Monty Hall With Envelopes
You are given three envelopes. One contains $\$2$ and the other two are empty. You pick one envelope at random but do not open it.
The interviewer, who knows where the money is, opens one of the remaining two envelopes and shows you that it is empty.
You now have a choice: stick with your original envelope, or switch to the other unopened envelope.
- What strategy maximizes your probability of winning the $\$2$?
- What is the probability of winning under each strategy?
Follow-up: Now suppose the interviewer does not know where the money is. They open one of the remaining two envelopes at random, and it happens to be empty. Should you still switch? What is the probability of winning if you switch vs. stay?
Hints
- Think about what information the interviewer's action gives you. Does opening an empty envelope change anything about your original pick?
- Your initial pick is correct with probability $1/3$. The two envelopes you did not pick collectively hold $2/3$ of the probability. What happens to that $2/3$ when one of them is eliminated?
- Set up Bayes' theorem: condition on the interviewer opening a specific envelope. The key is that $P(\text{open 3} \mid C_2) = 1$ (forced) while $P(\text{open 3} \mid C_1) = 1/2$ (random choice).
Worked Solution
How to Think About It: This is the Monty Hall problem dressed up with envelopes. The key is that the interviewer is not opening a random envelope -- they *know* which one has the money and they always reveal an empty one. That asymmetry is everything. Before you do any math, think about it this way: when you first picked, you had a 1-in-3 shot. The interviewer's reveal does not change what is inside your envelope. It just concentrates all the remaining probability onto one specific envelope. If you can internalize that the interviewer's action is informative (it tells you something about the envelope you did *not* pick), the answer falls out immediately.
Quick Estimate: You picked 1 of 3 envelopes, so your chance of having the money is $1/3$. The other two envelopes collectively hold $2/3$ of the probability. The interviewer removes one empty envelope from that pair, so the surviving envelope inherits the full $2/3$. Switching wins with probability $2/3$, staying wins with probability $1/3$. Switching doubles your odds.
Approach: We can confirm this with a direct application of Bayes' theorem, conditioning on which envelope the interviewer opens.
Formal Solution:
Label the envelopes 1, 2, 3. You pick envelope 1. Let $C_i$ denote the event that envelope $i$ contains the $\$2$. Each has prior probability $1/3$.
Suppose the interviewer opens envelope 3 and shows it is empty. We want $P(C_1 \mid \text{open 3})$ and $P(C_2 \mid \text{open 3})$.
First, compute the likelihood of the interviewer opening envelope 3 under each hypothesis:
- If the money is in envelope 1 (your pick): the interviewer can open either 2 or 3. Assuming they choose uniformly at random among valid options, $P(\text{open 3} \mid C_1) = 1/2$.
- If the money is in envelope 2: the interviewer *must* open envelope 3 (they cannot open 2, which has the money). So $P(\text{open 3} \mid C_2) = 1$.
- If the money is in envelope 3: the interviewer cannot open envelope 3. So $P(\text{open 3} \mid C_3) = 0$.
The total probability of the interviewer opening envelope 3:
$$P(\text{open 3}) = \frac{1}{2} \cdot \frac{1}{3} + 1 \cdot \frac{1}{3} + 0 \cdot \frac{1}{3} = \frac{1}{6} + \frac{1}{3} = \frac{1}{2}$$
Now apply Bayes' theorem:
$$P(C_1 \mid \text{open 3}) = \frac{P(\text{open 3} \mid C_1) \cdot P(C_1)}{P(\text{open 3})} = \frac{(1/2)(1/3)}{1/2} = \frac{1}{3}$$
$$P(C_2 \mid \text{open 3}) = \frac{P(\text{open 3} \mid C_2) \cdot P(C_2)}{P(\text{open 3})} = \frac{(1)(1/3)}{1/2} = \frac{2}{3}$$
The posterior probability that the money is in your original envelope is still $1/3$. The posterior probability that it is in the other unopened envelope is $2/3$.
Answer: You should always switch. Switching wins with probability $2/3$, while staying wins with probability $1/3$. The interviewer's forced reveal of an empty envelope concentrates the $2/3$ prior mass of the two unchosen envelopes onto the single remaining one.
Follow-up: Uninformed Interviewer
This variant changes everything. When the interviewer does not know where the money is and opens a random remaining envelope:
- There is a $1/3$ chance the interviewer reveals the money (game over — you lose or restart).
- Conditional on the interviewer revealing an empty envelope, the probability the money is in your original envelope is:
$$P(\text{your envelope} \mid \text{revealed empty}) = \frac{P(\text{revealed empty} \mid \text{your envelope has money}) \cdot P(\text{your envelope has money})}{P(\text{revealed empty})}$$
$$= \frac{1 \cdot 1/3}{2/3} = \frac{1}{2}$$
So switching gives no advantage — the probability is $1/2$ either way.
Why the difference? In the original problem, the interviewer's knowledge creates an asymmetry: they are *forced* to reveal an empty envelope, which transfers information. When the interviewer acts randomly, the reveal carries no strategic information — it is like a coin flip that happened to come up "empty." The posterior is symmetric.
This distinction (informed vs. uninformed host) is the most common follow-up in quant interviews and tests whether the candidate truly understands conditional probability vs. just memorizing "always switch."
Intuition
The Monty Hall problem is the canonical example of how *constrained information revelation* updates probabilities in a non-obvious way. The interviewer is not opening a random envelope -- they are forced to show you an empty one. That constraint is what makes the update asymmetric. Your original pick carries $1/3$ probability no matter what happens afterward, because the interviewer's action is conditioned on your choice and the true location of the prize. The remaining $2/3$ that was spread across two envelopes gets funneled into the single surviving envelope.
This same structure shows up constantly in trading and market-making. When someone lifts your offer, the fact that they chose to trade with you is informative -- it is not a random event. Adverse selection in market-making is essentially the Monty Hall problem: the counterparty's action reveals information that should cause you to update your beliefs about what you are holding. Any time an agent with private information takes a constrained action, you should ask what their action tells you about the states they *could not* have acted on.