diff --git a/tests/utils/test_log_handlers.py b/tests/utils/test_log_handlers.py
index b0f2d6f262e55..45a43fdba684c 100644
--- a/tests/utils/test_log_handlers.py
+++ b/tests/utils/test_log_handlers.py
@@ -21,6 +21,7 @@
 import logging.config
 import os
 import re
+from contextlib import suppress
 from http import HTTPStatus
 from importlib import reload
 from pathlib import Path
@@ -47,6 +48,7 @@
     _fetch_logs_from_service,
     _get_parsed_log_stream,
     _interleave_logs,
+    _parse_timestamp,
 )
 from airflow.utils.log.logging_mixin import set_context
 from airflow.utils.net import get_hostname
@@ -68,6 +70,20 @@
 FILE_TASK_HANDLER = "task"
 
 
+def _log_sample_to_parsed_log_stream(log_sample: str):
+    lines = log_sample.splitlines()
+    timestamp = None
+    next_timestamp = None
+    for idx, line in enumerate(lines):
+        if line:
+            with suppress(Exception):
+                # next_timestamp unchanged if line can't be parsed
+                next_timestamp = _parse_timestamp(line)
+            if next_timestamp:
+                timestamp = next_timestamp
+            yield timestamp, idx, line
+
+
 class TestFileTaskLogHandler:
     def clean_up(self):
         with create_session() as session:
@@ -633,6 +649,7 @@ def test_interleave_interleaves():
             "[2022-11-16T00:05:54.278-0800] {taskinstance.py:1258} INFO - Starting attempt 1 of 1",
         ]
     )
+    log_sample1_stream = _log_sample_to_parsed_log_stream(log_sample1)
     log_sample2 = "\n".join(
         [
             "[2022-11-16T00:05:54.295-0800] {taskinstance.py:1278} INFO - Executing <Task(TimeDeltaSensorAsync): wait> on 2022-11-16 08:05:52.324532+00:00",
@@ -643,6 +660,7 @@ def test_interleave_interleaves():
             "[2022-11-16T00:05:54.309-0800] {standard_task_runner.py:83} INFO - Job 33648: Subtask wait",
         ]
     )
+    log_sample2_stream = _log_sample_to_parsed_log_stream(log_sample2)
     log_sample3 = "\n".join(
         [
             "[2022-11-16T00:05:54.457-0800] {task_command.py:376} INFO - Running <TaskInstance: simple_async_timedelta.wait manual__2022-11-16T08:05:52.324532+00:00 [running]> on host daniels-mbp-2.lan",
@@ -655,6 +673,7 @@ def test_interleave_interleaves():
             "[2022-11-16T00:05:54.604-0800] {taskinstance.py:1360} INFO - Pausing task as DEFERRED. dag_id=simple_async_timedelta, task_id=wait, execution_date=20221116T080552, start_date=20221116T080554",
         ]
     )
+    log_sample3_stream = _log_sample_to_parsed_log_stream(log_sample3)
     expected = "\n".join(
         [
             "[2022-11-16T00:05:54.278-0800] {taskinstance.py:1258} INFO - Starting attempt 1 of 1",
@@ -672,7 +691,9 @@ def test_interleave_interleaves():
             "[2022-11-16T00:05:54.604-0800] {taskinstance.py:1360} INFO - Pausing task as DEFERRED. dag_id=simple_async_timedelta, task_id=wait, execution_date=20221116T080552, start_date=20221116T080554",
         ]
     )
-    assert "\n".join(_interleave_logs(log_sample2, log_sample1, log_sample3)) == expected
+    interleave_log_stream = _interleave_logs(log_sample1_stream, log_sample2_stream, log_sample3_stream)
+    interleave_log_str = "\n".join(line for line in interleave_log_stream)
+    assert interleave_log_str == expected
 
 
 long_sample = """
@@ -749,22 +770,31 @@ def test_interleave_logs_correct_ordering():
     [2023-01-17T12:47:11.883-0800] {triggerer_job.py:540} INFO - Trigger <airflow.triggers.temporal.DateTimeTrigger moment=2023-01-17T20:47:11.254388+00:00> (ID 1) fired: TriggerEvent<DateTime(2023, 1, 17, 20, 47, 11, 254388, tzinfo=Timezone('UTC'))>
     """
 
-    assert sample_with_dupe == "\n".join(_interleave_logs(sample_with_dupe, "", sample_with_dupe))
+    interleave_stream = _interleave_logs(
+        _log_sample_to_parsed_log_stream(sample_with_dupe),
+        _log_sample_to_parsed_log_stream(""),
+        _log_sample_to_parsed_log_stream(sample_with_dupe),
+    )
+    interleave_str = "\n".join(line for line in interleave_stream)
+    assert interleave_str == sample_with_dupe
 
 
 def test_interleave_logs_correct_dedupe():
     sample_without_dupe = """test,
-    test,
-    test,
-    test,
-    test,
-    test,
-    test,
-    test,
-    test,
-    test"""
-
-    assert sample_without_dupe == "\n".join(_interleave_logs(",\n    ".join(["test"] * 10)))
+test,
+test,
+test,
+test,
+test,
+test,
+test,
+test,
+test"""
+
+    interleave_stream = _interleave_logs(
+        _log_sample_to_parsed_log_stream(sample_without_dupe),
+    )
+    assert "\n".join(line for line in interleave_stream) == "test,\ntest"
 
 
 def test_permissions_for_new_directories(tmp_path):