diff --git a/src/paperless_tika/tests/test_live_tika.py b/src/paperless_tika/tests/test_live_tika.py
index e1af7cf86..b5efc7cef 100644
--- a/src/paperless_tika/tests/test_live_tika.py
+++ b/src/paperless_tika/tests/test_live_tika.py
@@ -1,10 +1,11 @@
-import datetime
 import os
+import time
 from pathlib import Path
 from typing import Final
 
 import pytest
 from django.test import TestCase
+from documents.parsers import ParseError
 from paperless_tika.parsers import TikaDocumentParser
 
 
@@ -24,6 +25,44 @@ class TestTikaParserAgainstServer(TestCase):
     def tearDown(self) -> None:
         self.parser.cleanup()
 
+    def try_parse_with_wait(self, test_file, mime_type):
+        """
+        For whatever reason, the image started during the test pipeline likes to
+        segfault sometimes, when run with the exact files that usually pass.
+
+        So, this function will retry the parsing up to 3 times, with larger backoff
+        periods between each attempt, in hopes the issue resolves itself during
+        one attempt to parse.
+
+        This will wait the following:
+            - Attempt 1 - 20s following failure
+            - Attempt 2 - 40s following failure
+            - Attempt 3 - 80s following failure
+
+        """
+        succeeded = False
+        retry_time = 20.0
+        retry_count = 0
+        max_retry_count = 3
+
+        while retry_count < max_retry_count and not succeeded:
+            try:
+                self.parser.parse(test_file, mime_type)
+
+                succeeded = True
+            except Exception as e:
+                print(f"{e} during try #{retry_count}", flush=True)
+
+                retry_count = retry_count + 1
+
+                time.sleep(retry_time)
+                retry_time = retry_time * 2.0
+
+        self.assertTrue(
+            succeeded,
+            "Continued Tika server errors after multiple retries",
+        )
+
     def test_basic_parse_odt(self):
         """
         GIVEN:
@@ -36,7 +75,7 @@ class TestTikaParserAgainstServer(TestCase):
         """
         test_file = self.SAMPLE_DIR / Path("sample.odt")
 
-        self.parser.parse(test_file, "application/vnd.oasis.opendocument.text")
+        self.try_parse_with_wait(test_file, "application/vnd.oasis.opendocument.text")
 
         self.assertEqual(
             self.parser.text,
@@ -62,7 +101,7 @@ class TestTikaParserAgainstServer(TestCase):
         """
         test_file = self.SAMPLE_DIR / Path("sample.docx")
 
-        self.parser.parse(
+        self.try_parse_with_wait(
             test_file,
             "application/vnd.openxmlformats-officedocument.wordprocessingml.document",
         )