Social Engineering Challenge 2: A Midday Stroll

Good Afternoon! Successful mission report follows.

My task for this week: "Follow someone (without their noticing) for five or more blocks."

Let me start off by saying that five blocks is farther than one might think. Only on my fourth attempt did I actually find someone traveling on foot for that long.

Before I got started, I had to take care of one thing first:

Stalkers Run on Dunkin'

My first target was a traveling couple waiting for the green line at North Station. I rode with them to Park Street. Unfortunately, they asked me for directions, so I had to choose another target. My second target was headed down Winter St from Tremont. She turned into an office building on Summer St at about 4 and a half blocks. I picked up my third target outside South Station. He led me through the financial district to Post Office Square and stopped at a cafe. Distance? About 4 and a half blocks. Damn. I doubled back to South Station and found another target finishing up at a food truck.

We start our journey on a snowy Thursday afternoon near South Station. The target is wearing a gray jacket with a hood, jeans, and boots with red soles. He's carrying a bag of food in his left hand and has a messenger bag over his shoulder.

We follow Summer Street northbound to Otis...

Up to Arch...

And finally to Washington (Downtown Crossing), where we stop to check our phones.

After doubling back on Summer St toward Otis, I wondered if I'd somehow been detected. I'd been keeping my eyes on target as often as was possible, and stayed behind him throughout the trip. By this point, I had already tailed my target for 10 blocks. I considered breaking off, but I wanted to see how far I could go. We took a left on Otis.

To be safe, I crossed the street and increased my follow distance. These streets were less crowded than Summer, so I couldn't blend in to the crowd as well. The target can be seen in the above photo on the left, in front of the white BMW. This is the intersection of Devonshire and Franklin (Otis merged with Devonshire about 50 feet behind me).

We followed Devonshire up to State St. The target is seen here at the intersection of Devonshire and Water.

After turning right on State, the target walked another 3-4 blocks to Commercial before entering an office building.

The journey ends here.

Total Distance Traveled: 1 mile (~17 blocks).

Now, how did I choose my targets? I looked for the casually dressed, as they would be less likely to duck into an office building. I looked for couples or those distracted by headphones or cell phones. I chose targets who hadn't seen me--that is, I started behind them and attempted to stay that way. This was very effective.

Morally, following someone through the city can be either neutral or wrong, depending on intent. In this case, I was merely playing a game by pushing my luck. I knew the longer I followed someone, the greater likelihood of being noticed and confronted.

Through this exercise, I likely discovered where this individual works. With malicious intent, I could sit and wait for him to leave. I could have followed him home. I could have come back tomorrow and been in the same place at the same time. If I encountered the target again, I would have established the beginning of a pattern. People who stick to routines are easy targets.

While completing the mission, I constantly ran through scenarios in my head. What would I do if he noticed me? How would he react? If he confronted me, how would I react? I will say I didn't feel completely wrong or immoral while doing this, as there can be no expectation of privacy in public. While I attempt to vary my schedule and identify any potential tails, it's possible someone was following me today. If I were followed home, or if the assignment were to follow a stranger home, I likely would have felt much different. I feel that identifying someone's home or family is a much greater invasion of privacy than just happening to take the same path through Boston for a few minutes.

Bottom line: Mission Accomplished.

- The Admiral