TSUploader can cease uploading files and get stuck with Waiting to Initialize... displayed in the window. Error messages like these may also pop-up: The connection to this website is untrusted, The certificate used to identify the website is not trusted, The certificate has expired.
This can happen when the SSL certificate of the TeleScope domain can't be verified by the TSUploader application or due to an issue in IIS where when certificate chains are updated but IIS still provides old root CA in the web responses. One such scenario is mentioned in this article.
Steps To Fix
If you're facing this issue, please create a support ticket for more help with this.
Once the issue is resolved try to upload with the TSUploader and it should work normally.