diff --git a/singer_sdk/helpers/jsonpath.py b/singer_sdk/helpers/jsonpath.py
index 9e2956f19..82c514b41 100644
--- a/singer_sdk/helpers/jsonpath.py
+++ b/singer_sdk/helpers/jsonpath.py
@@ -2,6 +2,7 @@
 
 from __future__ import annotations
 
+import logging
 import typing as t
 
 import memoization
@@ -11,6 +12,9 @@
     import jsonpath_ng
 
 
+logger = logging.getLogger(__name__)
+
+
 def extract_jsonpath(
     expression: str,
     input: dict | list,  # noqa: A002
@@ -27,7 +31,11 @@ def extract_jsonpath(
     compiled_jsonpath = _compile_jsonpath(expression)
 
     match: jsonpath_ng.DatumInContext
-    for match in compiled_jsonpath.find(input):
+    matches = compiled_jsonpath.find(input)
+
+    logger.info("JSONPath matches: %d", len(matches))
+
+    for match in matches:
         yield match.value