GoodRx Software Engineer Interview Questions & Guide 2026

The 60-second brief

As a Software Engineer at GoodRx, you are at the intersection of consumer technology and healthcare accessibility. Your work directly impacts how millions of Americans find affordable prescriptions and navigate the complex healthcare landscape. This role is not just about writing code; it is about building scalable, reliable systems that solve real-world problems for people who rely on GoodRx to manage their health and finances.

State every complexity claim with the assumption sitting under it. Hash lookup is O(1) on average and only for a hash that spreads your actual keys; comparison-based sorting cannot beat n log n, though counting or radix sort can when the keys are bounded integers.

Focus areas

• Evolve APIs without breaking pinned SDK clients
• Bound blast radius with per-tenant concurrency limits
• Keep money in integer minor units

Overview

You will contribute to a platform that handles high-traffic, data-intensive applications. Whether you are working on the core prescription search engine, integrating with pharmacy networks, or building out internal tools, your engineering decisions directly influence user experience and company growth. The environment is fast-paced, and you will be expected to balance rapid feature deployment with the architectural rigor required to maintain a trusted, mission-critical product.

Joining this team means you will be part of a collaborative, cross-functional culture where engineers work closely with product managers, designers, and operations teams. You will face challenges related to system performance, API design, and data integrity, all while keeping the user’s needs at the center of your development process. It is a high-impact role for engineers who thrive on solving complex problems in a mission-driven environment.

The GoodRx interview process

GoodRx candidates report 3 rounds · ≈ 3-5 weeks. The stages below are what candidates describe, not a published process.

Recruiter Screen

The title covers product work, platform work, infrastructure, mobile and frontend, and those are different jobs with different loops behind them. A screening call is the cheapest place to find out which one the seat is, and asking reads as experienced rather than fussy. The questions that separate them: what the team is on call for, what the last three projects were, and whether any round happens inside an existing repository instead of a blank file. Then say which of that you have done and which you have not. Claiming the whole posting is the fastest way to be found out one round later.

What to demonstrate

• Whether you can locate your experience inside one flavour of the role honestly instead of claiming the entire requirements list
• Whether you name what you have not done, which an experienced screener reads as a level signal and can plan the loop around
• Whether what you want next matches what the seat is: someone who wants greenfield work landing on a team that mostly operates an existing system is a hire that leaves within the year

How to prepare

• Mark every line of the posting as done, adjacent or new, and write one sentence for each adjacent line naming the closest thing you actually built
• Split your last two years into rough percentages across feature work, operating and debugging live systems, and design or review, so a question about scope gets numbers rather than adjectives
• Bring three questions that discriminate between seats: what the team is paged for, how much of the work is changing existing code versus standing up something new, and what shipped in the last quarter

Technical Deep-Dive

Input bounds are the part of the prompt most often skimmed, and they usually contain the answer. They tell you which complexity class is admissible, which narrows the search before you have thought about the problem itself. As a rough planning figure, a compiled language does on the order of 10^8 simple operations per second and an interpreted one roughly an order of magnitude less. So n up to about twenty admits enumerating subsets, a few thousand admits a quadratic pass, and a million admits neither: you need near-linear, or linear with a log factor. If the bounds are missing, ask for them.

What to demonstrate

• Whether the approach is justified by the stated input size rather than by whichever pattern you recognised first
• Whether you ask about the properties that change the algorithm: whether the input arrives sorted, whether duplicates occur, whether values are bounded integers, whether it all fits in memory
• Whether you can name the bottleneck in your own solution and what would remove it, even when you deliberately leave it in place
• Whether a claimed speedup is real, since memoising a recursion only helps when subproblems genuinely overlap and the state can be keyed cheaply

How to prepare

• For each algorithm you rely on, write down the largest n it handles in roughly a second, then check two of those figures by timing them in the language you will actually type in
• For two weeks, write one line naming your target complexity and the bound that justifies it before you write any code, then compare that line with what you ended up submitting
• Practise the conversion backwards: given a required O(n log n), list the mechanisms that get you there (sorting, a heap, an ordered map, divide and conquer) and choose by what the problem needs to query, not by what you used last

Behavioral Rounds

Your first answer is not really what is scored. It buys the follow-up questions, and those decide the round. An interviewer with fifteen minutes takes one thread and pushes on it four or five times, so a story you can only tell at a single level of detail collapses under the third why. That is an argument for fewer stories known deeply rather than one prepared per prompt. Four or five pieces of work you can still explain down to the code you changed and the argument you had about it will cover nearly anything asked in this round.

What to demonstrate

• Whether a story holds as the questioning moves from what you did to why that instead of the alternative, and then to what you would change knowing what you know now
• Whether you can re-cut a project to answer the question actually asked rather than delivering a rehearsed block that answers an adjacent one
• Whether your level of detail is chosen rather than habitual: going down to the schema when the question is about the data model, staying out of it when the question is about the person who disagreed with you

How to prepare

• Pick four projects and write the chain out four levels deep for each: what you did, why that, why not the alternative, and what would have to be true for the alternative to have won. Where you cannot reach the fourth level, you have a placeholder rather than a story
• Have someone ask why three times in a row on a single thread with nothing else added, and mark the point where you start repeating a sentence you already said. That point is where the interviewer stops learning anything
• Build a one-page index instead of an answer bank: the common prompts in this round (disagreement, a failure that was yours, thin requirements, a deadline you missed, work you inherited) mapped to which of your four projects you would use for each, so the choosing is done now rather than while an interviewer waits

Where candidates lose points

Holding money in a floating-point type, or rounding it more than once

Binary floating point cannot represent 0.01 or 0.1 exactly, so sums drift and two code paths that should agree disagree by cents nobody can trace back. The fix is integer minor units or an exact decimal type end to end, with sub-cent rates expressed as scaled integers such as micro-units, because a per-request price genuinely is smaller than a cent. The second half of the trap is rounding position: rounding each line and then summing gives a different total from summing and rounding once, and half-up and half-even diverge systematically across many lines, so rounding must happen at one named place and every downstream reader must carry the rounded value rather than recompute it from quantity and rate.

Serialising a tenant's writes through select ... for update on a single counter row

It is the first change that makes a counter correct, and it caps that tenant's write throughput at roughly one divided by the lock hold time. A transaction that takes the lock, makes a network call and then commits holds it for the entire round trip: at 2 ms that is about 500 writes per second for the whole tenant, and the largest tenants are exactly the ones that exceed it. The damage then spreads, because every waiter holds a database connection while it queues, so one hot tenant drains the shared pool and the symptom presents as a site-wide latency incident rather than as a lock problem. The repairs are to shrink the critical section to a single statement, to shard the counter into per-(tenant, hour) or per-(tenant, bucket) rows and sum on read, or to batch in memory and flush periodically while accepting the bounded loss that batching implies.

Quoting amortised or average cost as if it were a worst-case guarantee

Appending to a dynamic array is amortised O(1), but the append that triggers a resize copies every element, and hash lookup is constant only while the hash spreads the actual keys. Say which guarantee you are offering when the caller cares about the latency of one call rather than the total over many.

Assuming fixed-width integer arithmetic cannot overflow

In languages with fixed-width integers, including C, C++, Java, Go and Rust, computing a midpoint as (lo + hi) / 2 overflows once the sum passes the type's maximum, so write lo + (hi - lo) / 2 instead. Say which language you are in: arbitrary-precision integers, as in Python or Ruby, remove this specific hazard and none of the others.

Questions & practice

Work with a log file to fetch and process specific data.

Medium · data structures and algorithms

Approach

1. Choose the data structure from the access pattern, not from familiarity.
2. Restate the input: its shape, its size, and what is guaranteed about it.
3. Walk one small example through your approach before writing the whole thing.

Follow-up

• Which test case would catch an off-by-one here?
• What is the worst case, and how likely is it on real data?

Modify a structure that resembles a linked list.

Medium · data structures and algorithms

Approach

1. State the target complexity and say which constraint rules the naive version out.
2. Restate the input: its shape, its size, and what is guaranteed about it.
3. Choose the data structure from the access pattern, not from familiarity.

Follow-up

• How does this change if the input no longer fits in memory?
• Which test case would catch an off-by-one here?

Write a decorator that is rate-limited to run n times per second without using external libraries.

Medium · data structures and algorithms

Approach

1. Name the brute-force solution and its complexity before improving on it.
2. Choose the data structure from the access pattern, not from familiarity.
3. State the target complexity and say which constraint rules the naive version out.

Follow-up

• What is the worst case, and how likely is it on real data?
• How does this change if the input no longer fits in memory?

What is the Python package manager called?

Medium · languages, concurrency and fundamentals

Approach

1. Reach for the cheapest primitive that closes the race, not the broadest lock.
2. Say what the runtime actually does before reasoning about the code.
3. Identify the window where an invariant is briefly untrue.

Follow-up

• What happens if two callers reach this at the same time?
• Where could this allocate more than you expect?

What is the difference between promises and callbacks in JavaScript?

Medium · languages, concurrency and fundamentals

Approach

1. Name what is shared across threads and what owns each piece of state.
2. Reach for the cheapest primitive that closes the race, not the broadest lock.
3. Identify the window where an invariant is briefly untrue.

Follow-up

• What happens if two callers reach this at the same time?
• How would you prove the race exists rather than suspect it?

Find peak concurrent sandbox usage from run intervals

Medium · sweep-line · intervals · concurrency-caps · null-semantics

Given up to 5 million job_run rows for one tenant over one day, with run_id, started_at, finished_at, status and wall_clock_limit_seconds, report the maximum number of sandboxes running at once, the earliest instant that maximum is reached, and the first run_id that would breach a per-tenant cap of C. started_at is null while a run is queued; finished_at is null both for runs still executing and for runs in status lost. Treat a run as occupying [started_at, finished_at). Give the complexity and state how you handle each null.

Approach

1. Turn each run into two sweep events, (started_at, +1) and (end, -1), then sort the 2n events by timestamp with -1 ordered before +1 at equal timestamps. That tie-break is what makes the interval half-open, so a run finishing at 10:00:00 and one starting at 10:00:00 never overlap.
2. Decide each null out loud before sweeping, because each choice moves the answer. A null started_at means queued and contributes nothing. A null finished_at with status running or leased is clipped to the window end. Status lost has no observed end at all, so clip it at started_at + wall_clock_limit_seconds on the grounds that the supervisor owns the timeout, and record that you did. The table's check (finished_at is null or started_at is not null) guarantees you never see an end without a start.
3. Sweep once, maintaining a running counter, the maximum, and the timestamp at which the maximum was first attained (update peak_at only on a strict increase, or you will report the last such instant instead of the earliest). Capture the first run_id whose +1 takes the counter to C+1 during the same sweep rather than in a second pass.
4. Complexity: O(n log n) dominated by the sort, O(n) space. If rows already arrive ordered by started_at, a min-heap of end times gives O(n log k) time and O(k) space with k the peak concurrency, which is the better shape when the rows come from an index scan on (tenant_id, started_at).
5. If second resolution is acceptable, counting-sort the endpoints into an 86,400-slot delta array and prefix-sum it: O(n + T) time and O(T) space, which beats the comparison sort at 5 million rows. It answers only at second granularity, so state which resolution the cap is defined in.

Worked solution (20 min)

1. Write the null policy as three lines of prose first, one per case, and keep them beside the output.
2. Emit 2n endpoint tuples (timestamp, delta, run_id) and sort on the key (timestamp, delta) so -1 precedes +1.
3. Sweep, tracking cur, peak, peak_at updated only on a strict increase, and the first run_id whose +1 takes cur to C+1.
4. Build a fixture with two runs where one ends exactly when the next starts, three genuinely overlapping runs, one run with a null finished_at and status running, and one with status lost and a 300-second wall_clock_limit_seconds.
5. Re-run with every timestamp shifted by a constant and confirm the peak is unchanged while peak_at shifts by the same constant.

Expected result: Peak is 3, from the overlapping trio. The exact-handoff pair yields a peak of 1, not 2. peak_at is the start instant of the third overlapping run. The lost run occupies exactly [started_at, started_at + 300s) under the stated policy.

Verify it yourself

• Setting peak_at on >= rather than > moves the reported instant to the last time the peak was attained. Flip it and watch the fixture change.
• Sorting by timestamp alone, without the delta tie-break, raises the reported peak on the handoff fixture.
• The deltas over the whole sweep sum to zero once every open-ended run has been clipped.

Follow-up

• Now report peak concurrency per tenant for 10,000 tenants from one globally sorted stream. What changes about memory and about the sort?
• The cap has to be enforced at dispatch rather than reported afterwards. What does the admission check look like, and where does it race?
• How would you answer 'peak concurrency within any 5-minute window' without re-sorting?

Migrate a live partitioned event table without blocking ingest

Hard · online migration · ddl locks · expand and contract · partitioning

usage_event is range-partitioned daily on ingested_at, holds roughly 250M rows per day across 400 live partitions, and is written at 10-40k rows/second. Two changes are required: quantity must move from double precision to numeric(20,6), and a new environment column must become NOT NULL with a default of 'production'. Ingest cannot stop. Give the ordered plan, naming for each step the lock it takes, what that lock blocks, and roughly how long it is held. Identify the one step that cannot be rolled back cleanly once traffic depends on it.

Approach

1. Classify the two changes before planning anything. Adding a column with a non-volatile default has been metadata-only since PostgreSQL 11, so it is cheap. Changing double precision to numeric is not binary-coercible, so alter column ... type rewrites every partition under ACCESS EXCLUSIVE and rebuilds its indexes; on this volume that is hours of blocked ingest and is simply not an option, which is why the plan is expand-and-contract rather than one statement.
2. Expand: add quantity_numeric numeric(20,6) and environment with its default on the parent. Both are catalogue-only but both take a brief ACCESS EXCLUSIVE that cascades to partitions, so run each with lock_timeout set to a second or two and retry on failure. A queued ACCESS EXCLUSIVE request blocks every reader behind it, which is how a metadata-only change turns into an outage.
3. Dual-write: deploy producer code that populates both columns on every insert, and leave it running before anything reads the new column. This is the step that cannot be reverted cleanly. Once readers depend on quantity_numeric, reverting the writer leaves rows with a null there, and the gap is only discoverable by re-reading the old column, which the readers have stopped doing.
4. Backfill older partitions in batches keyed on the primary key, oldest first, committing every few thousand rows with a pause between batches, and skipping the partition still receiving writes until it rotates. Each batch is an ordinary UPDATE taking row locks only. The cost is bloat and WAL rather than blocking, so watch dead tuples and let autovacuum keep pace instead of wrapping 400 partitions in one transaction.
5. Make NOT NULL cheap with the three-step form: add constraint ... check (environment is not null) not valid (brief ACCESS EXCLUSIVE, no scan), then validate constraint (SHARE UPDATE EXCLUSIVE, scans while reads and writes continue), then set not null, which from PostgreSQL 12 uses the validated check and skips its own full scan. Do this per partition, then on the parent.
6. Switch and contract: move reads to the new column behind a flag, verify over a full period that both columns agree on freshly written rows, drop the old column (metadata-only), and only then remove the dual-write. Any index on the new column goes on with CREATE INDEX CONCURRENTLY per partition, since CIC is not supported on a partitioned parent: create the parent index with ONLY, build each child concurrently, then ALTER INDEX ... ATTACH PARTITION until the parent index becomes valid.

Worked solution (45 min)

1. On a scratch cluster, build 10 partitions of 2M rows each and run a writer at a few thousand inserts/second.
2. Run the naive type change and measure how long writes stall and how far ingest lag grows before killing it.
3. Run the expand step with lock_timeout = '2s' while the writer runs, and observe a clean lock timeout and retry instead of a pile-up of blocked readers.
4. Backfill in 5k-row batches and chart dead tuples and WAL generated per batch.
5. Run the not-valid, validate, set-not-null sequence and confirm from pg_stat_activity and timings that nothing held an exclusive lock through a full scan.
6. Add an index with CIC per partition plus ATTACH PARTITION and confirm the parent index reports valid only after the last attach.

Expected result: An ordered expand, dual-write, backfill, switch, contract plan with the lock named per step: metadata-only ADD COLUMN under a brief ACCESS EXCLUSIVE taken with lock_timeout; batched UPDATE backfill under row locks; CHECK NOT VALID, then VALIDATE under SHARE UPDATE EXCLUSIVE, then SET NOT NULL; CREATE INDEX CONCURRENTLY per partition with ATTACH PARTITION; and the dual-write-to-read switch identified as the step that cannot be reverted cleanly.

Verify it yourself

• No step in the plan holds ACCESS EXCLUSIVE for longer than the configured lock_timeout.
• The writer's error rate stays at zero through the rehearsal apart from the deliberate lock timeout.
• After VALIDATE, SET NOT NULL completes in milliseconds on a table where the naive form scanned every row.
• Freshly written rows agree on both columns for a full verification period before the old column is dropped.

Follow-up

• A CREATE INDEX CONCURRENTLY fails halfway through the partition list. What state is the table in, how do you detect it, and what do you run?
• The producer computes quantity itself. What happens to a request already in flight when the dual-write deploy lands, and does it matter?
• Give two queries that prove the backfill is complete: one cheap enough to run every minute, one authoritative.

Find the join that inflates every invoice total

Medium · join fan-out · aggregation grain · sql correctness

invoice_line_item holds line_id, invoice_id, tenant_id, sku, rate_tier, quantity, unit_price_micros, amount_minor (bigint), currency, kind, voided_at. invoice_payment_attempt holds attempt_id, invoice_id, tenant_id, amount_minor, status (succeeded, failed, pending), created_at, and an invoice has many attempts. A finance report runs select i.invoice_id, sum(l.amount_minor), count(p.attempt_id) from invoice i join invoice_line_item l using (invoice_id) join invoice_payment_attempt p using (invoice_id) group by 1 and the totals are wrong. Say precisely what the sum now equals, and write a version that is also correct for invoices with zero attempts.

Approach

1. Compute what the query actually returns before fixing it. The two joins form a Cartesian product per invoice, so each line row repeats once per attempt row: sum(l.amount_minor) is the true total multiplied by the attempt count, and count(p.attempt_id) is attempts times lines. Three lines and two attempts report double the money and six attempts.
2. Reject the reflex repair. count(distinct p.attempt_id) does fix the count, because attempt_id is unique. sum(distinct l.amount_minor) does not fix the sum, because two legitimate lines with equal amounts collapse into one. DISTINCT inside an aggregate deduplicates values, not rows, and the difference stays invisible until two lines happen to match.
3. Aggregate each branch to invoice grain before joining: one CTE summing lines by invoice_id, one counting attempts by invoice_id, then join the two results. A LATERAL subquery per invoice is equivalent and sometimes plans better when the outer set is small. Either way every aggregate stays at the grain it was defined at.
4. Keep invoices with no attempts by making the attempt branch a LEFT JOIN with coalesce(attempt_count, 0). An inner join here silently drops every unpaid invoice, which is usually the exact population finance is asking about.
5. Push each filter to its own grain: where l.voided_at is null belongs inside the line CTE, not the outer query, or it would also filter the attempt branch through the join. Put the tenant predicate on both branches, since the denormalised tenant_id is what stops a wrong join crossing tenants.
6. Leave yourself a standing check: an invoice total is a function of its non-voided lines and of nothing about payments, so if changing the payment filter moves the money figure, the fan-out is back.

Follow-up

• Add a third branch for credit notes applied to the invoice. Does the CTE shape still hold, and when would a single pass with filter (where ...) be better?
• Over 500k invoices this report takes minutes. Which grain would you materialise, and how do you keep it correct when a line is voided?
• The same report is needed per tenant per month. What index makes the line CTE cheap?

Design an API for a recipe app—how do you make it efficient?

Medium · system design and architecture

Approach

1. Name the read and write paths separately; they rarely have the same bottleneck.
2. Choose a partition key and say what query it makes expensive.
3. State the consistency you need, and where you are willing to be stale.

Follow-up

• How does this behave when that dependency is down for an hour?
• What breaks first when traffic grows ten times?

What are the pros and cons of the tools you have used in past projects?

Medium · system design and architecture

Approach

1. Choose a partition key and say what query it makes expensive.
2. State the consistency you need, and where you are willing to be stale.
3. Fix the scope first: who calls this, how often, and what they do when it fails.

Follow-up

• What would you drop to keep the system up under load?
• What breaks first when traffic grows ten times?

Compare monolithic versus microservices applications.

Medium · system design and architecture

Approach

1. State the consistency you need, and where you are willing to be stale.
2. Fix the scope first: who calls this, how often, and what they do when it fails.
3. Name the failure you are designing for, then the recovery path.

Follow-up

• How does this behave when that dependency is down for an hour?
• What breaks first when traffic grows ten times?

Design a machine-readable error contract for the gateway

Easy · error taxonomy · retries · api contract

The edge gateway serves roughly 30k requests/second to SDKs and CI pipelines that retry automatically. Today every failure returns 500 with a prose message that clients string-match on. Design the error contract: the response body fields, and the status code for a malformed body, a revoked credential, a scope the credential lacks, a row belonging to another tenant, a reused idempotency key sent with a different body, an exceeded rate limit, and an unreachable dependency. For each, state whether the client may retry and on what schedule. Deliverable: the envelope schema plus the status-to-retry table.

Approach

1. Split the envelope by audience: a stable code string for programs, a message documented as human-only and free to change, a request_id that joins to gateway logs, and a details array for per-field problems. The code list is an enum that only ever grows.
2. Assign status by who has to change something: 400/422 for the caller's bytes, 401 for a credential that no longer authenticates, 403 for a scope or entitlement, 404 rather than 403 for a row in another tenant because 403 confirms the identifier exists, 409 for an idempotency conflict, 429 for a limit, 503 for a dependency.
3. Derive retryability from the method and the idempotency key rather than from the status: a 5xx or a timeout is an unknown outcome, not a failure, so GET/PUT/DELETE may be retried under HTTP semantics and POST only when it carries an idempotency key.
4. Put the schedule in the response: Retry-After on 429 and 503 overrides the client's own backoff; otherwise capped exponential backoff with full jitter, sleeping uniformly in [0, min(cap, base * 2^attempt)], bounded by a total attempt budget so retries expire before the caller's deadline.
5. Write the negative rules into the published contract: clients must never parse message, must tolerate unknown code values by falling back to the status class, and a code's meaning is never redefined once shipped.

Worked solution (20 min)

1. Write the envelope as a JSON schema with four top-level fields and say which are guaranteed present on every error.
2. Fill a seven-row table: condition, status, code string, retryable yes/no, and the schedule or the reason retrying cannot help.
3. For each non-retryable row, write the one thing the caller must change (bytes, credential, plan, key) so nothing is marked non-retryable without a remedy.
4. Add the unknown-outcome row for timeouts and 5xx separately from the other rows, and give it an action other than 'treat as failed'.
5. Write two sentences of client guidance: honour Retry-After when present, apply full jitter otherwise, and stop at the attempt budget.

Expected result: An envelope of { code, message, request_id, details[] } plus a table in which only 429 and 503 are unconditionally retryable, 5xx and timeouts are retryable only for idempotent methods or keyed POSTs, and every other row names a caller-side change.

Verify it yourself

• No row requires the client to read message to decide what to do.
• The cross-tenant row returns 404 and the justification mentions existence disclosure.
• Timeout appears as its own outcome, distinct from both success and failure.
• Retry-After is stated as authoritative over any client-side backoff calculation.

Follow-up

• A customer reports they retried a 500 from POST /v1/runs and ended up with two sandboxes billed. Whose bug is it, and what in your contract permits their reading?
• You need to add a new error code next quarter without a version bump. What did the v1 contract have to say for that to be non-breaking?

A rare job-run overwrite that logging makes disappear

Hard · fencing tokens · leases · concurrency

About one job run in fifty thousand records billable_seconds matching no observed sandbox lifetime, and a few rows show worker_id changing after finished_at was already set. It does not reproduce: debug logging around the terminal write made it vanish for two weeks before it returned. Runs last from 200 ms to 30 minutes, the lease is 60 seconds and is renewed while a run executes. Give an ordered checklist, the mechanism, and a fix that makes the illegal write impossible rather than merely rarer.

Approach

1. Mine the evidence instead of chasing a repro: select rows where updated_at is later than finished_at, or where a terminal status was written twice, and join them to attempt history to recover both writer identities. The defect has already happened tens of times and the rows are the recording.
2. State the signature before measuring it. If the cause is a lease that expired while the original worker was stalled, affected runs should cluster where the gap between the last renewal and the terminal write exceeds the lease, and should correlate with worker pause metrics rather than with workload shape.
3. Read the disappearance honestly. Logging inside the window changed the timing and lowered the probability; it is evidence about how narrow the window is, not a fix. Reproduce by widening the window on purpose, shortening the lease and injecting a pause between sandbox exit and the terminal write, rather than by adding more instrumentation.
4. Name the mechanism precisely: the lease expires during a stall such as a long garbage-collection pause or a brief partition, the run is re-dispatched, and the original worker then wakes and writes its terminal state over the new attempt's row. A lease alone cannot stop this, because the check and the write are separated by the stall.
5. Fix by fencing the write itself: UPDATE job_run SET status = $2, finished_at = $3, billable_seconds = $4 WHERE run_id = $1 AND status = 'running' AND lease_token = $5, with zero rows affected interpreted as having been fenced rather than as success. The token lives on the row so the store arbitrates, not the worker's memory.
6. Keep the state machine honest: a retry inserts a new row pointing at parent_run_id rather than resetting the old one, and a run whose worker vanished terminates as lost with billable_seconds null, because recording failure asserts an outcome nobody observed and then bills and retries on that assertion.

Follow-up

• The supervisor also emits a usage event on completion. What does the fenced worker do about the event it already emitted, and how does metering absorb it?
• Lease renewal is itself a network call. What happens when a renewal times out, and how does the worker decide whether it still holds the lease?
• Why is lengthening the lease past the longest legitimate run the wrong lever, and what breaks if you do it anyway?

Suggested practice checklist

For someone fluent in a dynamic language who has shipped real work but has never had to say what the runtime is doing underneath. The week is built on measuring and deliberately breaking things, because the questions that expose this background are the ones where the interviewer asks why a second time.

Day 1 — Measure before reasoning

• Take a slow piece of your own code, write down in advance where you believe the time goes, then profile it and record how wrong the guess was. The cost is usually an allocation you did not notice or an accidental quadratic membership test.
• Replace one list membership test inside a loop with a set and measure at a thousand, ten thousand and a hundred thousand elements, confirming the shape of the curve rather than only that it got faster.
• Write down the three quantities you can now measure instead of assert: wall time, peak memory, and call count for the function you suspected.

Deliverable: A before-and-after profile of real code plus a written note on the size of the gap between the guess and the measurement.

Day 2 — References, copies, and the bugs they produce

• Write the function with a mutable default argument, call it three times, and explain the accumulating result: the default is evaluated once when the function is defined, so every call shares one object.
• Build a nested structure, take a shallow copy, mutate an inner element, and show that both views changed, because a shallow copy duplicates the container and not the elements. Then fix it with a deep copy and state the cost you just accepted.
• Write two functions, one mutating its argument in place and one rebinding the local name, and predict the caller's view of each before running it. That single distinction produces most of the bugs that pass their tests.

Deliverable: Three small programs whose output you predicted correctly before running, each with a one-line statement of the rule underneath.

Day 3 — Types, once, in a language that checks them

• Port one module you have already written, roughly a hundred lines, into a statically typed language, and record every place the compiler demanded an answer your original had left implicit: a value that can be absent, a numeric width, a case never handled.
• Write the same signature in both languages and state what the static one guarantees before the program runs and what it does not, since it will not save you from a wrong algorithm or an index out of range.
• Write the difference between an interface satisfied by declaration and one satisfied structurally, with one case each where the other approach would miss the mistake.

Deliverable: One module in two languages plus a list of the questions the type checker forced you to answer.

Day 4 — Concurrency, starting with what actually runs at the same time

• Run the same CPU-bound function across four threads and four processes and measure both. Under the default CPython build the threaded version will not speed up, because only one thread executes bytecode at a time; the process version will. Check which build you are on first, since free-threaded builds remove that lock and change the result.
• Then run a blocking I/O workload across four threads and measure it speeding up, because the interpreter releases that lock around blocking calls, which is why treating threads as useless is wrong as a general claim.
• Build the lost update: two threads each incrementing a shared counter a hundred thousand times, and show a final value below the expected sum, because an increment is a load, an add and a store and the thread can be suspended between them. Fix it with a lock and then measure what the lock costs.

Deliverable: Three measurements, threads against processes on CPU work, threads on I/O work, and a demonstrated lost update, each with the mechanism written underneath.

Day 5 — Debugging as a procedure rather than an instinct

• Work one real failure as a bisection: find a revision or an input size where it is good and one where it is bad, halve repeatedly, and state the two assumptions bisection needs, that the property changes exactly once across the range and that the test is reliable.
• Minimise one failing input to the smallest version that still fails, and record how many rounds it took.
• Keep a hypothesis log for one bug in three columns, what I believe, what would disprove it, what I observed, and stop yourself the first time you are about to change two things at once.

Deliverable: One bug worked to root cause with a written hypothesis log and a minimised reproducing input.

Day 6 — Tests that catch the bug you are about to write

• Implement an LRU cache with a capacity bound, then write the three test cases that would catch an off-by-one in eviction: insert exactly capacity items and assert nothing was evicted, insert one more and assert the least recently used key is the one gone, and read an old key just before that insert so the eviction victim changes.
• Add a property test comparing your implementation against a deliberately slow reference, an ordered list scanned linearly, over a few thousand random operation sequences, because a slow reference finds the cases you would not have thought to write.
• Write one numeric test that fails under exact equality and passes with a tolerance, and state why the tolerance has to be relative rather than absolute once the magnitudes grow.

Deliverable: An LRU implementation with three boundary tests, one property test against a slow reference, and one tolerance-based numeric test.

Day 7 — Debug something broken, out loud

• Have someone plant three defects in a two-hundred-line program, an off-by-one, a shared mutable state bug, and a wrong error-handling path, then find them while narrating, under a fixed rule: state the hypothesis before touching anything.
• Time each one and record which tool found it, reading, a printed value, a debugger, or a test, because the question asked in interviews is how you would find it rather than what it was.
• Write the sentence you will use when you do not yet know the cause, one that names the next measurement instead of offering a guess.

Deliverable: A recorded debugging session with time-to-find per defect and the method that found each.

Disagreement needs an outcome you did not choose

Conflict answers where you were right and everyone came round are the weakest ones. Stronger: the evidence you went and collected, what would have changed your mind, and what you did in the weeks after the call went against you. Implementing a design you argued against, properly, is a specific and checkable behaviour.

After perusing our website, what kind of changes would you suggest off the top of your head?

Medium · behavioural and engineering judgement

Approach

1. Name the disagreement and how you resolved it with evidence.
2. Give the blast radius: what could have broken, and what you measured.
3. Pick a story where you made the decision, not one where you watched it.

Follow-up

• What would you do differently if you ran that again?
• How did you know your change caused the improvement?

Disclose a cross-tenant webhook delivery to affected customers

Medium · cross-tenant leak · disclosure · blast radius · authorisation checks

An enqueue path took the subscription from one lookup and the payload from another. For nineteen minutes, webhook_delivery rows were created whose tenant_id did not match the subscription's tenant, and eleven payloads were signed and sent to four endpoints belonging to other customers. You hold payload_digest, delivery timestamps and response codes. Describe how you handle a disclosure of this kind: what the records prove, what they cannot prove, what you say before you know everything, the one code change that closes it, and which parts you personally drove.

Approach

1. Bound the population before saying anything externally. The affected set is deliveries in the window where the event's tenant and the subscription's tenant differ; the ones that actually left are those with delivered_at set and a 2xx in last_response_code. Attempted and delivered are two different counts and a disclosure has to use the right one in the right sentence.
2. Separate what the records prove from what they do not, and say both halves rather than the flattering one. They prove which payloads were signed, where they went, and — through payload_digest — exactly which bytes. They do not prove what the receiving system did with them, and they do not bound the window more precisely than your deploy timestamps do.
3. Communicate on the facts you hold, with the scope stated as an upper bound: 'at most eleven payloads, four recipient endpoints, these fields, this window' is more useful and more honest than waiting a day for certainty. The field list matters more than the event count, because a customer cannot assess exposure from 'an event'.
4. Name the code change precisely, because this class never originates in the delivery worker. Compare the event's tenant against the subscription's tenant at enqueue and again immediately before the payload is signed, and make the second comparison drop the delivery rather than log a warning. Say why one check is insufficient: the enqueue check protects against the bug you know about, the pre-signing check protects the boundary itself.
5. Run the history question in parallel and say so: a query over historical deliveries for the same mismatch tells you whether this was nineteen minutes or a year, and you would rather find the second case yourself than have a customer find it after your disclosure.
6. Split the response into workstreams with owners — recipients asked to delete, affected customers notified, the check landed with a test, history swept — and say which you personally drove and which you handed off. Claiming all four is not credible and claiming none is not ownership.

Follow-up

• The historical sweep finds two more instances from last year. What changes in what you have already told people?
• Who approves the wording, and what do you do when you are asked to soften the scope?
• A customer asks you to prove a redelivery contained the same bytes as the original. What do you show them?

Argue against failing open when the control plane is unreachable

Hard · revocation · cache staleness · fail-open vs fail-closed · influence

The gateway caches credential-to-context decisions with a sixty-second TTL. A design proposal says that when control-plane reads fail, pods should keep serving from expired entries indefinitely so a control-plane outage never becomes a product outage. You believe that converts every revocation into an unbounded one. Describe a design you argued against while it was still a live proposal: what you measured or modelled to make the case, what you conceded, who decided, and what happened afterwards. Say what would have changed your mind before the decision, not after it.

Approach

1. Reframe it from a values argument into a bounded-staleness argument. Both sides already accept the cache; the disagreement is only about the ceiling on how long a revoked credential keeps authorising. Put a number on the table — serve stale for up to fifteen minutes, then fail closed — and make the other side argue against a number rather than against a principle.
2. Bring arithmetic rather than adjectives: the rate of revocations with revoked_reason in ('suspected_leak','auth_version_bump'), the observed distribution of control-plane unavailability, and the product of the two, which is expected requests served by revoked credentials per outage-hour. At 30k requests/second the unbounded version is not a subtle exposure and the number says so.
3. Concede the strong half of the opposing case first, because that is what buys you the room: failing closed turns one service's outage into a total outage across three regions, and a control plane doing tens of writes per second is not engineered to the gateway's availability target. A proposal you have not steelmanned reads as reflex.
4. Propose the asymmetry that usually resolves this: stale entitlements cost bounded money (a quota fifteen minutes out of date over-serves by a computable amount), while a stale revocation costs unbounded access. Split the cached decision by what it authorises, give the two halves different staleness ceilings, and let the entitlement half fail open while the revocation half fails closed.
5. State the propagation dependency plainly, since it is the part that is missed: validity is also derived from the principal's auth_version, so password reset and sign-out-everywhere flow through this same cache. A design that bounds staleness for explicit revocation and not for auth_version bumps has only fixed half of it.
6. Say who decided, and what you did afterwards in either outcome: write the decision down with its number and a review date, and instrument the exposure you were worried about so the next round of the argument is settled by data instead of by seniority.

Follow-up

• Publish-subscribe invalidation is lossy under a partition, and a TTL is the only hard bound. What TTL do you pick, and what does it cost you at 30k requests/second?
• The key was revoked because it was found in a public repository. Does your answer change, and where does that urgency live in the design?
• You lost the argument and six weeks later the failure you predicted happens. What do you say in the review, and what do you not say?