Try uploading each file individually directly to your Acrobat.com account (at https://cloud.acrobat.com). Once uploaded, you can use Adobe Send to easily send them from there.
How long is each 200MB file taking to upload?
To upload one 200 MB file is about 8-10 minutes. I just tried to upload to Acrobat cloud. Status bar was almost to the end when I went downstairs for a minute. When I came back, the status bar was gone and no file was uploaded. And why would the extra step be necessary? I should be able to send directly
Would you mind testing your upload speed by going to testmy.net and running their tests?
I just uploaded a 150 MB file to cloud.acrobat.com in less than 1.5 minutes, and testmy.net reported that my upload speed is 7.9 Mbps (1 MB/s).
Yes, you should be able to do the upload/send operation in one action; I was asking you to separate them so that we could identify where the issue was.
Seems upload speed is slower than normal, but I could not upload anything with Adobe Send. Tech support had me use SendNow and it worked. So, Adobe Send is not working for me. It gets to the end of the status bar then has the error - after wasting all that time it took to upload.
It turns out the Adobe servers were down for maintenance all day. Seems to be working now.