Are you getting any error messages? When we try it here we are able to assign them with no problem both with single and multiple image uploads. If you're just starting the gallery, I recommend going into pages, REMOVING the gallery by clicking on the (<) assign after selecting your gallery, and then re-adding it using the (>) button. This basically restarts the gallery again. Sometimes the gallery can get corrupted and the main way to fix it is to basically re-load it.
If you have any further questions, please contact technical support or leave a comment at the bottom of the page.
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