If I upload an updated file to my Resource asset, will students automatically see the newest version?

Yes!

Once the resource item has been used, changing it's asset (attachment or URL) will delete the previous asset and replace it with the new.   From that moment forward, anyone who accesses the asset will automatically see the latest upload.

Update your resource asset by following these steps:

1. Select your existing resource from the search list
2. Edit the Select resource assets section 
3. Select to either upload a file, or enter a URL

Once the system confirms your asset has been saved, your new file will instantly take effect for anyone viewing that resource.