diff --git a/CHANGELOG.md b/CHANGELOG.md
index 57096d1ca..860db8c76 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -12,6 +12,9 @@ This project follows [Semantic Versioning](http://semver.org) guidelines.
 * Added ability to reinstall a server using the currently assigned service and option.
 * Added ability to change a server's service and service option, as well as change pack assignments and other management services in that regard.
 
+### Changed
+* Environment setting commands now attempt to auto-quote strings with spaces in them, as well as comment lines that are edited to avoid manual changes being overwritten.
+
 ## v0.6.0-beta.2.1 (Courageous Carniadactylus)
 ### Fixed
 * `[beta.2]` — Suspended servers now show as suspended.
diff --git a/app/Console/Commands/UpdateEmailSettings.php b/app/Console/Commands/UpdateEmailSettings.php
index 679d94ee7..1e316d6cb 100644
--- a/app/Console/Commands/UpdateEmailSettings.php
+++ b/app/Console/Commands/UpdateEmailSettings.php
@@ -147,7 +147,10 @@ class UpdateEmailSettings extends Command
 
         $this->line('Writing new email environment configuration to file.');
         foreach ($variables as $key => $value) {
-            $newValue = $key . '=' . $value;
+            if (str_contains($value, ' ') && ! str_contains($value, '"')) {
+                $value = '"' . $value . '"';
+            }
+            $newValue = $key . '=' . $value . ' # DO NOT EDIT! set using pterodactyl:mail';
 
             if (preg_match_all('/^' . $key . '=(.*)$/m', $envContents) < 1) {
                 $envContents = $envContents . "\n" . $newValue;
diff --git a/app/Console/Commands/UpdateEnvironment.php b/app/Console/Commands/UpdateEnvironment.php
index 009efab2e..6252a2824 100644
--- a/app/Console/Commands/UpdateEnvironment.php
+++ b/app/Console/Commands/UpdateEnvironment.php
@@ -186,7 +186,10 @@ class UpdateEnvironment extends Command
         $bar = $this->output->createProgressBar(count($variables));
 
         foreach ($variables as $key => $value) {
-            $newValue = $key . '=' . $value;
+            if (str_contains($value, ' ') && ! str_contains($value, '"')) {
+                $value = '"' . $value . '"';
+            }
+            $newValue = $key . '=' . $value . ' # DO NOT EDIT! set using pterodactyl:env';
 
             if (preg_match_all('/^' . $key . '=(.*)$/m', $envContents) < 1) {
                 $envContents = $envContents . "\n" . $newValue;