The exploitation of Industrial Control Systems (ICSs) has been described as both easy and impossible, where is the truth? Post- Stuxnet works have included a plethora of ICS focused cyber security research activities, with topics covering device maturity, network protocols, and overall cyber security culture. We often hear the notion of ICSs being highly vulnerable due to a lack of inbuilt security mechanisms, considered a low hanging fruit to a variety of low skilled threat actors. While there is substantial evidence to support such a notion, when considering targeted attacks on ICS, it is hard to believe an attacker with limited resources, such as a script kiddie or hacktivist, using publicly accessible tools and exploits alone, would have adequate knowledge and resources to achieve targeted operational process manipulation, while simultaneously evade detection. Through use of a testbed environment, this paper provides two practical examples based on a Man-In-The-Middle scenario, demonstrating the types of information an attacker would need obtain, collate, and comprehend, in order to begin targeted process manipulation and detection avoidance. This allows for a clearer view of associated challenges, and illustrate why targeted ICS exploitation might not be possible for every malicious actor.