diff --git a/apps/dav/lib/CalDAV/WebcalCaching/Connection.php b/apps/dav/lib/CalDAV/WebcalCaching/Connection.php
index 3d12c92c49a69..b274eb1845116 100644
--- a/apps/dav/lib/CalDAV/WebcalCaching/Connection.php
+++ b/apps/dav/lib/CalDAV/WebcalCaching/Connection.php
@@ -34,6 +34,14 @@ public function queryWebcalFeed(array $subscription): ?string {
 			return null;
 		}
 
+		// calendar/#7234 - ICS feeds hosted on O365 can return HTTP 500 when the UA string isn't satisfactory..
+		$uaString = 'Nextcloud Webcal Service';
+		if (parse_url($url, PHP_URL_HOST) === 'outlook.office365.com') {
+			// 2025/08/20 - the required format/values here are not documented; this string based on research 
+			// from: https://github.com/bitfireAT/icsx5/discussions/654#discussioncomment-14158051
+			$uaString = 'Nextcloud (Linux) Chrome/66';
+		}
+		
 		$allowLocalAccess = $this->config->getValueString('dav', 'webcalAllowLocalAccess', 'no');
 
 		$params = [
@@ -41,7 +49,7 @@ public function queryWebcalFeed(array $subscription): ?string {
 				'allow_local_address' => $allowLocalAccess === 'yes',
 			],
 			RequestOptions::HEADERS => [
-				'User-Agent' => 'Nextcloud Webcal Service',
+				'User-Agent' => $uaString,
 				'Accept' => 'text/calendar, application/calendar+json, application/calendar+xml',
 			],
 		];