diff --git a/tagstudio/resources/translations/en.json b/tagstudio/resources/translations/en.json
index caeb7149..8b954278 100644
--- a/tagstudio/resources/translations/en.json
+++ b/tagstudio/resources/translations/en.json
@@ -205,6 +205,7 @@
     "status.library_version_found": "Found:",
     "status.library_version_mismatch": "Library Version Mismatch!",
     "status.results_found": "{count} Results Found ({time_span})",
+    "status.results.invalid_syntax": "Invalid Search Syntax:",
     "status.results": "Results",
     "tag_manager.title": "Library Tags",
     "tag.add_to_search": "Add to Search",
diff --git a/tagstudio/src/core/library/alchemy/enums.py b/tagstudio/src/core/library/alchemy/enums.py
index 952b81cd..7ae865ed 100644
--- a/tagstudio/src/core/library/alchemy/enums.py
+++ b/tagstudio/src/core/library/alchemy/enums.py
@@ -2,11 +2,14 @@ import enum
 from dataclasses import dataclass, replace
 from pathlib import Path
 
+import structlog
 from src.core.query_lang import AST as Query  # noqa: N811
 from src.core.query_lang import Constraint, ConstraintType, Parser
 
 MAX_SQL_VARIABLES = 32766  # 32766 is the max sql bind parameter count as defined here: https://github.com/sqlite/sqlite/blob/master/src/sqliteLimit.h#L140
 
+logger = structlog.get_logger(__name__)
+
 
 class TagColorEnum(enum.IntEnum):
     DEFAULT = 1
diff --git a/tagstudio/src/core/library/alchemy/library.py b/tagstudio/src/core/library/alchemy/library.py
index 83466280..8d6299df 100644
--- a/tagstudio/src/core/library/alchemy/library.py
+++ b/tagstudio/src/core/library/alchemy/library.py
@@ -640,10 +640,11 @@ class Library:
             return session.query(exists().where(Entry.path == path)).scalar()
 
     def get_paths(self, glob: str | None = None) -> list[str]:
+        path_strings: list[str] = []
         with Session(self.engine) as session:
             paths = session.scalars(select(Entry.path)).unique()
+            path_strings = list(map(lambda x: x.as_posix(), paths))
 
-        path_strings: list[str] = list(map(lambda x: x.as_posix(), paths))
         return path_strings
 
     def search_library(
diff --git a/tagstudio/src/qt/ts_qt.py b/tagstudio/src/qt/ts_qt.py
index f04f4349..5b001290 100644
--- a/tagstudio/src/qt/ts_qt.py
+++ b/tagstudio/src/qt/ts_qt.py
@@ -66,6 +66,7 @@ from src.core.library.alchemy.enums import (
 from src.core.library.alchemy.fields import _FieldID
 from src.core.library.alchemy.library import Entry, LibraryStatus
 from src.core.media_types import MediaCategories
+from src.core.query_lang.util import ParsingError
 from src.core.ts_core import TagStudioCore
 from src.core.utils.refresh_dir import RefreshDirTracker
 from src.core.utils.web import strip_web_protocol
@@ -659,24 +660,26 @@ class QtDriver(DriverMixin, QObject):
         # in a global dict for methods to access for different DPIs.
         # adj_font_size = math.floor(12 * self.main_window.devicePixelRatio())
 
+        def _filter_items():
+            try:
+                self.filter_items(
+                    FilterState.from_search_query(self.main_window.searchField.text())
+                    .with_sorting_mode(self.sorting_mode)
+                    .with_sorting_direction(self.sorting_direction)
+                )
+            except ParsingError as e:
+                self.main_window.statusbar.showMessage(
+                    f"{Translations["status.results.invalid_syntax"]} "
+                    f"\"{self.main_window.searchField.text()}\""
+                )
+                logger.error("[QtDriver] Could not filter items", error=e)
+
         # Search Button
         search_button: QPushButton = self.main_window.searchButton
-        search_button.clicked.connect(
-            lambda: self.filter_items(
-                FilterState.from_search_query(self.main_window.searchField.text())
-                .with_sorting_mode(self.sorting_mode)
-                .with_sorting_direction(self.sorting_direction)
-            )
-        )
+        search_button.clicked.connect(_filter_items)
         # Search Field
         search_field: QLineEdit = self.main_window.searchField
-        search_field.returnPressed.connect(
-            lambda: self.filter_items(
-                FilterState.from_search_query(self.main_window.searchField.text())
-                .with_sorting_mode(self.sorting_mode)
-                .with_sorting_direction(self.sorting_direction)
-            )
-        )
+        search_field.returnPressed.connect(_filter_items)
         # Sorting Dropdowns
         sort_mode_dropdown: QComboBox = self.main_window.sorting_mode_combobox
         for sort_mode in SortingModeEnum: