diff --git a/crates/core/src/operations/cast/mod.rs b/crates/core/src/operations/cast/mod.rs
index 554373e623..278cb2bbfa 100644
--- a/crates/core/src/operations/cast/mod.rs
+++ b/crates/core/src/operations/cast/mod.rs
@@ -144,7 +144,19 @@ fn cast_field(
             add_missing,
         )?) as ArrayRef),
         _ if is_cast_required(col_type, field_type) => {
-            cast_with_options(col, field_type, cast_options)
+            cast_with_options(col, field_type, cast_options).map_err(|err| {
+                if let ArrowError::CastError(err) = err {
+                    ArrowError::CastError(format!(
+                        "Failed to cast {} from {} to {}: {}",
+                        field.name(),
+                        field_type,
+                        col_type,
+                        err
+                    ))
+                } else {
+                    err
+                }
+            })
         }
         _ => Ok(col.clone()),
     }
@@ -337,6 +349,11 @@ mod tests {
         assert!(!is_cast_required(&field1, &field2));
     }
 
+    #[test]
+    fn test_is_cast_required_with_smol_int() {
+        assert!(is_cast_required(&DataType::Int8, &DataType::Int32));
+    }
+
     #[test]
     fn test_is_cast_required_with_list_non_default_item() {
         let field1 = DataType::List(FieldRef::from(Field::new("item", DataType::Int32, false)));
diff --git a/python/tests/test_writer.py b/python/tests/test_writer.py
index c43e5d1136..a6662c48d6 100644
--- a/python/tests/test_writer.py
+++ b/python/tests/test_writer.py
@@ -273,7 +273,8 @@ def test_write_type_castable_types(existing_table: DeltaTable):
         engine="rust",
     )
     with pytest.raises(
-        Exception, match="Cast error: Cannot cast string 'hello' to value of Int8 type"
+        Exception,
+        match="Cast error: Failed to cast int8 from Int8 to Utf8: Cannot cast string 'hello' to value of Int8 type",
     ):
         write_deltalake(
             existing_table,
@@ -284,7 +285,8 @@ def test_write_type_castable_types(existing_table: DeltaTable):
         )
 
     with pytest.raises(
-        Exception, match="Cast error: Can't cast value 1000 to type Int8"
+        Exception,
+        match="Cast error: Failed to cast int8 from Int8 to Int64: Can't cast value 1000 to type Int8",
     ):
         write_deltalake(
             existing_table,