diff --git a/app.py b/app.py
index 16afbe6..047db12 100644
--- a/app.py
+++ b/app.py
@@ -111,19 +111,53 @@ def get_file_key(filepath):
     return filepath
 
 def is_file_protected(filepath):
-    """Check if a file is password protected."""
+    """Check if a file is password protected. Checks both encrypted and non-encrypted versions."""
     passwords = load_passwords()
     file_key = get_file_key(filepath)
-    return passwords.get(file_key, {}).get('protected', False)
+    
+    # Check if this exact key is protected
+    if passwords.get(file_key, {}).get('protected', False):
+        return True
+    
+    # If looking for encrypted version, also check non-encrypted key
+    if filepath.endswith('.enc'):
+        base_key = filepath[:-4]  # Remove .enc
+        if passwords.get(base_key, {}).get('protected', False):
+            return True
+    
+    # If looking for non-encrypted, also check encrypted key
+    else:
+        enc_key = filepath + '.enc'
+        if passwords.get(enc_key, {}).get('protected', False):
+            return True
+    
+    return False
 
 def is_authenticated(filepath):
     """Check if user is authenticated for a protected file."""
     if not is_file_protected(filepath):
         return True  # Not protected, so allowed
     
+    passwords = load_passwords()
     file_key = get_file_key(filepath)
     authenticated_files = session.get('authenticated_files', {})
-    return authenticated_files.get(file_key, False)
+    
+    # Check if authenticated for this exact key
+    if authenticated_files.get(file_key, False):
+        return True
+    
+    # If looking for encrypted version, also check non-encrypted key
+    if filepath.endswith('.enc'):
+        base_key = filepath[:-4]
+        if authenticated_files.get(base_key, False):
+            return True
+    # If looking for non-encrypted, also check encrypted key
+    else:
+        enc_key = filepath + '.enc'
+        if authenticated_files.get(enc_key, False):
+            return True
+    
+    return False
 
 def extract_email_text(email_content):
     """
@@ -631,11 +665,16 @@ def view_file(filepath):
             with open(file_path, 'r', encoding='utf-8') as f:
                 encrypted_content = f.read()
             
-            # Get password from session
+            # Get password from session - check multiple possible keys
             file_key = get_file_key(lookup_filepath)
             authenticated_files = session.get('authenticated_files', {})
             password = authenticated_files.get(file_key + '_password')
             
+            # If not found with lookup_filepath key, try base filename (without .enc)
+            if not password and lookup_filepath.endswith('.enc'):
+                base_key = lookup_filepath[:-4]
+                password = authenticated_files.get(base_key + '_password')
+            
             if not password:
                 return "Unable to decrypt: password not found in session", 500
             
@@ -685,19 +724,34 @@ def authenticate(filepath):
     
     passwords = load_passwords()
     file_data = passwords.get(file_key)
+    actual_key = file_key
+    
+    # If looking for .enc file, also check the base name
+    if not file_data and filepath.endswith('.enc'):
+        base_key = filepath[:-4]
+        file_data = passwords.get(base_key)
+        if file_data:
+            actual_key = base_key
+    
+    # If looking for base file, also check the .enc version
+    if not file_data and not filepath.endswith('.enc'):
+        enc_key = filepath + '.enc'
+        file_data = passwords.get(enc_key)
+        if file_data:
+            actual_key = enc_key
     
     if not file_data or not file_data.get('protected'):
         return jsonify({'success': False, 'error': 'File not protected'}), 400
     
     # Check password
     if check_password_hash(file_data['password_hash'], password):
-        # Store in session
+        # Store in session using the key where protection is stored
         if 'authenticated_files' not in session:
             session['authenticated_files'] = {}
-        session['authenticated_files'][file_key] = True
+        session['authenticated_files'][actual_key] = True
         # Store the password for decryption if file is encrypted
         if is_encrypted_file(filepath):
-            session['authenticated_files'][file_key + '_password'] = password
+            session['authenticated_files'][actual_key + '_password'] = password
         session.modified = True
         
         logger.info(f"User authenticated for {file_key}")