diff --git a/src/public/app/services/utils.js b/src/public/app/services/utils.js
index e8c92351e..0544c8622 100644
--- a/src/public/app/services/utils.js
+++ b/src/public/app/services/utils.js
@@ -527,6 +527,58 @@ function downloadSvg(nameWithoutExtension, svgContent) {
     document.body.removeChild(element);
 }
 
+/**
+ * Compares two semantic version strings.
+ * Returns:
+ *   1  if v1 is greater than v2
+ *   0  if v1 is equal to v2
+ *   -1 if v1 is less than v2
+ * 
+ * @param {string} v1 First version string
+ * @param {string} v2 Second version string
+ * @returns {number}
+ */
+function compareVersions(v1, v2) {
+
+    // Remove 'v' prefix and everything after dash if present
+    v1 = v1.replace(/^v/, '').split('-')[0];
+    v2 = v2.replace(/^v/, '').split('-')[0];
+    
+    const v1parts = v1.split('.').map(Number);
+    const v2parts = v2.split('.').map(Number);
+    
+    // Pad shorter version with zeros
+    while (v1parts.length < 3) v1parts.push(0);
+    while (v2parts.length < 3) v2parts.push(0);
+    
+    // Compare major version
+    if (v1parts[0] !== v2parts[0]) {
+        return v1parts[0] > v2parts[0] ? 1 : -1;
+    }
+    
+    // Compare minor version
+    if (v1parts[1] !== v2parts[1]) {
+        return v1parts[1] > v2parts[1] ? 1 : -1;
+    }
+    
+    // Compare patch version
+    if (v1parts[2] !== v2parts[2]) {
+        return v1parts[2] > v2parts[2] ? 1 : -1;
+    }
+    
+    return 0;
+}
+
+/**
+ * Compares two semantic version strings and returns `true` if the latest version is greater than the current version.
+ * @param {string} latestVersion
+ * @param {string} currentVersion
+ * @returns {boolean}
+ */
+function isUpdateAvailable(latestVersion, currentVersion) {
+    return compareVersions(latestVersion, currentVersion) > 0;
+}
+
 export default {
     reloadFrontendApp,
     parseDate,
@@ -567,5 +619,7 @@ export default {
     areObjectsEqual,
     copyHtmlToClipboard,
     createImageSrcUrl,
-    downloadSvg
+    downloadSvg,
+    compareVersions,
+    isUpdateAvailable
 };
diff --git a/src/public/app/widgets/buttons/global_menu.js b/src/public/app/widgets/buttons/global_menu.js
index d4e65b989..d760ecd5c 100644
--- a/src/public/app/widgets/buttons/global_menu.js
+++ b/src/public/app/widgets/buttons/global_menu.js
@@ -333,7 +333,8 @@ export default class GlobalMenuWidget extends BasicWidget {
 
         const latestVersion = await this.fetchLatestVersion();
         this.updateAvailableWidget.updateVersionStatus(latestVersion);
-        this.$updateToLatestVersionButton.toggle(latestVersion > glob.triliumVersion);
+        // Show "click to download" button in options menu if there's a new version available
+        this.$updateToLatestVersionButton.toggle(utils.isUpdateAvailable(latestVersion, glob.triliumVersion));
         this.$updateToLatestVersionButton.find(".version-text").text(`Version ${latestVersion} is available, click to download.`);
     }
 
diff --git a/src/public/app/widgets/buttons/update_available.js b/src/public/app/widgets/buttons/update_available.js
index 50351cf0e..39db4cfd2 100644
--- a/src/public/app/widgets/buttons/update_available.js
+++ b/src/public/app/widgets/buttons/update_available.js
@@ -1,5 +1,6 @@
 import { t } from "../../services/i18n.js";
 import BasicWidget from "../basic_widget.js";
+import utils from "../../services/utils.js";
 
 const TPL = `
 <div style="display: none;">
@@ -34,6 +35,6 @@ export default class UpdateAvailableWidget extends BasicWidget {
     }
 
     updateVersionStatus(latestVersion) {
-        this.$widget.toggle(latestVersion > glob.triliumVersion);
+        this.$widget.toggle(utils.isUpdateAvailable(latestVersion, glob.triliumVersion));
     }
 }