Grateful if you could also reply to my similar issue as below:
I am having the same issue with Adobe track and send, it will send smaller files but my larger files which include video (but are still under the size limits) will not send. The track and send seems to crash my outlook when I try to send these larger files. I have tried uploading my file to the Adobe document cloud and creating a link to share using https://cloud.acrobat.com/send but both come up with error messages last minute.
It would be great if you could help with this asap as I only have Adobe creative suite so that I am able to send and track these large files.