diff --git a/wrolpi/files/progress.py b/wrolpi/files/progress.py
index 584b292b..37e7e704 100644
--- a/wrolpi/files/progress.py
+++ b/wrolpi/files/progress.py
@@ -278,28 +278,33 @@ class RecentlyViewedConfig(ConfigFile):
             diff.removed = {i for i in diff.removed
                             if oldest and db_rows[i]['viewed'] >= oldest and i not in malformed}
 
-        # Without deletes (no database version), progress written after the config is kept; a newer plain view keeps
-        # its `viewed`, but it is not a newer place to resume.
-        if not self.import_deletes:
-            for key, row in list(diff.changed.items()):
-                if db_rows[key]['viewed'] >= row['viewed']:
-                    if db_rows[key]['progress'] is not None:
-                        del diff.changed[key]
-                    else:
-                        diff.changed[key] = dict(row, viewed=db_rows[key]['viewed'])
-
-        # The files of new entries which are not yet in the database; a deleted file's history goes with it.
+        # New entries which are in the database (outside the newest views), and which are not.
         from wrolpi.files.lib import glob_shared_stem
         from wrolpi.files.models import FileGroup
         media_directory = get_media_directory()
-        known = set()
+        known = dict()
         with get_db_session() as session:
             for paths in chunks([str(media_directory / i) for i in diff.added], 500):
-                known.update(str(i) for i, in
-                             session.query(FileGroup.primary_path).filter(FileGroup.primary_path.in_(paths)))
+                known.update((str(path.relative_to(media_directory)), _viewed_row(*values)) for path, *values in
+                             session.query(FileGroup.primary_path, FileGroup.viewed, FileGroup.progress,
+                                           FileGroup.position).filter(FileGroup.primary_path.in_(paths)))
+
+        # Without deletes (no database version), progress written after the config is kept; a newer plain view keeps
+        # its `viewed`, but it is not a newer place to resume.  This applies to a file that fell out of the newest
+        # views too.
+        if not self.import_deletes:
+            for rows, current in ((diff.changed, db_rows), (diff.added, known)):
+                for key, row in list(rows.items()):
+                    if key in current and current[key]['viewed'] and current[key]['viewed'] >= row['viewed']:
+                        if current[key]['progress'] is not None:
+                            del rows[key]
+                        else:
+                            rows[key] = dict(row, viewed=current[key]['viewed'])
+
+        # The files of new entries which are not yet in the database; a deleted file's history goes with it.
         for key, row in list(diff.added.items()):
             absolute_path = media_directory / key
-            if str(absolute_path) in known:
+            if key in known:
                 continue
             if absolute_path.is_file():
                 row['files'] = glob_shared_stem(absolute_path)
diff --git a/wrolpi/files/test/test_recently_viewed_import.py b/wrolpi/files/test/test_recently_viewed_import.py
index ef423f8e..977c3b84 100644
--- a/wrolpi/files/test/test_recently_viewed_import.py
+++ b/wrolpi/files/test/test_recently_viewed_import.py
@@ -156,3 +156,32 @@ async def test_refresh_changing_primary_file_counts(test_session, test_directory
     test_session.expire_all()
     assert test_session.query(FileGroup).one().primary_path != test_directory / 'video.mp4'
     assert get_config_version(test_session, 'recently_viewed.yaml') > 0
+
+
+@pytest.mark.asyncio
+async def test_without_deletes_newer_history_outside_the_window_is_kept(test_session, test_directory, async_client,
+                                                                        make_files_structure, monkeypatch):
+    """Without a database version, a newer view in the database wins even when it fell out of the newest views: its
+    progress is kept, or (a plain view) its `viewed` is kept and the config's position is taken."""
+    monkeypatch.setattr('wrolpi.files.progress.RECENTLY_VIEWED_LIMIT', 2)
+    now = dates.now()
+    file_groups = {name: FileGroup.from_paths(test_session, *make_files_structure([name]))
+                   for name in ('progress.txt', 'plain.txt', 'b.txt', 'c.txt')}
+    file_groups['progress.txt'].viewed, file_groups['progress.txt'].progress = now - timedelta(hours=3), 0.8
+    file_groups['plain.txt'].viewed = now - timedelta(hours=3)
+    file_groups['b.txt'].viewed, file_groups['c.txt'].viewed = now - timedelta(hours=2), now - timedelta(hours=1)
+    test_session.commit()
+    config = get_recently_viewed_config()
+    config.get_file().parent.mkdir(exist_ok=True)
+    config.get_file().write_text(yaml.dump(dict(version=1, files=[
+        dict(path='progress.txt', viewed=(now - timedelta(days=1)).isoformat(), progress=0.1),
+        dict(path='plain.txt', viewed=(now - timedelta(days=1)).isoformat(), progress=0.5,
+             position=dict(kind='time', seconds=60)),
+    ])))
+
+    config.import_config()
+
+    found = viewed(test_session)
+    assert (found['progress.txt'].viewed, found['progress.txt'].progress) == (now - timedelta(hours=3), 0.8)
+    assert (found['plain.txt'].viewed, found['plain.txt'].progress, found['plain.txt'].position) == \
+           (now - timedelta(hours=3), 0.5, dict(kind='time', seconds=60.0))