diff --git a/src/app/Jobs/WalletCheck.php b/src/app/Jobs/WalletCheck.php
--- a/src/app/Jobs/WalletCheck.php
+++ b/src/app/Jobs/WalletCheck.php
@@ -2,6 +2,7 @@
 
 namespace App\Jobs;
 
+use App\Http\Controllers\API\V4\PaymentsController;
 use App\Wallet;
 use Carbon\Carbon;
 use Illuminate\Bus\Queueable;
@@ -21,7 +22,9 @@
     public const THRESHOLD_DELETE = 'delete';
     public const THRESHOLD_BEFORE_DELETE = 'before_delete';
     public const THRESHOLD_SUSPEND = 'suspend';
+    public const THRESHOLD_BEFORE_SUSPEND = 'before_suspend';
     public const THRESHOLD_REMINDER = 'reminder';
+    public const THRESHOLD_BEFORE_REMINDER = 'before_reminder';
     public const THRESHOLD_INITIAL = 'initial';
 
     /** @var int The number of seconds to wait before retrying the job. */
@@ -52,12 +55,12 @@
     /**
      * Execute the job.
      *
-     * @return void
+     * @return ?string Executed action (THRESHOLD_*)
      */
     public function handle()
     {
         if ($this->wallet->balance >= 0) {
-            return;
+            return null;
         }
 
         $now = Carbon::now();
@@ -65,32 +68,46 @@
         // Delete the account
         if (self::threshold($this->wallet, self::THRESHOLD_DELETE) < $now) {
             $this->deleteAccount();
-            return;
+            return self::THRESHOLD_DELETE;
         }
 
         // Warn about the upcomming account deletion
         if (self::threshold($this->wallet, self::THRESHOLD_BEFORE_DELETE) < $now) {
             $this->warnBeforeDelete();
-            return;
+            return self::THRESHOLD_BEFORE_DELETE;
         }
 
         // Suspend the account
         if (self::threshold($this->wallet, self::THRESHOLD_SUSPEND) < $now) {
             $this->suspendAccount();
-            return;
+            return self::THRESHOLD_SUSPEND;
+        }
+
+        // Try to top-up the wallet before suspending the account
+        if (self::threshold($this->wallet, self::THRESHOLD_BEFORE_SUSPEND) < $now) {
+            PaymentsController::topUpWallet($this->wallet);
+            return self::THRESHOLD_BEFORE_SUSPEND;
         }
 
         // Send the second reminder
         if (self::threshold($this->wallet, self::THRESHOLD_REMINDER) < $now) {
             $this->secondReminder();
-            return;
+            return self::THRESHOLD_REMINDER;
+        }
+
+        // Try to top-up the wallet before the second reminder
+        if (self::threshold($this->wallet, self::THRESHOLD_BEFORE_REMINDER) < $now) {
+            PaymentsController::topUpWallet($this->wallet);
+            return self::THRESHOLD_BEFORE_REMINDER;
         }
 
         // Send the initial reminder
         if (self::threshold($this->wallet, self::THRESHOLD_INITIAL) < $now) {
             $this->initialReminder();
-            return;
+            return self::THRESHOLD_INITIAL;
         }
+
+        return null;
     }
 
     /**
@@ -295,11 +312,21 @@
             return $negative_since->addDays($suspend + $remind);
         }
 
+        // A day before account suspension
+        if ($type == self::THRESHOLD_BEFORE_SUSPEND) {
+            return $negative_since->addDays($suspend + $remind - 1);
+        }
+
         // Second notification
         if ($type == self::THRESHOLD_REMINDER) {
             return $negative_since->addDays($remind);
         }
 
+        // A day before the second reminder
+        if ($type == self::THRESHOLD_BEFORE_REMINDER) {
+            return $negative_since->addDays($remind - 1);
+        }
+
         // Initial notification
         // Give it an hour so the async recurring payment has a chance to be finished
         if ($type == self::THRESHOLD_INITIAL) {
diff --git a/src/tests/Feature/Jobs/WalletCheckTest.php b/src/tests/Feature/Jobs/WalletCheckTest.php
--- a/src/tests/Feature/Jobs/WalletCheckTest.php
+++ b/src/tests/Feature/Jobs/WalletCheckTest.php
@@ -115,10 +115,36 @@
     }
 
     /**
-     * Test job handle, reminder notification
+     * Test job handle, top-up before reminder notification
      *
      * @depends testHandleInitial
      */
+    public function testHandleBeforeReminder(): void
+    {
+        Mail::fake();
+
+        $user = $this->getTestUser('ned@kolab.org');
+        $wallet = $user->wallets()->first();
+        $now = Carbon::now();
+
+        // Balance turned negative 7-1 days ago
+        $wallet->setSetting('balance_negative_since', $now->subDays(7 - 1)->toDateTimeString());
+
+        $job = new WalletCheck($wallet);
+        $res = $job->handle();
+
+        Mail::assertNothingSent();
+
+        // TODO: Test that it actually executed the topUpWallet()
+        $this->assertSame(WalletCheck::THRESHOLD_BEFORE_REMINDER, $res);
+        $this->assertFalse($user->fresh()->isSuspended());
+    }
+
+    /**
+     * Test job handle, reminder notification
+     *
+     * @depends testHandleBeforeReminder
+     */
     public function testHandleReminder(): void
     {
         Mail::fake();
@@ -149,10 +175,37 @@
     }
 
     /**
-     * Test job handle, account suspending
+     * Test job handle, top-up wallet before account suspending
      *
      * @depends testHandleReminder
      */
+    public function testHandleBeforeSuspended(): void
+    {
+        Mail::fake();
+
+        $user = $this->getTestUser('ned@kolab.org');
+        $wallet = $user->wallets()->first();
+        $now = Carbon::now();
+
+        // Balance turned negative 7+14-1 days ago
+        $days = 7 + 14 - 1;
+        $wallet->setSetting('balance_negative_since', $now->subDays($days)->toDateTimeString());
+
+        $job = new WalletCheck($wallet);
+        $res = $job->handle();
+
+        Mail::assertNothingSent();
+
+        // TODO: Test that it actually executed the topUpWallet()
+        $this->assertSame(WalletCheck::THRESHOLD_BEFORE_SUSPEND, $res);
+        $this->assertFalse($user->fresh()->isSuspended());
+    }
+
+    /**
+     * Test job handle, account suspending
+     *
+     * @depends testHandleBeforeSuspended
+     */
     public function testHandleSuspended(): void
     {
         Mail::fake();
diff --git a/src/tests/Functional/Methods/DomainTest.php b/src/tests/Functional/Methods/DomainTest.php
--- a/src/tests/Functional/Methods/DomainTest.php
+++ b/src/tests/Functional/Methods/DomainTest.php
@@ -110,5 +110,4 @@
         $this->assertFalse($this->domain->isConfirmed());
         $this->assertTrue($this->domain->isVerified());
     }
-
 }