diff --git a/app/Actions/Server/InstallServer.php b/app/Actions/Server/InstallServer.php
index 058fefbe5..968353be2 100644
--- a/app/Actions/Server/InstallServer.php
+++ b/app/Actions/Server/InstallServer.php
@@ -18,6 +18,8 @@
 
 class InstallServer
 {
+    private const MAX_WAIT_SECONDS = 180;
+
     protected Server $server;
 
     /**
@@ -27,20 +29,33 @@ public function run(Server $server): void
     {
         $this->server = $server;
 
-        $maxWait = 180;
+        $maxWait = self::MAX_WAIT_SECONDS;
+        $connected = false;
+        $lastError = null;
+
         while ($maxWait > 0) {
-            if (! $this->server->provider()->isRunning()) {
-                continue;
-            }
-            try {
-                $this->server->ssh()->connect();
-                break;
-            } catch (SSHConnectionError) {
-                // ignore
+            if ($this->server->provider()->isRunning()) {
+                try {
+                    $this->server->ssh()->connect();
+                    $connected = true;
+
+                    break;
+                } catch (SSHConnectionError $e) {
+                    $lastError = $e;
+                }
             }
+
             Sleep::sleep(10);
             $maxWait -= 10;
         }
+
+        if (! $connected) {
+            throw new SSHConnectionError(
+                'The server did not become reachable within '.self::MAX_WAIT_SECONDS.' seconds.',
+                previous: $lastError,
+            );
+        }
+
         $this->install();
         $this->server->update([
             'status' => ServerStatus::READY,
diff --git a/tests/Feature/Jobs/ServerInstallJobTest.php b/tests/Feature/Jobs/ServerInstallJobTest.php
index e951f71b5..9734112d9 100644
--- a/tests/Feature/Jobs/ServerInstallJobTest.php
+++ b/tests/Feature/Jobs/ServerInstallJobTest.php
@@ -1,9 +1,17 @@
 <?php
 
+use App\Actions\Server\InstallServer;
 use App\Enums\ServerStatus;
+use App\Exceptions\SSHConnectionError;
+use App\Facades\SSH;
 use App\Jobs\Server\InstallJob;
+use App\Models\ServerProvider;
+use App\ServerProviders\DigitalOcean;
+use Carbon\CarbonInterval as Duration;
 use Illuminate\Foundation\Testing\RefreshDatabase;
+use Illuminate\Support\Facades\Http;
 use Illuminate\Support\Facades\Notification;
+use Illuminate\Support\Sleep;
 
 uses(RefreshDatabase::class);
 
@@ -24,3 +32,92 @@
         'type' => 'server-installation-failed',
     ]);
 });
+
+test('waiting for the provider is bounded and paced when the instance never becomes active', function () {
+    SSH::fake();
+
+    $polls = 0;
+    Http::fake([
+        'api.digitalocean.com/v2/droplets/*' => function () use (&$polls) {
+            $polls++;
+
+            if ($polls > 50) {
+                throw new Error('isRunning() was polled '.$polls.' times: the wait loop is unbounded.');
+            }
+
+            return Http::response([
+                'droplet' => [
+                    'id' => 599103218,
+                    'status' => 'new',
+                    'networks' => ['v4' => []],
+                ],
+            ]);
+        },
+        '*' => Http::response([]),
+    ]);
+
+    $serverProvider = ServerProvider::factory()->create([
+        'user_id' => $this->user->id,
+        'provider' => DigitalOcean::id(),
+        'credentials' => ['token' => 'secret-token'],
+    ]);
+
+    $this->server->update([
+        'provider' => DigitalOcean::id(),
+        'provider_id' => $serverProvider->id,
+        'provider_data' => ['plan' => 's-1vcpu-512mb-10gb', 'region' => 'nyc1', 'droplet_id' => 599103218],
+        'ip' => '',
+        'status' => ServerStatus::INSTALLING,
+    ]);
+
+    expect(fn () => app(InstallServer::class)->run($this->server->refresh()))
+        ->toThrow(SSHConnectionError::class, 'The server did not become reachable within 180 seconds.');
+
+    expect($polls)->toBe(18);
+
+    Sleep::assertSleptTimes(18);
+    Sleep::assertSlept(fn (Duration $duration) => (int) $duration->totalSeconds === 10, 18);
+
+    $this->server->refresh();
+
+    expect($this->server->status)->toEqual(ServerStatus::INSTALLING);
+});
+
+test('the underlying ssh failure is preserved when the server never becomes reachable', function () {
+    SSH::fake()->connectionWillFail();
+
+    Http::fake([
+        'api.digitalocean.com/v2/droplets/*' => Http::response([
+            'droplet' => [
+                'id' => 599103218,
+                'status' => 'active',
+                'networks' => ['v4' => [['type' => 'public', 'ip_address' => '164.92.1.1']]],
+            ],
+        ]),
+        '*' => Http::response([]),
+    ]);
+
+    $serverProvider = ServerProvider::factory()->create([
+        'user_id' => $this->user->id,
+        'provider' => DigitalOcean::id(),
+        'credentials' => ['token' => 'secret-token'],
+    ]);
+
+    $this->server->update([
+        'provider' => DigitalOcean::id(),
+        'provider_id' => $serverProvider->id,
+        'provider_data' => ['plan' => 's-1vcpu-512mb-10gb', 'region' => 'nyc1', 'droplet_id' => 599103218],
+        'ip' => '',
+        'status' => ServerStatus::INSTALLING,
+    ]);
+
+    try {
+        app(InstallServer::class)->run($this->server->refresh());
+
+        $this->fail('Expected InstallServer to throw.');
+    } catch (SSHConnectionError $e) {
+        expect($e->getMessage())->toBe('The server did not become reachable within 180 seconds.')
+            ->and($e->getPrevious())->toBeInstanceOf(SSHConnectionError::class)
+            ->and($e->getPrevious()?->getMessage())->toBe('Connection failed');
+    }
+});