diff --git a/pyproject.toml b/pyproject.toml
index 4f06cf884..92032439d 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -34,6 +34,7 @@ dependencies = [
     "typing_extensions~=4.13",
     "ujson~=5.10",
     "wcmatch==10.*",
+    "requests~=2.31.0",
 ]
 
 [project.optional-dependencies]
diff --git a/src/tagstudio/core/ts_core.py b/src/tagstudio/core/ts_core.py
index 19aebae88..19fd2d470 100644
--- a/src/tagstudio/core/ts_core.py
+++ b/src/tagstudio/core/ts_core.py
@@ -5,17 +5,22 @@
 """The core classes and methods of TagStudio."""
 
 import json
+import re
 from pathlib import Path
 
+import requests
 import structlog
 
 from tagstudio.core.constants import TS_FOLDER_NAME
 from tagstudio.core.library.alchemy.fields import FieldID
 from tagstudio.core.library.alchemy.library import Library
 from tagstudio.core.library.alchemy.models import Entry
+from tagstudio.core.utils.types import unwrap
 
 logger = structlog.get_logger(__name__)
 
+MOST_RECENT_RELEASE_VERSION: str | None = None
+
 
 class TagStudioCore:
     def __init__(self):
@@ -101,11 +106,11 @@ def match_conditions(cls, lib: Library, entry_id: int) -> bool:
         """Match defined conditions against a file to add Entry data."""
         # TODO - what even is this file format?
         # TODO: Make this stored somewhere better instead of temporarily in this JSON file.
-        cond_file = lib.library_dir / TS_FOLDER_NAME / "conditions.json"
+        cond_file = unwrap(lib.library_dir) / TS_FOLDER_NAME / "conditions.json"
         if not cond_file.is_file():
             return False
 
-        entry: Entry = lib.get_entry(entry_id)
+        entry: Entry = unwrap(lib.get_entry(entry_id))
 
         try:
             with open(cond_file, encoding="utf8") as f:
@@ -130,7 +135,9 @@ def match_conditions(cls, lib: Library, entry_id: int) -> bool:
                         is_new = field["id"] not in entry_field_types
                         field_key = field["id"]
                         if is_new:
-                            lib.add_field_to_entry(entry.id, field_key, field["value"])
+                            lib.add_field_to_entry(
+                                entry.id, field_id=field_key, value=field["value"]
+                            )
                         else:
                             lib.update_entry_field(entry.id, field_key, field["value"])
 
@@ -181,3 +188,23 @@ def _build_instagram_url(cls, entry: Entry):
         except Exception:
             logger.exception("Error building Instagram URL.", entry=entry)
             return ""
+
+    @staticmethod
+    def get_most_recent_release_version() -> str | None:
+        """Get the version of the most recent Github release."""
+        global MOST_RECENT_RELEASE_VERSION
+        if MOST_RECENT_RELEASE_VERSION is not None:
+            return MOST_RECENT_RELEASE_VERSION
+
+        resp = requests.get("https://api.github.com/repos/TagStudioDev/TagStudio/releases/latest")
+        assert resp.status_code == 200, "Could not fetch information on latest release."
+
+        data = resp.json()
+        tag: str = data["tag_name"]
+        assert tag.startswith("v")
+
+        version = tag[1:]
+        assert re.match(r"^\d+\.\d+\.\d+(-\w+)?$", version) is not None, "Invalid version format."
+
+        MOST_RECENT_RELEASE_VERSION = version
+        return version
diff --git a/src/tagstudio/core/utils/str_formatting.py b/src/tagstudio/core/utils/str_formatting.py
index e4a870cc6..e399a9e20 100644
--- a/src/tagstudio/core/utils/str_formatting.py
+++ b/src/tagstudio/core/utils/str_formatting.py
@@ -2,6 +2,10 @@
 # Licensed under the GPL-3.0 License.
 # Created for TagStudio: https://github.com/CyanVoxel/TagStudio
 
+import re
+
+from tagstudio.core.utils.types import unwrap
+
 
 def strip_punctuation(string: str) -> str:
     """Returns a given string stripped of all punctuation characters."""
@@ -32,3 +36,25 @@ def strip_web_protocol(string: str) -> str:
     for prefix in prefixes:
         string = string.removeprefix(prefix)
     return string
+
+
+def is_version_outdated(current, latest) -> bool:
+    regex = re.compile(r"^(\d+)\.(\d+)\.(\d+)(-\w+)?$")
+    mcurrent = unwrap(regex.match(current))
+    mlatest = unwrap(regex.match(latest))
+
+    return (
+        int(mlatest[1]) > int(mcurrent[1])
+        or (mlatest[1] == mcurrent[1] and int(mlatest[2]) > int(mcurrent[2]))
+        or (
+            mlatest[1] == mcurrent[1]
+            and mlatest[2] == mcurrent[2]
+            and int(mlatest[3]) > int(mcurrent[3])
+        )
+        or (
+            mlatest[1] == mcurrent[1]
+            and mlatest[2] == mcurrent[2]
+            and mlatest[3] == mcurrent[3]
+            and (mlatest[4] is None and mcurrent[4] is not None)
+        )
+    )
diff --git a/src/tagstudio/qt/controllers/out_of_date_message_box.py b/src/tagstudio/qt/controllers/out_of_date_message_box.py
new file mode 100644
index 000000000..5254e57e1
--- /dev/null
+++ b/src/tagstudio/qt/controllers/out_of_date_message_box.py
@@ -0,0 +1,39 @@
+import structlog
+from PySide6.QtCore import Qt
+from PySide6.QtWidgets import QMessageBox
+
+from tagstudio.core.constants import VERSION
+from tagstudio.core.ts_core import TagStudioCore
+from tagstudio.qt.models.palette import ColorType, UiColor, get_ui_color
+from tagstudio.qt.translations import Translations
+
+logger = structlog.get_logger(__name__)
+
+
+class OutOfDateMessageBox(QMessageBox):
+    """A warning dialog for if the TagStudio is not running under the latest release version."""
+
+    def __init__(self):
+        super().__init__()
+
+        title = Translations.format("version_modal.title")
+        self.setWindowTitle(title)
+        self.setIcon(QMessageBox.Icon.Warning)
+        self.setWindowModality(Qt.WindowModality.ApplicationModal)
+
+        self.setStandardButtons(
+            QMessageBox.StandardButton.Ignore | QMessageBox.StandardButton.Cancel
+        )
+        self.setDefaultButton(QMessageBox.StandardButton.Ignore)
+        # Enables the cancel button but hides it to allow for click X to close dialog
+        self.button(QMessageBox.StandardButton.Cancel).hide()
+
+        red = get_ui_color(ColorType.PRIMARY, UiColor.RED)
+        green = get_ui_color(ColorType.PRIMARY, UiColor.GREEN)
+        latest_release_version = TagStudioCore.get_most_recent_release_version()
+        status = Translations.format(
+            "version_modal.status",
+            installed_version=f"<span style='color:{red}'>{VERSION}</span>",
+            latest_release_version=f"<span style='color:{green}'>{latest_release_version}</span>",
+        )
+        self.setText(f"{Translations['version_modal.description']}<br><br>{status}")
diff --git a/src/tagstudio/qt/mixed/about_modal.py b/src/tagstudio/qt/mixed/about_modal.py
index e7d4a2ecb..12942df95 100644
--- a/src/tagstudio/qt/mixed/about_modal.py
+++ b/src/tagstudio/qt/mixed/about_modal.py
@@ -20,6 +20,7 @@
 
 from tagstudio.core.constants import VERSION, VERSION_BRANCH
 from tagstudio.core.enums import Theme
+from tagstudio.core.ts_core import TagStudioCore
 from tagstudio.qt.models.palette import ColorType, UiColor, get_ui_color
 from tagstudio.qt.previews.vendored import ffmpeg
 from tagstudio.qt.resource_manager import ResourceManager
@@ -103,6 +104,19 @@ def __init__(self, config_path):
         self.system_info_layout = QFormLayout(self.system_info_widget)
         self.system_info_layout.setLabelAlignment(Qt.AlignmentFlag.AlignRight)
 
+        # Version
+        version_title = QLabel("Version")
+        most_recent_release = TagStudioCore.get_most_recent_release_version()
+        version_content_style = self.form_content_style
+        if most_recent_release == VERSION:
+            version_content = QLabel(f"{VERSION}")
+        else:
+            version_content = QLabel(f"{VERSION} (Latest Release: {most_recent_release})")
+            version_content_style += "color: #d9534f;"
+        version_content.setStyleSheet(version_content_style)
+        version_content.setMaximumWidth(version_content.sizeHint().width())
+        self.system_info_layout.addRow(version_title, version_content)
+
         # License
         license_title = QLabel(f"{Translations['about.license']}")
         license_content = QLabel("GPLv3")
diff --git a/src/tagstudio/qt/ts_qt.py b/src/tagstudio/qt/ts_qt.py
index 8d7edde30..612ca7511 100644
--- a/src/tagstudio/qt/ts_qt.py
+++ b/src/tagstudio/qt/ts_qt.py
@@ -62,7 +62,7 @@
 from tagstudio.core.media_types import MediaCategories
 from tagstudio.core.query_lang.util import ParsingError
 from tagstudio.core.ts_core import TagStudioCore
-from tagstudio.core.utils.str_formatting import strip_web_protocol
+from tagstudio.core.utils.str_formatting import is_version_outdated, strip_web_protocol
 from tagstudio.core.utils.types import unwrap
 from tagstudio.qt.cache_manager import CacheManager
 from tagstudio.qt.controllers.ffmpeg_missing_message_box import FfmpegMissingMessageBox
@@ -71,6 +71,7 @@
 from tagstudio.qt.controllers.fix_ignored_modal_controller import FixIgnoredEntriesModal
 from tagstudio.qt.controllers.ignore_modal_controller import IgnoreModal
 from tagstudio.qt.controllers.library_info_window_controller import LibraryInfoWindow
+from tagstudio.qt.controllers.out_of_date_message_box import OutOfDateMessageBox
 from tagstudio.qt.global_settings import (
     DEFAULT_GLOBAL_SETTINGS_PATH,
     GlobalSettings,
@@ -590,6 +591,9 @@ def create_about_modal():
         if not which(FFMPEG_CMD) or not which(FFPROBE_CMD):
             FfmpegMissingMessageBox().show()
 
+        if is_version_outdated(VERSION, TagStudioCore.get_most_recent_release_version()):
+            OutOfDateMessageBox().exec()
+
         self.app.exec()
         self.shutdown()
 
diff --git a/src/tagstudio/resources/translations/en.json b/src/tagstudio/resources/translations/en.json
index edda02311..89fb04379 100644
--- a/src/tagstudio/resources/translations/en.json
+++ b/src/tagstudio/resources/translations/en.json
@@ -348,6 +348,9 @@
     "trash.dialog.title.singular": "Delete File",
     "trash.name.generic": "Trash",
     "trash.name.windows": "Recycle Bin",
+    "version_modal.title": "TagStudio Update Available",
+    "version_modal.description": "A new version of TagStudio is available! You can download the latest release from <a href=\"https://github.com/TagStudioDev/TagStudio\">Github</a>.",
+    "version_modal.status": "Installed Version: {installed_version}<br>Latest Release Version: {latest_release_version}",
     "view.size.0": "Mini",
     "view.size.1": "Small",
     "view.size.2": "Medium",