diff --git a/src/tinker/lib/retry_handler.py b/src/tinker/lib/retry_handler.py
index 174d825..fb0c161 100644
--- a/src/tinker/lib/retry_handler.py
+++ b/src/tinker/lib/retry_handler.py
@@ -61,6 +61,9 @@ class RetryConfig:
     enable_retry_logic: bool = True
     """Whether to enable automatic retries on failure."""
 
+    max_retries: int = 5
+    """Maximum number of retry attempts before giving up. Set to 0 for unlimited retries."""
+
     retryable_exceptions: tuple[Type[Exception], ...] = (
         asyncio.TimeoutError,
         tinker.APIConnectionError,
@@ -82,6 +85,7 @@ class RetryConfig:
                 self.retry_delay_max,
                 self.jitter_factor,
                 self.enable_retry_logic,
+                self.max_retries,
                 self.retryable_exceptions,
             )
         )
@@ -241,6 +245,13 @@ class RetryHandler(Generic[T]):  # noqa: UP046
                     logger.error(f"Request failed with non-retryable error: {exception_str}")
                     raise
 
+                # Check if we've exceeded max retries (0 means unlimited)
+                if self.config.max_retries > 0 and attempt_count >= self.config.max_retries:
+                    logger.error(
+                        f"Request failed after {attempt_count} attempts (max_retries={self.config.max_retries}): {exception_str}"
+                    )
+                    raise
+
                 self._log_retry_reason(e, attempt_count)
                 self._retry_count += 1
 
@@ -263,6 +274,14 @@ class RetryHandler(Generic[T]):  # noqa: UP046
         if isinstance(exception, tinker.APIStatusError):
             return is_retryable_status_code(exception.status_code)
 
+        # Retry RequestFailedError when the error category is Unknown, as these
+        # may be transient server-side issues that could succeed on retry.
+        # User errors (category=User) are not retried as they require client changes.
+        if isinstance(exception, tinker.RequestFailedError):
+            from tinker.types import RequestErrorCategory
+
+            return exception.category == RequestErrorCategory.Unknown
+
         return False
 
     def _log_retry_reason(self, exception: Exception, attempt_count: int):
@@ -275,6 +294,11 @@ class RetryHandler(Generic[T]):  # noqa: UP046
             logger.debug(
                 f"Request attempt #{attempt_count} failed with status {exception.status_code}"
             )
+        elif isinstance(exception, tinker.RequestFailedError):
+            logger.debug(
+                f"Request attempt #{attempt_count} failed with category {exception.category}: "
+                f"{exception.message}"
+            )
         else:
             logger.debug(f"Request attempt #{attempt_count} failed with error: {exception}")