Attachments missing after CDN upload

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Hello.

I found an interesting problem when uploading attachments to the CDN (s3). Most attachments are uploaded as expected.
If the attachment is on a post or page and the attachment has the link to: “media file” property set then the file is not uploaded to the CDN. I can change the attachment link to: “None” and the file will upload. I use the link to: “Media file” property to allow the image to display in a lightbox.

I have enabled debugging and see no errors in the logs that indicate an issue.

how do I upload file that have the image properties with link to: “Media File”.

Thanks!