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
@@ -54,6 +54,12 @@
             ->cursor();
 
         foreach ($wallets as $wallet) {
+            // Skip accounts with no trial period, or a period longer than a month
+            $plan = $wallet->plan();
+            if (!$plan || $plan->free_months != 1) {
+                continue;
+            }
+
             // Send the email asynchronously
             \App\Jobs\TrialEndEmail::dispatch($wallet->owner);
 
diff --git a/src/app/Entitlement.php b/src/app/Entitlement.php
--- a/src/app/Entitlement.php
+++ b/src/app/Entitlement.php
@@ -47,26 +47,6 @@
     ];
 
     /**
-     * Return the costs per day for this entitlement.
-     *
-     * @return float
-     */
-    public function costsPerDay()
-    {
-        if ($this->cost == 0) {
-            return (float) 0;
-        }
-
-        $discount = $this->wallet->getDiscountRate();
-
-        $daysInLastMonth = \App\Utils::daysInLastMonth();
-
-        $costsPerDay = (float) ($this->cost * $discount) / $daysInLastMonth;
-
-        return $costsPerDay;
-    }
-
-    /**
      * Create a transaction record for this entitlement.
      *
      * @param string $type The type of transaction ('created', 'billed', 'deleted'), but use the
diff --git a/src/app/Http/Controllers/API/V4/WalletsController.php b/src/app/Http/Controllers/API/V4/WalletsController.php
--- a/src/app/Http/Controllers/API/V4/WalletsController.php
+++ b/src/app/Http/Controllers/API/V4/WalletsController.php
@@ -232,10 +232,14 @@
             return null;
         }
 
-        // the owner was created less than a month ago
-        if ($wallet->owner->created_at > Carbon::now()->subMonthsWithoutOverflow(1)) {
-            // but more than two weeks ago, notice of trial ending
-            if ($wallet->owner->created_at <= Carbon::now()->subWeeks(2)) {
+        $plan = $wallet->plan();
+        $freeMonths = $plan ? $plan->free_months : 0;
+        $trialEnd = $freeMonths ? $wallet->owner->created_at->copy()->addMonthsWithoutOverflow($freeMonths) : null;
+
+        // the owner is still in the trial period
+        if ($trialEnd && $trialEnd > Carbon::now()) {
+            // notice of trial ending if less than 2 weeks left
+            if ($trialEnd < Carbon::now()->addWeeks(2)) {
                 return \trans('app.wallet-notice-trial-end');
             }
 
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
@@ -114,15 +114,22 @@
             return;
         }
 
-        // Determine if we're still within the free first month
-        $freeMonthEnds = $owner->created_at->copy()->addMonthsWithoutOverflow(1);
+        $now = Carbon::now();
 
-        if ($freeMonthEnds >= Carbon::now()) {
-            return;
+        // Determine if we're still within the trial period
+        $trial = $entitlement->wallet->trialInfo();
+        if (
+            !empty($trial)
+            && $entitlement->updated_at < $trial['end']
+            && in_array($entitlement->sku_id, $trial['skus'])
+        ) {
+            if ($trial['end'] >= $now) {
+                return;
+            }
+
+            $entitlement->updated_at = $trial['end'];
         }
 
-        $now = Carbon::now();
-
         // get the discount rate applied to the wallet.
         $discount = $entitlement->wallet->getDiscountRate();
 
@@ -168,6 +175,8 @@
             return;
         }
 
+        // FIXME: Shouldn't we create per-entitlement transaction record?
+
         $entitlement->wallet->debit($cost);
     }
 }
diff --git a/src/app/Plan.php b/src/app/Plan.php
--- a/src/app/Plan.php
+++ b/src/app/Plan.php
@@ -18,6 +18,7 @@
  * @property string         $description
  * @property int            $discount_qty
  * @property int            $discount_rate
+ * @property int            $free_months
  * @property string         $id
  * @property string         $mode           Plan signup mode (email|token)
  * @property string         $name
@@ -48,6 +49,8 @@
         'discount_qty',
         // the rate of the discount for this plan
         'discount_rate',
+        // number of free months (trial)
+        'free_months',
     ];
 
     /** @var array<string, string> The attributes that should be cast */
@@ -55,7 +58,8 @@
         'promo_from' => 'datetime:Y-m-d H:i:s',
         'promo_to' => 'datetime:Y-m-d H:i:s',
         'discount_qty' => 'integer',
-        'discount_rate' => 'integer'
+        'discount_rate' => 'integer',
+        'free_months' => 'integer'
     ];
 
     /** @var array<int, string> Translatable properties */
diff --git a/src/app/Wallet.php b/src/app/Wallet.php
--- a/src/app/Wallet.php
+++ b/src/app/Wallet.php
@@ -75,83 +75,77 @@
      */
     public function chargeEntitlements($apply = true): int
     {
-        // This wallet has been created less than a month ago, this is the trial period
-        if ($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;
-        }
-
+        $transactions = [];
         $profit = 0;
         $charges = 0;
         $discount = $this->getDiscountRate();
         $isDegraded = $this->owner->isDegraded();
+        $trial = $this->trialInfo();
 
         if ($apply) {
             DB::beginTransaction();
         }
 
-        // used to parent individual entitlement billings to the wallet debit.
-        $entitlementTransactions = [];
-
-        foreach ($this->entitlements()->get() as $entitlement) {
-            // This entitlement has been created less than or equal to 14 days ago (this is at
+        // Get all entitlements...
+        $entitlements = $this->entitlements()
+            // Skip entitlements created less than or equal to 14 days ago (this is at
             // maximum the fourteenth 24-hour period).
-            if ($entitlement->created_at > Carbon::now()->subDays(14)) {
-                continue;
-            }
+            // ->where('created_at', '<=', Carbon::now()->subDays(14))
+            // Skip entitlements created, or billed last, less than a month ago.
+            ->where('updated_at', '<=', Carbon::now()->subMonthsWithoutOverflow(1))
+            ->get();
+
+        foreach ($entitlements as $entitlement) {
+            // If in trial, move entitlement's updated_at timestamps forward to the trial end.
+            if (
+                !empty($trial)
+                && $entitlement->updated_at < $trial['end']
+                && in_array($entitlement->sku_id, $trial['skus'])
+            ) {
+                // TODO: Consider not updating the updated_at to a future date, i.e. bump it
+                // as many months as possible, but not into the future
+                // if we're in dry-run, you know...
+                if ($apply) {
+                    $entitlement->updated_at = $trial['end'];
+                    $entitlement->save();
+                }
 
-            // This entitlement was created, or billed last, less than a month ago.
-            if ($entitlement->updated_at > Carbon::now()->subMonthsWithoutOverflow(1)) {
                 continue;
             }
 
-            // 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());
+            $diff = $entitlement->updated_at->diffInMonths(Carbon::now());
 
-                $cost = (int) ($entitlement->cost * $discount * $diff);
-                $fee = (int) ($entitlement->fee * $diff);
-
-                if ($isDegraded) {
-                    $cost = 0;
-                }
+            if ($diff <= 0) {
+                continue;
+            }
 
-                $charges += $cost;
-                $profit += $cost - $fee;
+            $cost = (int) ($entitlement->cost * $discount * $diff);
+            $fee = (int) ($entitlement->fee * $diff);
 
-                // if we're in dry-run, you know...
-                if (!$apply) {
-                    continue;
-                }
+            if ($isDegraded) {
+                $cost = 0;
+            }
 
-                $entitlement->updated_at = $entitlement->updated_at->copy()
-                    ->addMonthsWithoutOverflow($diff);
+            $charges += $cost;
+            $profit += $cost - $fee;
 
-                $entitlement->save();
+            // if we're in dry-run, you know...
+            if (!$apply) {
+                continue;
+            }
 
-                if ($cost == 0) {
-                    continue;
-                }
+            $entitlement->updated_at = $entitlement->updated_at->copy()->addMonthsWithoutOverflow($diff);
+            $entitlement->save();
 
-                $entitlementTransactions[] = $entitlement->createTransaction(
-                    Transaction::ENTITLEMENT_BILLED,
-                    $cost
-                );
+            if ($cost == 0) {
+                continue;
             }
+
+            $transactions[] = $entitlement->createTransaction(Transaction::ENTITLEMENT_BILLED, $cost);
         }
 
         if ($apply) {
-            $this->debit($charges, '', $entitlementTransactions);
+            $this->debit($charges, '', $transactions);
 
             // Credit/debit the reseller
             if ($profit != 0 && $this->owner->tenant) {
@@ -182,26 +176,53 @@
             return null;
         }
 
-        // retrieve any expected charges
-        $expectedCharge = $this->expectedCharges();
-
-        // get the costs per day for all entitlements billed against this wallet
-        $costsPerDay = $this->costsPerDay();
+        $balance = $this->balance;
+        $discount = $this->getDiscountRate();
+        $trial = $this->trialInfo();
+
+        // Get all entitlements...
+        $entitlements = $this->entitlements()->orderBy('updated_at')->get()
+            ->filter(function ($entitlement) {
+                return $entitlement->cost > 0;
+            })
+            ->map(function ($entitlement) {
+                return [
+                    'date' => $entitlement->updated_at ?: $entitlement->created_at,
+                    'cost' => $entitlement->cost,
+                    'sku_id' => $entitlement->sku_id,
+                ];
+            })
+            ->all();
+
+        $max = 12 * 25;
+        while ($max > 0) {
+            foreach ($entitlements as &$entitlement) {
+                $until = $entitlement['date'] = $entitlement['date']->addMonthsWithoutOverflow(1);
+
+                if (
+                    !empty($trial)
+                    && $entitlement['date'] < $trial['end']
+                    && in_array($entitlement['sku_id'], $trial['skus'])
+                ) {
+                    continue;
+                }
 
-        if (!$costsPerDay) {
-            return null;
-        }
+                $balance -= (int) ($entitlement['cost'] * $discount);
 
-        // the number of days this balance, minus the expected charges, would last
-        $daysDelta = floor(($this->balance - $expectedCharge) / $costsPerDay);
+                if ($balance < 0) {
+                    break 2;
+                }
+            }
 
-        // calculate from the last entitlement billed
-        $entitlement = $this->entitlements()->orderBy('updated_at', 'desc')->first();
+            $max--;
+        }
 
-        $until = $entitlement->updated_at->copy()->addDays($daysDelta);
+        if (empty($until)) {
+            return null;
+        }
 
         // Don't return dates from the past
-        if ($until < Carbon::now() && !$until->isToday()) {
+        if ($until <= Carbon::now() && !$until->isToday()) {
             return null;
         }
 
@@ -224,22 +245,6 @@
     }
 
     /**
-     * Retrieve the costs per day of everything charged to this wallet.
-     *
-     * @return float
-     */
-    public function costsPerDay()
-    {
-        $costs = (float) 0;
-
-        foreach ($this->entitlements as $entitlement) {
-            $costs += $entitlement->costsPerDay();
-        }
-
-        return $costs;
-    }
-
-    /**
      * Add an amount of pecunia to this wallet's balance.
      *
      * @param int    $amount      The amount of pecunia to add (in cents).
@@ -406,6 +411,18 @@
     }
 
     /**
+     * Plan of the wallet.
+     *
+     * @return ?\App\Plan
+     */
+    public function plan()
+    {
+        $planId = $this->owner->getSetting('plan_id');
+
+        return $planId ? Plan::find($planId) : null;
+    }
+
+    /**
      * Remove a controller from this wallet.
      *
      * @param \App\User $user The user to remove as a controller from this wallet.
@@ -426,12 +443,50 @@
      */
     public function transactions()
     {
-        return Transaction::where(
-            [
-                'object_id' => $this->id,
-                'object_type' => Wallet::class
-            ]
-        );
+        return Transaction::where('object_id', $this->id)->where('object_type', Wallet::class);
+    }
+
+    /**
+     * Returns trial related information.
+     *
+     * @return ?array Plan ID, plan SKUs, trial end date, number of free months (planId, skus, end, months)
+     */
+    public function trialInfo(): ?array
+    {
+        $plan = $this->plan();
+        $freeMonths = $plan ? $plan->free_months : 0;
+        $trialEnd = $freeMonths ? $this->owner->created_at->copy()->addMonthsWithoutOverflow($freeMonths) : null;
+
+        if ($trialEnd) {
+            // Get all SKUs assigned to the plan (they are free in trial)
+            // TODO: We could store the list of plan's SKUs in the wallet settings, for two reasons:
+            //       - performance
+            //       - if we change plan definition at some point in time, the old users would use
+            //         the old definition, instead of the current one
+            // TODO: The same for plan's free_months value
+            $trialSkus = \App\Sku::select('id')
+                ->whereIn('id', function ($query) use ($plan) {
+                    $query->select('sku_id')
+                        ->from('package_skus')
+                        ->whereIn('package_id', function ($query) use ($plan) {
+                            $query->select('package_id')
+                                ->from('plan_packages')
+                                ->where('plan_id', $plan->id);
+                        });
+                })
+                ->whereNot('title', 'storage')
+                ->pluck('id')
+                ->all();
+
+            return [
+                'end' => $trialEnd,
+                'skus' => $trialSkus,
+                'planId' => $plan->id,
+                'months' => $freeMonths,
+            ];
+        }
+
+        return null;
     }
 
     /**
diff --git a/src/database/migrations/2022_09_08_100000_plans_free_months.php b/src/database/migrations/2022_09_08_100000_plans_free_months.php
new file mode 100644
--- /dev/null
+++ b/src/database/migrations/2022_09_08_100000_plans_free_months.php
@@ -0,0 +1,41 @@
+<?php
+
+use Illuminate\Database\Migrations\Migration;
+use Illuminate\Database\Schema\Blueprint;
+use Illuminate\Support\Facades\DB;
+use Illuminate\Support\Facades\Schema;
+
+return new class extends Migration
+{
+    /**
+     * Run the migrations.
+     *
+     * @return void
+     */
+    public function up()
+    {
+        Schema::table(
+            'plans',
+            function (Blueprint $table) {
+                $table->tinyInteger('free_months')->unsigned()->default(0);
+            }
+        );
+
+        DB::table('plans')->update(['free_months' => 1]);
+    }
+
+    /**
+     * Reverse the migrations.
+     *
+     * @return void
+     */
+    public function down()
+    {
+        Schema::table(
+            'plans',
+            function (Blueprint $table) {
+                $table->dropColumn('free_months');
+            }
+        );
+    }
+};
diff --git a/src/database/seeds/local/PlanSeeder.php b/src/database/seeds/local/PlanSeeder.php
--- a/src/database/seeds/local/PlanSeeder.php
+++ b/src/database/seeds/local/PlanSeeder.php
@@ -32,6 +32,7 @@
                 'title' => 'individual',
                 'name' => 'Individual Account',
                 'description' => $description,
+                'free_months' => 1,
                 'discount_qty' => 0,
                 'discount_rate' => 0
             ]
@@ -59,6 +60,7 @@
                 'title' => 'group',
                 'name' => 'Group Account',
                 'description' => $description,
+                'free_months' => 1,
                 'discount_qty' => 0,
                 'discount_rate' => 0
             ]
@@ -91,6 +93,7 @@
                 [
                     'title' => 'individual',
                     'name' => 'Individual Account',
+                    'free_months' => 1,
                     'description' => $description,
                     'discount_qty' => 0,
                     'discount_rate' => 0
@@ -122,6 +125,7 @@
                     'title' => 'group',
                     'name' => 'Group Account',
                     'description' => $description,
+                    'free_months' => 1,
                     'discount_qty' => 0,
                     'discount_rate' => 0
                 ]
diff --git a/src/database/seeds/production/PlanSeeder.php b/src/database/seeds/production/PlanSeeder.php
--- a/src/database/seeds/production/PlanSeeder.php
+++ b/src/database/seeds/production/PlanSeeder.php
@@ -32,6 +32,7 @@
                 'title' => 'individual',
                 'name' => 'Individual Account',
                 'description' => $description,
+                'free_months' => 1,
                 'discount_qty' => 0,
                 'discount_rate' => 0
             ]
@@ -59,6 +60,7 @@
                 'title' => 'group',
                 'name' => 'Group Account',
                 'description' => $description,
+                'free_months' => 1,
                 'discount_qty' => 0,
                 'discount_rate' => 0
             ]
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
@@ -38,12 +38,12 @@
     {
         Queue::fake();
 
-        $package = \App\Package::withEnvTenantContext()->where('title', 'lite')->first();
+        $plan = \App\Plan::withEnvTenantContext()->where('title', 'individual')->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);
+        $user->assignPlan($plan);
 
         DB::table('users')->update(['created_at' => \now()->clone()->subMonthsNoOverflow(2)->subHours(1)]);
 
@@ -104,6 +104,7 @@
         $user2 = $this->getTestUser('test-user2@kolabnow.com', [
                 'status' => User::STATUS_IMAP_READY | User::STATUS_LDAP_READY | User::STATUS_ACTIVE,
         ]);
+        $package = \App\Package::withEnvTenantContext()->where('title', 'lite')->first();
         $user->assignPackage($package, $user2);
         $user2->created_at = \now()->clone()->subMonthsNoOverflow(1);
         $user2->save();
diff --git a/src/tests/Feature/Controller/WalletsTest.php b/src/tests/Feature/Controller/WalletsTest.php
--- a/src/tests/Feature/Controller/WalletsTest.php
+++ b/src/tests/Feature/Controller/WalletsTest.php
@@ -37,8 +37,8 @@
     public function testGetWalletNotice(): void
     {
         $user = $this->getTestUser('wallets-controller@kolabnow.com');
-        $package = \App\Package::withObjectTenantContext($user)->where('title', 'kolab')->first();
-        $user->assignPackage($package);
+        $plan = \App\Plan::withObjectTenantContext($user)->where('title', 'individual')->first();
+        $user->assignPlan($plan);
         $wallet = $user->wallets()->first();
 
         $controller = new WalletsController();
@@ -50,7 +50,7 @@
 
         $this->assertSame('You are in your free trial period.', $notice);
 
-        $wallet->owner->created_at = Carbon::now()->subDays(15);
+        $wallet->owner->created_at = Carbon::now()->subWeeks(3);
         $wallet->owner->save();
 
         $notice = $method->invoke($controller, $wallet);
@@ -64,8 +64,8 @@
         $this->assertSame('You are out of credit, top up your balance now.', $notice);
 
         // User/entitlements created slightly more than a month ago, balance=9,99 CHF (monthly)
-        $wallet->owner->created_at = Carbon::now()->subMonthsWithoutOverflow(1)->subDays(1);
-        $wallet->owner->save();
+        $this->backdateEntitlements($wallet->entitlements, Carbon::now()->subMonthsWithoutOverflow(1)->subDays(1));
+        $wallet->refresh();
 
         // test "1 month"
         $wallet->balance = 990;
@@ -77,7 +77,7 @@
         $wallet->balance = 990 * 2.6;
         $notice = $method->invoke($controller, $wallet);
 
-        $this->assertMatchesRegularExpression('/\(2 months 2 weeks\)/', $notice);
+        $this->assertMatchesRegularExpression('/\(1 month 4 weeks\)/', $notice);
 
         // Change locale to make sure the text is localized by Carbon
         \app()->setLocale('de');
@@ -86,7 +86,7 @@
         $wallet->balance = 990 * 23.5;
         $notice = $method->invoke($controller, $wallet);
 
-        $this->assertMatchesRegularExpression('/\(1 Jahr 11 Monate\)/', $notice);
+        $this->assertMatchesRegularExpression('/\(1 Jahr 10 Monate\)/', $notice);
 
         // Old entitlements, 100% discount
         $this->backdateEntitlements($wallet->entitlements, Carbon::now()->subDays(40));
diff --git a/src/tests/Feature/EntitlementTest.php b/src/tests/Feature/EntitlementTest.php
--- a/src/tests/Feature/EntitlementTest.php
+++ b/src/tests/Feature/EntitlementTest.php
@@ -40,28 +40,6 @@
     }
 
     /**
-     * Test for Entitlement::costsPerDay()
-     */
-    public function testCostsPerDay(): void
-    {
-        // 500
-        // 28 days: 17.86
-        // 31 days: 16.129
-        $user = $this->getTestUser('entitlement-test@kolabnow.com');
-        $package = Package::withEnvTenantContext()->where('title', 'kolab')->first();
-        $mailbox = Sku::withEnvTenantContext()->where('title', 'mailbox')->first();
-
-        $user->assignPackage($package);
-
-        $entitlement = $user->entitlements->where('sku_id', $mailbox->id)->first();
-
-        $costsPerDay = $entitlement->costsPerDay();
-
-        $this->assertTrue($costsPerDay < 17.86);
-        $this->assertTrue($costsPerDay > 16.12);
-    }
-
-    /**
      * Tests for entitlements
      * @todo This really should be in User or Wallet tests file
      */
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
@@ -3,6 +3,7 @@
 namespace Tests\Feature;
 
 use App\Package;
+use App\Plan;
 use App\User;
 use App\Sku;
 use App\Transaction;
@@ -27,6 +28,9 @@
         'jane@kolabnow.com'
     ];
 
+    /**
+     * {@inheritDoc}
+     */
     public function setUp(): void
     {
         parent::setUp();
@@ -35,8 +39,13 @@
         foreach ($this->users as $user) {
             $this->deleteTestUser($user);
         }
+
+        Sku::select()->update(['fee' => 0]);
     }
 
+    /**
+     * {@inheritDoc}
+     */
     public function tearDown(): void
     {
         foreach ($this->users as $user) {
@@ -90,8 +99,8 @@
         // 31 days: 31.93 per day
 
         $user = $this->getTestUser('jane@kolabnow.com');
-        $package = Package::withEnvTenantContext()->where('title', 'kolab')->first();
-        $user->assignPackage($package);
+        $plan = Plan::withEnvTenantContext()->where('title', 'individual')->first();
+        $user->assignPlan($plan);
         $wallet = $user->wallets()->first();
 
         // User/entitlements created today, balance=0
@@ -138,29 +147,6 @@
     }
 
     /**
-     * Test for Wallet::costsPerDay()
-     */
-    public function testCostsPerDay(): void
-    {
-        // 990
-        // 28 days: 35.36
-        // 31 days: 31.93
-        $user = $this->getTestUser('jane@kolabnow.com');
-
-        $package = Package::withEnvTenantContext()->where('title', 'kolab')->first();
-        $mailbox = Sku::withEnvTenantContext()->where('title', 'mailbox')->first();
-
-        $user->assignPackage($package);
-
-        $wallet = $user->wallets()->first();
-
-        $costsPerDay = $wallet->costsPerDay();
-
-        $this->assertTrue($costsPerDay < 35.38);
-        $this->assertTrue($costsPerDay > 31.93);
-    }
-
-    /**
      * Verify a wallet is created, when a user is created.
      */
     public function testCreateUserCreatesWallet(): void
@@ -332,11 +318,11 @@
         // Add 40% fee to all SKUs
         Sku::select()->update(['fee' => DB::raw("`cost` * 0.4")]);
 
-        $package = Package::withEnvTenantContext()->where('title', 'kolab')->first();
+        $plan = Plan::withEnvTenantContext()->where('title', 'individual')->first();
         $storage = Sku::withEnvTenantContext()->where('title', 'storage')->first();
-        $user->assignPackage($package);
+        $user->assignPlan($plan);
         $user->assignSku($storage, 5);
-        $user->refresh();
+        $user->setSetting('plan_id', null); // disable plan and trial
 
         // Reset reseller's wallet balance and transactions
         $reseller_wallet = $user->tenant->wallet();
@@ -357,10 +343,11 @@
         $wallet->refresh();
         $reseller_wallet->refresh();
 
-        // TODO: Update these comments with what is actually being used to calculate these numbers
-        // 388 + 310 + 17 + 17 = 732
+        // User discount is 30%
+        // Expected: groupware: 490 x 70% + mailbox: 500 x 70% + storage: 5 x round(25x70%) = 778
         $this->assertSame(-778, $wallet->balance);
-        // 388 - 555 x 40% + 310 - 444 x 40% + 34 - 50 x 40% = 312
+        // Reseller fee is 40%
+        // Expected: groupware: 490 x 30% + mailbox: 500 x 30% + storage: 5 x round(25x30%) = 332
         $this->assertSame(332, $reseller_wallet->balance);
 
         $transactions = Transaction::where('object_id', $wallet->id)
@@ -381,7 +368,9 @@
         $this->assertSame(-778, $trans->amount);
         $this->assertSame(Transaction::WALLET_DEBIT, $trans->type);
 
-        // TODO: Test entitlement transaction records
+        // Assert all entitlements' updated_at timestamp
+        $date = $backdate->addMonthsWithoutOverflow(1);
+        $this->assertCount(12, $wallet->entitlements()->where('updated_at', $date)->get());
 
         // -----------------------------------
         // Test charging on entitlement delete
@@ -439,6 +428,107 @@
     }
 
     /**
+     * Test for charging and removing entitlements when in trial
+     */
+    public function testChargeAndDeleteEntitlementsTrial(): void
+    {
+        $user = $this->getTestUser('jane@kolabnow.com');
+        $wallet = $user->wallets()->first();
+
+        $plan = Plan::withEnvTenantContext()->where('title', 'individual')->first();
+        $storage = Sku::withEnvTenantContext()->where('title', 'storage')->first();
+        $user->assignPlan($plan);
+        $user->assignSku($storage, 5);
+
+        // ------------------------------------
+        // Test normal charging of entitlements
+        // ------------------------------------
+
+        // Backdate and charge entitlements, we're expecting one month to be charged
+        // Set fake NOW date to make simpler asserting results that depend on number of days in current/last month
+        Carbon::setTestNow(Carbon::create(2021, 5, 21, 12));
+        $backdate = Carbon::now()->subWeeks(7);
+        $this->backdateEntitlements($user->entitlements, $backdate);
+        $charge = $wallet->chargeEntitlements();
+        $wallet->refresh();
+
+        // Expected: storage: 5 x 25 = 125 (the rest is free in trial)
+        $this->assertSame($balance = -125, $wallet->balance);
+
+        // Assert wallet transaction
+        $transactions = $wallet->transactions()->get();
+
+        $this->assertCount(1, $transactions);
+        $trans = $transactions[0];
+        $this->assertSame('', $trans->description);
+        $this->assertSame($balance, $trans->amount);
+        $this->assertSame(Transaction::WALLET_DEBIT, $trans->type);
+
+        // Assert entitlement transactions
+        $etransactions = Transaction::where('transaction_id', $trans->id)->get();
+        $this->assertCount(5, $etransactions);
+        $trans = $etransactions[0];
+        $this->assertSame(null, $trans->description);
+        $this->assertSame(25, $trans->amount);
+        $this->assertSame(Transaction::ENTITLEMENT_BILLED, $trans->type);
+
+        // Assert all entitlements' updated_at timestamp
+        $date = $backdate->addMonthsWithoutOverflow(1);
+        $this->assertCount(12, $wallet->entitlements()->where('updated_at', $date)->get());
+
+        // Run again, expect no changes
+        $charge = $wallet->chargeEntitlements();
+        $wallet->refresh();
+
+        $this->assertSame($balance, $wallet->balance);
+        $this->assertCount(1, $wallet->transactions()->get());
+        $this->assertCount(12, $wallet->entitlements()->where('updated_at', $date)->get());
+
+        // -----------------------------------
+        // Test charging on entitlement delete
+        // -----------------------------------
+
+        $wallet->transactions()->delete();
+
+        $user->removeSku($storage, 2);
+
+        $wallet->refresh();
+
+        // we expect the wallet to have been charged for 19 days of use of
+        // 2 deleted storage entitlements: 2 x round(25 / 31 * 19) = 30
+        $this->assertSame($balance -= 30, $wallet->balance);
+
+        // Assert wallet transactions
+        $transactions = $wallet->transactions()->get();
+
+        $this->assertCount(2, $transactions);
+        $trans = $transactions[0];
+        $this->assertSame('', $trans->description);
+        $this->assertSame(-15, $trans->amount);
+        $this->assertSame(Transaction::WALLET_DEBIT, $trans->type);
+        $trans = $transactions[1];
+        $this->assertSame('', $trans->description);
+        $this->assertSame(-15, $trans->amount);
+        $this->assertSame(Transaction::WALLET_DEBIT, $trans->type);
+
+        // Assert entitlement transactions
+        /* Note: Commented out because the observer does not create per-entitlement transactions
+        $etransactions = Transaction::where('transaction_id', $transactions[0]->id)->get();
+        $this->assertCount(1, $etransactions);
+        $trans = $etransactions[0];
+        $this->assertSame(null, $trans->description);
+        $this->assertSame(15, $trans->amount);
+        $this->assertSame(Transaction::ENTITLEMENT_BILLED, $trans->type);
+        $etransactions = Transaction::where('transaction_id', $transactions[1]->id)->get();
+        $this->assertCount(1, $etransactions);
+        $trans = $etransactions[0];
+        $this->assertSame(null, $trans->description);
+        $this->assertSame(15, $trans->amount);
+        $this->assertSame(Transaction::ENTITLEMENT_BILLED, $trans->type);
+        */
+    }
+
+    /**
      * Tests for updateEntitlements()
      */
     public function testUpdateEntitlements(): void