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Has "Fit to Fill" been killed or disabled with the latest Adobe updates? Just asking, because this feature always worked for me in the past. And now I can't get it to work either in the regular version of Premiere or even the Beta version. It's now always greyed out as an option:
Is there a setting I'm missing???
 
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OK, not sure if this could have been the issue, but I'm now noticing that the video clips with "fit to fill" being greyed out were "mp4" files. I imported a "mov" file and "fit to fill" is now working. Was that the issue? That the files were mp4 format?