ReportAssist has two different ways to add pupil portraits. Layouts will have to have portrait components added to them in order for you to see portraits in reports.
The fastest way is to let ReportAssist 'know' where the portraits are locally. Local portraits are only visible whilst at school.
The more time-consuming second way is to upload the portraits. Uploaded portraits take priority over local portraits.
To upload a portrait, simply drag the portrait file to one of the reports. It will be uploaded and allocated to the pupil that has that report.