I've been having the same problem (when uploading videos directly to Canvas on a page and adding an .srt file), but not consistently. Two weeks ago, no problem. Last week, I had problems when adding about half of my videos. I walked away and tried later, and there was no problem. Today, it is happening consistently (using Chrome and Firefox).
Here's what happens:
I go to "upload media," select the video file, and I select "add captions." I can select English from the dropdown menu, but when I add the .srt file, the whole upload window disappears. OR, I can start by uploading the .srt, but when I select English from the dropdown menu, the upload window disappears. And, if I only add the .srt but do not select English, the video uploads, but without captions.
AARGH!
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