Unfortunately, there is currently no way to reliably determine the order of multi-uploaded files. All files are uploaded simultaneously, and the resulting order is determined by which files finish uploading first. So for example, a smaller file is likely to appear before a larger one, and small fluctuations in things like network performance can also have an impact. This may be something we can update in the future, but it's not a simple fix. 

One thing you can try that may help the images be somewhat more ordered (as long as they all have similar file size): When selecting files to be uploaded, click on the last file in the list, then hold <shift> and click on the first file in the list which should select the whole list. This will at least make sure that the files are sent to be uploaded in alphabetical order. In testing, I've found that they will end up uploading in mostly in that order, so this may help reduce the amount of manual re-ordering required.

Let me know if you have any more questions.

Thanks,

Why?

How can this be changed?

I have a client that uploads between 30 - to - 200 photos per record so using the mass uploader is critical BUT if he has to go back an reorder them again for each record it's extremely painful and thus uploading one at a time is potentially better. 

So, how can we have the mass uploader actually upload in the order that the images are selected?

Thanks in advance!