We are aware of an ongoing issue with the File Upload function in Collaborate. The issue presents as uploaded files failing to convert after an extended period.
We have reported this problem and can confirm Blackboard are currently investigating.
In the meantime, you can use the Share Content > Share Application/Screen function and choose either Share Entire Screen or Share Application options during your session.
We apologise for any inconvenience and will update here as soon as the issue has been fixed.