Harden JWT PEM normalization diagnostics

app/Http/Middleware/JwtAuthMiddleware.php

@@ -109,10 +109,11 @@ class JwtAuthMiddleware
             throw new \RuntimeException('JWT public key is empty');
         }
 
+        $this->flushOpenSslErrors();
         $keyResource = openssl_pkey_get_public($publicKey);
 
         if ($keyResource === false) {
-            throw new \RuntimeException(openssl_error_string() ?: 'OpenSSL could not read JWT public key');
+            throw new \RuntimeException($this->openSslErrorMessage('OpenSSL could not read JWT public key'));
         }
 
         $result = openssl_verify(
@@ -123,7 +124,7 @@ class JwtAuthMiddleware
         );
 
         if ($result === false) {
-            throw new \RuntimeException(openssl_error_string() ?: 'OpenSSL could not verify JWT signature');
+            throw new \RuntimeException($this->openSslErrorMessage('OpenSSL could not verify JWT signature'));
         }
 
         return $result === 1;
@@ -131,6 +132,15 @@ class JwtAuthMiddleware
 
     private function normalizePublicKey(string $publicKey): string
     {
+        $publicKey = trim($publicKey);
+
+        if (
+            (str_starts_with($publicKey, '"') && str_ends_with($publicKey, '"')) ||
+            (str_starts_with($publicKey, "'") && str_ends_with($publicKey, "'"))
+        ) {
+            $publicKey = substr($publicKey, 1, -1);
+        }
+
         $publicKey = trim(str_replace(['\\r\\n', '\\n', '\\r', "\r\n", "\r"], "\n", $publicKey));
 
         if ($publicKey === '') {
@@ -139,23 +149,52 @@ class JwtAuthMiddleware
 
         if (
             preg_match(
-                '/-----BEGIN PUBLIC KEY-----(.*?)-----END PUBLIC KEY-----/s',
+                '/-----BEGIN ([A-Z ]*PUBLIC KEY)-----(.*?)-----END \1-----/s',
                 $publicKey,
                 $matches
             )
         ) {
-            $body = preg_replace('/\s+/', '', $matches[1]);
+            $type = $matches[1];
+            $body = preg_replace('/[^A-Za-z0-9+\/=]/', '', $matches[2]);
 
             if ($body === '') {
                 return '';
             }
 
-            return "-----BEGIN PUBLIC KEY-----\n"
+            return "-----BEGIN {$type}-----\n"
                 . chunk_split($body, 64, "\n")
-                . "-----END PUBLIC KEY-----\n";
+                . "-----END {$type}-----\n";
         }
 
-        return $publicKey;
+        if (!str_contains($publicKey, '-----BEGIN')) {
+            $body = preg_replace('/[^A-Za-z0-9+\/=]/', '', $publicKey);
+
+            if (strlen($body) > 100) {
+                return "-----BEGIN PUBLIC KEY-----\n"
+                    . chunk_split($body, 64, "\n")
+                    . "-----END PUBLIC KEY-----\n";
+            }
+        }
+
+        return trim($publicKey) . "\n";
+    }
+
+    private function flushOpenSslErrors(): void
+    {
+        while (openssl_error_string() !== false) {
+            // Clear stale OpenSSL errors before reading the next operation result.
+        }
+    }
+
+    private function openSslErrorMessage(string $fallback): string
+    {
+        $errors = [];
+
+        while (($error = openssl_error_string()) !== false) {
+            $errors[] = $error;
+        }
+
+        return $errors === [] ? $fallback : implode(' | ', $errors);
     }
 
     private function tokenIsExpired(array $payload): bool

routes/api.php

@@ -30,31 +30,61 @@ Route::get('/health', function () {
 
 Route::get('/health-check-key', function () {
     $rawPublicKey = (string) config('jwt.public_key');
-    $formattedPublicKey = trim(str_replace(['\\r\\n', '\\n', '\\r', "\r\n", "\r"], "\n", $rawPublicKey));
+    $formattedPublicKey = trim($rawPublicKey);
 
     if (
-        preg_match(
+        (str_starts_with($formattedPublicKey, '"') && str_ends_with($formattedPublicKey, '"')) ||
-            '/-----BEGIN PUBLIC KEY-----(.*?)-----END PUBLIC KEY-----/s',
+        (str_starts_with($formattedPublicKey, "'") && str_ends_with($formattedPublicKey, "'"))
-            $formattedPublicKey,
-            $matches
-        )
     ) {
-        $body = preg_replace('/\s+/', '', $matches[1]);
+        $formattedPublicKey = substr($formattedPublicKey, 1, -1);
-        $formattedPublicKey = "-----BEGIN PUBLIC KEY-----\n"
+    }
+
+    $formattedPublicKey = trim(str_replace(['\\r\\n', '\\n', '\\r', "\r\n", "\r"], "\n", $formattedPublicKey));
+    $pemType = null;
+    $bodyLength = null;
+
+    if (preg_match('/-----BEGIN ([A-Z ]*PUBLIC KEY)-----(.*?)-----END \1-----/s', $formattedPublicKey, $matches)) {
+        $pemType = $matches[1];
+        $body = preg_replace('/[^A-Za-z0-9+\/=]/', '', $matches[2]);
+        $bodyLength = strlen($body);
+        $formattedPublicKey = "-----BEGIN {$pemType}-----\n"
             . chunk_split($body, 64, "\n")
-            . "-----END PUBLIC KEY-----\n";
+            . "-----END {$pemType}-----\n";
+    } elseif (!str_contains($formattedPublicKey, '-----BEGIN')) {
+        $body = preg_replace('/[^A-Za-z0-9+\/=]/', '', $formattedPublicKey);
+        $bodyLength = strlen($body);
+
+        if ($bodyLength > 100) {
+            $pemType = 'PUBLIC KEY';
+            $formattedPublicKey = "-----BEGIN PUBLIC KEY-----\n"
+                . chunk_split($body, 64, "\n")
+                . "-----END PUBLIC KEY-----\n";
+        }
+    }
+
+    while (openssl_error_string() !== false) {
+        // Clear stale OpenSSL errors before testing the current key.
     }
 
     $publicKeyResource = openssl_pkey_get_public($formattedPublicKey);
+    $openSslErrors = [];
+
+    while (($error = openssl_error_string()) !== false) {
+        $openSslErrors[] = $error;
+    }
 
     return response()->json([
         'raw_key_empty' => $rawPublicKey === '',
         'raw_key_length' => strlen($rawPublicKey),
         'formatted_key_length' => strlen($formattedPublicKey),
+        'pem_type' => $pemType,
+        'pem_body_length' => $bodyLength,
         'has_begin_marker' => str_contains($rawPublicKey, '-----BEGIN PUBLIC KEY-----'),
+        'has_rsa_begin_marker' => str_contains($rawPublicKey, '-----BEGIN RSA PUBLIC KEY-----'),
         'has_end_marker' => str_contains($rawPublicKey, '-----END PUBLIC KEY-----'),
+        'has_rsa_end_marker' => str_contains($rawPublicKey, '-----END RSA PUBLIC KEY-----'),
         'openssl_accepted' => $publicKeyResource !== false,
-        'openssl_error' => openssl_error_string(),
+        'openssl_errors' => $openSslErrors,
     ]);
 });
 

routes/web.php

@@ -17,31 +17,61 @@ Route::get('/health', function () {
 
 Route::get('/health-check-key', function () {
     $rawPublicKey = (string) config('jwt.public_key');
-    $formattedPublicKey = trim(str_replace(['\\r\\n', '\\n', '\\r', "\r\n", "\r"], "\n", $rawPublicKey));
+    $formattedPublicKey = trim($rawPublicKey);
 
     if (
-        preg_match(
+        (str_starts_with($formattedPublicKey, '"') && str_ends_with($formattedPublicKey, '"')) ||
-            '/-----BEGIN PUBLIC KEY-----(.*?)-----END PUBLIC KEY-----/s',
+        (str_starts_with($formattedPublicKey, "'") && str_ends_with($formattedPublicKey, "'"))
-            $formattedPublicKey,
-            $matches
-        )
     ) {
-        $body = preg_replace('/\s+/', '', $matches[1]);
+        $formattedPublicKey = substr($formattedPublicKey, 1, -1);
-        $formattedPublicKey = "-----BEGIN PUBLIC KEY-----\n"
+    }
+
+    $formattedPublicKey = trim(str_replace(['\\r\\n', '\\n', '\\r', "\r\n", "\r"], "\n", $formattedPublicKey));
+    $pemType = null;
+    $bodyLength = null;
+
+    if (preg_match('/-----BEGIN ([A-Z ]*PUBLIC KEY)-----(.*?)-----END \1-----/s', $formattedPublicKey, $matches)) {
+        $pemType = $matches[1];
+        $body = preg_replace('/[^A-Za-z0-9+\/=]/', '', $matches[2]);
+        $bodyLength = strlen($body);
+        $formattedPublicKey = "-----BEGIN {$pemType}-----\n"
             . chunk_split($body, 64, "\n")
-            . "-----END PUBLIC KEY-----\n";
+            . "-----END {$pemType}-----\n";
+    } elseif (!str_contains($formattedPublicKey, '-----BEGIN')) {
+        $body = preg_replace('/[^A-Za-z0-9+\/=]/', '', $formattedPublicKey);
+        $bodyLength = strlen($body);
+
+        if ($bodyLength > 100) {
+            $pemType = 'PUBLIC KEY';
+            $formattedPublicKey = "-----BEGIN PUBLIC KEY-----\n"
+                . chunk_split($body, 64, "\n")
+                . "-----END PUBLIC KEY-----\n";
+        }
+    }
+
+    while (openssl_error_string() !== false) {
+        // Clear stale OpenSSL errors before testing the current key.
     }
 
     $publicKeyResource = openssl_pkey_get_public($formattedPublicKey);
+    $openSslErrors = [];
+
+    while (($error = openssl_error_string()) !== false) {
+        $openSslErrors[] = $error;
+    }
 
     return response()->json([
         'raw_key_empty' => $rawPublicKey === '',
         'raw_key_length' => strlen($rawPublicKey),
         'formatted_key_length' => strlen($formattedPublicKey),
+        'pem_type' => $pemType,
+        'pem_body_length' => $bodyLength,
         'has_begin_marker' => str_contains($rawPublicKey, '-----BEGIN PUBLIC KEY-----'),
+        'has_rsa_begin_marker' => str_contains($rawPublicKey, '-----BEGIN RSA PUBLIC KEY-----'),
         'has_end_marker' => str_contains($rawPublicKey, '-----END PUBLIC KEY-----'),
+        'has_rsa_end_marker' => str_contains($rawPublicKey, '-----END RSA PUBLIC KEY-----'),
         'openssl_accepted' => $publicKeyResource !== false,
-        'openssl_error' => openssl_error_string(),
+        'openssl_errors' => $openSslErrors,
     ]);
 });