diff --git a/app/Models/Server.php b/app/Models/Server.php
index 16511a2d73..38068b17f6 100644
--- a/app/Models/Server.php
+++ b/app/Models/Server.php
@@ -7,6 +7,7 @@ use App\Actions\Server\InstallDocker;
 use App\Actions\Server\InstallPrerequisites;
 use App\Actions\Server\StartSentinel;
 use App\Actions\Server\ValidatePrerequisites;
+use App\Enums\ApplicationDeploymentStatus;
 use App\Enums\ProxyTypes;
 use App\Enums\ServerRole;
 use App\Events\ServerReachabilityChanged;
@@ -244,11 +245,35 @@ class Server extends BaseModel
             $server->notificationThrottles()->delete();
         });
 
+        static::deleted(function (Server $server) {
+            $server->failQueuedDeployments();
+        });
+
         static::updated(function () {
             static::flushIdentityMap();
         });
     }
 
+    /**
+     * Fail the queued deployments of a deleted server, because they can never start.
+     */
+    public function failQueuedDeployments(): void
+    {
+        ApplicationDeploymentQueue::query()
+            ->where('server_id', $this->id)
+            ->where('status', ApplicationDeploymentStatus::QUEUED->value)
+            ->eachById(function (ApplicationDeploymentQueue $deployment) {
+                $updated = ApplicationDeploymentQueue::query()
+                    ->whereKey($deployment->id)
+                    ->where('status', ApplicationDeploymentStatus::QUEUED->value)
+                    ->update(['status' => ApplicationDeploymentStatus::FAILED->value]);
+
+                if ($updated > 0) {
+                    $deployment->addLogEntry('The server was deleted.', 'stderr');
+                }
+            });
+    }
+
     /**
      * Find a Server by ID using the identity map cache.
      * This prevents N+1 queries when the same Server is accessed multiple times.
diff --git a/tests/Feature/ServerDeleteFailsQueuedDeploymentsTest.php b/tests/Feature/ServerDeleteFailsQueuedDeploymentsTest.php
new file mode 100644
index 0000000000..16c5b49786
--- /dev/null
+++ b/tests/Feature/ServerDeleteFailsQueuedDeploymentsTest.php
@@ -0,0 +1,78 @@
+<?php
+
+use App\Enums\ApplicationDeploymentStatus;
+use App\Livewire\Server\Delete;
+use App\Models\Application;
+use App\Models\ApplicationDeploymentQueue;
+use App\Models\Environment;
+use App\Models\InstanceSettings;
+use App\Models\PrivateKey;
+use App\Models\Project;
+use App\Models\Server;
+use App\Models\StandaloneDocker;
+use App\Models\Team;
+use App\Models\User;
+use Illuminate\Foundation\Testing\RefreshDatabase;
+use Illuminate\Support\Facades\Queue;
+use Livewire\Livewire;
+
+uses(RefreshDatabase::class);
+
+beforeEach(function () {
+    Server::flushIdentityMap();
+    Queue::fake();
+    config(['app.maintenance.store' => 'array']);
+    InstanceSettings::forceCreate(['id' => 0, 'is_api_enabled' => true]);
+
+    $this->team = Team::factory()->create();
+    $this->user = User::factory()->create();
+    $this->team->members()->attach($this->user->id, ['role' => 'owner']);
+    session(['currentTeam' => $this->team]);
+
+    $privateKey = PrivateKey::factory()->create(['team_id' => $this->team->id]);
+    $this->server = Server::factory()->create(['team_id' => $this->team->id, 'private_key_id' => $privateKey->id, 'ip' => '203.0.113.41']);
+    $destination = StandaloneDocker::where('server_id', $this->server->id)->firstOrFail();
+    $project = Project::factory()->create(['team_id' => $this->team->id]);
+    $environment = Environment::factory()->create(['project_id' => $project->id]);
+    $application = Application::factory()->create([
+        'environment_id' => $environment->id,
+        'destination_id' => $destination->id,
+        'destination_type' => $destination->getMorphClass(),
+    ]);
+
+    $makeDeployment = fn (string $status, string $uuid): ApplicationDeploymentQueue => ApplicationDeploymentQueue::create([
+        'application_id' => $application->id,
+        'deployment_uuid' => $uuid,
+        'status' => $status,
+        'server_id' => $this->server->id,
+        'destination_id' => $destination->id,
+        'commit' => 'HEAD',
+        'pull_request_id' => 0,
+    ]);
+    $this->queued = $makeDeployment(ApplicationDeploymentStatus::QUEUED->value, 'server-delete-queued');
+    $this->finished = $makeDeployment(ApplicationDeploymentStatus::FINISHED->value, 'server-delete-finished');
+});
+
+afterEach(function () {
+    Server::flushIdentityMap();
+});
+
+test('deleting a server fails its queued deployments', function (string $path) {
+    if ($path === 'api') {
+        $token = $this->user->createToken('server-delete', ['write'])->plainTextToken;
+        $this->withHeaders(['Authorization' => 'Bearer '.$token])
+            ->deleteJson("/api/v1/servers/{$this->server->uuid}?force=true")
+            ->assertOk();
+    } else {
+        $this->actingAs($this->user);
+        Livewire::test(Delete::class, ['server_uuid' => $this->server->uuid])
+            ->call('delete', 'password', ['force_delete_resources']);
+    }
+
+    expect(Server::withTrashed()->find($this->server->id)->trashed())->toBeTrue();
+
+    $queued = $this->queued->fresh();
+    expect($queued->status)->toBe(ApplicationDeploymentStatus::FAILED->value)
+        ->and(collect(json_decode($queued->logs, true))->pluck('output')->implode("\n"))->toContain('The server was deleted.')
+        ->and($this->finished->fresh()->status)->toBe(ApplicationDeploymentStatus::FINISHED->value);
+})->with(['api', 'ui']);