In relation to the section 26 of the Counter-Terrorism and Security Act 2015 statutory duty to prevent people from being drawn towards terrorism, the main focus of this chapter is the law regarding the right to freedom of expression. Due to lack of knowledge of the law relating to freedom of expression leading to a lack of confidence in challenging individuals who express certain views, staff in the specified authorities have concerns regarding how to carry out this duty. A comparative study between the law in the UK and the US is conducted in this chapter where initially similarities are present in relation to the right to freedom of expression, but as this chapter covers judicial interpretation of the right, differences are identified. With a view to assisting staff in specified authorities in identifying language and expressions that should raise a concern that a person is being drawn towards terrorism, the chapter explores the law surrounding hate crime, elucidating what legally amounts to a hate crime up to extremist commentary that can cross the legal boundary into terrorist activity.