diff --git a/src/app/Jobs/Password/RetentionEmailJob.php b/src/app/Jobs/Password/RetentionEmailJob.php
--- a/src/app/Jobs/Password/RetentionEmailJob.php
+++ b/src/app/Jobs/Password/RetentionEmailJob.php
@@ -53,6 +53,11 @@
      */
     public function handle()
     {
+        if (!$this->user->isLdapReady() || !$this->user->isImapReady()) {
+            // The account isn't ready for mail delivery
+            return;
+        }
+
         // TODO: Should we check if the password didn't update since
         //       the job has been created?
 
diff --git a/src/app/Jobs/PaymentEmail.php b/src/app/Jobs/PaymentEmail.php
--- a/src/app/Jobs/PaymentEmail.php
+++ b/src/app/Jobs/PaymentEmail.php
@@ -80,7 +80,7 @@
 
         list($to, $cc) = \App\Mail\Helper::userEmails($this->controller);
 
-        if (!empty($to)) {
+        if (!empty($to) || !empty($cc)) {
             $params = [
                 'to' => $to,
                 'cc' => $cc,
diff --git a/src/app/Jobs/PaymentMandateDisabledEmail.php b/src/app/Jobs/PaymentMandateDisabledEmail.php
--- a/src/app/Jobs/PaymentMandateDisabledEmail.php
+++ b/src/app/Jobs/PaymentMandateDisabledEmail.php
@@ -67,7 +67,7 @@
 
         list($to, $cc) = \App\Mail\Helper::userEmails($this->controller);
 
-        if (!empty($to)) {
+        if (!empty($to) || !empty($cc)) {
             $params = [
                 'to' => $to,
                 'cc' => $cc,
diff --git a/src/app/Jobs/TrialEndEmail.php b/src/app/Jobs/TrialEndEmail.php
--- a/src/app/Jobs/TrialEndEmail.php
+++ b/src/app/Jobs/TrialEndEmail.php
@@ -56,10 +56,13 @@
      */
     public function handle()
     {
-        \App\Mail\Helper::sendMail(
-            new TrialEnd($this->account),
-            $this->account->tenant_id,
-            ['to' => $this->account->email]
-        );
+        //  Skip accounts that aren't ready for mail delivery
+        if ($this->account->isLdapReady() && $this->account->isImapReady()) {
+            \App\Mail\Helper::sendMail(
+                new TrialEnd($this->account),
+                $this->account->tenant_id,
+                ['to' => $this->account->email]
+            );
+        }
     }
 }
diff --git a/src/app/Mail/Helper.php b/src/app/Mail/Helper.php
--- a/src/app/Mail/Helper.php
+++ b/src/app/Mail/Helper.php
@@ -110,12 +110,16 @@
      */
     public static function userEmails(\App\User $user, bool $external = false): array
     {
-        $to = $user->email;
+        $active = $user->isLdapReady() && $user->isImapReady();
+
+        // Sending an email to non-(ldap|imap)-ready user will fail, skip it
+        // (or send to the external email only, when appropriate)
+        $to = $active ? $user->email : null;
         $cc = [];
 
         // If user has no mailbox entitlement we should not send
         // the email to his main address, but use external address, if defined
-        if (!$user->hasSku('mailbox')) {
+        if ($active && !$user->hasSku('mailbox')) {
             $to = $user->getSetting('external_email');
         } elseif ($external) {
             $ext_email = $user->getSetting('external_email');
diff --git a/src/tests/Feature/Jobs/Password/RetentionEmailJobTest.php b/src/tests/Feature/Jobs/Password/RetentionEmailJobTest.php
--- a/src/tests/Feature/Jobs/Password/RetentionEmailJobTest.php
+++ b/src/tests/Feature/Jobs/Password/RetentionEmailJobTest.php
@@ -4,6 +4,7 @@
 
 use App\Jobs\Password\RetentionEmailJob;
 use App\Mail\PasswordExpirationReminder;
+use App\User;
 use Illuminate\Support\Facades\Mail;
 use Tests\TestCase;
 
@@ -40,7 +41,8 @@
      */
     public function testHandle()
     {
-        $user = $this->getTestUser('PasswordRetention@UserAccount.com');
+        $status = User::STATUS_ACTIVE | User::STATUS_LDAP_READY | User::STATUS_IMAP_READY;
+        $user = $this->getTestUser('PasswordRetention@UserAccount.com', ['status' => $status]);
         $expiresOn = now()->copy()->addDays(7)->toDateString();
 
         Mail::fake();
diff --git a/src/tests/Feature/Jobs/PaymentEmailTest.php b/src/tests/Feature/Jobs/PaymentEmailTest.php
--- a/src/tests/Feature/Jobs/PaymentEmailTest.php
+++ b/src/tests/Feature/Jobs/PaymentEmailTest.php
@@ -7,6 +7,7 @@
 use App\Mail\PaymentSuccess;
 use App\Payment;
 use App\Providers\PaymentProvider;
+use App\User;
 use Illuminate\Support\Facades\Mail;
 use Tests\TestCase;
 
@@ -43,7 +44,8 @@
      */
     public function testHandle()
     {
-        $user = $this->getTestUser('PaymentEmail@UserAccount.com');
+        $status = User::STATUS_ACTIVE | User::STATUS_LDAP_READY | User::STATUS_IMAP_READY;
+        $user = $this->getTestUser('PaymentEmail@UserAccount.com', ['status' => $status]);
         $user->setSetting('external_email', 'ext@email.tld');
         $wallet = $user->wallets()->first();
 
diff --git a/src/tests/Feature/Jobs/PaymentMandateDisabledEmailTest.php b/src/tests/Feature/Jobs/PaymentMandateDisabledEmailTest.php
--- a/src/tests/Feature/Jobs/PaymentMandateDisabledEmailTest.php
+++ b/src/tests/Feature/Jobs/PaymentMandateDisabledEmailTest.php
@@ -4,6 +4,7 @@
 
 use App\Jobs\PaymentMandateDisabledEmail;
 use App\Mail\PaymentMandateDisabled;
+use App\User;
 use Illuminate\Support\Facades\Mail;
 use Tests\TestCase;
 
@@ -40,7 +41,8 @@
      */
     public function testHandle()
     {
-        $user = $this->getTestUser('PaymentEmail@UserAccount.com');
+        $status = User::STATUS_ACTIVE | User::STATUS_LDAP_READY | User::STATUS_IMAP_READY;
+        $user = $this->getTestUser('PaymentEmail@UserAccount.com', ['status' => $status]);
         $user->setSetting('external_email', 'ext@email.tld');
         $wallet = $user->wallets()->first();
 
diff --git a/src/tests/Feature/Jobs/TrialEndEmailTest.php b/src/tests/Feature/Jobs/TrialEndEmailTest.php
--- a/src/tests/Feature/Jobs/TrialEndEmailTest.php
+++ b/src/tests/Feature/Jobs/TrialEndEmailTest.php
@@ -4,6 +4,7 @@
 
 use App\Jobs\TrialEndEmail;
 use App\Mail\TrialEnd;
+use App\User;
 use Illuminate\Support\Facades\Mail;
 use Tests\TestCase;
 
@@ -40,7 +41,8 @@
      */
     public function testHandle()
     {
-        $user = $this->getTestUser('PaymentEmail@UserAccount.com');
+        $status = User::STATUS_ACTIVE | User::STATUS_LDAP_READY | User::STATUS_IMAP_READY;
+        $user = $this->getTestUser('PaymentEmail@UserAccount.com', ['status' => $status]);
         $user->setSetting('external_email', 'ext@email.tld');
 
         Mail::fake();
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
@@ -384,7 +384,8 @@
      */
     private function prepareTestUser(&$wallet)
     {
-        $user = $this->getTestUser('wallet-check@kolabnow.com');
+        $status = User::STATUS_ACTIVE | User::STATUS_LDAP_READY | User::STATUS_IMAP_READY;
+        $user = $this->getTestUser('wallet-check@kolabnow.com', ['status' => $status]);
         $user->setSetting('external_email', 'external@test.com');
         $wallet = $user->wallets()->first();
 
diff --git a/src/tests/Unit/Mail/HelperTest.php b/src/tests/Unit/Mail/HelperTest.php
--- a/src/tests/Unit/Mail/HelperTest.php
+++ b/src/tests/Unit/Mail/HelperTest.php
@@ -3,6 +3,7 @@
 namespace Tests\Unit\Mail;
 
 use App\Mail\Helper;
+use App\User;
 use Illuminate\Support\Facades\Mail;
 use Tests\TestCase;
 
@@ -98,7 +99,8 @@
      */
     public function testUserEmails(): void
     {
-        $user = $this->getTestUser('mail-helper-test@kolabnow.com');
+        $status = User::STATUS_ACTIVE | User::STATUS_LDAP_READY | User::STATUS_IMAP_READY;
+        $user = $this->getTestUser('mail-helper-test@kolabnow.com', ['status' => $status]);
 
         // User with no mailbox and no external email
         list($to, $cc) = Helper::userEmails($user);
@@ -148,5 +150,15 @@
 
         $this->assertSame($user->email, $to);
         $this->assertSame([], $cc);
+
+        // Use with mailbox, but not ready
+        $user->setSetting('external_email', 'external@test.com');
+        $user->status = User::STATUS_ACTIVE | User::STATUS_LDAP_READY;
+        $user->save();
+
+        list($to, $cc) = Helper::userEmails($user, true);
+
+        $this->assertSame(null, $to);
+        $this->assertSame(['external@test.com'], $cc);
     }
 }