diff --git a/app/Http/Controllers/Licenses/LicenseCheckinController.php b/app/Http/Controllers/Licenses/LicenseCheckinController.php
index dd83d0154c..373a167642 100644
--- a/app/Http/Controllers/Licenses/LicenseCheckinController.php
+++ b/app/Http/Controllers/Licenses/LicenseCheckinController.php
@@ -71,7 +71,7 @@ class LicenseCheckinController extends Controller
 
         if (! $license->reassignable) {
             // Not allowed to checkin
-            Session::flash('error', 'License not reassignable.');
+            Session::flash('error', trans('admin/licenses/message.checkin.not_reassignable') . '.');
 
             return redirect()->back()->withInput();
         }
diff --git a/database/factories/LicenseSeatFactory.php b/database/factories/LicenseSeatFactory.php
index f9560af472..aaf75bdc2d 100644
--- a/database/factories/LicenseSeatFactory.php
+++ b/database/factories/LicenseSeatFactory.php
@@ -4,6 +4,7 @@ namespace Database\Factories;
 
 use App\Models\Asset;
 use App\Models\License;
+use App\Models\LicenseSeat;
 use App\Models\User;
 use Illuminate\Database\Eloquent\Factories\Factory;
 
@@ -33,4 +34,18 @@ class LicenseSeatFactory extends Factory
             ];
         });
     }
+
+    public function reassignable()
+    {
+        return $this->afterMaking(function (LicenseSeat $seat) {
+            $seat->license->update(['reassignable' => true]);
+        });
+    }
+
+    public function notReassignable()
+    {
+        return $this->afterMaking(function (LicenseSeat $seat) {
+            $seat->license->update(['reassignable' => false]);
+        });
+    }
 }
diff --git a/resources/lang/en-US/admin/licenses/message.php b/resources/lang/en-US/admin/licenses/message.php
index 7f5981aa05..74e1d7af5a 100644
--- a/resources/lang/en-US/admin/licenses/message.php
+++ b/resources/lang/en-US/admin/licenses/message.php
@@ -50,6 +50,7 @@ return array(
 
     'checkin' => array(
         'error'   => 'There was an issue checking in the license. Please try again.',
+        'not_reassignable' => 'License not reassignable',
         'success' => 'The license was checked in successfully'
     ),
 
diff --git a/tests/Feature/Checkins/Ui/LicenseCheckinTest.php b/tests/Feature/Checkins/Ui/LicenseCheckinTest.php
index f006e41866..7a6553d8ba 100644
--- a/tests/Feature/Checkins/Ui/LicenseCheckinTest.php
+++ b/tests/Feature/Checkins/Ui/LicenseCheckinTest.php
@@ -2,8 +2,11 @@
 
 namespace Tests\Feature\Checkins\Ui;
 
+use App\Events\CheckoutableCheckedIn;
+use App\Models\Asset;
 use App\Models\LicenseSeat;
 use App\Models\User;
+use Illuminate\Support\Facades\Event;
 use Tests\TestCase;
 
 class LicenseCheckinTest extends TestCase
@@ -17,10 +20,112 @@ class LicenseCheckinTest extends TestCase
             ->assertForbidden();
     }
 
+    public function testCannotCheckinNonReassignableLicense()
+    {
+        $licenseSeat = LicenseSeat::factory()
+            ->notReassignable()
+            ->assignedToUser()
+            ->create();
+
+        $this->actingAs(User::factory()->checkoutLicenses()->create())
+            ->post(route('licenses.checkin.save', $licenseSeat), [
+                'notes' => 'my note',
+                'redirect_option' => 'index',
+            ])
+            ->assertSessionHas('error', trans('admin/licenses/message.checkin.not_reassignable') . '.');
+
+        $this->assertNotNull($licenseSeat->fresh()->assigned_to);
+    }
+
+    public function testCannotCheckinLicenseThatIsNotAssigned()
+    {
+        $licenseSeat = LicenseSeat::factory()
+            ->reassignable()
+            ->create();
+
+        $this->assertNull($licenseSeat->assigned_to);
+        $this->assertNull($licenseSeat->asset_id);
+
+        $this->actingAs(User::factory()->checkoutLicenses()->create())
+            ->post(route('licenses.checkin.save', $licenseSeat), [
+                'notes' => 'my note',
+                'redirect_option' => 'index',
+            ])
+            ->assertSessionHas('error', trans('admin/licenses/message.checkin.error'));
+    }
+
+    public function testCanCheckInLicenseAssignedToAsset()
+    {
+        Event::fake([CheckoutableCheckedIn::class]);
+
+        $asset = Asset::factory()->create();
+
+        $licenseSeat = LicenseSeat::factory()
+            ->reassignable()
+            ->assignedToAsset($asset)
+            ->create();
+
+        $actor = User::factory()->checkoutLicenses()->create();
+
+        $this->actingAs($actor)
+            ->post(route('licenses.checkin.save', $licenseSeat), [
+                'notes' => 'my note',
+                'redirect_option' => 'index',
+            ])
+            ->assertRedirect(route('licenses.index'));
+
+        $this->assertNull($licenseSeat->fresh()->asset_id);
+        $this->assertNull($licenseSeat->fresh()->assigned_to);
+        $this->assertEquals('my note', $licenseSeat->fresh()->notes);
+
+        Event::assertDispatchedTimes(CheckoutableCheckedIn::class, 1);
+        Event::assertDispatched(CheckoutableCheckedIn::class, function (CheckoutableCheckedIn $event) use ($actor, $asset, $licenseSeat) {
+            return $event->checkoutable->is($licenseSeat)
+                && $event->checkedOutTo->is($asset)
+                && $event->checkedInBy->is($actor)
+                && $event->note === 'my note';
+        });
+    }
+
+    public function testCanCheckInLicenseAssignedToUser()
+    {
+        Event::fake([CheckoutableCheckedIn::class]);
+
+        $user = User::factory()->create();
+
+        $licenseSeat = LicenseSeat::factory()
+            ->reassignable()
+            ->assignedToUser($user)
+            ->create();
+
+        $actor = User::factory()->checkoutLicenses()->create();
+
+        $this->actingAs($actor)
+            ->post(route('licenses.checkin.save', $licenseSeat), [
+                'notes' => 'my note',
+                'redirect_option' => 'index',
+            ])
+            ->assertRedirect(route('licenses.index'));
+
+        $this->assertNull($licenseSeat->fresh()->asset_id);
+        $this->assertNull($licenseSeat->fresh()->assigned_to);
+        $this->assertEquals('my note', $licenseSeat->fresh()->notes);
+
+        Event::assertDispatchedTimes(CheckoutableCheckedIn::class, 1);
+        Event::assertDispatched(CheckoutableCheckedIn::class, function (CheckoutableCheckedIn $event) use ($actor, $licenseSeat, $user) {
+            return $event->checkoutable->is($licenseSeat)
+                && $event->checkedOutTo->is($user)
+                && $event->checkedInBy->is($actor)
+                && $event->note === 'my note';
+        });
+
+    }
+  
     public function testPageRenders()
     {
         $this->actingAs(User::factory()->superuser()->create())
             ->get(route('licenses.checkin', LicenseSeat::factory()->assignedToUser()->create()->id))
             ->assertOk();
+
     }
 }