diff --git a/REUSE.toml b/REUSE.toml
index 70e2cf7c..1d39078d 100644
--- a/REUSE.toml
+++ b/REUSE.toml
@@ -45,6 +45,12 @@ SPDX-FileCopyrightText = "(c) 2026 Boxicons"
 SPDX-License-Identifier = "MIT"
 
 [[annotations]]
-path = ["src/tagstudio/resources/qt/images/dupe_file_stat.png"]
+path = [
+    "src/tagstudio/resources/qt/images/dupe_file_stat.png",
+    "src/tagstudio/resources/qt/images/hint_field_add.png",
+    "src/tagstudio/resources/qt/images/hint_field_create.png",
+    "src/tagstudio/resources/qt/images/hint_tag_add.png",
+    "src/tagstudio/resources/qt/images/hint_tag_create.png",
+]
 SPDX-FileCopyrightText = "(c) github:google/material-design-icons Contributors"
 SPDX-License-Identifier = "Apache-2.0"
diff --git a/docs/assets/tag_field_bars/field_bar_search.png b/docs/assets/tag_field_bars/field_bar_search.png
index 10f4fca6..c7c8063c 100644
Binary files a/docs/assets/tag_field_bars/field_bar_search.png and b/docs/assets/tag_field_bars/field_bar_search.png differ
diff --git a/docs/assets/tag_field_bars/tag_bar_new.png b/docs/assets/tag_field_bars/tag_bar_new.png
index 7327d906..3a8b83f1 100644
Binary files a/docs/assets/tag_field_bars/tag_bar_new.png and b/docs/assets/tag_field_bars/tag_bar_new.png differ
diff --git a/docs/assets/tag_field_bars/tag_bar_search_match.png b/docs/assets/tag_field_bars/tag_bar_search_match.png
index 3e993c4d..24431ccc 100644
Binary files a/docs/assets/tag_field_bars/tag_bar_search_match.png and b/docs/assets/tag_field_bars/tag_bar_search_match.png differ
diff --git a/docs/assets/tag_field_bars/tag_bar_shift_off.png b/docs/assets/tag_field_bars/tag_bar_shift_off.png
index a52deb6b..32b16034 100644
Binary files a/docs/assets/tag_field_bars/tag_bar_shift_off.png and b/docs/assets/tag_field_bars/tag_bar_shift_off.png differ
diff --git a/docs/assets/tag_field_bars/tag_bar_shift_on.png b/docs/assets/tag_field_bars/tag_bar_shift_on.png
index be3179a0..f3d72833 100644
Binary files a/docs/assets/tag_field_bars/tag_bar_shift_on.png and b/docs/assets/tag_field_bars/tag_bar_shift_on.png differ
diff --git a/src/tagstudio/qt/controllers/field_suggest_box.py b/src/tagstudio/qt/controllers/field_suggest_box.py
index 42250dfe..54fc36d8 100644
--- a/src/tagstudio/qt/controllers/field_suggest_box.py
+++ b/src/tagstudio/qt/controllers/field_suggest_box.py
@@ -86,6 +86,24 @@ class FieldSuggestBox(SuggestBox[BaseFieldTemplate]):
         else:
             return ([], [])
 
+    @override
+    def _on_shift_held(self, held: bool) -> None:
+        if held:
+            self.set_hint_icon(self._rm.hint_field_create)
+        else:
+            self._update_hint_icon()
+
+        return super()._on_shift_held(held)
+
+    @override
+    def _update_hint_icon(self) -> None:
+        if self.layout().search_field.text() and len(self._search_results) > 0:
+            self.set_hint_icon(self._rm.hint_field_add)
+        elif self.layout().search_field.text():
+            self.set_hint_icon(self._rm.hint_field_create)
+        else:
+            self.set_hint_icon(None)
+
     @override
     def _set_item_widget(self, item: BaseFieldTemplate | None, index: int) -> None:
         """Set the field template of a field template widget at a specific index."""
diff --git a/src/tagstudio/qt/controllers/suggest_box.py b/src/tagstudio/qt/controllers/suggest_box.py
index 7b3bd13f..48de05ef 100644
--- a/src/tagstudio/qt/controllers/suggest_box.py
+++ b/src/tagstudio/qt/controllers/suggest_box.py
@@ -4,8 +4,9 @@
 from typing import Any, override
 
 import structlog
+from PIL import Image, ImageQt
 from PySide6.QtCore import Signal
-from PySide6.QtGui import QShowEvent
+from PySide6.QtGui import QPixmap, QShowEvent
 from PySide6.QtWidgets import QGraphicsOpacityEffect, QWidget
 
 from tagstudio.core.library.alchemy.library import Library
@@ -13,6 +14,8 @@ from tagstudio.qt.controllers.autofill_line_edit import QtCore, QtGui
 from tagstudio.qt.controllers.modal_content import ModalContent
 from tagstudio.qt.controllers.underlined_widget import UnderlinedWidget
 from tagstudio.qt.global_settings import GlobalSettings
+from tagstudio.qt.helpers.color_overlay import auto_theme_overlay
+from tagstudio.qt.resource_manager import ResourceManager
 from tagstudio.qt.views.stylesheets.stylesheets import (
     autofill_line_edit_style,
     autofill_line_edit_top_style,
@@ -50,6 +53,7 @@ class SuggestBox[T](QWidget):
         super().__init__()
         self._lib = library
         self._settings = settings
+        self._rm = ResourceManager()
         self._limit = 5
         self._is_shift_held = False
         self._search_results: list[T] = []
@@ -81,6 +85,13 @@ class SuggestBox[T](QWidget):
 
         self.layout().search_field.shift_holding.connect(lambda held: self._on_shift_held(held))
 
+    def set_hint_icon(self, icon: Image.Image | None) -> None:
+        if icon:
+            pixmap = QPixmap.fromImage(ImageQt.ImageQt(auto_theme_overlay(icon)))
+            self.layout().hint_icon_action.setIcon(pixmap)
+        else:
+            self.layout().hint_icon_action.setIcon(QPixmap())
+
     def _on_shift_held(self, held: bool) -> None:
         if held:
             self._is_shift_held = True
@@ -105,6 +116,7 @@ class SuggestBox[T](QWidget):
 
     def _on_search_query_changed(self, query: str) -> None:
         self._update_items(query)
+        self._update_hint_icon()
 
     def _on_search_query_submitted(self, query: str, always_create: bool = False) -> None:
         # Focus search field if no query
@@ -137,6 +149,9 @@ class SuggestBox[T](QWidget):
     def _is_excluded(self, item: T) -> bool:
         return _item_id(item) in self.excluded
 
+    def _update_hint_icon(self) -> None:
+        raise NotImplementedError()
+
     def _update_items(self, query: str | None = None) -> None:
         """Update the item list given a search query."""
         logger.info("[SearchPanel] Updating items", limit=self._limit)
diff --git a/src/tagstudio/qt/controllers/tag_suggest_box.py b/src/tagstudio/qt/controllers/tag_suggest_box.py
index 27f9030a..bf38b7ae 100644
--- a/src/tagstudio/qt/controllers/tag_suggest_box.py
+++ b/src/tagstudio/qt/controllers/tag_suggest_box.py
@@ -91,6 +91,24 @@ class TagSuggestBox(SuggestBox[Tag]):
         self.item_chosen.emit(item.id)
         self.done.emit()
 
+    @override
+    def _on_shift_held(self, held: bool) -> None:
+        if held:
+            self.set_hint_icon(self._rm.hint_tag_create)
+        else:
+            self._update_hint_icon()
+
+        return super()._on_shift_held(held)
+
+    @override
+    def _update_hint_icon(self) -> None:
+        if self.layout().search_field.text() and len(self._search_results) > 0:
+            self.set_hint_icon(self._rm.hint_tag_add)
+        elif self.layout().search_field.text():
+            self.set_hint_icon(self._rm.hint_tag_create)
+        else:
+            self.set_hint_icon(None)
+
     @override
     def _search_items(self, query: str) -> tuple[list[Tag], list[Tag]]:
         if query != "":
diff --git a/src/tagstudio/qt/resource_manager.pyi b/src/tagstudio/qt/resource_manager.pyi
index 986ed884..46e6ca58 100644
--- a/src/tagstudio/qt/resource_manager.pyi
+++ b/src/tagstudio/qt/resource_manager.pyi
@@ -36,6 +36,10 @@ class ResourceManager:
     edit: Image.Image
     file_generic: Image.Image
     font: Image.Image
+    hint_field_add: Image.Image
+    hint_field_create: Image.Image
+    hint_tag_add: Image.Image
+    hint_tag_create: Image.Image
     icon: Image.Image
     ignored_stat: Image.Image
     ignored: Image.Image
diff --git a/src/tagstudio/qt/resources.json b/src/tagstudio/qt/resources.json
index 6533ce38..3fbdefba 100644
--- a/src/tagstudio/qt/resources.json
+++ b/src/tagstudio/qt/resources.json
@@ -71,6 +71,22 @@
         "mode": "pil",
         "path": "qt/images/file_icons/font.png"
     },
+    "hint_field_add": {
+        "mode": "pil",
+        "path": "qt/images/hint_field_add.png"
+    },
+    "hint_field_create": {
+        "mode": "pil",
+        "path": "qt/images/hint_field_create.png"
+    },
+    "hint_tag_add": {
+        "mode": "pil",
+        "path": "qt/images/hint_tag_add.png"
+    },
+    "hint_tag_create": {
+        "mode": "pil",
+        "path": "qt/images/hint_tag_create.png"
+    },
     "icon": {
         "mode": "pil",
         "path": "icon.png"
diff --git a/src/tagstudio/qt/views/suggest_box_view.py b/src/tagstudio/qt/views/suggest_box_view.py
index 39184e61..763b9744 100644
--- a/src/tagstudio/qt/views/suggest_box_view.py
+++ b/src/tagstudio/qt/views/suggest_box_view.py
@@ -4,6 +4,7 @@
 
 import structlog
 from PySide6.QtCore import Qt
+from PySide6.QtGui import QPixmap
 from PySide6.QtWidgets import QFrame, QHBoxLayout, QScrollArea, QSizePolicy, QVBoxLayout, QWidget
 
 from tagstudio.qt.controllers.autofill_line_edit import AutofillLineEdit
@@ -18,6 +19,7 @@ logger = structlog.get_logger(__name__)
 class SuggestBoxView(QVBoxLayout):
     def __init__(self, placeholder_text: str = "") -> None:
         super().__init__()
+
         self.setContentsMargins(0, 0, 0, 0)
         self.setSpacing(0)
 
@@ -70,6 +72,9 @@ class SuggestBoxView(QVBoxLayout):
         self.search_field.setObjectName("search_field")
         self.search_field.setMinimumHeight(28)
         self.search_field.setPlaceholderText(placeholder_text)
+        self.hint_icon_action = self.search_field.addAction(
+            QPixmap(), AutofillLineEdit.ActionPosition.TrailingPosition
+        )
         self.scroll_area.setFocusProxy(self.search_field)
 
         # Finalize Layout
diff --git a/src/tagstudio/resources/qt/images/hint_field_add.png b/src/tagstudio/resources/qt/images/hint_field_add.png
new file mode 100644
index 00000000..dabe8d92
Binary files /dev/null and b/src/tagstudio/resources/qt/images/hint_field_add.png differ
diff --git a/src/tagstudio/resources/qt/images/hint_field_create.png b/src/tagstudio/resources/qt/images/hint_field_create.png
new file mode 100644
index 00000000..f8ee8f19
Binary files /dev/null and b/src/tagstudio/resources/qt/images/hint_field_create.png differ
diff --git a/src/tagstudio/resources/qt/images/hint_tag_add.png b/src/tagstudio/resources/qt/images/hint_tag_add.png
new file mode 100644
index 00000000..50a1e89a
Binary files /dev/null and b/src/tagstudio/resources/qt/images/hint_tag_add.png differ
diff --git a/src/tagstudio/resources/qt/images/hint_tag_create.png b/src/tagstudio/resources/qt/images/hint_tag_create.png
new file mode 100644
index 00000000..10c94b30
Binary files /dev/null and b/src/tagstudio/resources/qt/images/hint_tag_create.png differ