diff --git a/app/Http/Controllers/Licenses/LicensesController.php b/app/Http/Controllers/Licenses/LicensesController.php
index b1728469b4..bdc0dc74e1 100755
--- a/app/Http/Controllers/Licenses/LicensesController.php
+++ b/app/Http/Controllers/Licenses/LicensesController.php
@@ -256,6 +256,9 @@ class LicensesController extends Controller
         else {
             $checkedout_seats_count = ($total_seats_count - $available_seats_count);
         }
+        if($license->isInactive()){
+            session()->flash('warning', (trans('admin/licenses/message.checkout.license_is_inactive')));
+        }
 
         $this->authorize('view', $license);
         return view('licenses.view', compact('license'))
diff --git a/app/Http/Transformers/LicenseSeatsTransformer.php b/app/Http/Transformers/LicenseSeatsTransformer.php
index 17025e7f9f..d018934e18 100644
--- a/app/Http/Transformers/LicenseSeatsTransformer.php
+++ b/app/Http/Transformers/LicenseSeatsTransformer.php
@@ -51,7 +51,7 @@ class LicenseSeatsTransformer
             'reassignable' => (bool) $seat->license->reassignable,
             'notes' => e($seat->notes),
             'user_can_checkout' => (($seat->assigned_to == '') && ($seat->asset_id == '')),
-            'disabled' => $seat->unreassignable_seat,
+            'disabled' => $seat->unreassignable_seat || $seat->license->isInactive(),
         ];
 
         $permissions_array['available_actions'] = [
diff --git a/app/Http/Transformers/LicensesTransformer.php b/app/Http/Transformers/LicensesTransformer.php
index 24822efeca..39079c6ec5 100644
--- a/app/Http/Transformers/LicensesTransformer.php
+++ b/app/Http/Transformers/LicensesTransformer.php
@@ -54,7 +54,7 @@ class LicensesTransformer
             'updated_at' => Helper::getFormattedDateObject($license->updated_at, 'datetime'),
             'deleted_at' => Helper::getFormattedDateObject($license->deleted_at, 'datetime'),
             'user_can_checkout' => (bool) ($license->free_seats_count > 0),
-
+            'disabled' => $license->isInactive(),
         ];
 
         $permissions_array['available_actions'] = [
diff --git a/app/Models/License.php b/app/Models/License.php
index ecd1b003e3..f80886236c 100755
--- a/app/Models/License.php
+++ b/app/Models/License.php
@@ -296,6 +296,18 @@ class License extends Depreciable
         }
         $this->attributes['termination_date'] = $value;
     }
+
+    public function isInactive(): bool
+{
+    $day = now()->startOfDay();
+
+    $expired = $this->expiration_date && $this->asDateTime($this->expiration_date)->startofDay()->lessThanOrEqualTo($day);
+
+    $terminated = $this->termination_date && $this->asDateTime($this->termination_date)->startofDay()->lessThanOrEqualTo($day);
+
+
+    return $expired || $terminated;
+}
     /**
      * Sets free_seat_count attribute
      *
diff --git a/app/Presenters/LicensePresenter.php b/app/Presenters/LicensePresenter.php
index b0518ef264..a1edf2cf76 100644
--- a/app/Presenters/LicensePresenter.php
+++ b/app/Presenters/LicensePresenter.php
@@ -202,7 +202,7 @@ class LicensePresenter extends Presenter
             'switchable' => false,
             'title' => trans('general.checkin').'/'.trans('general.checkout'),
             'visible' => true,
-            'formatter' => 'licensesInOutFormatter',
+            'formatter' => 'licenseInOutFormatter',
             'printIgnore' => true,
         ];
 
diff --git a/resources/lang/en-US/admin/licenses/message.php b/resources/lang/en-US/admin/licenses/message.php
index 9a0219d857..29ab06cbd9 100644
--- a/resources/lang/en-US/admin/licenses/message.php
+++ b/resources/lang/en-US/admin/licenses/message.php
@@ -46,6 +46,7 @@ return array(
         'not_enough_seats' => 'Not enough license seats available for checkout',
         'mismatch' => 'The license seat provided does not match the license',
         'unavailable' => 'This seat is not available for checkout.',
+        'license_is_inactive' => 'This license is expired or terminated.',
     ),
 
     'checkin' => array(
diff --git a/resources/views/partials/bootstrap-table.blade.php b/resources/views/partials/bootstrap-table.blade.php
index b325e89f1b..7c3468537d 100644
--- a/resources/views/partials/bootstrap-table.blade.php
+++ b/resources/views/partials/bootstrap-table.blade.php
@@ -556,21 +556,30 @@
         }
     }
 
-
+    function licenseInOutFormatter(value, row) {
+        if(row.disabled || row.user_can_checkout === false) {
+            return '<a href="{{ config('app.url') }}/licenses/' + row.id + '/checkin" class="btn btn-sm bg-maroon disabled" data-tooltip="true" title="{{ trans('general.checkin_tooltip') }}">{{ trans('general.checkout') }}</a>';
+        } else
+            // The user is allowed to check the license seat out and it's available
+        if ((row.available_actions.checkout === true) && (row.user_can_checkout === true)) {
+            return '<a href="{{ config('app.url') }}/licenses/' + row.id + '/checkout/'+row.id+'" class="btn btn-sm bg-maroon" data-tooltip="true" title="{{ trans('general.checkout_tooltip') }}">{{ trans('general.checkout') }}</a>';
+        }
+    }
     // We need a special formatter for license seats, since they don't work exactly the same
     // Checkouts need the license ID, checkins need the specific seat ID
 
     function licenseSeatInOutFormatter(value, row) {
+        if (row.disabled && (row.assigned_user || row.assigned_asset)) {
+            return '<a href="{{ config('app.url') }}/licenses/' + row.id + '/checkin" class="btn btn-sm bg-purple" data-tooltip="true" title="{{ trans('general.checkin_tooltip') }}">{{ trans('general.checkin') }}</a>';
+        }
         if(row.disabled) {
             return '<a href="{{ config('app.url') }}/licenses/' + row.id + '/checkin" class="btn btn-sm bg-maroon disabled" data-tooltip="true" title="{{ trans('general.checkin_tooltip') }}">{{ trans('general.checkout') }}</a>';
-        } else
+        }
         // The user is allowed to check the license seat out and it's available
-        if ((row.available_actions.checkout === true) && (row.user_can_checkout === true) && ((!row.asset_id) && (!row.assigned_to))) {
+        if ((row.available_actions.checkout === true) && (row.user_can_checkout === true) && ((!row.assigned_asset) && (!row.assigned_user))) {
             return '<a href="{{ config('app.url') }}/licenses/' + row.license_id + '/checkout/'+row.id+'" class="btn btn-sm bg-maroon" data-tooltip="true" title="{{ trans('general.checkout_tooltip') }}">{{ trans('general.checkout') }}</a>';
         }
-        else {
-                return '<a href="{{ config('app.url') }}/licenses/' + row.id + '/checkin" class="btn btn-sm bg-purple" data-tooltip="true" title="{{ trans('general.checkin_tooltip') }}">{{ trans('general.checkin') }}</a>';
-            }
+
     }
 
     function genericCheckinCheckoutFormatter(destination) {