diff --git a/src/app/Backends/LDAP.php b/src/app/Backends/LDAP.php
--- a/src/app/Backends/LDAP.php
+++ b/src/app/Backends/LDAP.php
@@ -760,6 +760,7 @@
     {
         $firstName = $user->getSetting('first_name');
         $lastName = $user->getSetting('last_name');
+        $isDegraded = $user->wallet()->owner->isDegraded();
 
         $cn = "unknown";
         $displayname = "";
@@ -820,13 +821,19 @@
             $entry['nsroledn'][] = "cn=2fa-user,{$hostedRootDN}";
         }
 
-        if (in_array("activesync", $roles)) {
+        if (!$isDegraded && in_array("activesync", $roles)) {
             $entry['nsroledn'][] = "cn=activesync-user,{$hostedRootDN}";
         }
 
-        if (!in_array("groupware", $roles)) {
+        if (!$isDegraded && !in_array("groupware", $roles)) {
             $entry['nsroledn'][] = "cn=imap-user,{$hostedRootDN}";
         }
+
+        if ($isDegraded) {
+            // FIXME: Should we use a role instead?
+            $entry['inetuserstatus'] = $user->status | User::STATUS_DEGRADED;
+            $entry['mailquota'] = 2 * 1048576;
+        }
     }
 
     /**
diff --git a/src/app/Console/Commands/UserDegrade.php b/src/app/Console/Commands/UserDegrade.php
new file mode 100644
--- /dev/null
+++ b/src/app/Console/Commands/UserDegrade.php
@@ -0,0 +1,48 @@
+<?php
+
+namespace App\Console\Commands;
+
+use Illuminate\Console\Command;
+
+class UserDegrade extends Command
+{
+    /**
+     * The name and signature of the console command.
+     *
+     * @var string
+     */
+    protected $signature = 'user:degrade {user}';
+
+    /**
+     * The console command description.
+     *
+     * @var string
+     */
+    protected $description = 'Degrade a user';
+
+    /**
+     * Create a new command instance.
+     *
+     * @return void
+     */
+    public function __construct()
+    {
+        parent::__construct();
+    }
+
+    /**
+     * Execute the console command.
+     *
+     * @return mixed
+     */
+    public function handle()
+    {
+        $user = \App\User::where('email', $this->argument('user'))->first();
+
+        if (!$user) {
+            return 1;
+        }
+
+        $user->degrade();
+    }
+}
diff --git a/src/app/Console/Commands/UserUndegrade.php b/src/app/Console/Commands/UserUndegrade.php
new file mode 100644
--- /dev/null
+++ b/src/app/Console/Commands/UserUndegrade.php
@@ -0,0 +1,48 @@
+<?php
+
+namespace App\Console\Commands;
+
+use Illuminate\Console\Command;
+
+class UserUndegrade extends Command
+{
+    /**
+     * The name and signature of the console command.
+     *
+     * @var string
+     */
+    protected $signature = 'user:undegrade {user}';
+
+    /**
+     * The console command description.
+     *
+     * @var string
+     */
+    protected $description = 'Un-degrade a user';
+
+    /**
+     * Create a new command instance.
+     *
+     * @return void
+     */
+    public function __construct()
+    {
+        parent::__construct();
+    }
+
+    /**
+     * Execute the console command.
+     *
+     * @return mixed
+     */
+    public function handle()
+    {
+        $user = \App\User::where('email', $this->argument('user'))->first();
+
+        if (!$user) {
+            return 1;
+        }
+
+        $user->undegrade();
+    }
+}
diff --git a/src/app/Console/Commands/WalletCharge.php b/src/app/Console/Commands/WalletCharge.php
--- a/src/app/Console/Commands/WalletCharge.php
+++ b/src/app/Console/Commands/WalletCharge.php
@@ -68,7 +68,9 @@
             }
 
             if ($wallet->balance < 0) {
-                // Check the account balance, send notifications, suspend, delete
+                // Check the account balance, send notifications, (suspend, delete,) degrade
+                // TODO: For performance reasons we should probably skip the job
+                //       if the wallet owner is degraded already
                 \App\Jobs\WalletCheck::dispatch($wallet);
             }
         }
diff --git a/src/app/Http/Controllers/API/V4/OpenViduController.php b/src/app/Http/Controllers/API/V4/OpenViduController.php
--- a/src/app/Http/Controllers/API/V4/OpenViduController.php
+++ b/src/app/Http/Controllers/API/V4/OpenViduController.php
@@ -213,7 +213,7 @@
         $room = Room::where('name', $id)->first();
 
         // Room does not exist, or the owner is deleted
-        if (!$room || !$room->owner) {
+        if (!$room || !$room->owner || $room->owner->isDegraded(true)) {
             return $this->errorResponse(404, \trans('meet.room-not-found'));
         }
 
@@ -349,7 +349,7 @@
         $room = Room::where('name', $id)->first();
 
         // Room does not exist, or the owner is deleted
-        if (!$room || !$room->owner) {
+        if (!$room || !$room->owner || $room->owner->isDegraded(true)) {
             return $this->errorResponse(404);
         }
 
diff --git a/src/app/Http/Controllers/API/V4/UsersController.php b/src/app/Http/Controllers/API/V4/UsersController.php
--- a/src/app/Http/Controllers/API/V4/UsersController.php
+++ b/src/app/Http/Controllers/API/V4/UsersController.php
@@ -525,6 +525,8 @@
             'isSuspended' => $user->isSuspended(),
             'isActive' => $user->isActive(),
             'isDeleted' => $user->isDeleted() || $user->trashed(),
+            'isDegraded' => $user->isDegraded(),
+            'isAccountDegraded' => $user->isDegraded(true),
         ];
     }
 
diff --git a/src/app/Jobs/WalletCheck.php b/src/app/Jobs/WalletCheck.php
--- a/src/app/Jobs/WalletCheck.php
+++ b/src/app/Jobs/WalletCheck.php
@@ -19,6 +19,8 @@
     use Queueable;
     use SerializesModels;
 
+    public const THRESHOLD_DEGRADE = 'degrade';
+    public const THRESHOLD_BEFORE_DEGRADE = 'before_degrade';
     public const THRESHOLD_DELETE = 'delete';
     public const THRESHOLD_BEFORE_DELETE = 'before_delete';
     public const THRESHOLD_SUSPEND = 'suspend';
@@ -64,62 +66,80 @@
         }
 
         $now = Carbon::now();
-
-        // Delete the account
-        if (self::threshold($this->wallet, self::THRESHOLD_DELETE) < $now) {
-            $this->deleteAccount();
-            return self::THRESHOLD_DELETE;
-        }
-
-        // Warn about the upcomming account deletion
-        if (self::threshold($this->wallet, self::THRESHOLD_BEFORE_DELETE) < $now) {
-            $this->warnBeforeDelete();
-            return self::THRESHOLD_BEFORE_DELETE;
+/*
+        // Steps for old "first suspend then delete" approach
+        $steps = [
+            // Send the initial reminder
+            self::THRESHOLD_INITIAL => 'initialReminder',
+            // Try to top-up the wallet before the second reminder
+            self::THRESHOLD_BEFORE_REMINDER => 'topUpWallet',
+            // Send the second reminder
+            self::THRESHOLD_REMINDER => 'secondReminder',
+            // Try to top-up the wallet before suspending the account
+            self::THRESHOLD_BEFORE_SUSPEND => 'topUpWallet',
+            // Suspend the account
+            self::THRESHOLD_SUSPEND => 'suspendAccount',
+            // Warn about the upcomming account deletion
+            self::THRESHOLD_BEFORE_DELETE => 'warnBeforeDelete',
+            // Delete the account
+            self::THRESHOLD_DELETE => 'deleteAccount',
+        ];
+*/
+        // Steps for "demote instead of suspend+delete" approach
+        $steps = [
+            // Send the initial reminder
+            self::THRESHOLD_INITIAL => 'initialReminderForDegrade',
+            // Try to top-up the wallet before the second reminder
+            self::THRESHOLD_BEFORE_REMINDER => 'topUpWallet',
+            // Send the second reminder
+            self::THRESHOLD_REMINDER => 'secondReminderForDegrade',
+            // Try to top-up the wallet before the account degradation
+            self::THRESHOLD_BEFORE_DEGRADE => 'topUpWallet',
+            // Degrade the account
+            self::THRESHOLD_DEGRADE => 'degradeAccount',
+        ];
+
+        foreach (array_reverse($steps, true) as $type => $method) {
+            if (self::threshold($this->wallet, $type) < $now) {
+                $this->{$method}();
+                return $type;
+            }
         }
 
-        // Suspend the account
-        if (self::threshold($this->wallet, self::THRESHOLD_SUSPEND) < $now) {
-            $this->suspendAccount();
-            return self::THRESHOLD_SUSPEND;
-        }
+        return null;
+    }
 
-        // Try to top-up the wallet before suspending the account
-        if (self::threshold($this->wallet, self::THRESHOLD_BEFORE_SUSPEND) < $now) {
-            PaymentsController::topUpWallet($this->wallet);
-            return self::THRESHOLD_BEFORE_SUSPEND;
+    /**
+     * Send the initial reminder (for the suspend+delete process)
+     */
+    protected function initialReminder()
+    {
+        if ($this->wallet->getSetting('balance_warning_initial')) {
+            return;
         }
 
-        // Send the second reminder
-        if (self::threshold($this->wallet, self::THRESHOLD_REMINDER) < $now) {
-            $this->secondReminder();
-            return self::THRESHOLD_REMINDER;
-        }
+        // TODO: Should we check if the account is already suspended?
 
-        // Try to top-up the wallet before the second reminder
-        if (self::threshold($this->wallet, self::THRESHOLD_BEFORE_REMINDER) < $now) {
-            PaymentsController::topUpWallet($this->wallet);
-            return self::THRESHOLD_BEFORE_REMINDER;
-        }
+        $label = "Notification sent for";
 
-        // Send the initial reminder
-        if (self::threshold($this->wallet, self::THRESHOLD_INITIAL) < $now) {
-            $this->initialReminder();
-            return self::THRESHOLD_INITIAL;
-        }
+        $this->sendMail(\App\Mail\NegativeBalance::class, false, $label);
 
-        return null;
+        $now = \Carbon\Carbon::now()->toDateTimeString();
+        $this->wallet->setSetting('balance_warning_initial', $now);
     }
 
     /**
-     * Send the initial reminder
+     * Send the initial reminder (for the process of degrading a account)
      */
-    protected function initialReminder()
+    protected function initialReminderForDegrade()
     {
         if ($this->wallet->getSetting('balance_warning_initial')) {
             return;
         }
 
-        // TODO: Should we check if the account is already suspended?
+        if ($this->wallet->owner && $this->wallet->owner->isDegraded()) {
+            return;
+        }
 
         $label = "Notification sent for";
 
@@ -130,7 +150,7 @@
     }
 
     /**
-     * Send the second reminder
+     * Send the second reminder (for the suspend+delete process)
      */
     protected function secondReminder()
     {
@@ -148,6 +168,27 @@
         $this->wallet->setSetting('balance_warning_reminder', $now);
     }
 
+    /**
+     * Send the second reminder (for the process of degrading a account)
+     */
+    protected function secondReminderForDegrade()
+    {
+        if ($this->wallet->getSetting('balance_warning_reminder')) {
+            return;
+        }
+
+        if ($this->wallet->owner && $this->wallet->owner->isDegraded()) {
+            return;
+        }
+
+        $label = "Reminder sent for";
+
+        $this->sendMail(\App\Mail\NegativeBalanceReminderDegrade::class, true, $label);
+
+        $now = \Carbon\Carbon::now()->toDateTimeString();
+        $this->wallet->setSetting('balance_warning_reminder', $now);
+    }
+
     /**
      * Suspend the account (and send the warning)
      */
@@ -203,6 +244,36 @@
         $this->wallet->setSetting('balance_warning_before_delete', $now);
     }
 
+    /**
+     * Degrade the account
+     */
+    protected function degradeAccount()
+    {
+        // TODO: This will not work when we actually allow multiple-wallets per account
+        //       but in this case we anyway have to change the whole thing
+        //       and calculate summarized balance from all wallets.
+        if (!$this->wallet->owner || $this->wallet->owner->isDegraded()) {
+            return;
+        }
+
+        $email = $this->wallet->owner->email;
+
+        // The dirty work will be done by UserObserver
+        $this->wallet->owner->degrade();
+
+        \Log::info(
+            sprintf(
+                "[WalletCheck] Account degraded %s (%s)",
+                $this->wallet->id,
+                $email
+            )
+        );
+
+        $label = "Degradation notification sent for";
+
+        $this->sendMail(\App\Mail\NegativeBalanceDegraded::class, true, $label);
+    }
+
     /**
      * Delete the account
      */
@@ -292,47 +363,50 @@
             $negative_since = new Carbon($negative_since);
         }
 
-        $remind = 7;   // remind after first X days
-        $suspend = 14; // suspend after next X days
-        $delete = 21;  // delete after next X days
-        $warn = 3;     // warn about delete on X days before delete
-
-        // Acount deletion
-        if ($type == self::THRESHOLD_DELETE) {
-            return $negative_since->addDays($delete + $suspend + $remind);
-        }
-
-        // Warning about the upcomming account deletion
-        if ($type == self::THRESHOLD_BEFORE_DELETE) {
-            return $negative_since->addDays($delete + $suspend + $remind - $warn);
-        }
-
-        // Account suspension
-        if ($type == self::THRESHOLD_SUSPEND) {
-            return $negative_since->addDays($suspend + $remind);
-        }
-
-        // A day before account suspension
-        if ($type == self::THRESHOLD_BEFORE_SUSPEND) {
-            return $negative_since->addDays($suspend + $remind - 1);
-        }
-
-        // Second notification
-        if ($type == self::THRESHOLD_REMINDER) {
-            return $negative_since->addDays($remind);
-        }
-
-        // A day before the second reminder
-        if ($type == self::THRESHOLD_BEFORE_REMINDER) {
-            return $negative_since->addDays($remind - 1);
-        }
-
         // Initial notification
         // Give it an hour so the async recurring payment has a chance to be finished
         if ($type == self::THRESHOLD_INITIAL) {
             return $negative_since->addHours(1);
         }
+/*
+        $thresholds = [
+            // A day before the second reminder
+            self::THRESHOLD_BEFORE_REMINDER => 7 - 1,
+            // Second notification
+            self::THRESHOLD_REMINDER => 7,
+            // A day before account suspension
+            self::THRESHOLD_BEFORE_SUSPEND => 14 + 7 - 1,
+            // Account suspension
+            self::THRESHOLD_SUSPEND => 14 + 7,
+            // Warning about the upcomming account deletion
+            self::THRESHOLD_BEFORE_DELETE => 21 + 14 + 7 - 3,
+            // Acount deletion
+            self::THRESHOLD_DELETE => 21 + 14 + 7,
+        ];
+*/
+        $thresholds = [
+            // Top-up a walet before the second notification
+            self::THRESHOLD_BEFORE_REMINDER => 7 - 1,
+            // Second notification
+            self::THRESHOLD_REMINDER => 7,
+            // Last chance to top-up the wallet
+            self::THRESHOLD_BEFORE_DEGRADE => 13,
+            // Account degradation
+            self::THRESHOLD_DEGRADE => 14,
+        ];
+
+        if (!empty($thresholds[$type])) {
+            return $negative_since->addDays($thresholds[$type]);
+        }
 
         return null;
     }
+
+    /**
+     * Try to automatically top-up the wallet
+     */
+    protected function topUpWallet(): void
+    {
+        PaymentsController::topUpWallet($this->wallet);
+    }
 }
diff --git a/src/app/Mail/NegativeBalanceDegraded.php b/src/app/Mail/NegativeBalanceDegraded.php
new file mode 100644
--- /dev/null
+++ b/src/app/Mail/NegativeBalanceDegraded.php
@@ -0,0 +1,78 @@
+<?php
+
+namespace App\Mail;
+
+use App\Jobs\WalletCheck;
+use App\User;
+use App\Utils;
+use App\Wallet;
+use Illuminate\Bus\Queueable;
+use Illuminate\Mail\Mailable;
+use Illuminate\Queue\SerializesModels;
+
+class NegativeBalanceDegraded extends Mailable
+{
+    use Queueable;
+    use SerializesModels;
+
+    /** @var \App\Wallet A wallet with a negative balance */
+    protected $wallet;
+
+    /** @var \App\User A wallet controller to whom the email is being sent */
+    protected $user;
+
+
+    /**
+     * Create a new message instance.
+     *
+     * @param \App\Wallet $wallet A wallet
+     * @param \App\User   $user   An email recipient
+     *
+     * @return void
+     */
+    public function __construct(Wallet $wallet, User $user)
+    {
+        $this->wallet = $wallet;
+        $this->user = $user;
+    }
+
+    /**
+     * Build the message.
+     *
+     * @return $this
+     */
+    public function build()
+    {
+        $subject = \trans('mail.negativebalancedegraded-subject', ['site' => \config('app.name')]);
+
+        $this->view('emails.html.negative_balance_degraded')
+            ->text('emails.plain.negative_balance_degraded')
+            ->subject($subject)
+            ->with([
+                    'site' => \config('app.name'),
+                    'subject' => $subject,
+                    'username' => $this->user->name(true),
+                    'supportUrl' => \config('app.support_url'),
+                    'walletUrl' => Utils::serviceUrl('/wallet'),
+            ]);
+
+        return $this;
+    }
+
+    /**
+     * Render the mail template with fake data
+     *
+     * @param string $type Output format ('html' or 'text')
+     *
+     * @return string HTML or Plain Text output
+     */
+    public static function fakeRender(string $type = 'html'): string
+    {
+        $wallet = new Wallet();
+        $user = new User();
+
+        $mail = new self($wallet, $user);
+
+        return Helper::render($mail, $type);
+    }
+}
diff --git a/src/app/Mail/NegativeBalanceReminderDegrade.php b/src/app/Mail/NegativeBalanceReminderDegrade.php
new file mode 100644
--- /dev/null
+++ b/src/app/Mail/NegativeBalanceReminderDegrade.php
@@ -0,0 +1,81 @@
+<?php
+
+namespace App\Mail;
+
+use App\Jobs\WalletCheck;
+use App\User;
+use App\Utils;
+use App\Wallet;
+use Illuminate\Bus\Queueable;
+use Illuminate\Mail\Mailable;
+use Illuminate\Queue\SerializesModels;
+
+class NegativeBalanceReminderDegrade extends Mailable
+{
+    use Queueable;
+    use SerializesModels;
+
+    /** @var \App\Wallet A wallet with a negative balance */
+    protected $wallet;
+
+    /** @var \App\User A wallet controller to whom the email is being sent */
+    protected $user;
+
+
+    /**
+     * Create a new message instance.
+     *
+     * @param \App\Wallet $wallet A wallet
+     * @param \App\User   $user   An email recipient
+     *
+     * @return void
+     */
+    public function __construct(Wallet $wallet, User $user)
+    {
+        $this->wallet = $wallet;
+        $this->user = $user;
+    }
+
+    /**
+     * Build the message.
+     *
+     * @return $this
+     */
+    public function build()
+    {
+        $threshold = WalletCheck::threshold($this->wallet, WalletCheck::THRESHOLD_DEGRADE);
+
+        $subject = \trans('mail.negativebalancereminder-subject', ['site' => \config('app.name')]);
+
+        $this->view('emails.html.negative_balance_reminder')
+            ->text('emails.plain.negative_balance_reminder')
+            ->subject($subject)
+            ->with([
+                    'site' => \config('app.name'),
+                    'subject' => $subject,
+                    'username' => $this->user->name(true),
+                    'supportUrl' => \config('app.support_url'),
+                    'walletUrl' => Utils::serviceUrl('/wallet'),
+                    'date' => $threshold->toDateString(),
+            ]);
+
+        return $this;
+    }
+
+    /**
+     * Render the mail template with fake data
+     *
+     * @param string $type Output format ('html' or 'text')
+     *
+     * @return string HTML or Plain Text output
+     */
+    public static function fakeRender(string $type = 'html'): string
+    {
+        $wallet = new Wallet();
+        $user = new User();
+
+        $mail = new self($wallet, $user);
+
+        return Helper::render($mail, $type);
+    }
+}
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
@@ -116,6 +116,10 @@
 
         $owner = $entitlement->wallet->owner;
 
+        if ($owner->isDegraded()) {
+            return;
+        }
+
         // Determine if we're still within the free first month
         $freeMonthEnds = $owner->created_at->copy()->addMonthsWithoutOverflow(1);
 
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
@@ -349,14 +349,43 @@
     }
 
     /**
-     * Handle the "updating" event.
+     * Handle the "updated" event.
      *
      * @param User $user The user that is being updated.
      *
      * @return void
      */
-    public function updating(User $user)
+    public function updated(User $user)
     {
         \App\Jobs\User\UpdateJob::dispatch($user->id);
+
+        $oldStatus = $user->getOriginal('status');
+        $newStatus = $user->status;
+
+        if (($oldStatus & User::STATUS_DEGRADED) !== ($newStatus & User::STATUS_DEGRADED)) {
+            $wallets = [];
+
+            // Charge all entitlements as if they were being deleted,
+            // but don't delete them. Just debit the wallet and update
+            // entitlements' updated_at timestamp. On un-degrade we still
+            // update updated_at, but with no debit (the cost is 0 on a degraded account).
+            foreach ($user->wallets as $wallet) {
+                $wallet->updateEntitlements($user->isDegraded());
+                $wallets[] = $wallet->id;
+            }
+
+            // (Un-)degrade users by invoking an update job.
+            // LDAP backend will read the wallet owner's degraded status and
+            // set LDAP attributes accordingly.
+            // We do not change their status as their wallets have its own state
+            \App\Entitlement::whereIn('wallet_id', $wallets)
+                ->where('entitleable_id', '!=', $user->id)
+                ->where('entitleable_type', User::class)
+                ->pluck('entitleable_id')
+                ->unique()
+                ->each(function ($user_id) {
+                    \App\Jobs\User\UpdateJob::dispatch($user_id);
+                });
+        }
     }
 }
diff --git a/src/app/Observers/WalletObserver.php b/src/app/Observers/WalletObserver.php
--- a/src/app/Observers/WalletObserver.php
+++ b/src/app/Observers/WalletObserver.php
@@ -95,10 +95,12 @@
                     'balance_warning_before_delete' => null,
             ]);
 
-            // Unsuspend the account/domains/users
+            // Un-suspend and un-degrade the account/domains/users
             if ($wallet->owner) {
                 $wallet->owner->unsuspend();
+                $wallet->owner->undegrade();
             }
+
             foreach ($wallet->entitlements as $entitlement) {
                 if (
                     $entitlement->entitleable_type == \App\Domain::class
diff --git a/src/app/User.php b/src/app/User.php
--- a/src/app/User.php
+++ b/src/app/User.php
@@ -42,6 +42,8 @@
     public const STATUS_LDAP_READY = 1 << 4;
     // user mailbox has been created in IMAP
     public const STATUS_IMAP_READY = 1 << 5;
+    // user in "limited feature-set" state
+    public const STATUS_DEGRADED   = 1 << 6;
 
 
     // change the default primary key type
@@ -262,6 +264,21 @@
         return $this->canDelete($object);
     }
 
+    /**
+     * Degrade the user
+     *
+     * @return void
+     */
+    public function degrade(): void
+    {
+        if ($this->isDegraded()) {
+            return;
+        }
+
+        $this->status |= User::STATUS_DEGRADED;
+        $this->save();
+    }
+
     /**
      * Return the \App\Domain for this user.
      *
@@ -449,7 +466,7 @@
     }
 
     /**
-     * Returns whether this domain is active.
+     * Returns whether this user is active.
      *
      * @return bool
      */
@@ -459,7 +476,28 @@
     }
 
     /**
-     * Returns whether this domain is deleted.
+     * Returns whether this user (or its wallet owner) is degraded.
+     *
+     * @param bool $owner Check also the wallet owner instead just the user himself
+     *
+     * @return bool
+     */
+    public function isDegraded(bool $owner = false): bool
+    {
+        if ($this->status & self::STATUS_DEGRADED) {
+            return true;
+        }
+
+        if ($owner) {
+            $owner = $this->wallet()->owner;
+            return $owner && $owner->isDegraded();
+        }
+
+        return false;
+    }
+
+    /**
+     * Returns whether this user is deleted.
      *
      * @return bool
      */
@@ -469,8 +507,7 @@
     }
 
     /**
-     * Returns whether this (external) domain has been verified
-     * to exist in DNS.
+     * Returns whether this user is registered in IMAP.
      *
      * @return bool
      */
@@ -500,7 +537,7 @@
     }
 
     /**
-     * Returns whether this domain is suspended.
+     * Returns whether this user is suspended.
      *
      * @return bool
      */
@@ -574,7 +611,7 @@
     }
 
     /**
-     * Suspend this domain.
+     * Suspend this user.
      *
      * @return void
      */
@@ -589,7 +626,22 @@
     }
 
     /**
-     * Unsuspend this domain.
+     * Un-degrade this user.
+     *
+     * @return void
+     */
+    public function undegrade(): void
+    {
+        if (!$this->isDegraded()) {
+            return;
+        }
+
+        $this->status ^= User::STATUS_DEGRADED;
+        $this->save();
+    }
+
+    /**
+     * Unsuspend this user.
      *
      * @return void
      */
@@ -705,6 +757,7 @@
             self::STATUS_DELETED,
             self::STATUS_LDAP_READY,
             self::STATUS_IMAP_READY,
+            self::STATUS_DEGRADED,
         ];
 
         foreach ($allowed_values as $value) {
diff --git a/src/app/Wallet.php b/src/app/Wallet.php
--- a/src/app/Wallet.php
+++ b/src/app/Wallet.php
@@ -58,7 +58,14 @@
         }
     }
 
-    public function chargeEntitlements($apply = true)
+    /**
+     * Charge entitlements in the wallet
+     *
+     * @param bool $apply Set to false for a dry-run mode
+     *
+     * @return int Charged amount in cents
+     */
+    public function chargeEntitlements($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)) {
@@ -78,8 +85,11 @@
 
         $charges = 0;
         $discount = $this->getDiscountRate();
+        $isDegraded = $this->owner->isDegraded();
 
-        DB::beginTransaction();
+        if ($apply) {
+            DB::beginTransaction();
+        }
 
         // used to parent individual entitlement billings to the wallet debit.
         $entitlementTransactions = [];
@@ -102,6 +112,10 @@
 
                 $cost = (int) ($entitlement->cost * $discount * $diff);
 
+                if ($isDegraded) {
+                    $cost = 0;
+                }
+
                 $charges += $cost;
 
                 // if we're in dry-run, you know...
@@ -127,10 +141,9 @@
 
         if ($apply) {
             $this->debit($charges, $entitlementTransactions);
+            DB::commit();
         }
 
-        DB::commit();
-
         return $charges;
     }
 
@@ -397,4 +410,72 @@
             ]
         );
     }
+
+    /**
+     * Force-update entitlements' updated_at, charge if needed.
+     *
+     * @param bool $withCost When enabled the cost will be charged
+     *
+     * @return int Charged amount in cents
+     */
+    public function updateEntitlements($withCost = true): int
+    {
+        $charges = 0;
+        $discount = $this->getDiscountRate();
+        $now = Carbon::now();
+
+        DB::beginTransaction();
+
+        // used to parent individual entitlement billings to the wallet debit.
+        $entitlementTransactions = [];
+
+        foreach ($this->entitlements()->get()->fresh() as $entitlement) {
+            $cost = 0;
+            $diffInDays = $entitlement->updated_at->diffInDays($now);
+
+            // This entitlement has been 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)) {
+                // $cost=0
+            } elseif ($withCost && $diffInDays > 0) {
+                // The price per day is based on the number of days in the last month
+                // or the current month if the period does not overlap with the previous month
+                // FIXME: This really should be simplified to constant $daysInMonth=30
+                if ($now->day >= $diffInDays && $now->month == $entitlement->updated_at->month) {
+                    $daysInMonth = $now->daysInMonth;
+                } else {
+                    $daysInMonth = \App\Utils::daysInLastMonth();
+                }
+
+                $pricePerDay = $entitlement->cost / $daysInMonth;
+
+                $cost = (int) (round($pricePerDay * $discount * $diffInDays, 0));
+            }
+
+            if ($diffInDays > 0) {
+                $entitlement->updated_at->setDateFrom($now);
+                $entitlement->save();
+            }
+
+            if ($cost == 0) {
+                continue;
+            }
+
+            $charges += $cost;
+
+            // FIXME: Shouldn't we store also cost=0 transactions (to have the full history)?
+            $entitlementTransactions[] = $entitlement->createTransaction(
+                \App\Transaction::ENTITLEMENT_BILLED,
+                $cost
+            );
+        }
+
+        if ($charges > 0) {
+            $this->debit($charges, $entitlementTransactions);
+        }
+
+        DB::commit();
+
+        return $charges;
+    }
 }
diff --git a/src/resources/js/app.js b/src/resources/js/app.js
--- a/src/resources/js/app.js
+++ b/src/resources/js/app.js
@@ -300,6 +300,9 @@
 
             return 'Active'
         },
+        isDegraded() {
+            return store.state.authInfo.isAccountDegraded
+        },
         pageName(path) {
             let page = this.$route.path
 
@@ -337,7 +340,7 @@
                 return 'text-muted'
             }
 
-            if (user.isSuspended) {
+            if (user.isDegraded || user.isSuspended) {
                 return 'text-warning'
             }
 
@@ -352,6 +355,10 @@
                 return 'Deleted'
             }
 
+            if (user.isDegraded) {
+                return 'Degraded'
+            }
+
             if (user.isSuspended) {
                 return 'Suspended'
             }
diff --git a/src/resources/lang/en/mail.php b/src/resources/lang/en/mail.php
--- a/src/resources/lang/en/mail.php
+++ b/src/resources/lang/en/mail.php
@@ -29,6 +29,14 @@
     'negativebalancereminder-body-warning' => "Please, be aware that your account will be suspended "
         . "if your account balance is not settled by :date.",
 
+    'negativebalancereminderdegrade-body-warning' => "Please, be aware that your account will be degraded "
+        . "if your account balance is not settled by :date.",
+
+    'negativebalancedegraded-subject' => ":site Account Degraded",
+    'negativebalancedegraded-body' => "Your :site account has been degraded for having a negative balance for too long. "
+        . "Consider setting up an automatic payment to avoid messages like this in the future.",
+    'negativebalancedegraded-body-ext' => "Settle up now to undegrade your account:",
+
     'negativebalancesuspended-subject' => ":site Account Suspended",
     'negativebalancesuspended-body' => "Your :site account has been suspended for having a negative balance for too long. "
         . "Consider setting up an automatic payment to avoid messages like this in the future.",
diff --git a/src/resources/views/emails/html/negative_balance_degraded.blade.php b/src/resources/views/emails/html/negative_balance_degraded.blade.php
new file mode 100644
--- /dev/null
+++ b/src/resources/views/emails/html/negative_balance_degraded.blade.php
@@ -0,0 +1,21 @@
+<!DOCTYPE html>
+<html lang="{{ str_replace('_', '-', app()->getLocale()) }}">
+    <head>
+        <meta charset="utf-8">
+    </head>
+    <body>
+        <p>{{ __('mail.header', ['name' => $username]) }}</p>
+
+        <p>{{ __('mail.negativebalancedegraded-body', ['site' => $site]) }}</p>
+        <p>{{ __('mail.negativebalancedegraded-body-ext', ['site' => $site]) }}</p>
+        <p><a href="{{ $walletUrl }}">{{ $walletUrl }}</a></p>
+
+@if ($supportUrl)
+        <p>{{ __('mail.support', ['site' => $site]) }}</p>
+        <p><a href="{{ $supportUrl }}">{{ $supportUrl }}</a></p>
+@endif
+
+        <p>{{ __('mail.footer1') }}</p>
+        <p>{{ __('mail.footer2', ['site' => $site]) }}</p>
+    </body>
+</html>
diff --git a/src/resources/views/emails/html/negative_balance_reminder_degrade.blade.php b/src/resources/views/emails/html/negative_balance_reminder_degrade.blade.php
new file mode 100644
--- /dev/null
+++ b/src/resources/views/emails/html/negative_balance_reminder_degrade.blade.php
@@ -0,0 +1,22 @@
+<!DOCTYPE html>
+<html lang="{{ str_replace('_', '-', app()->getLocale()) }}">
+    <head>
+        <meta charset="utf-8">
+    </head>
+    <body>
+        <p>{{ __('mail.header', ['name' => $username]) }}</p>
+
+        <p>{{ __('mail.negativebalancereminder-body', ['site' => $site]) }}</p>
+        <p>{{ __('mail.negativebalancereminder-body-ext', ['site' => $site]) }}</p>
+        <p><a href="{{ $walletUrl }}">{{ $walletUrl }}</a></p>
+        <p><b>{{ __('mail.negativebalancereminderdegrade-body-warning', ['site' => $site, 'date' => $date]) }}</b></p>
+
+@if ($supportUrl)
+        <p>{{ __('mail.support', ['site' => $site]) }}</p>
+        <p><a href="{{ $supportUrl }}">{{ $supportUrl }}</a></p>
+@endif
+
+        <p>{{ __('mail.footer1') }}</p>
+        <p>{{ __('mail.footer2', ['site' => $site]) }}</p>
+    </body>
+</html>
diff --git a/src/resources/views/emails/plain/negative_balance_degraded.blade.php b/src/resources/views/emails/plain/negative_balance_degraded.blade.php
new file mode 100644
--- /dev/null
+++ b/src/resources/views/emails/plain/negative_balance_degraded.blade.php
@@ -0,0 +1,17 @@
+{!! __('mail.header', ['name' => $username]) !!}
+
+{!! __('mail.negativebalancedegraded-body', ['site' => $site]) !!}
+
+{!! __('mail.negativebalancedegraded-body-ext', ['site' => $site]) !!}
+
+{!! $walletUrl !!}
+
+@if ($supportUrl)
+{!! __('mail.support', ['site' => $site]) !!}
+
+{!! $supportUrl !!}
+@endif
+
+-- 
+{!! __('mail.footer1') !!}
+{!! __('mail.footer2', ['site' => $site]) !!}
diff --git a/src/resources/views/emails/plain/negative_balance_reminder_degrade.blade.php b/src/resources/views/emails/plain/negative_balance_reminder_degrade.blade.php
new file mode 100644
--- /dev/null
+++ b/src/resources/views/emails/plain/negative_balance_reminder_degrade.blade.php
@@ -0,0 +1,19 @@
+{!! __('mail.header', ['name' => $username]) !!}
+
+{!! __('mail.negativebalancereminder-body', ['site' => $site]) !!}
+
+{!! __('mail.negativebalancereminder-body-ext', ['site' => $site]) !!}
+
+{!! $walletUrl !!}
+
+{!! __('mail.negativebalancereminderdegrade-body-warning', ['site' => $site, 'date' => $date]) !!}
+
+@if ($supportUrl)
+{!! __('mail.support', ['site' => $site]) !!}
+
+{!! $supportUrl !!}
+@endif
+
+-- 
+{!! __('mail.footer1') !!}
+{!! __('mail.footer2', ['site' => $site]) !!}
diff --git a/src/resources/vue/Dashboard.vue b/src/resources/vue/Dashboard.vue
--- a/src/resources/vue/Dashboard.vue
+++ b/src/resources/vue/Dashboard.vue
@@ -2,6 +2,12 @@
     <div class="container" dusk="dashboard-component">
         <status-component :status="status" @status-update="statusUpdate"></status-component>
 
+        <div id="status-degraded" v-if="$root.isDegraded()" class="d-flex justify-content-center">
+            <p class="alert alert-danger">
+                The account is degraded. Some features has been disabled. Please, make a payment.
+            </p>
+        </div>
+
         <div id="dashboard-nav">
             <router-link class="card link-profile" :to="{ name: 'profile' }">
                 <svg-icon icon="user-cog"></svg-icon><span class="name">Your profile</span>
@@ -16,7 +22,7 @@
                 <svg-icon icon="wallet"></svg-icon><span class="name">Wallet</span>
                 <span v-if="balance < 0" class="badge badge-danger">{{ $root.price(balance) }}</span>
             </router-link>
-            <router-link v-if="$root.hasSKU('meet')" class="card link-chat" :to="{ name: 'rooms' }">
+            <router-link v-if="$root.hasSKU('meet') && !$root.isDegraded()" class="card link-chat" :to="{ name: 'rooms' }">
                 <svg-icon icon="comments"></svg-icon><span class="name">Video chat</span>
                 <span class="badge badge-primary">beta</span>
             </router-link>
diff --git a/src/resources/vue/Rooms.vue b/src/resources/vue/Rooms.vue
--- a/src/resources/vue/Rooms.vue
+++ b/src/resources/vue/Rooms.vue
@@ -81,7 +81,7 @@
             }
         },
         mounted() {
-            if (!this.$root.hasSKU('meet')) {
+            if (!this.$root.hasSKU('meet') || this.$root.isDegraded()) {
                 this.$root.errorPage(403)
                 return
             }
diff --git a/src/resources/vue/User/List.vue b/src/resources/vue/User/List.vue
--- a/src/resources/vue/User/List.vue
+++ b/src/resources/vue/User/List.vue
@@ -4,7 +4,7 @@
             <div class="card-body">
                 <div class="card-title">
                     User Accounts
-                    <router-link class="btn btn-primary float-right create-user" :to="{ path: 'user/new' }" tag="button">
+                    <router-link v-if="!$root.isDegraded()" class="btn btn-primary float-right create-user" :to="{ path: 'user/new' }" tag="button">
                         <svg-icon icon="user"></svg-icon> Create user
                     </router-link>
                 </div>