diff --git a/app/Http/Requests/CreateKeyLookupRequest.php b/app/Http/Requests/CreateKeyLookupRequest.php
index a3f037ae8b..58d4f32d95 100644
--- a/app/Http/Requests/CreateKeyLookupRequest.php
+++ b/app/Http/Requests/CreateKeyLookupRequest.php
@@ -18,7 +18,7 @@ public function authorize(): Response
     {
         return $this->publicKey() instanceof SshPublicKey
             ? Response::allow()
-            : Response::denyAsNotFound('None of your SSH keys are on the GitHub account of a /dev/null user. Add your key on GitHub (Settings → SSH and GPG keys), then sign in on '.url('/').'.');
+            : Response::denyAsNotFound('None of your SSH keys are on the GitHub account of a /dev/null user. Add your key on GitHub (Settings → SSH and GPG keys), then click Sync from GitHub on '.route('user-profile.edit').'.');
     }
 
     /**
diff --git a/tests/Feature/Controllers/Cli/KeyLookupControllerTest.php b/tests/Feature/Controllers/Cli/KeyLookupControllerTest.php
index 2bb5d1d7ca..93c03a312e 100644
--- a/tests/Feature/Controllers/Cli/KeyLookupControllerTest.php
+++ b/tests/Feature/Controllers/Cli/KeyLookupControllerTest.php
@@ -2,7 +2,9 @@
 
 declare(strict_types=1);
 
+use App\Contracts\Services\GitHubProvider;
 use App\Models\SshKey;
+use App\Models\User;
 use Illuminate\Support\Facades\Http;
 use Tests\Support\SshKeyPair;
 
@@ -33,7 +35,26 @@
 
     $response->assertNotFound()
         ->assertHeader('Content-Type', 'text/plain; charset=utf-8')
-        ->assertSee('None of your SSH keys are on the GitHub account of a /dev/null user.');
+        ->assertSee('None of your SSH keys are on the GitHub account of a /dev/null user.')
+        ->assertSee('then click Sync from GitHub on '.route('user-profile.edit').'.');
+});
+
+it('finds a key added on github after signing in once the user syncs from github', function (): void {
+    $user = User::factory()->create(['github_id' => '42']);
+    $key = SshKeyPair::generate()->publicKey;
+    $github = $this->mock(GitHubProvider::class);
+    $github->shouldReceive('account')->with('42')->andReturn(['login' => 'taylor']);
+    $github->shouldReceive('login')->with('42')->andReturn('taylor');
+    $github->shouldReceive('sshKeys')->with('taylor')->andReturn([$key->toOpenSsh()]);
+
+    $this->call('POST', route('cli-key-lookup.store'), content: $key->toOpenSsh())->assertNotFound();
+
+    $this->actingAs($user)->put(route('user-profile.update'))
+        ->assertInertiaFlash('toast', ['type' => 'success', 'message' => 'Synced from GitHub.']);
+
+    $this->call('POST', route('cli-key-lookup.store'), content: $key->toOpenSsh())
+        ->assertOk()
+        ->assertContent($key->toOpenSsh()."\n");
 });
 
 it('only considers the first 20 keys', function (): void {