Image file upload fails

I try and upload images to my site and after ~5 files it is unable to upload anymore. The process goes slowly no matter what. It has been happening for months and occurs during CSV Import and when manually editing files. Error log is:

[Fri Oct 13 12:31:45 2017] [error] [client] Premature end of script headers: index.php, referer: (same error repeatedly)

My site uses Omeka 2.4.1 on a Dreamhost server.

Also, failed uploads direct me to a 404 page and I get this message:

404 Page Not Found
/admin/items/edit/567 is not a valid URL

The permissions on all files on the site are 755 if you’re thinking that may be an issue.

The other thing I’m wondering is if now that the site is https something else needs to change. The 404 error is at the url whereas the site now uses https. Is there a way to ensure the file path is correct?

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