diff --git a/ra_aid/__main__.py b/ra_aid/__main__.py
index 24b941e..748acd7 100644
--- a/ra_aid/__main__.py
+++ b/ra_aid/__main__.py
@@ -55,6 +55,15 @@ def launch_webui(host: str, port: int):
 def parse_arguments(args=None):
     ANTHROPIC_DEFAULT_MODEL = "claude-3-7-sonnet-20250219"
     OPENAI_DEFAULT_MODEL = "gpt-4o"
+    
+    # Case-insensitive log level argument type
+    def log_level_type(value):
+        value = value.lower()
+        if value not in ["debug", "info", "warning", "error", "critical"]:
+            raise argparse.ArgumentTypeError(
+                f"Invalid log level: {value}. Choose from debug, info, warning, error, critical."
+            )
+        return value
 
     parser = argparse.ArgumentParser(
         description="RA.Aid - AI Agent for executing programming and research tasks",
@@ -148,6 +157,12 @@ Examples:
     parser.add_argument(
         "--pretty-logger", action="store_true", help="Enable pretty logging output"
     )
+    parser.add_argument(
+        "--log-level",
+        type=log_level_type,
+        default="warning",
+        help="Set specific logging level (case-insensitive, overrides --verbose)",
+    )
     parser.add_argument(
         "--temperature",
         type=float,
@@ -333,7 +348,7 @@ def build_status(
 def main():
     """Main entry point for the ra-aid command line tool."""
     args = parse_arguments()
-    setup_logging(args.verbose, args.pretty_logger)
+    setup_logging(args.verbose, args.pretty_logger, args.log_level)
     logger.debug("Starting RA.Aid with arguments: %s", args)
 
     # Launch web interface if requested
diff --git a/ra_aid/logging_config.py b/ra_aid/logging_config.py
index 781b14f..1af5ae4 100644
--- a/ra_aid/logging_config.py
+++ b/ra_aid/logging_config.py
@@ -1,7 +1,12 @@
 import logging
+import os
 import sys
+from datetime import datetime
+from logging.handlers import RotatingFileHandler
+from pathlib import Path
 from typing import Optional
 
+
 from rich.console import Console
 from rich.markdown import Markdown
 from rich.panel import Panel
@@ -36,21 +41,89 @@ class PrettyHandler(logging.Handler):
             self.handleError(record)
 
 
-def setup_logging(verbose: bool = False, pretty: bool = False) -> None:
+def setup_logging(verbose: bool = False, pretty: bool = False, log_level: Optional[str] = None) -> None:
+    """
+    Configure logging for ra_aid.
+    
+    Args:
+        verbose: Set to True to enable verbose logging (implies DEBUG level if log_level not specified)
+        pretty: Set to True to enable pretty console logging
+        log_level: Optional explicit log level (DEBUG, INFO, WARNING, ERROR, CRITICAL)
+                  Takes precedence over verbose flag if specified
+    """
+    # Create .ra-aid/logs directory if it doesn't exist
+    cwd = os.getcwd()
+    ra_aid_dir_str = os.path.join(cwd, ".ra-aid")
+    logs_dir_str = os.path.join(ra_aid_dir_str, "logs")
+    
+    # Create directory structure
+    for directory in [ra_aid_dir_str, logs_dir_str]:
+        path = Path(directory)
+        if not path.exists():
+            try:
+                path.mkdir(mode=0o755, parents=True, exist_ok=True)
+            except Exception as e:
+                print(f"Warning: Failed to create log directory {directory}: {str(e)}")
+    
+    # Determine log level
+    if log_level is not None:
+        # Use provided log level if specified (case-insensitive)
+        numeric_level = getattr(logging, log_level.upper(), None)
+        if not isinstance(numeric_level, int):
+            # If invalid log level is provided, fall back to default
+            print(f"Invalid log level: {log_level}")
+            numeric_level = logging.DEBUG if verbose else logging.WARNING
+    else:
+        # Use verbose flag to determine log level
+        numeric_level = logging.DEBUG if verbose else logging.WARNING
+    
+    # Configure root logger
     logger = logging.getLogger("ra_aid")
-    logger.setLevel(logging.DEBUG if verbose else logging.WARNING)
-
-    if not logger.handlers:
-        if pretty:
-            handler = PrettyHandler()
-        else:
-            handler = logging.StreamHandler(sys.stdout)
-            formatter = logging.Formatter(
-                "%(asctime)s - %(name)s - %(levelname)s - %(message)s"
-            )
-            handler.setFormatter(formatter)
-        logger.addHandler(handler)
+    logger.setLevel(numeric_level)
+    
+    # Clear existing handlers to avoid duplicates
+    if logger.handlers:
+        logger.handlers.clear()
+    
+    # Create console handler
+    if pretty:
+        console_handler = PrettyHandler()
+    else:
+        console_handler = logging.StreamHandler(sys.stdout)
+        formatter = logging.Formatter(
+            "%(asctime)s - %(name)s - %(levelname)s - %(message)s"
+        )
+        console_handler.setFormatter(formatter)
+    
+    # Add console handler to logger
+    logger.addHandler(console_handler)
+    
+    # Create file handler with rotation
+    try:
+        timestamp = datetime.now().strftime("%Y%m%d_%H%M%S")
+        log_filename = os.path.join(logs_dir_str, f"ra_aid_{timestamp}.log")
+        
+        # RotatingFileHandler with 5MB max size and 100 backup files
+        file_handler = RotatingFileHandler(
+            log_filename,
+            maxBytes=5 * 1024 * 1024,  # 5MB
+            backupCount=100,
+            encoding="utf-8"
+        )
+        
+        file_formatter = logging.Formatter(
+            "%(asctime)s - %(name)s - %(levelname)s - %(message)s"
+        )
+        file_handler.setFormatter(file_formatter)
+        file_handler.setLevel(numeric_level)
+        
+        # Add file handler to logger
+        logger.addHandler(file_handler)
+        
+        logger.info(f"Log file created: {log_filename}")
+    except Exception as e:
+        logger.error(f"Failed to set up file logging: {str(e)}")
 
 
 def get_logger(name: Optional[str] = None) -> logging.Logger:
-    return logging.getLogger(f"ra_aid.{name}" if name else "ra_aid")
+    return logging.getLogger(f"ra_aid.{name}" if name else "ra_aid")
\ No newline at end of file