diff --git a/server/models/documentSyncQueue.js b/server/models/documentSyncQueue.js
index 4c5ee71a..b4e9790c 100644
--- a/server/models/documentSyncQueue.js
+++ b/server/models/documentSyncQueue.js
@@ -53,6 +53,8 @@ const DocumentSyncQueue = {
    * @returns {boolean} - true if the document can be watched, false otherwise
    */
   canWatch: function ({ title, chunkSource = null } = {}) {
+    if (!chunkSource) return false;
+
     if (chunkSource.startsWith("link://") && title.endsWith(".html"))
       return true; // If is web-link material (prior to feature most chunkSources were links://)
     if (chunkSource.startsWith("youtube://")) return true; // If is a youtube link
diff --git a/server/utils/files/index.js b/server/utils/files/index.js
index 3f186f35..47c358d4 100644
--- a/server/utils/files/index.js
+++ b/server/utils/files/index.js
@@ -361,9 +361,6 @@ async function fileToPickerData({
   const filename = path.basename(pathToFile);
   const fileStats = fs.statSync(pathToFile);
   const cachedStatus = await cachedVectorInformation(cachefilename, true);
-  const canWatchStatus = liveSyncAvailable
-    ? DocumentSyncQueue.canWatch(metadata)
-    : false;
 
   if (fileStats.size < FILE_READ_SIZE_THRESHOLD) {
     const rawData = fs.readFileSync(pathToFile, "utf8");
@@ -381,7 +378,9 @@ async function fileToPickerData({
       type: "file",
       ...metadata,
       cached: cachedStatus,
-      canWatch: canWatchStatus,
+      canWatch: liveSyncAvailable
+        ? DocumentSyncQueue.canWatch(metadata)
+        : false,
       // pinnedWorkspaces: [], // This is the list of workspaceIds that have pinned this document
       // watched: false, // boolean to indicate if this document is watched in ANY workspace
     };
@@ -429,7 +428,7 @@ async function fileToPickerData({
     type: "file",
     ...metadata,
     cached: cachedStatus,
-    canWatch: canWatchStatus,
+    canWatch: liveSyncAvailable ? DocumentSyncQueue.canWatch(metadata) : false,
   };
 }