diff --git a/src/sentry/grouping/parameterization.py b/src/sentry/grouping/parameterization.py
index a1be4c4a3376a7..87957ace6824cd 100644
--- a/src/sentry/grouping/parameterization.py
+++ b/src/sentry/grouping/parameterization.py
@@ -1,18 +1,42 @@
 import dataclasses
+import logging
 import re
-from collections import OrderedDict, defaultdict
+from collections import Counter, OrderedDict, defaultdict
 from collections.abc import Sequence
 from ipaddress import ip_address, ip_interface, ip_network
-from typing import Callable
+from typing import Any, Callable
 
 from sentry.utils import metrics
 
+logger = logging.getLogger("sentry.events.grouping")
+
+
+# Counter for logging a set amount of example data. Not meant to be used directly. (Use the
+# `_log_example_data` helper instead.)
+LOGGING_COUNTER: Counter[str] = Counter()
+
 # Function parameterization regexes can specify to provide a customized replacement string. Can also
 # be used to do conditional replacement, by returning the original value in cases where replacement
 # shouldn't happen.
 ParameterizationReplacementFunction = Callable[[str], str]
 
 
+# Log examples, up to the given limit.
+def _log_example_data(
+    key: str,  # Key used for tracking log count and in logger `event` string
+    extra: dict[str, Any],  # Extra data to add to the log (should include example data)
+    limit: int = 100,  # Number of logs to be gathered per deployment
+) -> None:
+    # Note: In a multi-threaded environment, it's possible to run into a race condition where
+    # multiple threads are simultaneously logging what should theoretically be the last example. As
+    # result, we may end up logging a few more examples than the given limit. To fix this, we'd need
+    # to wrap everything here in a lock, but given that a few extra logs don't hurt anything, it's
+    # not worth blocking ingest by doing so.
+    if LOGGING_COUNTER[key] < limit:
+        logger.info(f"grouping.parameterization.{key}", extra=extra)
+        LOGGING_COUNTER[key] += 1
+
+
 @dataclasses.dataclass
 class ParameterizationRegex:
     name: str  # name of the pattern (also used as group name in combined regex)
@@ -445,6 +469,10 @@ def _handle_regex_match(match: re.Match[str]) -> str:
                     metrics.incr(
                         "grouping.parameterization_false_positive", tags={"key": matched_key}
                     )
+                    # TODO: Remove this once we have enough sample data
+                    _log_example_data(
+                        "ip_false_positive", extra={"input_str": input_str, "value": orig_value}
+                    )
 
             return replacement_string
 
diff --git a/tests/sentry/grouping/test_parameterization.py b/tests/sentry/grouping/test_parameterization.py
index 48cfb97bc31fc5..0bf373a68765f0 100644
--- a/tests/sentry/grouping/test_parameterization.py
+++ b/tests/sentry/grouping/test_parameterization.py
@@ -13,6 +13,7 @@
 from sentry.grouping.parameterization import (
     ParameterizationRegex,
     Parameterizer,
+    _log_example_data,
     experimental_parameterizer,
     is_valid_ip,
     parameterizer,
@@ -717,3 +718,33 @@ def test_replacement_callback_false_positive_triggers_individual_regex_fallback(
             )
             == 1
         )
+
+
+@patch("sentry.grouping.parameterization.logger")
+def test_example_data_logging(mock_logger: MagicMock) -> None:
+    for i in range(15):
+        _log_example_data("dog_fact_1", extra={"input_str": "dogs are great", "num": i}, limit=10)
+
+    for i in range(105):
+        _log_example_data("dog_fact_2", extra={"input_str": "all dogs are good dogs", "num": i})
+
+    # In the first loop, we specified a limit of 10, so the logger was called 10 times, even though
+    # we called the helper 15 times
+    assert (
+        count_matching_calls(
+            mock_logger.info,
+            "grouping.parameterization.dog_fact_1",
+            extra={"input_str": "dogs are great", "num": ANY},
+        )
+        == 10
+    )
+    # In the second loop, we didn't specify a limit, so the logger was called 100 times (the
+    # default limit), even though we called the helper 105 times
+    assert (
+        count_matching_calls(
+            mock_logger.info,
+            "grouping.parameterization.dog_fact_2",
+            extra={"input_str": "all dogs are good dogs", "num": ANY},
+        )
+        == 100
+    )