diff --git a/misc/python/materialize/buildkite_insights/annotation_search/annotation_match.py b/misc/python/materialize/buildkite_insights/annotation_search/annotation_match.py
new file mode 100755
index 000000000000..87d782206704
--- /dev/null
+++ b/misc/python/materialize/buildkite_insights/annotation_search/annotation_match.py
@@ -0,0 +1,18 @@
+#!/usr/bin/env python3
+
+# Copyright Materialize, Inc. and contributors. All rights reserved.
+#
+# Use of this software is governed by the Business Source License
+# included in the LICENSE file at the root of this repository.
+#
+# As of the Change Date specified in that file, in accordance with
+# the Business Source License, use of this software will be governed
+# by the Apache License, Version 2.0.
+
+from dataclasses import dataclass
+
+
+@dataclass
+class AnnotationMatch:
+    title: str | None
+    title_and_text: str
diff --git a/misc/python/materialize/buildkite_insights/annotation_search/annotation_search.py b/misc/python/materialize/buildkite_insights/annotation_search/annotation_search.py
index 54ecb46d78a4..be7ad6c7247a 100755
--- a/misc/python/materialize/buildkite_insights/annotation_search/annotation_search.py
+++ b/misc/python/materialize/buildkite_insights/annotation_search/annotation_search.py
@@ -13,6 +13,9 @@
 import re
 from typing import Any
 
+from materialize.buildkite_insights.annotation_search.annotation_match import (
+    AnnotationMatch,
+)
 from materialize.buildkite_insights.annotation_search.annotation_search_presentation import (
     print_annotation_match,
     print_before_search_results,
@@ -92,7 +95,7 @@ def search_annotations(
     annotations: list[Any],
     search_value: str,
     use_regex: bool,
-) -> list[str]:
+) -> list[AnnotationMatch]:
     matched_annotations = []
 
     search_pattern = _search_value_to_pattern(search_value, use_regex)
@@ -101,7 +104,12 @@ def search_annotations(
         annotation_text = clean_annotation_text(annotation_html)
 
         if search_pattern.search(annotation_text) is not None:
-            matched_annotations.append(annotation_text)
+            annotation_title = try_extracting_title_from_annotation_html(
+                annotation_html
+            )
+            matched_annotations.append(
+                AnnotationMatch(annotation_title, annotation_text)
+            )
 
     return matched_annotations
 
@@ -110,6 +118,25 @@ def clean_annotation_text(annotation_html: str) -> str:
     return re.sub(r"<[^>]+>", "", annotation_html)
 
 
+def try_extracting_title_from_annotation_html(annotation_html: str) -> str | None:
+    # match <p>...</p> header
+    header_paragraph_match = re.search("<p>(.*?)</p>", annotation_html)
+
+    if header_paragraph_match is None:
+        return None
+
+    header_paragraph = header_paragraph_match.group(1)
+
+    build_step_name_match = re.search(
+        "<a href=.*?>(.*?)</a> (failed|succeeded)", header_paragraph
+    )
+
+    if build_step_name_match:
+        return build_step_name_match.group(1)
+    else:
+        return clean_annotation_text(header_paragraph)
+
+
 def filter_builds(
     builds_data: list[Any],
     only_failed_build_step_keys: list[str],
diff --git a/misc/python/materialize/buildkite_insights/annotation_search/annotation_search_presentation.py b/misc/python/materialize/buildkite_insights/annotation_search/annotation_search_presentation.py
index 7d4edcdd376a..45cddf0e6b46 100755
--- a/misc/python/materialize/buildkite_insights/annotation_search/annotation_search_presentation.py
+++ b/misc/python/materialize/buildkite_insights/annotation_search/annotation_search_presentation.py
@@ -11,6 +11,9 @@
 
 from typing import Any
 
+from materialize.buildkite_insights.annotation_search.annotation_match import (
+    AnnotationMatch,
+)
 from materialize.buildkite_insights.util.search_utility import (
     highlight_match,
     trim_match,
@@ -35,13 +38,13 @@ def print_annotation_match(
     build_pipeline: str,
     branch: str,
     web_url: str,
-    annotation_text: str,
+    annotation: AnnotationMatch,
     search_value: str,
     use_regex: bool,
     short_result_presentation: bool,
 ) -> None:
     matched_snippet = trim_match(
-        input=annotation_text, search_value=search_value, use_regex=use_regex
+        input=annotation.title_and_text, search_value=search_value, use_regex=use_regex
     )
     matched_snippet = highlight_match(
         input=matched_snippet,
@@ -57,6 +60,9 @@ def print_annotation_match(
     )
     print(f"URL: {with_formatting(web_url, COLOR_CYAN)}")
 
+    if annotation.title is not None:
+        print(f"Annotation: {with_formatting(annotation.title, COLOR_CYAN)}")
+
     if not short_result_presentation:
         print(SHORT_SEPARATOR)
         print(matched_snippet)