Files Added To WordPress Library With Current Path

Is it possible for it to insert them with the current date WordPress uploads directory month folder?

If you set the Set the imported date to the: o Current Time x File Time to the File Time option then that’ll re-use the date from the file path such as in this case: 2016/02/filename.jpg.
(Note: Those options are at the bottom of the import selection table)

Your mileage may vary though, if fiddling with that option doesn’t achieve what you want, you’d have to set the file timestamps correctly.

I’ll try the file time option and see what that does. Otherwise I will just move them all into the current month directory and import. The only issue I have is that I have thousands of files to upload and the plugin fails to upload any files when you selected them all. No errors are reported when I do this so I find I can only upload a couple of hundred at a time which is tedious. I fully understand this is a PHP/server limitation.

The only issue I have is that I have thousands of files to upload and the plugin fails to upload any files when you selected them all.

You may also want to look into using WP-CLI to import the media: https://wp-cli.org/commands/media/import/
Unfortunately it doesn’t look like it has a date-setting option though.

Hmm I don’t have a VPS to allow me to install WP-CLI but I could probably build the site on a localhost and then upload it later…

Cheers for the suggestion!