diff --git a/src/Phaseolies/Application.php b/src/Phaseolies/Application.php
index b505d15..182c7fc 100644
--- a/src/Phaseolies/Application.php
+++ b/src/Phaseolies/Application.php
@@ -156,6 +156,7 @@ class Application extends Container
      *
      * Initializes the application by:
      * - Setting the application instance in the container.
+     * - Loading environment variables from .env before anything else.
      * - Setting up exception handling.
      * - Loading configuration.
      * - Defining necessary folder paths.
diff --git a/src/Phaseolies/Auth/Security/Authenticate.php b/src/Phaseolies/Auth/Security/Authenticate.php
index ecac875..8347e7e 100644
--- a/src/Phaseolies/Auth/Security/Authenticate.php
+++ b/src/Phaseolies/Auth/Security/Authenticate.php
@@ -284,9 +284,7 @@ public function user(): ?Model
         if (session()->has($cacheKey)) {
             $cache = session($cacheKey);
             if ($this->isUserCacheValid($cache)) {
-                if ($this->isUserCacheValid($cache)) {
-                    return $this->resolvedUser = $cache['user'];
-                }
+                return $this->resolvedUser = $cache['user'];
             }
         }
 
diff --git a/src/Phaseolies/Config/Config.php b/src/Phaseolies/Config/Config.php
index 49620e2..60b872b 100644
--- a/src/Phaseolies/Config/Config.php
+++ b/src/Phaseolies/Config/Config.php
@@ -27,6 +27,13 @@ final class Config
      */
     protected static bool $loadedFromCache = false;
 
+    /**
+     * Tracks whether config was modified after loading from cache.
+     *
+     * @var bool
+     */
+    protected static bool $configModified = false;
+
     /**
      * Stores hashes of configuration files used to detect changes.
      *
@@ -34,6 +41,13 @@ final class Config
      */
     protected static array $fileHashes = [];
 
+    /**
+     * Cached list of config file paths
+     *
+     * @var array|null
+     */
+    protected static ?array $configFiles = null;
+
     /**
      * Initialize the configuration system.
      *
@@ -48,7 +62,17 @@ public static function initialize(): void
     }
 
     /**
-     * Generate a unique cache key based on all configuration files.
+     * Get all config file paths, cached for the request lifetime.
+     *
+     * @return array
+     */
+    protected static function getConfigFiles(): array
+    {
+        return self::$configFiles ??= glob(base_path('config/*.php')) ?: [];
+    }
+
+    /**
+     * Generate a unique cache key based on all configuration files and .env.
      *
      * @return string
      */
@@ -57,9 +81,9 @@ protected static function getCacheKey(): string
         static $cacheKey = null;
 
         if ($cacheKey === null) {
-            $files = glob(base_path('config/*.php'));
             $hashes = [];
-            foreach ($files as $file) {
+
+            foreach (self::getConfigFiles() as $file) {
                 $hashes[] = md5_file($file) . '|' . filemtime($file);
             }
 
@@ -83,7 +107,7 @@ public static function loadAll(): void
     {
         self::$config = [];
 
-        foreach (glob(base_path('config/*.php')) as $file) {
+        foreach (self::getConfigFiles() as $file) {
             $key = basename($file, '.php');
             self::$config[$key] = include $file;
         }
@@ -98,13 +122,23 @@ public static function loadAll(): void
      */
     public static function loadFromCache(): void
     {
-        if (!file_exists(self::$cacheFile) || !self::isCacheValid()) {
+        if (!file_exists(self::$cacheFile)) {
             self::$loadedFromCache = false;
             self::loadAll();
             return;
         }
 
         $cached = include self::$cacheFile;
+
+        if (
+            !isset($cached['_meta']['cache_key']) ||
+            $cached['_meta']['cache_key'] !== self::getCacheKey()
+        ) {
+            self::$loadedFromCache = false;
+            self::loadAll();
+            return;
+        }
+
         self::$config = $cached['data'] ?? [];
         self::$fileHashes = $cached['_meta']['file_hashes'] ?? [];
         self::$loadedFromCache = true;
@@ -121,7 +155,7 @@ public static function cacheConfig(): void
             return;
         }
 
-        if (self::$loadedFromCache && !self::configWasModified()) {
+        if (self::$loadedFromCache && !self::$configModified) {
             return;
         }
 
@@ -130,10 +164,8 @@ public static function cacheConfig(): void
             throw new RuntimeException("Failed to create cache directory: {$cacheDir}");
         }
 
-        $files = glob(base_path('config/*.php'));
-
         $hashes = [];
-        foreach ($files as $file) {
+        foreach (self::getConfigFiles() as $file) {
             $hashes[basename($file)] = md5_file($file) . '|' . filemtime($file);
         }
 
@@ -151,23 +183,10 @@ public static function cacheConfig(): void
         rename($tempFile, self::$cacheFile);
 
         self::$loadedFromCache = true;
+        self::$configModified = false;
         self::$fileHashes = $hashes;
     }
 
-    /**
-     * Check if the configuration data has been modified compared to cache.
-     *
-     * @return bool
-     */
-    protected static function configWasModified(): bool
-    {
-        if (!file_exists(self::$cacheFile)) return true;
-
-        $cached = include self::$cacheFile;
-
-        return $cached['data'] !== self::$config;
-    }
-
     /**
      * Get a configuration value using dot notation.
      *
@@ -225,6 +244,7 @@ public static function set(string $key, mixed $value): void
             $current = $value;
         }
 
+        self::$configModified = true;
         self::cacheConfig();
     }
 
@@ -261,8 +281,9 @@ public static function clearCache(): void
         if (file_exists(self::$cacheFile)) @unlink(self::$cacheFile);
 
         self::$config = [];
-
         self::$fileHashes = [];
+        self::$configFiles = null;
+        self::$configModified = false;
     }
 
     /**