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Orwell: Keeping an Eye on You is broken up into 5 episodes. I have organized this guide accordingly for ease of navigation. I tried to be thorough without ruining all of the game's surprises. There are spoilers in this guide, since several of them steer the plot and therefore cannot be avoided. The story will require you to upload certain Datachunks, which I have bolded. Keep in mind that Datachunks not necessary for plot progression still impact the outcomes of the story. Disclaimers aside, I hope this guide is helpful!
Introduction:
Enter a name and choose a profile picture. Agree to Orwell’s terms, then proceed to the next screen. There will be a cutscene which depicts a pleasant-looking plaza. Scans are performed on several of the people in the plaza and no results are found. Then, a scan of a blue-haired woman finds that she has a police record. She boards a bus and disappears. Moments later, a memorial explodes, and the people in the area start screaming and running away from the scene. Who was the blue-haired woman, and was she responsible for the bombing?
Episode 1: The Clocks Were Striking Thirteen
Your new coworker, Symes, will briefly introduce himself. He will then explain the Reader tool, which helps you flag information relevant to your current targets. Symes requests that you read an article from The National Beholder (TNB) which covers the bombing incident from the introductory cutscene. Once you're done, click on the file that says "Unknown Person".
Continue to follow Symes's directions by opening the arrest record of the woman with the blue hair. Symes explains how to upload Datachunks to Orwell's servers (just drag the chunks to the Profile section of the screen with the appropriate target selected). Go ahead and upload the woman's name (Cassandra Watergate) and portrait. Then Symes will unlock a new TNB article with the title "Is this woman a terrorist?". He'll tell you to upload the information in the article. Follow his instructions.
After you upload the Datachunk about Cassandra's art career, you will unlock her portfolio on a website called - you guessed it - Port.Folio. This page presents the first opportunity to upload inaccurate information. If you upload the Datachunk “a colorful inhabitant of Wonderland, right behind the rainbow”, Symes will scold you and warn you to be more careful in the future. It's pretty funny to watch him get worked up and it has no impact on the story, so I recommend uploading it.
If you submit the Datachunk “quit my dull day job, focus on my art career”, Symes will prompt you to find more information about her previous job. Uploading Cassi’s uTell account name is also necessary to proceed. Upon uploading it you will unlock the Listener, which allows you to track conversations. You can upload the Datachunk about Cassi’s Christmas gift to her boyfriend if you want, but it’s not necessary. You also have the option of adding a new portrait to Cassi's profile, but as far as I can tell this action has no meaningful impact.
Eavesdropping on Cassi via the Listener exposes a conversation between herself and an unknown person. This person is quickly revealed to be Josef Langley, her attorney and boyfriend. Cassi took Josef’s credit card without his knowledge. If you upload this Datachunk to Orwell, Symes will disable the card. Uploading the “Josef Langley, my fearless attorney” Datachunk will unlock the TNB article “Procedure closing raises manipulation suspicions”. Uploading the Datachunk “big pharma aka my parents then?” unlocks the Watergate Pharmaceuticals website.
When you open the TNB article, Symes will explain a new feature: conflicting Datachunks. Conflicting Datachunks are highlighted in yellow instead of blue. Be careful with these – try to find as much information as possible before committing to a conflicting Datachunk. The Datachunks you choose to upload influence the course of the plot!
I recommend investigating the Watergate Pharmaceuticals website before committing to either of the conflicting Datachunks.
Under the website’s Company tab, you find that Cassi is listed as the Chief Operating Officer (COO) of Watergate Pharmaceuticals. Uploading these Datachunks prompts Symes to wonder if this was the “dull day job” that Cassi had previously mentioned. A quick look at the Jobs tab on the site confirms Symes’s suspicions. The Datachunk says, “We are urgently looking for a Chief Operating Officer to replace the retired, formerly appointed predecessor.” Upload it to her profile.
You can also submit the Datachunk identifying Cassi’s parents, Alice and Bruno.
To progress, you must return to the TNB article about Cassi’s court case and decide between the two conflicting Datachunks.
TNB: Procedure closing raises manipulation suspicions
The two Datachunks presented to you are as follows:
1 “with the case being closed due to lack of evidence”
2 “the wealthy family of the accused might have influenced the outcome in her favor”
If you choose to submit the first Datachunk, Symes will tell you that he expected as much and is unsurprised. If you upload the second chunk along with the names of Cassi's parents, Symes will launch an investigation into the conduct of Alice and Bruno in relation to their daughter's court case.
At this point, you can view Cassi's Timeline. I recommend waiting to upload most of the Datachunks until you have more information. The ones that are pertinent at the moment can be found under the post where Cassi shows off her newly-dyed hair. Upload the comments from Juliet Kerrington and Harrison O’Donnell. These Datachunks reveal that Juliet gave Cassi the alias Cassarthis and that Harrison invited her to join an activist group.
The Listener will pick up another conversation between Cassi and Josef. There are several Datachunks in this conversation, but for now just upload the one that says “i was so happy when goldfels accepted me into thought”.
After you upload the Datachunk, Symes will ask you to find information about Cassandra’s current beliefs. Be careful about which Datachunks you choose to upload. The pieces of information you send Symes will determine whether or not he perceives Cassi to be a threat. This will have a lasting impact on the course of the game.
If you want to go back and upload any Datachunks that you previously ignored, now is the time to do it.
At this point you can eavesdrop on a conversation between Cassi and Juliet. Cassi admits to attacking the officer (!), and Juliet tries to console her by reminding her that she attacked him to defend Juliet. Cassi contradicts her by saying that she attacked the officer because she "lost it". You must upload one of the two Datachunks.
!! Small Spoilers Ahead !!
No matter which answers you choose, Cassi will be taken into custody. After that, one of three scenarios will play out:
1 If you only submitted Datachunks that lead Symes to believe Cassi is opposed to violence, he will say, "But if we don't get clear evidence she was involved in the assault, she will not stay there for long. We don't have enough against her to charge and hold her."
2 If you submitted Datachunks that lead Symes to believe Cassi is violent or unstable (anti-government comments, disclosing her Metharin usage, etc), and you also said she attacked the officer to defend Juliet, Symes will say, "Despite acting in defense of this Juliet, she seems to be quite unstable and a threat."
3 If you submitted the Datachunk in which Cassi says she attacked the officer because she "lost it", Symes will express shock at her admission and say, "And with that admission of guilt, she will probably serve some time."
Double check that you have uploaded all of the desired Datachunks, and then click on the little symbol in the top right corner of the screen to end the day. Congratulations on finishing Episode 1!