If you encounter any error through UI when uploading any file and there is no clear error message, you may debug this by checking these things to quickly identify the issue.
1. Check if your current user has enough permission to deploy to this repository.
2. Check if this is failing over large files only. If this is only failing on large files, first check the file size limitation for the GUI which can be found in UI under Admin -> General -> File Upload Max Size. If tuning this option does not help, you should then check reverse proxy, try uploading through api, and temp folder for file upload. More details on these below:
3. Check if there is an reverse proxy in front of your server. Try visiting the server with direct ip and port to Tomcat to confirm if the issue is related to reverse proxy.
4. Check if you can upload with REST api. If REST api upload also fails, The issue could be related to network or your binary provider and you would need to further debug this using your artifactory log or contact support.
5. Check the permission and available disk space for the following folder. UI upload may failed if artifactory can not write to these temp folder.