diff --git a/src/app/Observers/EntitlementObserver.php b/src/app/Observers/EntitlementObserver.php
--- a/src/app/Observers/EntitlementObserver.php
+++ b/src/app/Observers/EntitlementObserver.php
@@ -97,11 +97,21 @@
     {
         // Start calculating the costs for the consumption of this entitlement if the
         // existing consumption spans >= 14 days.
-        // anything's free for 14 days
+        //
+        // Effect is that anything's free for the first 14 days
         if ($entitlement->created_at >= Carbon::now()->subDays(14)) {
             return;
         }
 
+        $owner = $entitlement->wallet->owner;
+
+        // Determine if we're still within the free first month
+        $freeMonthEnds = $owner->created_at->copy()->addMonthsWithoutOverflow(1);
+
+        if ($freeMonthEnds >= Carbon::now()) {
+            return;
+        }
+
         $cost = 0;
 
         // get the discount rate applied to the wallet.
diff --git a/src/app/Wallet.php b/src/app/Wallet.php
--- a/src/app/Wallet.php
+++ b/src/app/Wallet.php
@@ -60,6 +60,22 @@
 
     public function chargeEntitlements($apply = true)
     {
+        // This wallet has been created less than a month ago, this is the trial period
+        if ($this->owner->created_at >= Carbon::now()->subMonthsWithoutOverflow(1)) {
+            // Move all the current entitlement's updated_at timestamps forward to one month after
+            // this wallet was created.
+            $freeMonthEnds = $this->owner->created_at->copy()->addMonthsWithoutOverflow(1);
+
+            foreach ($this->entitlements()->get()->fresh() as $entitlement) {
+                if ($entitlement->updated_at < $freeMonthEnds) {
+                    $entitlement->updated_at = $freeMonthEnds;
+                    $entitlement->save();
+                }
+            }
+
+            return 0;
+        }
+
         $charges = 0;
         $discount = $this->getDiscountRate();
 
@@ -80,7 +96,7 @@
                 continue;
             }
 
-            // created more than a month ago -- was it billed?
+            // updated last more than a month ago -- was it billed?
             if ($entitlement->updated_at <= Carbon::now()->subMonthsWithoutOverflow(1)) {
                 $diff = $entitlement->updated_at->diffInMonths(Carbon::now());
 
@@ -93,7 +109,9 @@
                     continue;
                 }
 
-                $entitlement->updated_at = $entitlement->updated_at->copy()->addMonthsWithoutOverflow($diff);
+                $entitlement->updated_at = $entitlement->updated_at->copy()
+                    ->addMonthsWithoutOverflow($diff);
+
                 $entitlement->save();
 
                 if ($cost == 0) {
diff --git a/src/database/seeds/production/PackageSeeder.php b/src/database/seeds/production/PackageSeeder.php
--- a/src/database/seeds/production/PackageSeeder.php
+++ b/src/database/seeds/production/PackageSeeder.php
@@ -15,6 +15,7 @@
      */
     public function run()
     {
+        $skuActiveSync = Sku::firstOrCreate(['title' => 'activesync']);
         $skuGroupware = Sku::firstOrCreate(['title' => 'groupware']);
         $skuMailbox = Sku::firstOrCreate(['title' => 'mailbox']);
         $skuStorage = Sku::firstOrCreate(['title' => 'storage']);
@@ -31,7 +32,8 @@
         $skus = [
             $skuMailbox,
             $skuGroupware,
-            $skuStorage
+            $skuStorage,
+            $skuActiveSync
         ];
 
         $package->skus()->saveMany($skus);
diff --git a/src/tests/Feature/BillingTest.php b/src/tests/Feature/BillingTest.php
--- a/src/tests/Feature/BillingTest.php
+++ b/src/tests/Feature/BillingTest.php
@@ -82,7 +82,10 @@
      */
     public function testFullTrial(): void
     {
-        $this->backdateEntitlements($this->wallet->entitlements, Carbon::now()->subMonthsWithoutOverflow(1));
+        $this->backdateEntitlements(
+            $this->wallet->entitlements,
+            Carbon::now()->subMonthsWithoutOverflow(1)
+        );
 
         $this->assertEquals(999, $this->wallet->expectedCharges());
     }
diff --git a/src/tests/Feature/WalletTest.php b/src/tests/Feature/WalletTest.php
--- a/src/tests/Feature/WalletTest.php
+++ b/src/tests/Feature/WalletTest.php
@@ -44,8 +44,6 @@
         parent::tearDown();
     }
 
-
-
     /**
      * Test that turning wallet balance from negative to positive
      * unsuspends the account
@@ -88,7 +86,10 @@
         // User/entitlements created today, balance=0
         $until = $wallet->balanceLastsUntil();
 
-        $this->assertSame(Carbon::now()->toDateString(), $until->toDateString());
+        $this->assertSame(
+            Carbon::now()->addMonthWithoutOverflow(1)->toDateString(),
+            $until->toDateString()
+        );
 
         // User/entitlements created today, balance=-10 CHF
         $wallet->balance = -1000;
@@ -103,7 +104,7 @@
         $daysInLastMonth = \App\Utils::daysInLastMonth();
 
         $this->assertSame(
-            Carbon::now()->addDays($daysInLastMonth)->toDateString(),
+            Carbon::now()->addMonthsWithoutOverflow(1)->addDays($daysInLastMonth)->toDateString(),
             $until->toDateString()
         );
 
diff --git a/src/tests/TestCase.php b/src/tests/TestCase.php
--- a/src/tests/TestCase.php
+++ b/src/tests/TestCase.php
@@ -14,6 +14,10 @@
             $entitlement->created_at = $targetDate;
             $entitlement->updated_at = $targetDate;
             $entitlement->save();
+
+            $owner = $entitlement->wallet->owner;
+            $owner->created_at = $targetDate;
+            $owner->save();
         }
     }