According to the plot Orwell: Keeping an Eye On You the government spies on its citizens. The game is an episodic adventure consisting of 5 parts and touches on current issues regarding the tensions between privacy and national security. It's a visual novel where the player takes on the role of a spy forced to observe a group of activists while trying to determine who is responsible for a series of bombings.

Orwell: Keeping an Eye On You features a civilian surveillance program. The player finds himself as an investigator whose task is to analyze the digital footprint of people whom the Party has flagged as a potential threat. He first looks through government documents, as well as newspapers, websites and police databases, but soon dives deeper into his investigation. You'll have to read emails and chat logs, listen to phone calls, and, in extreme cases, dig into your target's computer. As private information is obtained, the game system highlights relevant passages of text in the form of information blocks.

The primary role of a researcher is to separate fact from fiction. The gamer is literally the brain of the operation, and the problem is to understand what information to filter and take into account. Sometimes this is easy because many pieces of information are quirks of language or clearly have no meaning. Others are clearly important, and the difficulty arises when conflicting data emerges. In the end, it is necessary to find out who is the main suspect – a naive activist or a dangerous terrorist?