"Failed to Import Media"

I’ve just set up a new wp.org site, go-everywhere.com.

I’m trying to import my old wp.com site, tessa-rose.com.

I downloaded the XML from my wp.com and used the import plugin for the wp.org site, but it’s not all uploading correctly.

My images are fine from 2011 to May 2014, but after May all of the images are saying “Failed to Import Media”. The pics show up in the posts, but embedded with their old wp.com URLs. They’re not uploading into my new Media Library, and none of their featured images show up.

I also tried to just export all posts starting from May, thinking it might be a file size issue, but had the same problem. Media failed to import.

I’m not sure if it’s related, but I also can’t check the “Import Attachments” when I do the import. If I check that box then I just get a 500 Internal Server Error message. So I’m not really sure what I’m missing since I can’t import attachments.