diff --git a/app/Actions/AccessToken/ListConnectedMcpClients.php b/app/Actions/AccessToken/ListConnectedMcpClients.php
index 0e2922a1..26166974 100644
--- a/app/Actions/AccessToken/ListConnectedMcpClients.php
+++ b/app/Actions/AccessToken/ListConnectedMcpClients.php
@@ -7,6 +7,7 @@
 use App\Models\AccessToken;
 use App\Models\User;
 use App\Models\Workspace;
+use Carbon\CarbonInterface;
 use Illuminate\Support\Collection;
 
 class ListConnectedMcpClients
@@ -16,7 +17,7 @@ class ListConnectedMcpClients
      * OAuth client. Matches API keys: each person only sees what they connected
      * for the workspace they are viewing.
      *
-     * @return list<array{client_id: string, name: string, can_disconnect: bool, last_used_at: mixed}>
+     * @return list<array{client_id: string, name: string, can_disconnect: bool, last_used_at: ?CarbonInterface}>
      */
     public static function forUser(User $user, Workspace $workspace): array
     {
@@ -41,7 +42,8 @@ public static function forUser(User $user, Workspace $workspace): array
                     'last_used_at' => $group->max('last_used_at'),
                 ];
             })
-            ->sortByDesc(fn (array $client): mixed => $client['last_used_at'] ?? 0)
+            // Timestamp, not the date object: never-used clients are null.
+            ->sortByDesc(fn (array $client): int => $client['last_used_at']?->getTimestamp() ?? 0)
             ->values()
             ->all();
     }
diff --git a/tests/Feature/McpSettingsControllerTest.php b/tests/Feature/McpSettingsControllerTest.php
index d4a8c38d..ca300d35 100644
--- a/tests/Feature/McpSettingsControllerTest.php
+++ b/tests/Feature/McpSettingsControllerTest.php
@@ -313,6 +313,35 @@
             ->where('connectedClients.1.name', 'Older Agent'));
 });
 
+it('orders a never-used client last instead of crashing', function (): void {
+    $used = mcpAccessToken($this->user, mcpOauthClient('Used Agent'), $this->workspace);
+    $neverUsed = mcpAccessToken($this->user, mcpOauthClient('Fresh Agent'), $this->workspace);
+
+    $used->forceFill(['last_used_at' => now()->subHour()])->saveQuietly();
+    $neverUsed->forceFill(['last_used_at' => null])->saveQuietly();
+
+    $this->actingAs($this->user)
+        ->get(route('app.mcp.index'))
+        ->assertOk()
+        ->assertInertia(fn ($page) => $page
+            ->has('connectedClients', 2)
+            ->where('connectedClients.0.name', 'Used Agent')
+            ->where('connectedClients.1.name', 'Fresh Agent'));
+});
+
+it('lists clients that have never been used', function (): void {
+    $first = mcpAccessToken($this->user, mcpOauthClient('First Agent'), $this->workspace);
+    $second = mcpAccessToken($this->user, mcpOauthClient('Second Agent'), $this->workspace);
+
+    $first->forceFill(['last_used_at' => null])->saveQuietly();
+    $second->forceFill(['last_used_at' => null])->saveQuietly();
+
+    $this->actingAs($this->user)
+        ->get(route('app.mcp.index'))
+        ->assertOk()
+        ->assertInertia(fn ($page) => $page->has('connectedClients', 2));
+});
+
 it('does not list unbound mcp grants', function (): void {
     mcpAccessToken($this->user, mcpOauthClient('Legacy Agent'), workspace: null);