diff --git a/app.json b/app.json
index fe4b84ffd70..053530f04af 100644
--- a/app.json
+++ b/app.json
@@ -19,7 +19,7 @@
     }
   ],
   "scripts": {
-    "postdeploy": "php artisan monica:update --force"
+    "postdeploy": "php artisan monica:update --force -vvv"
   },
   "env": {
     "APP_KEY": {
diff --git a/app/Console/Commands/Helpers/CommandExecutor.php b/app/Console/Commands/Helpers/CommandExecutor.php
index 0208762dbae..a1c9a3cba38 100644
--- a/app/Console/Commands/Helpers/CommandExecutor.php
+++ b/app/Console/Commands/Helpers/CommandExecutor.php
@@ -37,17 +37,14 @@ public function exec($message, $commandline)
 
     public function artisan($message, $commandline, array $arguments = [])
     {
-        $this->command->info($message);
         $info = '';
         foreach ($arguments as $key => $value) {
-            $info = $info.' '.$key.'='.$value;
-        }
-        $this->command->line('php artisan '.$commandline.$info);
-        if ($this->command->getOutput()->getVerbosity() >= OutputInterface::VERBOSITY_VERBOSE) {
-            $this->command->call($commandline, $arguments);
-        } else {
-            $this->command->callSilent($commandline, $arguments);
+            if (is_string($key)) {
+                $info .= ' '.$key.'="'.$value.'"';
+            } else {
+                $info .= ' '.$value;
+            }
         }
-        $this->command->line('');
+        $this->exec($message, 'php artisan '.$commandline.$info);
     }
 }
diff --git a/app/Console/Commands/Update.php b/app/Console/Commands/Update.php
index 0fd9be85395..786fa91fdac 100644
--- a/app/Console/Commands/Update.php
+++ b/app/Console/Commands/Update.php
@@ -60,11 +60,12 @@ public function handle()
                     ]);
 
                 // Clear or rebuild all cache
-                if (config('cache.default') != 'database' || Schema::hasTable('cache')) {
+                if (config('cache.default') != 'database' || Schema::hasTable(config('cache.stores.database.table'))) {
                     $this->commandExecutor->artisan('✓ Resetting application cache', 'cache:clear');
                 }
 
                 if ($this->getLaravel()->environment() == 'production') {
+                    $this->commandExecutor->artisan('✓ Clear config cache', 'config:clear');
                     $this->commandExecutor->artisan('✓ Resetting route cache', 'route:cache');
                     if ($this->getLaravel()->version() > '5.6') {
                         $this->commandExecutor->artisan('✓ Resetting view cache', 'view:cache');
@@ -86,12 +87,18 @@ public function handle()
                 }
 
                 if ($this->migrateCollationTest()) {
-                    $this->commandExecutor->artisan('✓ Performing collation migrations', 'migrate:collation', ['--force' => 'true']);
+                    $this->commandExecutor->artisan('✓ Performing collation migrations', 'migrate:collation', ['--force']);
                 }
 
-                $this->commandExecutor->artisan('✓ Performing migrations', 'migrate', ['--force' => 'true']);
+                $this->commandExecutor->artisan('✓ Performing migrations', 'migrate', ['--force']);
+
+                $this->commandExecutor->artisan('✓ Ping for new version', 'monica:ping', ['--force']);
 
-                $this->commandExecutor->artisan('✓ Ping for new version', 'monica:ping', ['--force' => 'true']);
+                // Cache config
+                if ($this->getLaravel()->environment() == 'production'
+                    && (config('cache.default') != 'database' || Schema::hasTable(config('cache.stores.database.table')))) {
+                    $this->commandExecutor->artisan('✓ Cache configuraton', 'config:cache');
+                }
             } finally {
                 $this->commandExecutor->artisan('✓ Maintenance mode: off', 'up');
             }
diff --git a/config/trustedproxy.php b/config/trustedproxy.php
index 8caa659f786..3a4b6b8b691 100644
--- a/config/trustedproxy.php
+++ b/config/trustedproxy.php
@@ -44,6 +44,6 @@
     /*
      * Enable cloudflare trusted proxies
      */
-    'cloudflare' => env('APP_TRUSTED_CLOUDFLARE', false),
+    'cloudflare' => (bool) env('APP_TRUSTED_CLOUDFLARE', false),
 
 ];
diff --git a/database/migrations/2018_07_08_104306_update-timestamps-timezone.php b/database/migrations/2018_07_08_104306_update-timestamps-timezone.php
index 313553899cc..c85d62a71ac 100644
--- a/database/migrations/2018_07_08_104306_update-timestamps-timezone.php
+++ b/database/migrations/2018_07_08_104306_update-timestamps-timezone.php
@@ -15,7 +15,7 @@ public function up()
     {
         $timezone = env('APP_DEFAULT_TIMEZONE', 'UTC');
 
-        if ($timezone == 'UTC') {
+        if ($timezone == null || $timezone == 'UTC') {
             return;
         }
 
diff --git a/docs/installation/generic.md b/docs/installation/generic.md
index 1eaa656a9d7..1b479ba4a27 100644
--- a/docs/installation/generic.md
+++ b/docs/installation/generic.md
@@ -95,6 +95,9 @@ exit
 1. Run `php artisan setup:production` to run the migrations, seed the database and symlink folders.
 1. Optional: run `php artisan passport:install` to create the access tokens required for the API (Optional).
 
+The `setup:production` command will run migrations scripts for database, and flush all cache for config, route, and view, as an optimization process.
+As the configuration of the application is cached, any update on the `.env` file will not be detected after that. You may have to run `php artisan config:cache` manually after every update of `.env` file.
+
 ### 4. Configure cron job
 
 Monica requires some background processes to continuously run. The list of things Monica does in the background is described [here](https://github.com/monicahq/monica/blob/master/app/Console/Kernel.php#L33).
diff --git a/docs/installation/update.md b/docs/installation/update.md
index fbbb4e150f7..7d7e430d625 100644
--- a/docs/installation/update.md
+++ b/docs/installation/update.md
@@ -27,6 +27,10 @@ steps below to update it, **every single time**, or you will run into problems.
    php artisan monica:update --force
    ```
 
+The `monica:update` command will run migrations scripts for database, and flush all cache for config, route, and view, as an optimization process.
+As the configuration of the application is cached, any update on the `.env` file will not be detected after that. You may have to run `php artisan config:cache` manually after every update of `.env` file.
+
+
 Your instance should be updated.
 
 ## Importing vCards (CLI only)
diff --git a/scripts/docker/test-server.sh b/scripts/docker/test-server.sh
index f22c0ab02d4..ed6dfb178a6 100755
--- a/scripts/docker/test-server.sh
+++ b/scripts/docker/test-server.sh
@@ -20,7 +20,7 @@ else
 fi
 
 # Run migrations
-${ARTISAN} monica:update --force
+${ARTISAN} monica:update --force -v
 
 # Run cron
 crond -b &
diff --git a/scripts/vagrant/Vagrantfile b/scripts/vagrant/Vagrantfile
index 8bc5c69de4a..3df996e1c8a 100644
--- a/scripts/vagrant/Vagrantfile
+++ b/scripts/vagrant/Vagrantfile
@@ -18,7 +18,7 @@ else
 fi
 
 # Run migrations
-${ARTISAN} monica:update --force
+${ARTISAN} monica:update --force -v
 
 echo -e "\n\n\033[1;32mDone! You can access Monica by visiting \033[4;96mhttp://localhost:8080\033[0;40m\033[1;32m from your host machine\033[0;40m"