diff --git a/src/app/Console/Commands/Wallet/TrialEndCommand.php b/src/app/Console/Commands/Wallet/TrialEndCommand.php
--- a/src/app/Console/Commands/Wallet/TrialEndCommand.php
+++ b/src/app/Console/Commands/Wallet/TrialEndCommand.php
@@ -27,19 +27,30 @@
      */
     public function handle()
     {
-        // Get all wallets, excluding deleted/inactive accounts
-        // created precisely a month ago
+        // Get all wallets...
         $wallets = \App\Wallet::select('wallets.*')
             ->join('users', 'users.id', '=', 'wallets.user_id')
-            ->leftJoin('wallet_settings', function ($join) {
-                $join->on('wallet_settings.wallet_id', '=', 'wallets.id')
-                    ->where('wallet_settings.key', 'trial_end_notice');
-            })
             ->withEnvTenantContext('users')
+            // exclude deleted accounts
             ->whereNull('users.deleted_at')
+            // exclude "inactive" accounts
             ->where('users.status', '&', \App\User::STATUS_IMAP_READY)
+            // consider only these created 1 to 2 months ago
             ->where('users.created_at', '>', \now()->subMonthsNoOverflow(2))
-            ->whereNull('wallet_settings.value')
+            ->where('users.created_at', '<=', \now()->subMonthsNoOverflow(1))
+            // skip wallets with the notification already sent
+            ->whereNotExists(function ($query) {
+                $query->from('wallet_settings')
+                    ->where('wallet_settings.key', 'trial_end_notice')
+                    ->whereColumn('wallet_settings.wallet_id', 'wallets.id');
+            })
+            // skip users that aren't account owners
+            ->whereExists(function ($query) {
+                $query->from('entitlements')
+                    ->where('entitlements.entitleable_type', \App\User::class)
+                    ->whereColumn('entitlements.entitleable_id', 'wallets.user_id')
+                    ->whereColumn('entitlements.wallet_id', 'wallets.id');
+            })
             ->cursor();
 
         foreach ($wallets as $wallet) {
diff --git a/src/tests/Feature/Console/Wallet/TrialEndTest.php b/src/tests/Feature/Console/Wallet/TrialEndTest.php
--- a/src/tests/Feature/Console/Wallet/TrialEndTest.php
+++ b/src/tests/Feature/Console/Wallet/TrialEndTest.php
@@ -16,7 +16,8 @@
     {
         parent::setUp();
 
-        $this->deleteTestUser('wallets-controller@kolabnow.com');
+        $this->deleteTestUser('test-user1@kolabnow.com');
+        $this->deleteTestUser('test-user22@kolabnow.com');
     }
 
     /**
@@ -24,7 +25,8 @@
      */
     public function tearDown(): void
     {
-        $this->deleteTestUser('wallets-controller@kolabnow.com');
+        $this->deleteTestUser('test-user1@kolabnow.com');
+        $this->deleteTestUser('test-user22@kolabnow.com');
 
         parent::tearDown();
     }
@@ -36,20 +38,30 @@
     {
         Queue::fake();
 
-        $user = $this->getTestUser('wallets-controller@kolabnow.com', [
+        $package = \App\Package::withEnvTenantContext()->where('title', 'lite')->first();
+        $user = $this->getTestUser('test-user1@kolabnow.com', [
                 'status' => User::STATUS_IMAP_READY | User::STATUS_LDAP_READY | User::STATUS_ACTIVE,
         ]);
         $wallet = $user->wallets()->first();
+        $user->assignPackage($package);
 
         DB::table('users')->update(['created_at' => \now()->clone()->subMonthsNoOverflow(2)->subHours(1)]);
 
-        // Expect no wallets in after-trial state
+        // No wallets in after-trial state, no email sent
+        Queue::fake();
+        $code = \Artisan::call("wallet:trial-end");
+        Queue::assertNothingPushed();
+
+        // Expect no email sent (out of time boundaries)
+        $user->created_at = \now()->clone()->subMonthsNoOverflow(1)->addHour();
+        $user->save();
+
         Queue::fake();
         $code = \Artisan::call("wallet:trial-end");
         Queue::assertNothingPushed();
 
         // Test an email sent
-        $user->created_at = \now()->clone()->subMonthNoOverflow();
+        $user->created_at = \now()->clone()->subMonthsNoOverflow(1);
         $user->save();
 
         Queue::fake();
@@ -87,5 +99,17 @@
         Queue::assertNothingPushed();
 
         $this->assertNull($wallet->getSetting('trial_end_notice'));
+
+        // Make sure the non-controller users are omitted
+        $user2 = $this->getTestUser('test-user2@kolabnow.com', [
+                'status' => User::STATUS_IMAP_READY | User::STATUS_LDAP_READY | User::STATUS_ACTIVE,
+        ]);
+        $user->assignPackage($package, $user2);
+        $user2->created_at = \now()->clone()->subMonthsNoOverflow(1);
+        $user2->save();
+
+        Queue::fake();
+        $code = \Artisan::call("wallet:trial-end");
+        Queue::assertNothingPushed();
     }
 }