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The more you use Sites in Office 365, the more likely you’ll need to copy or move documents around, either between your desktop computer and a site, or from one site to another. Uploading files gets easier after your sites are upgraded to the new SharePoint Online experience, thanks to new drag and drop functionality. (To learn more about the service upgrade, see Upgrading to the new SharePoint Online.)
A new video on Office.com shows how to move files between sites whether or not your site has been upgraded to the latest user interface.
Note: Using File Explorer to move SharePoint files does not preserve metadata, such as the original creation date, unfortunately. If preserving the original file metadata is important to you, consider searching the Office 365 Marketplace for a file migration solution available from one of our partners.
Some users in the Office 365 Community have had issues with Open with Explorer recently, and we are working on solutions to those. In the meantime, for additional help with Open with Explorer, see Troubleshoot the 'Open with Explorer' command in Microsoft SharePoint Online or search here in the Office 365 Community forums.
--Matt Evans, SharePoint Writer
It is all nice that there are ways to move files around, however I came up against one major problem: the original date of creation and modified of existing files is always changed to the date/time of this operation. All moved files (previously existing in Sharepoint libraries or on my file system) are ending with a new date in stead of their original (and correct date/ time of creation and modifying.
For me this is a MAJOR issue that makes moving files useless: I loose all my history !
E.G. I cannot upload all my existing documents from my file system into Sharepoint without loosing this important information. Does this makes sense?
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Might also want to give SkySync (www.skysync.com) a whirl. A bit simpler (2007,2010, 2013, and O365 all have the same look and operation).