Most software evaluations test the happy path. Document systems need a less cooperative fixture set: phone scans, repeated names, signed revisions, office files, and access rules. Build a test set of 20 synthetic or non-sensitive files: clean PDFs and phone scans; invoices, receipts, agreements...
Source: [Dev.to](https://dev.to/jun-stoatify/how-to-test-document-management-software-with-20-real-files-32e6)