diff --git a/backend/app/Http/Controllers/Api/MeetingsController.php b/backend/app/Http/Controllers/Api/MeetingsController.php
index 3c0d7c7d..9db5ffb2 100644
--- a/backend/app/Http/Controllers/Api/MeetingsController.php
+++ b/backend/app/Http/Controllers/Api/MeetingsController.php
@@ -799,6 +799,15 @@ class MeetingsController extends Controller {
                     Storage::disk('private')->put($filename, $pdf);
                 }
             }
+            else {
+                // DBにミーティングがある場合
+                if ($chk = Meeting::select('pdf')->where('id', (int)$meeting_id)->first()) {
+                    $opdf = str_replace('/files/', '', $chk->pdf);
+                    if (Storage::disk('private')->get($opdf)) {
+                        Storage::disk('private')->delete($opdf);
+                    }
+                }
+            }
 
             // データベースに保存します。
             DB::beginTransaction();
@@ -809,6 +818,7 @@ class MeetingsController extends Controller {
             $meeting->text = $update['text'];
             if (isset($update['memo'])) $meeting->memo = $update['memo'];
             if (isset($update['pdf'])) $meeting->pdf = $update['pdf'];
+            else $meeting->pdf = null;
 
             $meeting->save();