diff --git a/src/app/Changelog.php b/src/app/Changelog.php
new file mode 100644
--- /dev/null
+++ b/src/app/Changelog.php
@@ -0,0 +1,15 @@
+<?php
+
+namespace App;
+
+use Illuminate\Database\Eloquent\Model;
+use Illuminate\Database\Eloquent\SoftDeletes;
+
+class Changelog extends Model
+{
+    use SoftDeletes;
+
+    protected $fillable = [
+        'entitlement_id'
+    ];
+}
diff --git a/src/app/Console/Commands/WalletCharge.php b/src/app/Console/Commands/WalletCharge.php
new file mode 100644
--- /dev/null
+++ b/src/app/Console/Commands/WalletCharge.php
@@ -0,0 +1,58 @@
+<?php
+
+namespace App\Console\Commands;
+
+use App\Domain;
+use App\User;
+use Carbon\Carbon;
+use Illuminate\Console\Command;
+use Illuminate\Support\Facades\DB;
+
+class WalletCharge extends Command
+{
+    /**
+     * The name and signature of the console command.
+     *
+     * @var string
+     */
+    protected $signature = 'wallet:charge';
+
+    /**
+     * The console command description.
+     *
+     * @var string
+     */
+    protected $description = 'Charge wallets';
+
+    /**
+     * Create a new command instance.
+     *
+     * @return void
+     */
+    public function __construct()
+    {
+        parent::__construct();
+    }
+
+    /**
+     * Execute the console command.
+     *
+     * @return mixed
+     */
+    public function handle()
+    {
+        $wallets = \App\Wallet::all();
+
+        foreach ($wallets as $wallet) {
+            $charge = $wallet->expectedCharges();
+
+            if ($charge > 0) {
+                $this->info("charging wallet {$wallet->id} for user {$wallet->owner->email} with {$charge}");
+
+                foreach ($wallet->entitlements as $entitlement) {
+                    $entitlement->chargeWallet();
+                }
+            }
+        }
+    }
+}
diff --git a/src/app/Console/Commands/WalletExpected.php b/src/app/Console/Commands/WalletExpected.php
new file mode 100644
--- /dev/null
+++ b/src/app/Console/Commands/WalletExpected.php
@@ -0,0 +1,55 @@
+<?php
+
+namespace App\Console\Commands;
+
+use App\Domain;
+use App\User;
+use Carbon\Carbon;
+use Illuminate\Console\Command;
+use Illuminate\Support\Facades\DB;
+
+class WalletExpected extends Command
+{
+    /**
+     * The name and signature of the console command.
+     *
+     * @var string
+     */
+    protected $signature = 'wallet:expected';
+
+    /**
+     * The console command description.
+     *
+     * @var string
+     */
+    protected $description = 'Show expected charges to wallets';
+
+    /**
+     * Create a new command instance.
+     *
+     * @return void
+     */
+    public function __construct()
+    {
+        parent::__construct();
+    }
+
+    /**
+     * Execute the console command.
+     *
+     * @return mixed
+     */
+    public function handle()
+    {
+        $wallets = \App\Wallet::all();
+
+        foreach ($wallets as $wallet) {
+            $charge = 0;
+            $expected = $wallet->expectedCharges();
+
+            if ($expected > 0) {
+                $this->info("expect charging wallet {$wallet->id} for user {$wallet->owner->email} with {$expected}");
+            }
+        }
+    }
+}
diff --git a/src/app/Domain.php b/src/app/Domain.php
--- a/src/app/Domain.php
+++ b/src/app/Domain.php
@@ -68,6 +68,7 @@
                         'owner_id' => $user->id,
                         'wallet_id' => $wallet_id,
                         'sku_id' => $sku->id,
+                        'cost' => $sku->pivot->cost(),
                         'entitleable_id' => $this->id,
                         'entitleable_type' => Domain::class
                     ]
diff --git a/src/app/Entitlement.php b/src/app/Entitlement.php
--- a/src/app/Entitlement.php
+++ b/src/app/Entitlement.php
@@ -2,7 +2,9 @@
 
 namespace App;
 
+use Carbon\Carbon;
 use Illuminate\Database\Eloquent\Model;
+use Illuminate\Database\Eloquent\SoftDeletes;
 
 /**
  * The eloquent definition of an Entitlement.
@@ -16,6 +18,8 @@
  */
 class Entitlement extends Model
 {
+    use SoftDeletes;
+
     /**
      * This table does not use auto-increment.
      *
@@ -41,9 +45,51 @@
         'wallet_id',
         'entitleable_id',
         'entitleable_type',
+        'cost',
         'description'
     ];
 
+    public function changelogEntry()
+    {
+        return \App\Changelog::where('entitlement_id', $this->id)->latest()->first();
+    }
+
+    public function chargeWallet()
+    {
+        $charges = 0;
+
+        $entry = $this->changelogEntry();
+
+        \Log::debug("entry: " . var_export($entry->toArray(), true));
+
+        if ($entry->updated_at >= Carbon::now()->subDays(14)) {
+            \Log::debug(">= 14 days ago, skipping");
+            return $charges;
+        }
+
+        if ($entry->updated_at > Carbon::now()->subMonths(1)) {
+            \Log::debug("> 1 month ago, skipping");
+            return $charges;
+        }
+
+        $diff = $entry->updated_at->diffInMonths(Carbon::now());
+
+        if ($this->cost < 1) {
+            \Log::debug("{$this->sku->title} is a free entitlement, skipping");
+            $entry->updated_at = $entry->updated_at->addMonths($diff);
+            $entry->save();
+            return $charges;
+        }
+
+        $charges += $this->cost * $diff;
+
+        $this->wallet->debit($this->cost * $diff);
+        $entry->updated_at = $entry->updated_at->addMonths($diff);
+        $entry->save();
+
+        return $charges;
+    }
+
     /**
      * Principally entitleable objects such as 'Domain' or 'User'.
      *
diff --git a/src/app/Handlers/Domain.php b/src/app/Handlers/Domain.php
--- a/src/app/Handlers/Domain.php
+++ b/src/app/Handlers/Domain.php
@@ -2,8 +2,6 @@
 
 namespace App\Handlers;
 
-use App\Sku;
-
 class Domain extends \App\Handlers\Base
 {
     public static function entitleableClass()
diff --git a/src/app/Handlers/DomainHosting.php b/src/app/Handlers/DomainHosting.php
--- a/src/app/Handlers/DomainHosting.php
+++ b/src/app/Handlers/DomainHosting.php
@@ -2,8 +2,6 @@
 
 namespace App\Handlers;
 
-use App\Sku;
-
 class DomainHosting extends \App\Handlers\Base
 {
     public static function entitleableClass()
diff --git a/src/app/Handlers/DomainRegistration.php b/src/app/Handlers/DomainRegistration.php
--- a/src/app/Handlers/DomainRegistration.php
+++ b/src/app/Handlers/DomainRegistration.php
@@ -2,8 +2,6 @@
 
 namespace App\Handlers;
 
-use App\Sku;
-
 class DomainRegistration extends \App\Handlers\Base
 {
     public static function entitleableClass()
diff --git a/src/app/Handlers/Groupware.php b/src/app/Handlers/Groupware.php
--- a/src/app/Handlers/Groupware.php
+++ b/src/app/Handlers/Groupware.php
@@ -2,8 +2,6 @@
 
 namespace App\Handlers;
 
-use App\Sku;
-
 class Groupware extends \App\Handlers\Base
 {
     public static function entitleableClass()
diff --git a/src/app/Handlers/Mailbox.php b/src/app/Handlers/Mailbox.php
--- a/src/app/Handlers/Mailbox.php
+++ b/src/app/Handlers/Mailbox.php
@@ -2,10 +2,6 @@
 
 namespace App\Handlers;
 
-use App\Entitlement;
-use App\Sku;
-use App\User;
-
 class Mailbox extends \App\Handlers\Base
 {
     public static function entitleableClass()
diff --git a/src/app/Handlers/Resource.php b/src/app/Handlers/Resource.php
--- a/src/app/Handlers/Resource.php
+++ b/src/app/Handlers/Resource.php
@@ -2,8 +2,6 @@
 
 namespace App\Handlers;
 
-use App\Sku;
-
 class Resource extends \App\Handlers\Base
 {
     public static function entitleableClass()
diff --git a/src/app/Handlers/SharedFolder.php b/src/app/Handlers/SharedFolder.php
--- a/src/app/Handlers/SharedFolder.php
+++ b/src/app/Handlers/SharedFolder.php
@@ -2,8 +2,6 @@
 
 namespace App\Handlers;
 
-use App\Sku;
-
 class SharedFolder extends \App\Handlers\Base
 {
     public static function entitleableClass()
diff --git a/src/app/Handlers/Storage.php b/src/app/Handlers/Storage.php
--- a/src/app/Handlers/Storage.php
+++ b/src/app/Handlers/Storage.php
@@ -6,7 +6,7 @@
 {
     public static function entitleableClass()
     {
-        return null;
+        return \App\User::class;
     }
 
     public static function preReq($entitlement, $object)
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
@@ -3,6 +3,7 @@
 namespace App\Observers;
 
 use App\Entitlement;
+use Carbon\Carbon;
 
 /**
  * This is an observer for the Entitlement model definition.
@@ -62,11 +63,15 @@
         if (!$result) {
             return false;
         }
+    }
 
-        // TODO: Handle the first free unit here?
-
-        // TODO: Execute the Sku handler class or function?
+    public function created(Entitlement $entitlement)
+    {
+        \App\Changelog::create(['entitlement_id' => $entitlement->id]);
+    }
 
-        $wallet->debit($sku->cost);
+    public function deleting(Entitlement $entitlement)
+    {
+        \App\Changelog::where('entitlement_id', $entitlement->id)->delete();
     }
 }
diff --git a/src/app/Observers/PackageSkuObserver.php b/src/app/Observers/PackageSkuObserver.php
new file mode 100644
--- /dev/null
+++ b/src/app/Observers/PackageSkuObserver.php
@@ -0,0 +1,23 @@
+<?php
+
+namespace App\Observers;
+
+class PackageSkuObserver
+{
+    public function created(\App\PackageSku $packageSku)
+    {
+        // TODO: free units...
+        $package = $packageSku->package;
+        $sku = $packageSku->sku;
+
+        $cost = ($sku->cost * (100 - $package->discount_rate)) / 100;
+
+        \Log::debug("Setting costs for {$sku->title} on package {$package->title} to {$cost}");
+
+        $package->skus()->updateExistingPivot(
+            $sku,
+            ['cost' => ($sku->cost * (100 - $package->discount_rate)) / 100],
+            false
+        );
+    }
+}
diff --git a/src/app/Observers/UserObserver.php b/src/app/Observers/UserObserver.php
--- a/src/app/Observers/UserObserver.php
+++ b/src/app/Observers/UserObserver.php
@@ -79,6 +79,8 @@
      */
     public function deleting(User $user)
     {
+        \Log::debug("where deleting user {$user->email}");
+
         // Entitlements do not have referential integrity on the entitled object, so this is our
         // way of doing an onDelete('cascade') without the foreign key.
         $entitlements = \App\Entitlement::where('entitleable_id', $user->id)
diff --git a/src/app/Package.php b/src/app/Package.php
--- a/src/app/Package.php
+++ b/src/app/Package.php
@@ -34,12 +34,26 @@
         'discount_rate'
     ];
 
+    /**
+     * The costs of this package at its pre-defined, existing configuration.
+     *
+     * @return int The costs in cents.
+     */
     public function cost()
     {
         $costs = 0;
 
         foreach ($this->skus as $sku) {
-            $costs += ($sku->pivot->qty - $sku->units_free) * $sku->cost;
+            $units = $sku->pivot->qty - $sku->units_free;
+
+            if ($units < 0) {
+                \Log::debug("Package {$this->id} is misconfigured for more free units than qty.");
+                $units = 0;
+            }
+
+            $ppu = $sku->cost * ((100 - $this->discount_rate) / 100);
+
+            $costs += $units * $ppu;
         }
 
         return $costs;
diff --git a/src/app/PackageSku.php b/src/app/PackageSku.php
--- a/src/app/PackageSku.php
+++ b/src/app/PackageSku.php
@@ -12,10 +12,48 @@
     protected $fillable = [
         'package_id',
         'sku_id',
+        'cost',
         'qty'
     ];
 
     protected $casts = [
+        'cost' => 'integer',
         'qty' => 'integer'
     ];
+
+    /**
+     * Under this package, how much does this SKU cost?
+     *
+     * @return int The costs of this SKU under this package in cents.
+     */
+    public function cost()
+    {
+        $costs = 0;
+
+        $units = $this->qty - $this->sku->units_free;
+
+        if ($units < 0) {
+            \Log::debug(
+                "Package {$this->package_id} is misconfigured for more free units than qty."
+            );
+
+            $units = 0;
+        }
+
+        $ppu = $this->sku->cost * ((100 - $this->package->discount_rate) / 100);
+
+        $costs += $units * $ppu;
+
+        return $costs;
+    }
+
+    public function package()
+    {
+        return $this->belongsTo('App\Package');
+    }
+
+    public function sku()
+    {
+        return $this->belongsTo('App\Sku');
+    }
 }
diff --git a/src/app/Plan.php b/src/app/Plan.php
--- a/src/app/Plan.php
+++ b/src/app/Plan.php
@@ -49,7 +49,11 @@
         'description',
     ];
 
-
+    /**
+     * The list price for this package at the minimum configuration.
+     *
+     * @return int The costs in cents.
+     */
     public function cost()
     {
         $costs = 0;
diff --git a/src/app/Providers/AppServiceProvider.php b/src/app/Providers/AppServiceProvider.php
--- a/src/app/Providers/AppServiceProvider.php
+++ b/src/app/Providers/AppServiceProvider.php
@@ -28,6 +28,7 @@
         \App\Domain::observe(\App\Observers\DomainObserver::class);
         \App\Entitlement::observe(\App\Observers\EntitlementObserver::class);
         \App\Package::observe(\App\Observers\PackageObserver::class);
+        \App\PackageSku::observe(\App\Observers\PackageSkuObserver::class);
         \App\Plan::observe(\App\Observers\PlanObserver::class);
         \App\SignupCode::observe(\App\Observers\SignupCodeObserver::class);
         \App\Sku::observe(\App\Observers\SkuObserver::class);
diff --git a/src/app/Sku.php b/src/app/Sku.php
--- a/src/app/Sku.php
+++ b/src/app/Sku.php
@@ -21,6 +21,7 @@
         'description',
         'cost',
         'units_free',
+        // persist for annual domain registration
         'period',
         'handler_class',
         'active'
@@ -41,6 +42,6 @@
         return $this->belongsToMany(
             'App\Package',
             'package_skus'
-        )->using('App\PackageSku')->withPivot(['qty']);
+        )->using('App\PackageSku')->withPivot(['cost', 'qty']);
     }
 }
diff --git a/src/app/User.php b/src/app/User.php
--- a/src/app/User.php
+++ b/src/app/User.php
@@ -118,6 +118,7 @@
                         'owner_id' => $this->id,
                         'wallet_id' => $wallet_id,
                         'sku_id' => $sku->id,
+                        'cost' => $sku->pivot->cost(),
                         'entitleable_id' => $user->id,
                         'entitleable_type' => User::class
                     ]
diff --git a/src/app/Wallet.php b/src/app/Wallet.php
--- a/src/app/Wallet.php
+++ b/src/app/Wallet.php
@@ -3,6 +3,7 @@
 namespace App;
 
 use App\User;
+use Carbon\Carbon;
 use Iatstuti\Database\Support\NullableFields;
 use Illuminate\Database\Eloquent\Model;
 
@@ -55,6 +56,44 @@
         }
     }
 
+    /**
+     * Calculate the expected charges to this wallet.
+     *
+     * @return int
+     */
+    public function expectedCharges()
+    {
+        $charges = 0;
+
+        foreach ($this->entitlements()->get()->fresh() as $entitlement) {
+            $entry = \App\Changelog::withTrashed()
+                ->where('entitlement_id', $entitlement->id)->latest()->first();
+
+            // created less than or equal to 14 days ago (this is the fourteenth 24-hour period)
+            if ($entry->updated_at >= Carbon::now()->subDays(14)) {
+                continue;
+            }
+
+            // created less than or equal to a month ago, can't have been billed
+            if ($entry->updated_at >= Carbon::now()->subMonths(1)) {
+                $charges += $entitlement->cost;
+            }
+
+            // created more than a month ago -- was it billed?
+            if ($entry->updated_at < Carbon::now()->subMonths(1)) {
+                $diff = $entry->updated_at->diffInMonths(Carbon::now());
+                $charges += $entitlement->cost * $diff;
+            }
+
+            if ($entry->deleted_at) {
+                // TODO
+                \Log::debug("should consider deleted_at");
+            }
+        }
+
+        return $charges;
+    }
+
     /**
      * Remove a controller from this wallet.
      *
@@ -94,6 +133,8 @@
      */
     public function debit(float $amount)
     {
+        \Log::debug("debitting wallet {$this->id} with {$amount}");
+
         $this->balance -= $amount;
 
         $this->save();
diff --git a/src/database/migrations/2019_09_17_102628_create_sku_entitlements.php b/src/database/migrations/2019_09_17_102628_create_sku_entitlements.php
--- a/src/database/migrations/2019_09_17_102628_create_sku_entitlements.php
+++ b/src/database/migrations/2019_09_17_102628_create_sku_entitlements.php
@@ -36,6 +36,7 @@
                 $table->bigInteger('owner_id');
                 $table->bigInteger('entitleable_id');
                 $table->string('entitleable_type');
+                $table->integer('cost')->default(0)->nullable();
                 $table->string('wallet_id', 36);
                 $table->string('sku_id', 36);
                 $table->string('description')->nullable();
diff --git a/src/database/migrations/2019_12_10_100355_create_package_skus_table.php b/src/database/migrations/2019_12_10_100355_create_package_skus_table.php
--- a/src/database/migrations/2019_12_10_100355_create_package_skus_table.php
+++ b/src/database/migrations/2019_12_10_100355_create_package_skus_table.php
@@ -4,6 +4,7 @@
 use Illuminate\Database\Schema\Blueprint;
 use Illuminate\Database\Migrations\Migration;
 
+// phpcs:ignore
 class CreatePackageSkusTable extends Migration
 {
     /**
@@ -21,6 +22,8 @@
                 $table->string('sku_id', 36);
                 $table->integer('qty')->default(1);
 
+                $table->integer('cost')->default(0)->nullable();
+
                 $table->foreign('package_id')->references('id')->on('packages')
                     ->onDelete('cascade')->onUpdate('cascade');
 
diff --git a/src/database/migrations/2020_02_11_110959_add_deleted_at.php b/src/database/migrations/2020_02_11_110959_users_add_deleted_at.php
rename from src/database/migrations/2020_02_11_110959_add_deleted_at.php
rename to src/database/migrations/2020_02_11_110959_users_add_deleted_at.php
--- a/src/database/migrations/2020_02_11_110959_add_deleted_at.php
+++ b/src/database/migrations/2020_02_11_110959_users_add_deleted_at.php
@@ -4,7 +4,8 @@
 use Illuminate\Database\Schema\Blueprint;
 use Illuminate\Database\Migrations\Migration;
 
-class AddDeletedAt extends Migration
+// phpcs:ignore
+class UsersAddDeletedAt extends Migration
 {
     /**
      * Run the migrations.
@@ -13,13 +14,6 @@
      */
     public function up()
     {
-        Schema::table(
-            'domains',
-            function (Blueprint $table) {
-                $table->softDeletes();
-            }
-        );
-
         Schema::table(
             'users',
             function (Blueprint $table) {
@@ -35,12 +29,6 @@
      */
     public function down()
     {
-        Schema::table(
-            'domains',
-            function (Blueprint $table) {
-                $table->dropColumn(['deleted_at']);
-            }
-        );
         Schema::table(
             'users',
             function (Blueprint $table) {
diff --git a/src/database/migrations/2020_02_11_110959_add_deleted_at.php b/src/database/migrations/2020_02_11_110960_domains_add_deleted_at.php
copy from src/database/migrations/2020_02_11_110959_add_deleted_at.php
copy to src/database/migrations/2020_02_11_110960_domains_add_deleted_at.php
--- a/src/database/migrations/2020_02_11_110959_add_deleted_at.php
+++ b/src/database/migrations/2020_02_11_110960_domains_add_deleted_at.php
@@ -4,7 +4,8 @@
 use Illuminate\Database\Schema\Blueprint;
 use Illuminate\Database\Migrations\Migration;
 
-class AddDeletedAt extends Migration
+// phpcs:ignore
+class DomainsAddDeletedAt extends Migration
 {
     /**
      * Run the migrations.
@@ -19,13 +20,6 @@
                 $table->softDeletes();
             }
         );
-
-        Schema::table(
-            'users',
-            function (Blueprint $table) {
-                $table->softDeletes();
-            }
-        );
     }
 
     /**
@@ -41,11 +35,5 @@
                 $table->dropColumn(['deleted_at']);
             }
         );
-        Schema::table(
-            'users',
-            function (Blueprint $table) {
-                $table->dropColumn(['deleted_at']);
-            }
-        );
     }
 }
diff --git a/src/database/migrations/2020_02_24_095604_create_changelogs_table.php b/src/database/migrations/2020_02_24_095604_create_changelogs_table.php
new file mode 100644
--- /dev/null
+++ b/src/database/migrations/2020_02_24_095604_create_changelogs_table.php
@@ -0,0 +1,41 @@
+<?php
+
+use Illuminate\Support\Facades\Schema;
+use Illuminate\Database\Schema\Blueprint;
+use Illuminate\Database\Migrations\Migration;
+
+// phpcs:ignore
+class CreateChangelogsTable extends Migration
+{
+    /**
+     * Run the migrations.
+     *
+     * @return void
+     */
+    public function up()
+    {
+        Schema::create(
+            'changelogs',
+            function (Blueprint $table) {
+                $table->bigIncrements('id');
+                $table->string('entitlement_id', 36);
+                $table->timestamps();
+
+                $table->softDeletes();
+
+                $table->foreign('entitlement_id')->references('id')
+                    ->on('entitlements')->onDelete('cascade');
+            }
+        );
+    }
+
+    /**
+     * Reverse the migrations.
+     *
+     * @return void
+     */
+    public function down()
+    {
+        Schema::dropIfExists('changelogs');
+    }
+}
diff --git a/src/database/migrations/2020_02_11_110959_add_deleted_at.php b/src/database/migrations/2020_02_26_085835_entitlements_add_deleted_at.php
rename from src/database/migrations/2020_02_11_110959_add_deleted_at.php
rename to src/database/migrations/2020_02_26_085835_entitlements_add_deleted_at.php
--- a/src/database/migrations/2020_02_11_110959_add_deleted_at.php
+++ b/src/database/migrations/2020_02_26_085835_entitlements_add_deleted_at.php
@@ -4,7 +4,8 @@
 use Illuminate\Database\Schema\Blueprint;
 use Illuminate\Database\Migrations\Migration;
 
-class AddDeletedAt extends Migration
+// phpcs:ignore
+class EntitlementsAddDeletedAt extends Migration
 {
     /**
      * Run the migrations.
@@ -14,14 +15,7 @@
     public function up()
     {
         Schema::table(
-            'domains',
-            function (Blueprint $table) {
-                $table->softDeletes();
-            }
-        );
-
-        Schema::table(
-            'users',
+            'entitlements',
             function (Blueprint $table) {
                 $table->softDeletes();
             }
@@ -36,13 +30,7 @@
     public function down()
     {
         Schema::table(
-            'domains',
-            function (Blueprint $table) {
-                $table->dropColumn(['deleted_at']);
-            }
-        );
-        Schema::table(
-            'users',
+            'entitlements',
             function (Blueprint $table) {
                 $table->dropColumn(['deleted_at']);
             }
diff --git a/src/database/seeds/PackageSeeder.php b/src/database/seeds/PackageSeeder.php
--- a/src/database/seeds/PackageSeeder.php
+++ b/src/database/seeds/PackageSeeder.php
@@ -14,6 +14,10 @@
      */
     public function run()
     {
+        $skuGroupware = Sku::firstOrCreate(['title' => 'groupware']);
+        $skuMailbox = Sku::firstOrCreate(['title' => 'mailbox']);
+        $skuStorage = Sku::firstOrCreate(['title' => 'storage']);
+
         $package = Package::create(
             [
                 'title' => 'kolab',
@@ -23,9 +27,9 @@
         );
 
         $skus = [
-            Sku::firstOrCreate(['title' => 'mailbox']),
-            Sku::firstOrCreate(['title' => 'storage']),
-            Sku::firstOrCreate(['title' => 'groupware'])
+            $skuMailbox,
+            $skuGroupware,
+            $skuStorage
         ];
 
         $package->skus()->saveMany($skus);
@@ -33,7 +37,7 @@
         // This package contains 2 units of the storage SKU, which just so happens to also
         // be the number of SKU free units.
         $package->skus()->updateExistingPivot(
-            Sku::firstOrCreate(['title' => 'storage']),
+            $skuStorage,
             ['qty' => 2],
             false
         );
@@ -47,8 +51,8 @@
         );
 
         $skus = [
-            Sku::firstOrCreate(['title' => 'mailbox']),
-            Sku::firstOrCreate(['title' => 'storage'])
+            $skuMailbox,
+            $skuStorage
         ];
 
         $package->skus()->saveMany($skus);
diff --git a/src/database/seeds/UserSeeder.php b/src/database/seeds/UserSeeder.php
--- a/src/database/seeds/UserSeeder.php
+++ b/src/database/seeds/UserSeeder.php
@@ -1,10 +1,11 @@
 <?php
 
-use Illuminate\Database\Seeder;
 use App\Domain;
 use App\Entitlement;
 use App\User;
 use App\Sku;
+use Carbon\Carbon;
+use Illuminate\Database\Seeder;
 
 // phpcs:ignore
 class UserSeeder extends Seeder
@@ -42,7 +43,7 @@
             ]
         );
 
-        $user_wallets = $john->wallets()->get();
+        $wallet = $john->wallets->first();
 
         $package_domain = \App\Package::where('title', 'domain-hosting')->first();
         $package_kolab = \App\Package::where('title', 'kolab')->first();
@@ -70,6 +71,14 @@
 
         $john->assignPackage($package_kolab, $jack);
 
+        foreach ($john->entitlements as $entitlement) {
+            $entry = \App\Changelog::where('entitlement_id', $entitlement->id)->latest()->first();
+
+            $entry->created_at = Carbon::now()->subMonths(1);
+            $entry->updated_at = Carbon::now()->subMonths(1);
+            $entry->save();
+        }
+
         factory(User::class, 10)->create();
     }
 }
diff --git a/src/tests/Feature/BillingTest.php b/src/tests/Feature/BillingTest.php
new file mode 100644
--- /dev/null
+++ b/src/tests/Feature/BillingTest.php
@@ -0,0 +1,340 @@
+<?php
+
+namespace Tests\Feature;
+
+use Carbon\Carbon;
+use Illuminate\Support\Facades\Queue;
+use Tests\TestCase;
+
+class BillingTest extends TestCase
+{
+    public function setUp(): void
+    {
+        parent::setUp();
+
+        $this->deleteTestUser('jane@kolabnow.com');
+        $this->deleteTestUser('jack@kolabnow.com');
+
+        \App\Package::where('title', 'kolab-kube')->delete();
+
+        $this->user = $this->getTestUser('jane@kolabnow.com');
+        $this->package = \App\Package::where('title', 'kolab')->first();
+        $this->user->assignPackage($this->package);
+
+        $this->wallet = $this->user->wallets->first();
+
+        $this->wallet_id = $this->wallet->id;
+    }
+
+    public function tearDown(): void
+    {
+        //$this->deleteTestUser('jane@kolabnow.com');
+        $this->deleteTestUser('jack@kolabnow.com');
+
+        \App\Package::where('title', 'kolab-kube')->delete();
+
+        parent::tearDown();
+    }
+
+    /**
+     * Test the expected results for a user that registers and is almost immediately gone.
+     */
+    public function testTouchAndGo(): void
+    {
+        $this->assertCount(4, $this->changelogEntries($this->wallet));
+
+        $this->assertEquals(0, $this->wallet->expectedCharges());
+
+        $this->user->delete();
+
+        $this->assertCount(0, $this->changelogEntries($this->wallet));
+
+        $this->assertCount(4, $this->changelogEntries($this->wallet, true));
+    }
+
+    /**
+     * Verify the 13th 24-hour period does not incur charges to the wallet.
+     */
+    public function testNearFullTrial(): void
+    {
+        $entries = $this->changelogEntries($this->wallet);
+
+        $this->assertCount(4, $entries);
+
+        foreach ($entries as $entry) {
+            $entry->created_at = Carbon::now()->subDays(13);
+            $entry->updated_at = Carbon::now()->subDays(13);
+            $entry->save();
+        }
+
+        $this->assertEquals(0, $this->wallet->expectedCharges());
+    }
+
+    /**
+     * Verify the 14th 24-hour period does incur charges to the wallet.
+     */
+    public function testFullTrial(): void
+    {
+        $entries = $this->changelogEntries($this->wallet);
+
+        $this->assertCount(4, $entries);
+
+        foreach ($entries as $entry) {
+            $entry->created_at = Carbon::now()->subDays(14);
+            $entry->updated_at = Carbon::now()->subDays(14);
+            $entry->save();
+        }
+
+        $this->assertEquals(999, $this->wallet->expectedCharges());
+    }
+
+    /**
+     * Verify additional storage configuration entitlement created 'early' does incur additional
+     * charges to the wallet.
+     */
+    public function testAddtStorageEarly(): void
+    {
+        $entries = $this->changelogEntries($this->wallet);
+
+        foreach ($entries as $entry) {
+            $entry->created_at = Carbon::now()->subDays(16);
+            $entry->updated_at = Carbon::now()->subDays(16);
+            $entry->save();
+        }
+
+        $this->assertCount(4, $entries);
+
+        $this->assertEquals(999, $this->wallet->expectedCharges());
+
+        $sku = \App\Sku::where(['title' => 'storage'])->first();
+
+        $entitlement = \App\Entitlement::create(
+            [
+                'owner_id' => $this->user->id,
+                'wallet_id' => $this->wallet_id,
+                'sku_id' => $sku->id,
+                'cost' => $sku->cost,
+                'entitleable_id' => $this->user->id,
+                'entitleable_type' => \App\User::class
+            ]
+        );
+
+        $entries = $this->changelogEntries($this->wallet);
+
+        $this->assertCount(5, $entries);
+
+        $entry = \App\Changelog::where('entitlement_id', $entitlement->id)->first();
+        $entry->created_at = Carbon::now()->subDays(16);
+        $entry->updated_at = Carbon::now()->subDays(16);
+        $entry->save();
+
+        $this->assertEquals(1024, $this->wallet->expectedCharges());
+    }
+
+    /**
+     * Verify additional storage configuration entitlement created 'late' does not incur additional
+     * charges to the wallet.
+     */
+    public function testAddtStorageLate(): void
+    {
+        $entries = $this->changelogEntries($this->wallet);
+
+        foreach ($entries as $entry) {
+            $entry->created_at = Carbon::now()->subDays(16);
+            $entry->updated_at = Carbon::now()->subDays(16);
+            $entry->save();
+        }
+
+        $this->assertCount(4, $entries);
+
+        $this->assertEquals(999, $this->wallet->expectedCharges());
+
+        $sku = \App\Sku::where(['title' => 'storage'])->first();
+
+        $entitlement = \App\Entitlement::create(
+            [
+                'owner_id' => $this->user->id,
+                'wallet_id' => $this->wallet_id,
+                'sku_id' => $sku->id,
+                'cost' => $sku->cost,
+                'entitleable_id' => $this->user->id,
+                'entitleable_type' => \App\User::class
+            ]
+        );
+
+        $entries = $this->changelogEntries($this->wallet);
+
+        $this->assertCount(5, $entries);
+
+        $entry = \App\Changelog::where('entitlement_id', $entitlement->id)->first();
+        $entry->created_at = Carbon::now()->subDays(7);
+        $entry->updated_at = Carbon::now()->subDays(7);
+        $entry->save();
+
+        $this->assertEquals(999, $this->wallet->expectedCharges());
+    }
+
+    /**
+     * Verify that over-running the trial by a single day causes charges to be incurred.
+     */
+    public function testOutRunTrial(): void
+    {
+        $entries = $this->changelogEntries($this->wallet);
+
+        foreach ($entries as $entry) {
+            $entry->created_at = Carbon::now()->subDays(15);
+            $entry->updated_at = Carbon::now()->subDays(15);
+            $entry->save();
+        }
+
+        $this->assertCount(4, $entries);
+
+        $this->assertEquals(999, $this->wallet->expectedCharges());
+    }
+
+    public function testFifthWeek(): void
+    {
+        $entries = $this->changelogEntries($this->wallet);
+
+        $this->assertCount(4, $entries);
+
+        $targetDateA = Carbon::now()->subWeeks(5);
+        $targetDateB = $targetDateA->copy()->addMonths(1);
+
+        foreach ($entries as $entry) {
+            $entry->created_at = $targetDateA;
+            $entry->updated_at = $targetDateA;
+            $entry->save();
+        }
+
+        $this->assertEquals(999, $this->wallet->expectedCharges());
+
+        foreach ($this->wallet->entitlements as $entitlement) {
+            $entitlement->chargeWallet();
+        }
+
+        $this->wallet->refresh();
+
+        $this->assertEquals(-999, $this->wallet->balance);
+
+        $entries = $this->changelogEntries($this->wallet);
+
+        foreach ($entries as $entry) {
+            $this->assertTrue($entry->created_at->isSameSecond($targetDateA));
+            $this->assertTrue($entry->updated_at->isSameSecond($targetDateB));
+        }
+    }
+
+    public function testSecondMonth(): void
+    {
+        $entries = $this->changelogEntries($this->wallet);
+
+        foreach ($entries as $entry) {
+            $entry->created_at = Carbon::now()->subMonths(2);
+            $entry->updated_at = Carbon::now()->subMonths(2);
+            $entry->save();
+        }
+
+        $this->assertCount(4, $entries);
+
+        $this->assertEquals(1998, $this->wallet->expectedCharges());
+
+        $sku = \App\Sku::where(['title' => 'storage'])->first();
+
+        $entitlement = \App\Entitlement::create(
+            [
+                'owner_id' => $this->user->id,
+                'entitleable_id' => $this->user->id,
+                'entitleable_type' => \App\User::class,
+                'cost' => $sku->cost,
+                'sku_id' => $sku->id,
+                'wallet_id' => $this->wallet_id
+            ]
+        );
+
+        // A fresh query should now return 5 entries.
+        $entries = $this->changelogEntries($this->wallet);
+        $this->assertCount(5, $entries);
+
+        $entry = \App\Changelog::where('entitlement_id', $entitlement->id)->first();
+        $entry->created_at = Carbon::now()->subMonths(1);
+        $entry->updated_at = Carbon::now()->subMonths(1);
+        $entry->save();
+
+        $this->assertEquals(2023, $this->wallet->expectedCharges());
+    }
+
+    public function testWithDiscount(): void
+    {
+        $package = \App\Package::create(
+            [
+                'title' => 'kolab-kube',
+                'description' => 'Kolab for Kube fans',
+                'discount_rate' => 50
+            ]
+        );
+
+        $skus = [
+            \App\Sku::firstOrCreate(['title' => 'mailbox']),
+            \App\Sku::firstOrCreate(['title' => 'storage']),
+            \App\Sku::firstOrCreate(['title' => 'groupware'])
+        ];
+
+        $package->skus()->saveMany($skus);
+
+        $package->skus()->updateExistingPivot(
+            \App\Sku::firstOrCreate(['title' => 'storage']),
+            ['qty' => 2],
+            false
+        );
+
+        $user = $this->getTestUser('jack@kolabnow.com');
+
+        $user->assignPackage($package);
+
+        $wallet = $user->wallets->first();
+
+        $wallet_id = $wallet->id;
+
+        $entries = $this->changelogEntries($wallet);
+
+        $this->assertCount(4, $entries);
+
+        foreach ($entries as $entry) {
+            $entry->created_at = Carbon::now()->subDays(15);
+            $entry->updated_at = Carbon::now()->subDays(15);
+            $entry->save();
+        }
+
+        $this->assertEquals(500, $wallet->expectedCharges());
+    }
+
+    private function changelogEntries($wallet, $withTrashed = false)
+    {
+        $entitlement_ids = $this->walletEntitlements($wallet, $withTrashed);
+
+        if ($withTrashed) {
+            return \App\Changelog::withTrashed()
+                ->whereIn('entitlement_id', $entitlement_ids)->get();
+        }
+
+        return \App\Changelog::whereIn('entitlement_id', $entitlement_ids)->get();
+    }
+
+    private function walletEntitlements($wallet, $withTrashed = false)
+    {
+        $entitlement_ids = [];
+
+        if ($withTrashed) {
+            $entitlements = $wallet->entitlements()->withTrashed()->get()->fresh();
+        } else {
+            $entitlements = $wallet->entitlements()->get()->fresh();
+        }
+
+        foreach ($entitlements as $entitlement) {
+            $entitlement_ids[] = $entitlement->id;
+        }
+
+        return $entitlement_ids;
+    }
+}
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
@@ -4,8 +4,10 @@
 
 use App\Domain;
 use App\Entitlement;
+use App\Package;
 use App\Sku;
 use App\User;
+use Carbon\Carbon;
 use Tests\TestCase;
 
 class EntitlementTest extends TestCase
@@ -32,10 +34,15 @@
      */
     public function testUserAddEntitlement(): void
     {
-        $sku_domain = Sku::firstOrCreate(['title' => 'domain']);
-        $sku_mailbox = Sku::firstOrCreate(['title' => 'mailbox']);
+        $package_domain = Package::where('title', 'domain-hosting')->first();
+        $package_kolab = Package::where('title', 'kolab')->first();
+
+        $sku_domain = Sku::where('title', 'domain-hosting')->first();
+        $sku_mailbox = Sku::where('title', 'mailbox')->first();
+
         $owner = $this->getTestUser('entitlement-test@kolabnow.com');
         $user = $this->getTestUser('entitled-user@custom-domain.com');
+
         $domain = $this->getTestDomain(
             'custom-domain.com',
             [
@@ -44,50 +51,28 @@
             ]
         );
 
-        $wallet = $owner->wallets()->first();
+        $domain->assignPackage($package_domain, $owner);
 
-        $entitlement_own_mailbox = new Entitlement(
-            [
-                'owner_id' => $owner->id,
-                'entitleable_id' => $owner->id,
-                'entitleable_type' => User::class,
-                'wallet_id' => $wallet->id,
-                'sku_id' => $sku_mailbox->id,
-                'description' => "Owner Mailbox Entitlement Test"
-            ]
-        );
+        $owner->assignPackage($package_kolab);
+        $owner->assignPackage($package_kolab, $user);
 
-        $entitlement_domain = new Entitlement(
-            [
-                'owner_id' => $owner->id,
-                'entitleable_id' => $domain->id,
-                'entitleable_type' => Domain::class,
-                'wallet_id' => $wallet->id,
-                'sku_id' => $sku_domain->id,
-                'description' => "User Domain Entitlement Test"
-            ]
-        );
+        $wallet = $owner->wallets->first();
 
-        $entitlement_mailbox = new Entitlement(
-            [
-                'owner_id' => $owner->id,
-                'entitleable_id' => $user->id,
-                'entitleable_type' => User::class,
-                'wallet_id' => $wallet->id,
-                'sku_id' => $sku_mailbox->id,
-                'description' => "User Mailbox Entitlement Test"
-            ]
-        );
+        $this->assertCount(4, $owner->entitlements()->get());
+        $this->assertCount(1, $sku_domain->entitlements()->where('owner_id', $owner->id)->get());
+        $this->assertCount(2, $sku_mailbox->entitlements()->where('owner_id', $owner->id)->get());
+        $this->assertCount(9, $wallet->entitlements);
+
+        foreach ($owner->entitlements()->get() as $entitlement) {
+            $entry = \App\Changelog::where('entitlement_id', $entitlement->id)->first();
+            $entry->created_at = Carbon::now()->subMonths(1);
+            $entry->updated_at = Carbon::now()->subMonths(1);
+            $entry->save();
 
-        $owner->addEntitlement($entitlement_own_mailbox);
-        $owner->addEntitlement($entitlement_domain);
-        $owner->addEntitlement($entitlement_mailbox);
+            $entitlement->chargeWallet();
+        }
 
-        $this->assertTrue($owner->entitlements()->count() == 3);
-        $this->assertTrue($sku_domain->entitlements()->where('owner_id', $owner->id)->count() == 1);
-        $this->assertTrue($sku_mailbox->entitlements()->where('owner_id', $owner->id)->count() == 2);
-        $this->assertTrue($wallet->entitlements()->count() == 3);
-        $this->assertTrue($wallet->fresh()->balance < 0.00);
+        $this->assertTrue($wallet->fresh()->balance < 0);
     }
 
     public function testAddExistingEntitlement(): void
diff --git a/src/tests/Feature/SkuTest.php b/src/tests/Feature/SkuTest.php
--- a/src/tests/Feature/SkuTest.php
+++ b/src/tests/Feature/SkuTest.php
@@ -2,11 +2,12 @@
 
 namespace Tests\Feature;
 
-use App\Domain;
+use App\Changelog;
 use App\Entitlement;
 use App\Handlers;
+use App\Package;
 use App\Sku;
-use App\User;
+use Carbon\Carbon;
 use Tests\TestCase;
 
 class SkuTest extends TestCase
@@ -16,228 +17,79 @@
     {
         parent::setUp();
 
-        $this->deleteTestUser('sku-test-user@custom-domain.com');
-        $this->deleteTestDomain('custom-domain.com');
+        $this->deleteTestUser('jane@kolabnow.com');
     }
 
     public function tearDown(): void
     {
-        $this->deleteTestUser('sku-test-user@custom-domain.com');
-        $this->deleteTestDomain('custom-domain.com');
+        $this->deleteTestUser('jane@kolabnow.com');
 
         parent::tearDown();
     }
 
-    /**
-     * Tests for Sku::registerEntitlements()
-     */
-    public function testRegisterEntitlement(): void
+    public function testPackageEntitlements(): void
     {
-        // TODO: This test depends on seeded SKUs, but probably should not
-        $domain = $this->getTestDomain(
-            'custom-domain.com',
-            [
-                'status' => Domain::STATUS_NEW,
-                'type' => Domain::TYPE_EXTERNAL,
-            ]
-        );
-
-        \Log::debug(var_export($domain->toArray(), true));
+        $user = $this->getTestUser('jane@kolabnow.com');
 
-        $user = $this->getTestUser('sku-test-user@custom-domain.com');
         $wallet = $user->wallets()->first();
 
-        // \App\Handlers\Mailbox SKU
-        // Note, we're testing mailbox SKU before domain SKU as it may potentially fail in that
-        // order
-        $sku = Sku::where('title', 'mailbox')->first();
-        Entitlement::create(
-            [
-                'owner_id' => $user->id,
-                'wallet_id' => $wallet->id,
-                'sku_id' => $sku->id,
-                'entitleable_id' => $user->id,
-                'entitleable_type' => User::class
-            ]
-        );
+        $package = Package::where('title', 'lite')->first();
 
-        $entitlements = $sku->entitlements()->where('owner_id', $user->id)->get();
-        $wallet->refresh();
-
-        if ($sku->active) {
-            $balance = -$sku->cost;
-            $this->assertCount(1, $entitlements);
-            $this->assertEquals($user->id, $entitlements[0]->entitleable_id);
-            $this->assertSame(
-                Handlers\Mailbox::entitleableClass(),
-                $entitlements[0]->entitleable_type
-            );
-        } else {
-            $this->assertCount(0, $entitlements);
-        }
-
-        $this->assertEquals($balance, $wallet->balance);
-
-        // \App\Handlers\Domain SKU
-        $sku = Sku::where('title', 'domain')->first();
-        Entitlement::create(
-            [
-                'owner_id' => $user->id,
-                'wallet_id' => $wallet->id,
-                'sku_id' => $sku->id,
-                'entitleable_id' => $domain->id,
-                'entitleable_type' => Domain::class
-            ]
-        );
-
-        $entitlements = $sku->entitlements->where('owner_id', $user->id);
-
-        foreach ($entitlements as $entitlement) {
-            \Log::debug(var_export($entitlement->toArray(), true));
-        }
-
-        $wallet->refresh();
-
-        if ($sku->active) {
-            $balance -= $sku->cost;
-            $this->assertCount(1, $entitlements);
-
-            $_domain = Domain::find($entitlements->first()->entitleable_id);
-
-            $this->assertEquals(
-                $domain->id,
-                $entitlements->first()->entitleable_id,
-                var_export($_domain->toArray(), true)
-            );
-
-            $this->assertSame(
-                Handlers\Domain::entitleableClass(),
-                $entitlements->first()->entitleable_type
-            );
-        } else {
-            $this->assertCount(0, $entitlements);
-        }
-
-        $this->assertEquals($balance, $wallet->balance);
-
-        // \App\Handlers\DomainRegistration SKU
-        $sku = Sku::where('title', 'domain-registration')->first();
-        Entitlement::create(
-            [
-                'owner_id' => $user->id,
-                'wallet_id' => $user->wallets()->get()[0]->id,
-                'sku_id' => $sku->id,
-                'entitleable_id' => $domain->id,
-                'entitleable_type' => Domain::class
-            ]
-        );
+        $sku_mailbox = Sku::where('title', 'mailbox')->first();
+        $sku_storage = Sku::where('title', 'storage')->first();
 
-        $entitlements = $sku->entitlements->where('owner_id', $user->id);
-        $wallet->refresh();
+        $user = $user->assignPackage($package);
 
-        if ($sku->active) {
-            $balance -= $sku->cost;
-            $this->assertCount(1, $entitlements);
-            $this->assertEquals($domain->id, $entitlements->first()->entitleable_id);
-            $this->assertSame(
-                Handlers\DomainRegistration::entitleableClass(),
-                $entitlements->first()->entitleable_type
-            );
-        } else {
-            $this->assertCount(0, $entitlements);
-        }
+        $this->backdateChangelogs($user->fresh()->entitlements, Carbon::now()->subMonths(1));
 
-        $this->assertEquals($balance, $wallet->balance);
+        $wallet = $this->chargeWallet($wallet);
 
-        // \App\Handlers\DomainHosting SKU
-        $sku = Sku::where('title', 'domain-hosting')->first();
-        Entitlement::create(
-            [
-                'owner_id' => $user->id,
-                'wallet_id' => $wallet->id,
-                'sku_id' => $sku->id,
-                'entitleable_id' => $domain->id,
-                'entitleable_type' => Domain::class
-            ]
-        );
+        $this->assertTrue($wallet->balance < 0);
+    }
 
-        $entitlements = $sku->entitlements->where('owner_id', $user->id);
-        $wallet->refresh();
-
-        if ($sku->active) {
-            $balance -= $sku->cost;
-            $this->assertCount(1, $entitlements);
-            $this->assertEquals($domain->id, $entitlements->first()->entitleable_id);
-            $this->assertSame(
-                Handlers\DomainHosting::entitleableClass(),
-                $entitlements->first()->entitleable_type
-            );
-        } else {
-            $this->assertCount(0, $entitlements);
-        }
-
-        $this->assertEquals($balance, $wallet->balance);
-
-        // \App\Handlers\Groupware SKU
-        $sku = Sku::where('title', 'groupware')->first();
-        Entitlement::create(
-            [
-                'owner_id' => $user->id,
-                'wallet_id' => $user->wallets()->get()[0]->id,
-                'sku_id' => $sku->id,
-                'entitleable_id' => $user->id,
-                'entitleable_type' => User::class
-            ]
-        );
+    public function testSkuEntitlements(): void
+    {
+        $this->assertCount(2, Sku::where('title', 'mailbox')->first()->entitlements);
+    }
 
-        $entitlements = $sku->entitlements->where('owner_id', $user->id);
-        $wallet->refresh();
+    public function testSkuPackages(): void
+    {
+        $this->assertCount(2, Sku::where('title', 'mailbox')->first()->packages);
+    }
 
-        if ($sku->active) {
-            $balance -= $sku->cost;
-            $this->assertCount(1, $entitlements);
-            $this->assertEquals($user->id, $entitlements->first()->entitleable_id);
-            $this->assertSame(
-                Handlers\Mailbox::entitleableClass(),
-                $entitlements->first()->entitleable_type
-            );
-        } else {
-            $this->assertCount(0, $entitlements);
-        }
+    public function testSkuHandlerDomainHosting(): void
+    {
+        $sku = Sku::where('title', 'domain-hosting')->first();
 
-        $this->assertEquals($balance, $wallet->balance);
+        $entitlement = $sku->entitlements->first();
 
-        // \App\Handlers\Storage SKU
-        $sku = Sku::where('title', 'storage')->first();
-        Entitlement::create(
-            [
-                'owner_id' => $user->id,
-                'wallet_id' => $wallet->id,
-                'sku_id' => $sku->id,
-                'entitleable_id' => $user->id,
-                'entitleable_type' => User::class
-            ]
+        $this->assertSame(
+            Handlers\DomainHosting::entitleableClass(),
+            $entitlement->entitleable_type
         );
+    }
 
-        $entitlements = $sku->entitlements->where('owner_id', $user->id);
-        $wallet->refresh();
+    public function testSkuHandlerMailbox(): void
+    {
+        $sku = Sku::where('title', 'mailbox')->first();
 
-        if ($sku->active) {
-            $balance -= $sku->cost;
-            $this->assertCount(1, $entitlements);
-        } else {
-            $this->assertCount(0, $entitlements);
-        }
+        $entitlement = $sku->entitlements->first();
 
-        $this->assertEquals($balance, $wallet->balance);
+        $this->assertSame(
+            Handlers\Mailbox::entitleableClass(),
+            $entitlement->entitleable_type
+        );
     }
 
-    public function testSkuPackages(): void
+    public function testSkuHandlerStorage(): void
     {
-        $sku = Sku::where('title', 'mailbox')->first();
+        $sku = Sku::where('title', 'storage')->first();
 
-        $packages = $sku->packages;
+        $entitlement = $sku->entitlements->first();
 
-        $this->assertCount(2, $packages);
+        $this->assertSame(
+            Handlers\Storage::entitleableClass(),
+            $entitlement->entitleable_type
+        );
     }
 }
diff --git a/src/tests/Feature/VerificationCodeTest.php b/src/tests/Feature/VerificationCodeTest.php
--- a/src/tests/Feature/VerificationCodeTest.php
+++ b/src/tests/Feature/VerificationCodeTest.php
@@ -48,6 +48,7 @@
         $this->assertSame($data['mode'], $code->mode);
         $this->assertEquals($user->id, $code->user->id);
         $this->assertInstanceOf(\DateTime::class, $code->expires_at);
+
         $this->assertSame($code_exp_hrs, $code->expires_at->diff($now)->h + 1);
 
         $inst = VerificationCode::find($code->code);
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
@@ -47,7 +47,7 @@
     {
         $user = $this->getTestUser('UserWallet1@UserWallet.com');
 
-        $this->assertTrue($user->wallets()->count() == 1);
+        $this->assertCount(1, $user->wallets);
     }
 
     /**
@@ -61,11 +61,11 @@
             new Wallet(['currency' => 'USD'])
         );
 
-        $this->assertTrue($user->wallets()->count() >= 2);
+        $this->assertCount(2, $user->wallets);
 
         $user->wallets()->each(
             function ($wallet) {
-                $this->assertTrue($wallet->balance === 0.00);
+                $this->assertEquals(0, $wallet->balance);
             }
         );
     }
@@ -79,7 +79,7 @@
 
         $user->wallets()->each(
             function ($wallet) {
-                $wallet->credit(1.00)->save();
+                $wallet->credit(100)->save();
             }
         );
 
@@ -97,7 +97,7 @@
     {
         $user = $this->getTestUser('UserWallet4@UserWallet.com');
 
-        $this->assertTrue($user->wallets()->count() == 1);
+        $this->assertCount(1, $user->wallets);
 
         $user->wallets()->each(
             function ($wallet) {
@@ -140,15 +140,12 @@
             }
         );
 
-        $this->assertTrue(
-            $userB->accounts()->count() == 1,
-            "number of accounts (1 expected): {$userB->accounts()->count()}"
-        );
+        $this->assertCount(1, $userB->accounts);
 
-        $aWallet = $userA->wallets()->get();
-        $bAccount = $userB->accounts()->get();
+        $aWallet = $userA->wallets()->first();
+        $bAccount = $userB->accounts()->first();
 
-        $this->assertTrue($bAccount[0]->id === $aWallet[0]->id);
+        $this->assertTrue($bAccount->id === $aWallet->id);
     }
 
     /**
@@ -173,6 +170,6 @@
             }
         );
 
-        $this->assertTrue($userB->accounts()->count() == 0);
+        $this->assertCount(0, $userB->accounts);
     }
 }
diff --git a/src/tests/TestCase.php b/src/tests/TestCase.php
--- a/src/tests/TestCase.php
+++ b/src/tests/TestCase.php
@@ -11,10 +11,37 @@
 {
     use CreatesApplication;
 
+    protected function backdateChangelogs($entitlements, $targetDate)
+    {
+        foreach ($entitlements as $entitlement) {
+            $entitlement->created_at = $targetDate;
+            $entitlement->updated_at = $targetDate;
+            $entitlement->save();
+
+            $entry = \App\Changelog::where('entitlement_id', $entitlement->id)->first();
+            $entry->created_at = $targetDate;
+            $entry->updated_at = $targetDate;
+            $entry->save();
+        }
+    }
+
+    protected function chargeWallet($wallet)
+    {
+        foreach ($wallet->entitlements as $entitlement) {
+            $entitlement->chargeWallet();
+        }
+
+        $wallet->refresh();
+
+        return $wallet;
+    }
+
     protected function deleteTestDomain($name)
     {
         Queue::fake();
+
         $domain = Domain::withTrashed()->where('namespace', $name)->first();
+
         if (!$domain) {
             return;
         }
@@ -28,6 +55,7 @@
     protected function deleteTestUser($email)
     {
         Queue::fake();
+
         $user = User::withTrashed()->where('email', $email)->first();
 
         if (!$user) {
@@ -59,7 +87,17 @@
     {
         // Disable jobs (i.e. skip LDAP oprations)
         Queue::fake();
-        return User::firstOrCreate(['email' => $email], $attrib);
+        $user = User::withTrashed()->where('email', $email)->first();
+
+        if (!$user) {
+            return User::firstOrCreate(['email' => $email], $attrib);
+        }
+
+        if ($user->deleted_at) {
+            $user->restore();
+        }
+
+        return $user;
     }
 
     /**