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Usability testing is known as cake-walk, but that isn't true. Is it easy or challenging is a perspective based on individual's knowledge and how much depth has to be covered in order to meet the purpose of usability testing.
This checklist is going to help you kick-start security testing for web application from day 1.
Cross Browser Testing - Know the basics and this mindmap will help you get started.
Are you doing BVA (Boundary Value Analysis) tests? May be you are doing it wrong. No matter how you are doing it, this mindmap shall shed light on some cool tests to be done or which may help your brain trigger more test ideas based on your testing context or project context.
In most of the application you find file upload feature. Are you testing it in a better way or you just check whether file uploads or not which is very basic test to be done. However, your users do not always choose optimal path. They could cancel upload in between, they could close web browser while upload is in progress and several such cases which can be edge cases.