diff --git a/CHANGELOG.md b/CHANGELOG.md
index 553b4beb2f4b8..c1881821210b2 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -58,6 +58,7 @@ Inspired from [Keep a Changelog](https://keepachangelog.com/en/1.0.0/)
 - [Bug]: Alias filter lost after rollover ([#4499](https://github.com/opensearch-project/OpenSearch/pull/4499))
 - Fixing Gradle warnings associated with publishPluginZipPublicationToXxx tasks ([#4696](https://github.com/opensearch-project/OpenSearch/pull/4696))
 - Fixed randomly failing test ([4774](https://github.com/opensearch-project/OpenSearch/pull/4774))
+- Skip uppercase regex tests before 2.4.0 ([4869](https://github.com/opensearch-project/OpenSearch/pull/4869))
 ### Security
 - CVE-2022-25857 org.yaml:snakeyaml DOS vulnerability ([#4341](https://github.com/opensearch-project/OpenSearch/pull/4341))
 
diff --git a/rest-api-spec/src/main/resources/rest-api-spec/test/search/190_index_prefix_search.yml b/rest-api-spec/src/main/resources/rest-api-spec/test/search/190_index_prefix_search.yml
index ca8e89aa2d5b5..4532a26451c05 100644
--- a/rest-api-spec/src/main/resources/rest-api-spec/test/search/190_index_prefix_search.yml
+++ b/rest-api-spec/src/main/resources/rest-api-spec/test/search/190_index_prefix_search.yml
@@ -84,6 +84,9 @@ setup:
 
 ---
 "search with uppercase regex":
+  - skip:
+      version: " - 2.3.99"
+      reason: uppercase regex not supported before 2.4.0
   - do:
       search:
         rest_total_hits_as_int: true