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I'd like to expand files and filter using a substring like so:

Is it possible?

/sites/Training/_api/web/lists/getbytitle('production_library')/files?$expand&?$filter=substringof(%27https://gumdropsgc.sharepoint.com/sites/Training/Production_Library/Communication%20Management%27,url)%20eq%20true
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Yes, it is supported.

The following query returns files from Documents library located under Guides folder with associated list items those names contains SharePoint keyword:

/_api/web/GetFolderByServerRelativeUrl('documents/guides')/files?$expand=ListItemAllFields&$filter=substringof('SharePoint',Name)

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