diff --git a/app/Http/Controllers/Assets/AssetCheckinController.php b/app/Http/Controllers/Assets/AssetCheckinController.php
index 80667c9cea..e1a30b30cc 100644
--- a/app/Http/Controllers/Assets/AssetCheckinController.php
+++ b/app/Http/Controllers/Assets/AssetCheckinController.php
@@ -111,6 +111,13 @@ class AssetCheckinController extends Controller
             $checkin_at = $request->input('checkin_at');
         }
 
+        if(!empty($asset->licenseseats->all())){
+            foreach ($asset->licenseseats as $seat){
+                $seat->assigned_to = null;
+                $seat->save();
+            }
+        }
+
         // Get all pending Acceptances for this asset and delete them
         $acceptances = CheckoutAcceptance::pending()->whereHasMorph('checkoutable',
             [Asset::class],
diff --git a/app/Http/Controllers/Assets/AssetCheckoutController.php b/app/Http/Controllers/Assets/AssetCheckoutController.php
index dc4ea8fb50..38f7460986 100644
--- a/app/Http/Controllers/Assets/AssetCheckoutController.php
+++ b/app/Http/Controllers/Assets/AssetCheckoutController.php
@@ -80,6 +80,15 @@ class AssetCheckoutController extends Controller
                 $asset->status_id = $request->get('status_id');
             }
 
+            if(!empty($asset->licenseseats->all())){
+                if(request('checkout_to_type') == 'user') {
+                    foreach ($asset->licenseseats as $seat){
+                        $seat->assigned_to = $target->id;
+                        $seat->save();
+                    }
+                }
+            }
+
             if ($asset->checkOut($target, $admin, $checkout_at, $expected_checkin, e($request->get('note')), $request->get('name'))) {
                 return redirect()->route('hardware.index')->with('success', trans('admin/hardware/message.checkout.success'));
             }