diff --git a/_config/forms.yml b/_config/forms.yml
index a6d1b214b..b3dc4d4ea 100644
--- a/_config/forms.yml
+++ b/_config/forms.yml
@@ -16,3 +16,7 @@ SilverStripe\Forms\Form:
 SilverStripe\Forms\FormField:
   extensions:
   - SilverStripe\Forms\FormMessageBootstrapExtension
+
+SilverStripe\Admin\LeftAndMain:
+  extensions:
+    - SilverStripe\Admin\LeftAndMainErrorExtension
diff --git a/code/LeftAndMain.php b/code/LeftAndMain.php
index af700f103..8e1f87c63 100644
--- a/code/LeftAndMain.php
+++ b/code/LeftAndMain.php
@@ -175,6 +175,11 @@ class LeftAndMain extends Controller implements PermissionProvider
      */
     protected $pageID = null;
 
+    /**
+     * Set by {@link LeftAndMainErrorExtension} if an http error occurs
+     */
+    private string $httpErrorMessage;
+
     /**
      * Assign themes to use for cms
      *
@@ -773,6 +778,32 @@ protected function init()
         Versioned::set_default_reading_mode(Versioned::get_reading_mode());
     }
 
+    public function afterHandleRequest()
+    {
+        if ($this->response->isError()) {
+            $this->init();
+            $errorCode = $this->response->getStatusCode();
+            $errorType = $this->response->getStatusDescription();
+            $defaultMessage = _t(
+                self::class . '.ErrorMessage',
+                'Sorry, it seems there was a {errorcode} error.',
+                ['errorcode' => $errorCode]
+            );
+            $this->response = HTTPResponse::create($this->render([
+                'Title' => $this->getApplicationName() . ' - ' . $errorType,
+                'Content' => $this->renderWith($this->getTemplatesWithSuffix('_NotFound'), [
+                    'ErrorCode' => $errorCode,
+                    'ErrorType' => $errorType,
+                    'Message' => DBField::create_field(
+                        'HTMLFragment',
+                        _t(self::class . '.ErrorMessage' . $errorCode, $defaultMessage)
+                    ),
+                ]),
+            ]), $errorCode, $errorType);
+        }
+        parent::afterHandleRequest();
+    }
+
     public function handleRequest(HTTPRequest $request)
     {
         try {
@@ -1998,4 +2029,23 @@ public function getVersionProvider()
     {
         return $this->versionProvider;
     }
+
+    /**
+     * Get the HTTP error message if one has occurred during HandleRequest.
+     */
+    public function getHttpErrorMessage(): string
+    {
+        return $this->httpErrorMessage;
+    }
+
+    /**
+     * Set the HTTP error message when one occurs during HandleRequest.
+     * Called by {@link LeftAndMainErrorExtension}
+     * @internal
+     */
+    public function setHttpErrorMessage(string $message): self
+    {
+        $this->httpErrorMessage = $message;
+        return $this;
+    }
 }
diff --git a/code/LeftAndMainErrorExtension.php b/code/LeftAndMainErrorExtension.php
new file mode 100644
index 000000000..6f8fe0f78
--- /dev/null
+++ b/code/LeftAndMainErrorExtension.php
@@ -0,0 +1,21 @@
+<?php
+
+namespace SilverStripe\Admin;
+
+use SilverStripe\Control\Director;
+use SilverStripe\Control\HTTPRequest;
+use SilverStripe\Core\Extension;
+
+class LeftAndMainErrorExtension extends Extension
+{
+    /**
+     * Used by {@see RequestHandler::httpError}
+     */
+    public function onBeforeHTTPError($statusCode, HTTPRequest $request, $errorMessage = null)
+    {
+        if (Director::is_ajax($request)) {
+            return;
+        }
+        $this->owner->setHttpErrorMessage($errorMessage);
+    }
+}
diff --git a/lang/en.yml b/lang/en.yml
index f133800c4..eac3cb08a 100644
--- a/lang/en.yml
+++ b/lang/en.yml
@@ -33,6 +33,12 @@ en:
     CollapsePanel: 'Collapse panel'
     DELETED: Deleted.
     DropdownBatchActionsDefault: 'Choose an action...'
+    ErrorDetail: 'Error detail: {detail}'
+    ErrorMessage: '<p>Sorry, it seems there was a {errorcode} error.</p>'
+    ErrorMessage403: '<p>Sorry, it seems the action you were trying to perform is forbidden.</p>'
+    ErrorMessage404: '<p>Sorry, it seems you were trying to access a page that doesn''t exist.</p>'
+    ErrorMessage500: '<p>Sorry, it seems there was an internal server error.</p>'
+    ErrorMessage503: '<p>Sorry, it seems the service is temporarily unavailable.</p>'
     ExpandPanel: 'Expand panel'
     HelpMenu: 'Help menu'
     LOGOUT: 'Log out'
diff --git a/templates/SilverStripe/Admin/Includes/LeftAndMain_NotFound.ss b/templates/SilverStripe/Admin/Includes/LeftAndMain_NotFound.ss
new file mode 100644
index 000000000..9f03eed30
--- /dev/null
+++ b/templates/SilverStripe/Admin/Includes/LeftAndMain_NotFound.ss
@@ -0,0 +1,24 @@
+<div class="cms-content flexbox-area-grow $BaseCSSClasses" data-layout-type="border" data-pjax-fragment="Content">
+
+	<div class="cms-content-header north">
+		<div class="cms-content-header-info vertical-align-items flexbox-area-grow">
+			<div class="breadcrumbs-wrapper">
+				<span class="cms-panel-link crumb last">
+					$ErrorType
+				</span>
+			</div>
+		</div>
+    </div>
+
+	$Tools
+
+    <div class="panel panel--padded">
+        $Message
+        <% if $isDev && $HttpErrorMessage %>
+            <p>
+                <strong><%t SilverStripe\Admin\LeftAndMain.ErrorDetail "Error detail: {detail}" detail=$HttpErrorMessage %></strong>
+            </p>
+        <% end_if %>
+    </div>
+
+</div>