diff --git a/helpers/exceptions.py b/helpers/exceptions.py
index 94d241b73..5e4c8b6dd 100644
--- a/helpers/exceptions.py
+++ b/helpers/exceptions.py
@@ -1,5 +1,7 @@
 class ReportExpiredException(Exception):
-    pass
+    def __init__(self, message=None, filename=None) -> None:
+        super().__init__(message)
+        self.filename = filename
 
 
 class ReportEmptyError(Exception):
diff --git a/services/report/__init__.py b/services/report/__init__.py
index 914e73e90..20e04afb8 100644
--- a/services/report/__init__.py
+++ b/services/report/__init__.py
@@ -1016,11 +1016,16 @@ def build_report_from_raw_content(
                 raw_report=result.raw_report,
                 upload_obj=upload,
             )
-        except ReportExpiredException:
+        except ReportExpiredException as r:
             log.info(
                 "Report %s is expired",
                 reportid,
-                extra=dict(repoid=commit.repoid, commit=commit.commitid),
+                extra=dict(
+                    repoid=commit.repoid,
+                    commit=commit.commitid,
+                    archive_path=archive_url,
+                    file_name=r.filename,
+                ),
             )
             return ProcessingResult(
                 report=None,
diff --git a/services/report/raw_upload_processor.py b/services/report/raw_upload_processor.py
index c9146d592..2a67fafa0 100644
--- a/services/report/raw_upload_processor.py
+++ b/services/report/raw_upload_processor.py
@@ -11,7 +11,7 @@
 from shared.utils.sessions import Session, SessionType
 
 from database.models.reports import Upload
-from helpers.exceptions import ReportEmptyError
+from helpers.exceptions import ReportEmptyError, ReportExpiredException
 from helpers.labels import get_all_report_labels, get_labels_per_session
 from rollouts import USE_LABEL_INDEX_IN_REPORT_PROCESSING_BY_REPO_ID
 from services.path_fixer import PathFixer
@@ -155,9 +155,13 @@ def process_raw_upload(
                 path_fixer_to_use,
                 should_use_encoded_labels,
             )
-            report = process_report(
-                report=report_file, report_builder=report_builder_to_use
-            )
+            try:
+                report = process_report(
+                    report=report_file, report_builder=report_builder_to_use
+                )
+            except ReportExpiredException as r:
+                r.filename = current_filename
+                raise
             if report:
                 if should_use_encoded_labels:
                     # Copies the labels from report into temporary_report
diff --git a/services/report/tests/unit/test_process.py b/services/report/tests/unit/test_process.py
index 425fb05d6..7ef6c6737 100644
--- a/services/report/tests/unit/test_process.py
+++ b/services/report/tests/unit/test_process.py
@@ -11,7 +11,11 @@
 from shared.utils.sessions import Session, SessionType
 from shared.yaml import UserYaml
 
-from helpers.exceptions import CorruptRawReportError, ReportEmptyError
+from helpers.exceptions import (
+    CorruptRawReportError,
+    ReportEmptyError,
+    ReportExpiredException,
+)
 from services.report import raw_upload_processor as process
 from services.report.parser import LegacyReportParser
 from services.report.parser.types import LegacyParsedRawReport, ParsedUploadedReportFile
@@ -984,6 +988,38 @@ def test_process_raw_upload_multiple_raw_reports(self, mocker):
         assert sorted(res.sessions.keys()) == [0, 1]
         assert res.sessions[1] == session
 
+    def test_process_raw_upload_expired_report(self, mocker):
+        filename = "/Users/path/to/app.coverage.txt"
+        uploaded_reports = LegacyParsedRawReport(
+            toc=None,
+            env=None,
+            report_fixes=None,
+            uploaded_files=[
+                ParsedUploadedReportFile(
+                    filename="/Users/path/to/app.coverage.txt",
+                    file_contents=BytesIO("<data>".encode()),
+                ),
+            ],
+        )
+        mocker.patch.object(
+            process,
+            "process_report",
+            side_effect=[
+                ReportExpiredException(),
+            ],
+        )
+        session = Session()
+        with pytest.raises(ReportExpiredException) as e:
+            _ = process.process_raw_upload(
+                UserYaml({}),
+                None,
+                uploaded_reports,
+                ["flag_one", "flag_two"],
+                session=session,
+            )
+
+        assert e.value.filename == filename
+
 
 class TestProcessRawUploadCarryforwardFlags(BaseTestCase):
     def _generate_sample_report(self) -> EditableReport: