To replace a video’s existing Transcript and captions file you need to first delete the existing file.
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Open Video settings
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Expand the Transcript and captions field
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Select the Delete icon next to the file. You can now upload a new file.
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Select Upload
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Select the language of the file you want to upload
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Choose Select file to pick the WebVTT file from your computer
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Once uploaded, the file name will appear in the Transcript and captions field
Note: Support for attaching multiple transcript and captions files to a video is coming later in 2022.