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The problem with this is that there is no standard place where the data is stored. So it would have to be done on a case by case basis. So while possible (especially in this case as Microsoft has documented how they do it here) it is a lot of work to grab it from all the various methods programs use. Maybe eventually there will be a standard and it will make ...
I have been using Lightroom since 1.0 and it has had been taking the captions and keywords up with the image. I also have used Star*Explorer and it was successful at uploading with the keywords. I have not used WLPG so I am not sure about the compatibility but with LR I have not had any issues, both using internal uploader and separate.
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