diff --git a/app/views/media_objects/_thumbnail.html.erb b/app/views/media_objects/_thumbnail.html.erb
index 4512344d44..2310c1a2b7 100644
--- a/app/views/media_objects/_thumbnail.html.erb
+++ b/app/views/media_objects/_thumbnail.html.erb
@@ -61,6 +61,17 @@ Unless required by applicable law or agreed to in writing, software distributed
           }
           clearInterval(timeCheck);
         });
+        /*
+          Browsers on MacOS sometimes miss the 'loadedmetadata' event resulting in a disabled add to playlist button indefinitely.
+          This timeout enables the add to playlist button, when this happens. It checks the button's state and enables it as needed.
+        */
+        setTimeout(() => {
+          let thumbnailBtn = document.getElementById('create-thumbnail-btn');
+          if (thumbnailBtn && thumbnailBtn.disabled) {
+            thumbnailBtn.disabled = false;
+          }
+          clearInterval(timeCheck);
+        }, 500);
       }
 
       $('#thumbnailModal').on('show.bs.modal', function(e) {
diff --git a/app/views/media_objects/_timeline.html.erb b/app/views/media_objects/_timeline.html.erb
index 1d546e0a32..f5f3f22f27 100644
--- a/app/views/media_objects/_timeline.html.erb
+++ b/app/views/media_objects/_timeline.html.erb
@@ -51,11 +51,22 @@ $(document).ready(function() {
     if(player && player != undefined) {
       player.player.on('loadedmetadata', () => {
         let timelineBtn = document.getElementById('timelineBtn');
-        if(timelineBtn) {
+        if (timelineBtn) {
           timelineBtn.disabled = false;
         }
         clearInterval(timeCheck);
       });
+      /*
+        Browsers on MacOS sometimes miss the 'loadedmetadata' event resulting in a disabled add to playlist button indefinitely.
+        This timeout enables the add to playlist button, when this happens. It checks the button's state and enables it as needed.
+      */
+      setTimeout(() => {
+        let timelineBtn = document.getElementById('timelineBtn');
+        if (timelineBtn && timelineBtn.disabled) {
+          timelineBtn.disabled = false;
+        }
+        clearInterval(timeCheck);
+      }, 500);
     }
 
     $('#timelineModal').on('shown.bs.modal', function (e) {