+            <input type="hidden" data-reset-input name="{{ $name }}_reset" value="true" disabled="disabled">
+            @if(isset($removeName))
+                <input type="hidden" data-remove-input name="{{ $removeName }}" value="{{ $removeValue }}" disabled="disabled">
+            @endif
+
             <br>
             <button class="text-button text-muted" data-action="reset-image" type="button">{{ trans('common.reset') }}</button>
 
-            @if ($showRemove)
+            @if(isset($removeName))
                 <span class="sep">|</span>
                 <button class="text-button text-muted" data-action="remove-image" type="button">{{ trans('common.remove') }}</button>
             @endif
         </div>
     </div>
 
-    <input type="hidden" name="{{$name}}" id="{{$name}}" value="{{ isset($currentId) && ($currentId !== 0 && $currentId !== false) ? $currentId : $currentImage}}">
+    @if($errors->has($name))
+        <div class="text-neg text-small">{{ $errors->first($name) }}</div>
+    @endif
+
 </div>
\ No newline at end of file
diff --git a/resources/views/settings/index.blade.php b/resources/views/settings/index.blade.php
index 582bb078e..2dabe9dec 100644
--- a/resources/views/settings/index.blade.php
+++ b/resources/views/settings/index.blade.php
@@ -79,7 +79,7 @@
 
         <div class="card content-wrap auto-height">
             <h2 class="list-heading">{{ trans('settings.app_customization') }}</h2>
-            <form action="{{ baseUrl("/settings") }}" method="POST">
+            <form action="{{ baseUrl("/settings") }}" method="POST" enctype="multipart/form-data">
                 {!! csrf_field() !!}
 
                 <div class="setting-list">
@@ -119,14 +119,12 @@
                         </div>
                         <div>
                             @include('components.image-picker', [
-                                     'resizeHeight' => '43',
-                                     'resizeWidth' => '200',
-                                     'showRemove' => true,
+                                     'removeName' => 'setting-app-logo',
+                                     'removeValue' => 'none',
                                      'defaultImage' => baseUrl('/logo.png'),
                                      'currentImage' => setting('app-logo'),
-                                     'name' => 'setting-app-logo',
+                                     'name' => 'app_logo',
                                      'imageClass' => 'logo-image',
-                                     'currentId' => false
                                  ])
                         </div>
                     </div>
diff --git a/resources/views/shelves/create.blade.php b/resources/views/shelves/create.blade.php
index 72bf904fe..706e15d07 100644
--- a/resources/views/shelves/create.blade.php
+++ b/resources/views/shelves/create.blade.php
@@ -26,6 +26,4 @@
 
     </div>
 
-    @include('components.image-manager', ['imageType' => 'cover'])
-
 @stop
\ No newline at end of file
diff --git a/resources/views/shelves/edit.blade.php b/resources/views/shelves/edit.blade.php
index 8b99e8b51..8c2cd4f45 100644
--- a/resources/views/shelves/edit.blade.php
+++ b/resources/views/shelves/edit.blade.php
@@ -16,12 +16,11 @@
 
         <div class="card content-wrap">
             <h1 class="list-heading">{{ trans('entities.shelves_edit') }}</h1>
-            <form action="{{ $shelf->getUrl() }}" method="POST">
+            <form action="{{ $shelf->getUrl() }}" method="POST" enctype="multipart/form-data">
                 <input type="hidden" name="_method" value="PUT">
                 @include('shelves.form', ['model' => $shelf])
             </form>
         </div>
     </div>
 
-    @include('components.image-manager', ['imageType' => 'cover'])
 @stop
\ No newline at end of file
diff --git a/resources/views/shelves/form.blade.php b/resources/views/shelves/form.blade.php
index 8a270a894..4191f421d 100644
--- a/resources/views/shelves/form.blade.php
+++ b/resources/views/shelves/form.blade.php
@@ -53,13 +53,9 @@
         <p class="small">{{ trans('common.cover_image_description') }}</p>
 
         @include('components.image-picker', [
-            'resizeHeight' => '512',
-            'resizeWidth' => '512',
-            'showRemove' => false,
             'defaultImage' => baseUrl('/book_default_cover.png'),
-            'currentImage' => isset($shelf) ? $shelf->getBookCover() : baseUrl('/book_default_cover.png') ,
-            'currentId' => isset($shelf) && $shelf->image_id ? $shelf->image_id : 0,
-            'name' => 'image_id',
+            'currentImage' => (isset($shelf) && $shelf->cover) ? $shelf->getBookCover() : baseUrl('/book_default_cover.png') ,
+            'name' => 'image',
             'imageClass' => 'cover'
         ])
     </div>
diff --git a/resources/views/users/edit.blade.php b/resources/views/users/edit.blade.php
index b9ad052c7..377500193 100644
--- a/resources/views/users/edit.blade.php
+++ b/resources/views/users/edit.blade.php
@@ -9,7 +9,7 @@
 
         <div class="card content-wrap">
             <h1 class="list-heading">{{ $user->id === $currentUser->id ? trans('settings.users_edit_profile') : trans('settings.users_edit') }}</h1>
-            <form action="{{ baseUrl("/settings/users/{$user->id}") }}" method="post">
+            <form action="{{ baseUrl("/settings/users/{$user->id}") }}" method="post" enctype="multipart/form-data">
                 {!! csrf_field() !!}
                 <input type="hidden" name="_method" value="PUT">
 
@@ -29,7 +29,7 @@
                                 'defaultImage' => baseUrl('/user_avatar.png'),
                                 'currentImage' => $user->getAvatar(80),
                                 'currentId' => $user->image_id,
-                                'name' => 'image_id',
+                                'name' => 'profile_image',
                                 'imageClass' => 'avatar large'
                             ])
                         </div>
@@ -87,5 +87,4 @@
         @endif
     </div>
 
-    @include('components.image-manager', ['imageType' => 'user'])
 @stop
diff --git a/routes/web.php b/routes/web.php
index 695f61654..25d7ab692 100644
--- a/routes/web.php
+++ b/routes/web.php
@@ -6,7 +6,8 @@ Route::get('/robots.txt', 'HomeController@getRobots');
 // Authenticated routes...
 Route::group(['middleware' => 'auth'], function () {
 
-    Route::get('/uploads/images/{path}', 'ImageController@showImage')
+    // Secure images routing
+    Route::get('/uploads/images/{path}', 'Images\ImageController@showImage')
         ->where('path', '.*$');
 
     Route::group(['prefix' => 'pages'], function() {
@@ -103,22 +104,21 @@ Route::group(['middleware' => 'auth'], function () {
     Route::get('/user/{userId}', 'UserController@showProfilePage');
 
     // Image routes
-    Route::group(['prefix' => 'images'], function() {
-        // Get for user images
-        Route::get('/user/all', 'ImageController@getAllForUserType');
-        Route::get('/user/all/{page}', 'ImageController@getAllForUserType');
-        // Standard get, update and deletion for all types
-        Route::get('/thumb/{id}/{width}/{height}/{crop}', 'ImageController@getThumbnail');
-        Route::get('/base64/{id}', 'ImageController@getBase64Image');
-        Route::put('/update/{imageId}', 'ImageController@update');
-        Route::post('/drawing/upload', 'ImageController@uploadDrawing');
-        Route::get('/usage/{id}', 'ImageController@usage');
-        Route::post('/{type}/upload', 'ImageController@uploadByType');
-        Route::get('/{type}/all', 'ImageController@getAllByType');
-        Route::get('/{type}/all/{page}', 'ImageController@getAllByType');
-        Route::get('/{type}/search/{page}', 'ImageController@searchByType');
-        Route::get('/gallery/{filter}/{page}', 'ImageController@getGalleryFiltered');
-        Route::delete('/{id}', 'ImageController@destroy');
+    Route::group(['prefix' => 'images'], function () {
+
+        // Gallery
+        Route::get('/gallery', 'Images\GalleryImageController@list');
+        Route::post('/gallery', 'Images\GalleryImageController@create');
+
+        // Drawio
+        Route::get('/drawio', 'Images\DrawioImageController@list');
+        Route::get('/drawio/base64/{id}', 'Images\DrawioImageController@getAsBase64');
+        Route::post('/drawio', 'Images\DrawioImageController@create');
+
+        // Shared gallery & draw.io endpoint
+        Route::get('/usage/{id}', 'Images\ImageController@usage');
+        Route::put('/{id}', 'Images\ImageController@update');
+        Route::delete('/{id}', 'Images\ImageController@destroy');
     });
 
     // Attachments routes
diff --git a/tests/Uploads/ImageTest.php b/tests/Uploads/ImageTest.php
index 8373a809c..01bf23d5b 100644
--- a/tests/Uploads/ImageTest.php
+++ b/tests/Uploads/ImageTest.php
@@ -17,14 +17,10 @@ class ImageTest extends TestCase
         $admin = $this->getAdmin();
         $this->actingAs($admin);
 
-        $imageName = 'first-image.png';
-        $relPath = $this->getTestImagePath('gallery', $imageName);
-        $this->deleteImage($relPath);
+        $imgDetails = $this->uploadGalleryImage($page);
+        $relPath = $imgDetails['path'];
 
-        $upload = $this->uploadImage($imageName, $page->id);
-        $upload->assertStatus(200);
-
-        $this->assertTrue(file_exists(public_path($relPath)), 'Uploaded image not found at path: '. public_path($relPath));
+        $this->assertTrue(file_exists(public_path($relPath)), 'Uploaded image found at path: '. public_path($relPath));
 
         $this->deleteImage($relPath);
 
@@ -35,10 +31,93 @@ class ImageTest extends TestCase
             'path' => $relPath,
             'created_by' => $admin->id,
             'updated_by' => $admin->id,
-            'name' => $imageName
+            'name' => $imgDetails['name'],
         ]);
     }
 
+    public function test_image_edit()
+    {
+        $editor = $this->getEditor();
+        $this->actingAs($editor);
+
+        $imgDetails = $this->uploadGalleryImage();
+        $image = Image::query()->first();
+
+        $newName = str_random();
+        $update = $this->put('/images/' . $image->id, ['name' => $newName]);
+        $update->assertSuccessful();
+        $update->assertJson([
+            'id' => $image->id,
+            'name' => $newName,
+            'type' => 'gallery',
+        ]);
+
+        $this->deleteImage($imgDetails['path']);
+
+        $this->assertDatabaseHas('images', [
+            'type' => 'gallery',
+            'name' => $newName
+        ]);
+    }
+
+    public function test_gallery_get_list_format()
+    {
+        $this->asEditor();
+
+        $imgDetails = $this->uploadGalleryImage();
+        $image = Image::query()->first();
+
+        $emptyJson = ['images' => [], 'has_more' => false];
+        $resultJson = [
+            'images' => [
+                [
+                    'id' => $image->id,
+                    'name' => $imgDetails['name'],
+                ]
+            ],
+            'has_more' => false,
+        ];
+
+        $pageId = $imgDetails['page']->id;
+        $firstPageRequest = $this->get("/images/gallery?page=1&uploaded_to={$pageId}");
+        $firstPageRequest->assertSuccessful()->assertJson($resultJson);
+
+        $secondPageRequest = $this->get("/images/gallery?page=2&uploaded_to={$pageId}");
+        $secondPageRequest->assertSuccessful()->assertExactJson($emptyJson);
+
+        $namePartial = substr($imgDetails['name'], 0, 3);
+        $searchHitRequest = $this->get("/images/gallery?page=1&uploaded_to={$pageId}&search={$namePartial}");
+        $searchHitRequest->assertSuccessful()->assertJson($resultJson);
+
+        $namePartial = str_random(16);
+        $searchHitRequest = $this->get("/images/gallery?page=1&uploaded_to={$pageId}&search={$namePartial}");
+        $searchHitRequest->assertSuccessful()->assertExactJson($emptyJson);
+    }
+
+    public function test_image_usage()
+    {
+        $page = Page::first();
+        $editor = $this->getEditor();
+        $this->actingAs($editor);
+
+        $imgDetails = $this->uploadGalleryImage($page);
+
+        $image = Image::query()->first();
+        $page->html = '<img src="'.$image->url.'">';
+        $page->save();
+
+        $usage = $this->get('/images/usage/' . $image->id);
+        $usage->assertSuccessful();
+        $usage->assertJson([
+            [
+                'id' => $page->id,
+                'name' => $page->name
+            ]
+        ]);
+
+        $this->deleteImage($imgDetails['path']);
+    }
+
     public function test_php_files_cannot_be_uploaded()
     {
         $page = Page::first();
@@ -50,7 +129,7 @@ class ImageTest extends TestCase
         $this->deleteImage($relPath);
 
         $file = $this->getTestImage($fileName);
-        $upload = $this->withHeader('Content-Type', 'image/jpeg')->call('POST', '/images/gallery/upload', ['uploaded_to' => $page->id], [], ['file' => $file], []);
+        $upload = $this->withHeader('Content-Type', 'image/jpeg')->call('POST', '/images/gallery', ['uploaded_to' => $page->id], [], ['file' => $file], []);
         $upload->assertStatus(302);
 
         $this->assertFalse(file_exists(public_path($relPath)), 'Uploaded php file was uploaded but should have been stopped');
@@ -72,7 +151,7 @@ class ImageTest extends TestCase
         $this->deleteImage($relPath);
 
         $file = $this->getTestImage($fileName);
-        $upload = $this->withHeader('Content-Type', 'image/jpeg')->call('POST', '/images/gallery/upload', ['uploaded_to' => $page->id], [], ['file' => $file], []);
+        $upload = $this->withHeader('Content-Type', 'image/jpeg')->call('POST', '/images/gallery', ['uploaded_to' => $page->id], [], ['file' => $file], []);
         $upload->assertStatus(302);
 
         $this->assertFalse(file_exists(public_path($relPath)), 'Uploaded php file was uploaded but should have been stopped');
@@ -89,7 +168,7 @@ class ImageTest extends TestCase
         $this->deleteImage($relPath);
 
         $file = $this->getTestImage($fileName);
-        $upload = $this->withHeader('Content-Type', 'image/png')->call('POST', '/images/gallery/upload', ['uploaded_to' => $page->id], [], ['file' => $file], []);
+        $upload = $this->withHeader('Content-Type', 'image/png')->call('POST', '/images/gallery', ['uploaded_to' => $page->id], [], ['file' => $file], []);
         $upload->assertStatus(302);
 
         $this->assertFalse(file_exists(public_path($relPath)), 'Uploaded double extension file was uploaded but should have been stopped');
@@ -101,9 +180,9 @@ class ImageTest extends TestCase
         $this->asEditor();
         $galleryFile = $this->getTestImage('my-secure-test-upload.png');
         $page = Page::first();
-        $expectedPath = storage_path('uploads/images/gallery/' . Date('Y-m-M') . '/my-secure-test-upload.png');
+        $expectedPath = storage_path('uploads/images/gallery/' . Date('Y-m') . '/my-secure-test-upload.png');
 
-        $upload = $this->call('POST', '/images/gallery/upload', ['uploaded_to' => $page->id], [], ['file' => $galleryFile], []);
+        $upload = $this->call('POST', '/images/gallery', ['uploaded_to' => $page->id], [], ['file' => $galleryFile], []);
         $upload->assertStatus(200);
 
         $this->assertTrue(file_exists($expectedPath), 'Uploaded image not found at path: '. $expectedPath);
@@ -119,9 +198,9 @@ class ImageTest extends TestCase
         $this->asEditor();
         $galleryFile = $this->getTestImage('my-secure-test-upload.png');
         $page = Page::first();
-        $expectedPath = storage_path('uploads/images/gallery/' . Date('Y-m-M') . '/my-secure-test-upload.png');
+        $expectedPath = storage_path('uploads/images/gallery/' . Date('Y-m') . '/my-secure-test-upload.png');
 
-        $upload = $this->call('POST', '/images/gallery/upload', ['uploaded_to' => $page->id], [], ['file' => $galleryFile], []);
+        $upload = $this->call('POST', '/images/gallery', ['uploaded_to' => $page->id], [], ['file' => $galleryFile], []);
         $imageUrl = json_decode($upload->getContent(), true)['url'];
         $page->html .= "<img src=\"{$imageUrl}\">";
         $page->save();
@@ -139,13 +218,12 @@ class ImageTest extends TestCase
     public function test_system_images_remain_public()
     {
         config()->set('filesystems.default', 'local_secure');
-        $this->asEditor();
+        $this->asAdmin();
         $galleryFile = $this->getTestImage('my-system-test-upload.png');
-        $page = Page::first();
-        $expectedPath = public_path('uploads/images/system/' . Date('Y-m-M') . '/my-system-test-upload.png');
+        $expectedPath = public_path('uploads/images/system/' . Date('Y-m') . '/my-system-test-upload.png');
 
-        $upload = $this->call('POST', '/images/system/upload', ['uploaded_to' => $page->id], [], ['file' => $galleryFile], []);
-        $upload->assertStatus(200);
+        $upload = $this->call('POST', '/settings', [], [], ['app_logo' => $galleryFile], []);
+        $upload->assertRedirect('/settings');
 
         $this->assertTrue(file_exists($expectedPath), 'Uploaded image not found at path: '. $expectedPath);
 
@@ -183,8 +261,10 @@ class ImageTest extends TestCase
 
         $this->uploadImage($imageName, $page->id);
         $image = Image::first();
+        $image->type = 'drawio';
+        $image->save();
 
-        $imageGet = $this->getJson("/images/base64/{$image->id}");
+        $imageGet = $this->getJson("/images/drawio/base64/{$image->id}");
         $imageGet->assertJson([
             'content' => 'iVBORw0KGgoAAAANSUhEUgAAAAUAAAAFCAIAAAACDbGyAAAACXBIWXMAAAsTAAALEwEAmpwYAAAAB3RJTUUH4gEcDCo5iYNs+gAAAB1pVFh0Q29tbWVudAAAAAAAQ3JlYXRlZCB3aXRoIEdJTVBkLmUHAAAAFElEQVQI12O0jN/KgASYGFABqXwAZtoBV6Sl3hIAAAAASUVORK5CYII='
         ]);
@@ -196,7 +276,7 @@ class ImageTest extends TestCase
         $editor = $this->getEditor();
         $this->actingAs($editor);
 
-        $upload = $this->postJson('images/drawing/upload', [
+        $upload = $this->postJson('images/drawio', [
             'uploaded_to' => $page->id,
             'image' => 'image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAAUAAAAFCAIAAAACDbGyAAAACXBIWXMAAAsTAAALEwEAmpwYAAAAB3RJTUUH4gEcDCo5iYNs+gAAAB1pVFh0Q29tbWVudAAAAAAAQ3JlYXRlZCB3aXRoIEdJTVBkLmUHAAAAFElEQVQI12O0jN/KgASYGFABqXwAZtoBV6Sl3hIAAAAASUVORK5CYII='
         ]);
@@ -217,28 +297,58 @@ class ImageTest extends TestCase
         $this->assertTrue($testImageData === $uploadedImageData, "Uploaded image file data does not match our test image as expected");
     }
 
+    protected function getTestProfileImage()
+    {
+        $imageName = 'profile.png';
+        $relPath = $this->getTestImagePath('user', $imageName);
+        $this->deleteImage($relPath);
+
+        return $this->getTestImage($imageName);
+    }
+
+    public function test_user_image_upload()
+    {
+        $editor = $this->getEditor();
+        $admin = $this->getAdmin();
+        $this->actingAs($admin);
+
+        $file = $this->getTestProfileImage();
+        $this->call('PUT', '/settings/users/' . $editor->id, [], [], ['profile_image' => $file], []);
+
+        $this->assertDatabaseHas('images', [
+            'type' => 'user',
+            'uploaded_to' => $editor->id,
+            'created_by' => $admin->id,
+        ]);
+    }
+
     public function test_user_images_deleted_on_user_deletion()
     {
         $editor = $this->getEditor();
         $this->actingAs($editor);
 
-        $imageName = 'profile.png';
-        $relPath = $this->getTestImagePath('gallery', $imageName);
-        $this->deleteImage($relPath);
-
-        $file = $this->getTestImage($imageName);
-        $this->call('POST', '/images/user/upload', [], [], ['file' => $file], []);
-        $this->call('POST', '/images/user/upload', [], [], ['file' => $file], []);
+        $file = $this->getTestProfileImage();
+        $this->call('PUT', '/settings/users/' . $editor->id, [], [], ['profile_image' => $file], []);
 
         $profileImages = Image::where('type', '=', 'user')->where('created_by', '=', $editor->id)->get();
-        $this->assertTrue($profileImages->count() === 2, "Found profile images does not match upload count");
+        $this->assertTrue($profileImages->count() === 1, "Found profile images does not match upload count");
+
+        $imagePath = public_path($profileImages->first()->path);
+        $this->assertTrue(file_exists($imagePath));
 
         $userDelete = $this->asAdmin()->delete("/settings/users/{$editor->id}");
         $userDelete->assertStatus(302);
+
         $this->assertDatabaseMissing('images', [
             'type' => 'user',
             'created_by' => $editor->id
         ]);
+        $this->assertDatabaseMissing('images', [
+            'type' => 'user',
+            'uploaded_to' => $editor->id
+        ]);
+
+        $this->assertFalse(file_exists($imagePath));
     }
 
     public function test_deleted_unused_images()
diff --git a/tests/Uploads/UsesImages.php b/tests/Uploads/UsesImages.php
index 93bf278e2..aa5ffe4c7 100644
--- a/tests/Uploads/UsesImages.php
+++ b/tests/Uploads/UsesImages.php
@@ -1,6 +1,7 @@
 <?php namespace Tests\Uploads;
 
 
+use BookStack\Entities\Page;
 use Illuminate\Http\UploadedFile;
 
 trait UsesImages
@@ -41,7 +42,7 @@ trait UsesImages
      */
     protected function getTestImagePath($type, $fileName)
     {
-        return '/uploads/images/' . $type . '/' . Date('Y-m-M') . '/' . $fileName;
+        return '/uploads/images/' . $type . '/' . Date('Y-m') . '/' . $fileName;
     }
 
     /**
@@ -55,7 +56,33 @@ trait UsesImages
     {
         $file = $this->getTestImage($name);
         return $this->withHeader('Content-Type', $contentType)
-            ->call('POST', '/images/gallery/upload', ['uploaded_to' => $uploadedTo], [], ['file' => $file], []);
+            ->call('POST', '/images/gallery', ['uploaded_to' => $uploadedTo], [], ['file' => $file], []);
+    }
+
+    /**
+     * Upload a new gallery image.
+     * Returns the image name.
+     * Can provide a page to relate the image to.
+     * @param Page|null $page
+     * @return array
+     */
+    protected function uploadGalleryImage(Page $page = null)
+    {
+        if ($page === null) {
+            $page = Page::query()->first();
+        }
+
+        $imageName = 'first-image.png';
+        $relPath = $this->getTestImagePath('gallery', $imageName);
+        $this->deleteImage($relPath);
+
+        $upload = $this->uploadImage($imageName, $page->id);
+        $upload->assertStatus(200);
+        return [
+            'name' => $imageName,
+            'path' => $relPath,
+            'page' => $page
+        ];
     }
 
     /**