diff --git a/python/lancedb/context.py b/python/lancedb/context.py
index 83d10771..dee4180c 100644
--- a/python/lancedb/context.py
+++ b/python/lancedb/context.py
@@ -13,7 +13,7 @@
 from __future__ import annotations
 
 import pandas as pd
-
+from .exceptions import MissingValueError, MissingColumnError
 
 def contextualize(raw_df: pd.DataFrame) -> Contextualizer:
     """Create a Contextualizer object for the given DataFrame.
@@ -140,6 +140,17 @@ class Contextualizer:
     def to_df(self) -> pd.DataFrame:
         """Create the context windows and return a DataFrame."""
 
+        if self._text_col not in self._raw_df.columns.tolist():
+            raise MissingColumnError(self._text_col)
+
+        if self._window is None or self._window < 1:
+            raise MissingValueError("The value of window is None or less than 1. Specify the "
+                "window size (number of rows to include in each window)")
+
+        if self._stride is None or self._stride < 1:
+            raise MissingValueError("The value of stride is None or less than 1. Specify the "
+                "stride (number of rows to skip between each window)")
+
         def process_group(grp):
             # For each group, create the text rolling window
             text = grp[self._text_col].values
diff --git a/python/lancedb/exceptions.py b/python/lancedb/exceptions.py
new file mode 100644
index 00000000..10def337
--- /dev/null
+++ b/python/lancedb/exceptions.py
@@ -0,0 +1,16 @@
+"""Custom exception handling"""
+
+class MissingValueError(ValueError):
+    """Exception raised when a required value is missing."""
+    pass
+
+class MissingColumnError(KeyError):
+    """
+    Exception raised when a column name specified is not in 
+    the  DataFrame object
+    """
+    def __init__(self, column_name):
+        self.column_name = column_name
+
+    def __str__(self):
+        return f"Error: Column '{self.column_name}' does not exist in the DataFrame object"