Interview guides · Icapital

Icapital Software Engineer Interview Questions & Guide 2026

A prep plan for Icapital software engineer candidates: answer first, read the solution second, repeat the misses later.

The 60-second brief

As a Software Engineer at iCapital, you play a foundational role in building, scaling, and evolving the cutting-edge financial technology platform powering global alternative investments. Your day-to-day contributions directly impact how wealth managers, asset managers, and individual investors seamlessly navigate complex financial markets through intuitive, highly performant applications. Whether you are architecting microservices, optimizing database schemas, or delivering robust client-facing features, your work drives operational efficiency across the entire ecosystem.

Ask whether any round happens inside an existing repository instead of a blank file. Reading unfamiliar code, isolating a fault and making the smallest correct change is a different skill from writing a function from scratch, and it needs its own practice.

Focus areas

Evolve APIs without breaking pinned SDK clients
Make every write idempotent under client retries
Bound blast radius with per-tenant concurrency limits

Overview

You will operate within dynamic, collaborative product pods, partnering closely with Product Management, QA, and adjacent engineering teams throughout the entire software development lifecycle. The technical landscape at iCapital spans modern full-stack development—predominantly leveraging Ruby on Rails, Python/Django, Scala, and Node.js on the backend, paired with React on the frontend. The platform relies on secure, cloud-native microservices architecture hosted on major cloud providers and container orchestration layers like.

Success in this role requires more than just checking technical boxes; it demands a deep curiosity for financial domains, a passion for solving intricate architectural problems, and a collaborative mindset. You will tackle real-world challenges around data integrity, secure API integrations, and user experience, all while maintaining high standards for code quality and test automation. Expect a fast-paced environment where your technical ownership grows rapidly, giving you the platform to influence core product components and mentor emerging engineering talent.

The Icapital interview process

Icapital candidates report 6 rounds · ≈ 4-6 weeks. The stages below are what candidates describe, not a published process.

Initial Screening

Half of this call is the part candidates treat as small talk: start date, notice period, work authorisation and its timing, location and time zone, on-call, and the number. Those are what kill offers late, after several engineers have each spent a day. Surfacing a hard constraint now costs you nothing and occasionally buys you something, since a loop compressed to fit a competing deadline can usually only be arranged if it is asked for early. The common failure is deflecting the compensation question twice, then discovering at offer stage that the band never reached your number.

What to demonstrate

Whether your hard constraints are compatible with the role before a loop gets booked: earliest start, notice period, what authorisation you hold and when it needs action, days on site, willingness to carry a pager
Whether you give a compensation range with something behind it, such as current total compensation or a competing timeline, rather than leaving the band untested
Whether your stated timeline is real, since a competing deadline raised now is something scheduling can sometimes work around and the same deadline raised at offer stage usually is not

How to prepare

Write each constraint down in one line before the call and state them as facts rather than negotiating them live under a question you were not expecting
Set your range from two or three current data points for that level and location, and name the structure you are quoting in, so the number is comparable to the one they are holding
If another process is running, say where it stands and by when, and ask directly whether this loop can be scheduled inside that window

Technical Assessments

Most of the time lost in this format is not lost to thinking. It goes to a standard-library call you half-remember, an off-by-one in a loop bound, and a debugging loop that mutates code at random until something passes. When output is wrong, stop re-reading the whole function: take the smallest input that reproduces it and walk the state through by hand, printing intermediates if the environment allows. Guessing at a fix without a failing case you understand is how a five-minute bug becomes twenty, and the clock does not pause while you do it.

What to demonstrate

Whether you reach the right structure without a detour, and can write it from memory rather than only recall that one exists
Whether overflow is considered where the language has fixed-width integers, since a signed 32-bit value stops at 2,147,483,647 and then wraps in Java, is undefined behaviour in C++, and does not arise in Python, whose integers grow instead
Whether recursion depth is treated as a constraint on large inputs, given that CPython's default limit is 1000 frames and a deep recursion can exhaust the stack in any language where an iterative version would not
Whether a failing case is isolated and explained before any edit is made to the code

How to prepare

From an empty file and with no references open, implement the pieces you lean on most: a heap push and pop, an iterative DFS with an explicit stack, and a binary search whose midpoint is written lo + (hi - lo) / 2, which avoids the overflow that (lo + hi) / 2 can hit in a fixed-width integer type
Time yourself on the ten library calls you look up most, such as sorting with a custom comparator, splitting and joining strings, and finding the next key at or above a value in an ordered map, until the lookup is gone
Take a solution you know is broken and, before touching it, write one sentence naming the input, the expected value and the actual value. Repeat until you do it without deciding to.

Behavioral Interviews

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

Team Interactions

You cannot drill a format you do not know, so put the preparation into material that travels. Three pieces of your own work, each rehearsed until you can take a follow-up you did not anticipate, will carry a conversation or a code walkthrough equally well. Specificity is what separates that from filler. A number needs its definition before it means anything: a p99 is over some window and measured at some hop, and a server-side figure excludes the queueing and network time a client would see. The number you cannot qualify is the one to leave out.

What to demonstrate

Whether your examples carry detail only someone who did the work would hold, such as what the binding constraint actually was, which alternative you rejected and why it was worse, and what you measured on each side of the change
Whether a number survives one follow-up, meaning you can say what it was measured over and whether it moved because of your change or merely alongside it
Whether a failure is described with the specific change that followed it, rather than a lesson stated in general terms
Whether your part in a team effort is stated accurately, including what other people did

How to prepare

Write a page on each of three projects covering the constraint, the option you rejected, the measurement before and after, and what went wrong. Cut any line you cannot take a follow-up on, since you are writing the parts you will be pressed on rather than a summary.
Recover the real figures while you still have access: request volume, data size, latency with its percentile and window, team size, timeline. Note where each came from, whether a dashboard, a design document or memory, and mark the estimates so you can say which they are out loud.
Take your weakest project story to someone who works in a different area and have them ask why four times in succession. The point where you run out of answer is the part to go and re-read before the round.

Coding Challenges

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

Technical Discussions

What this round decides is narrow: whether you can produce code that runs and is correct on inputs nobody showed you. An elegant solution that does not compile scores below a plain one that does, so write a correct brute force first, say out loud that you know its cost, and improve it with the working version still on screen. What separates strong answers is who finds the broken case. Trace your own code against an empty input, a single element, and duplicate keys before you say you are finished, because being told is far more expensive than noticing.

What to demonstrate

Whether degenerate inputs get checked without being asked for: an empty collection, one element, every element equal, and the extreme value the input type allows
Whether the complexity you state matches the code you actually wrote, including a sort or a copy sitting inside a loop
Whether the finished answer is verified against the worked examples before you call it done, rather than assumed correct because the code reads correctly

How to prepare

Take five problems you have already solved and, without running anything, write down what each returns for empty input, a single element, and all-duplicates. Then run them and count how many you predicted wrong.
Drill the brute force as its own skill: on ten problems, write only the obviously-correct slow version and time how long it takes to get it passing. If that is more than a few minutes, that is what to practise, not the optimal version.
Add a fixed last step before you submit anything, reading only the loop bounds and the initial value of each accumulator, which is where most off-by-one errors live

Where candidates lose points

Treating a timed-out write as a failed write

A timeout says the response did not arrive, not that the work did not happen; the server may well have committed and then lost the connection. Retrying a non-idempotent create after a timeout is the standard way to end up with two of something, and those duplicates land precisely when the system is already degraded and least able to absorb them. The discipline is to treat a timeout as unknown: either the write carries an idempotency key so the retry is safe by construction, or the client re-reads authoritative state before deciding what to do, and the interface says unknown rather than showing a failure that invites a second click.

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.

Issuing one query per row of a result set

Fetch related rows in a single batched query keyed by the ids you already hold, or join them into the original query. A per-row round trip multiplies network latency by the row count, and it looks perfectly fine against the ten rows in your development database.

Saying 'eventually consistent' without naming the anomaly a user would see

Describe the concrete symptom you are choosing to accept: the author reloads and their own comment is missing for two seconds, or two devices show different balances for a minute. The class of consistency model is a technical label; the tolerable anomaly is the actual product decision.

Questions & practice

Describe how you would check for a word to be a palindrome using clean, optimal logic.

Medium · data structures and algorithms

Approach

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

Follow-up

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

Write and explain code during a live-coding Hackerrank session.

Medium · data structures and algorithms

Approach

Walk one small example through your approach before writing the whole thing.
Restate the input: its shape, its size, and what is guaranteed about it.
State the target complexity and say which constraint rules the naive version out.

Follow-up

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

Schedule ordered webhook retries with a heap of subscription queues

Medium · heap · scheduling · backoff · head-of-line-blocking

Design the in-memory scheduler for webhook delivery. Up to 20 million rows sit in status pending or failed_retryable across 200,000 subscriptions, each row carrying next_attempt_at and attempt_count, and each endpoint having a circuit breaker. Deliveries for one subscription must be attempted in order, so at most one attempt per subscription may be in flight. Support due(now), complete(delivery, outcome) and insert(delivery) in O(log S), where S is the subscription count rather than the delivery count. Give the backoff formula you schedule retries with.

Approach

Key the global heap by subscription, not by delivery. Each subscription owns a FIFO of its due deliveries in event order; the heap holds one entry per eligible subscription, keyed by its head's next_attempt_at. That is 200,000 heap entries instead of 20 million, and it makes the one-in-flight rule structural rather than a check somebody can forget.
due(now): peek the minimum. If its key is in the future, sleep until then instead of spinning. Otherwise pop it, move the subscription into an in-flight set, and do not re-push it. A subscription absent from the heap cannot be dispatched twice, which is precisely how ordering is preserved.
complete: on success, drop the head and re-push the subscription keyed by its new head, or leave it out when the queue empties. On a retryable failure, increment attempt_count and set next_attempt_at = now + uniform(0, min(cap, base * 2^attempt)), sampled uniformly across the whole interval. That is full jitter; deterministic backoff re-synchronises the herd you just created.
Circuit breaker: park the subscription in a second heap keyed by its half-open time, so an endpoint dead for six hours costs one heap entry and zero attempts rather than consuming worker slots. Admit exactly one probe at half-open and close the breaker only on its success.
Say the price of the ordering guarantee out loud. One in-flight attempt per subscription means an endpoint answering in 10 seconds drains at 0.1 deliveries/second however many workers you run, and its backlog grows until it recovers. If the customer does not need order, allow k in flight and document delivery as unordered; that is the trade, and it is a product decision.
All three operations are O(log S) with O(S) resident heap memory and the queues themselves backed by the store. The database-backed equivalent is a partial index on (subscription_id, next_attempt_at) where status in ('pending','failed_retryable') claimed with FOR UPDATE SKIP LOCKED, and the write-back must be fenced on lease_token so a worker that stalled and resumed cannot overwrite a newer attempt.

Worked solution (30 min)

Define the four structures explicitly: queues: subscription_id -> deque[delivery], ready: min-heap of (next_attempt_at, subscription_id), inflight: set[subscription_id], breaker: min-heap of (half_open_at, subscription_id).
Write down the invariant you will assert after every operation: a subscription appears in at most one of ready, inflight and breaker, never in two.
Implement due, complete and insert, then simulate 200,000 subscriptions with Zipf-distributed queue depths totalling 20 million deliveries.
Add one endpoint that always times out after 10 seconds and one that always answers in 20 ms, then measure the fast endpoint's throughput with and without the per-endpoint breaker.
Instrument heap size across the run.

Expected result: Heap size stays at or below 200,000 regardless of the 20 million deliveries. The fast endpoint's throughput is unaffected by the dead one once the breaker trips. The dead endpoint's deliveries accumulate in their own deque and cost exactly one heap entry.

Verify it yourself

The asserted invariant never fires under concurrent workers.
Replaying the same delivery set twice produces identical per-subscription ordering, even though the interleaving across subscriptions differs.
Replacing full jitter with fixed backoff makes retry attempts cluster visibly in a histogram of attempt timestamps.

Follow-up

One subscription has 4 million queued deliveries. What stops it from starving the other 199,999, and what does your heap look like under that load?
A customer requests redelivery of last Tuesday's events. Where do those rows enter your structure, and what keeps them from reordering live traffic?
The process restarts. How much state do you rebuild, and what stops every subscription from being attempted in the same second?

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

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.
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.
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.
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.
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.
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.

Worked solution (25 min)

Create one invoice with three lines of 1000, 1000 and 500 minor units and two payment attempts, then run the original query.
Confirm it reports 5000 and 6 rather than 2500 and 2.
Apply sum(distinct l.amount_minor) and confirm the total becomes 1500, which is worse rather than better.
Write the two-CTE version with a LEFT JOIN and coalesce, and confirm 2500 and 2.
Add a second invoice with lines and no attempts and confirm it still appears.

Expected result: The original sum equals the true line total multiplied by the number of payment attempts and the count equals attempts times lines; the corrected query pre-aggregates each branch to invoice grain in separate CTEs and LEFT JOINs them with coalesce, with voided lines excluded inside the line CTE and the tenant predicate applied to both branches.

Verify it yourself

The money total is unchanged by adding or removing payment attempts.
An invoice with zero attempts appears with its total and a zero count.
Two lines with identical amounts both contribute to the total.
Voiding a line changes the money figure and leaves the attempt count alone.

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?

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

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.
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.
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.
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.
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.
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.

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.

Are you familiar with identity management tools like Okta or container platforms like Kubernetes?

Medium · system design and architecture

Approach

Choose a partition key and say what query it makes expensive.
Fix the scope first: who calls this, how often, and what they do when it fails.
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 would you drop to keep the system up under load?

Discuss basic Azure, AWS, or cloud infrastructure concepts.

Medium · system design and architecture

Approach

Fix the scope first: who calls this, how often, and what they do when it fails.
Name the failure you are designing for, then the recovery path.
Choose a partition key and say what query it makes expensive.

Follow-up

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

Explain how Single Sign-On (SSO) works and how it integrates into enterprise applications.

Medium · system design and architecture

Approach

Choose a partition key and say what query it makes expensive.
State the consistency you need, and where you are willing to be stale.
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 would you drop to keep the system up under load?

Walk through a technically difficult project from your resume and explain your architectural choices.

Medium

Approach

Say what you would check first and why it is the highest-information step.
State your assumptions explicitly before working the problem.
Work from the requirement backwards to the design.

Follow-up

What assumption would you test first?
How would you know your answer was wrong?

Describe how the CSS styling and modular components would be structured for a scalable web application.

Medium

Approach

Say what you would check first and why it is the highest-information step.
Clarify what is being asked and what a complete answer contains.
Work from the requirement backwards to the design.

Follow-up

What assumption would you test first?
How would you know your answer was wrong?

Design the batch ingest endpoint metering agents retry into

Hard · batch api · partial failure · deduplication

A customer-run agent posts usage events in batches of up to 1,000 to metering-ingest with a 30-second timeout and at-least-once retry of the whole batch. Each event carries event_id, idempotency_key, sku, quantity and occurred_at; the server adds ingested_at, and usage_event is partitioned daily on ingested_at with unique (ingested_day, tenant_id, idempotency_key). Design the endpoint: the request shape, what the response says when 900 events are new, 90 are duplicates and 10 are malformed, the status code, and the agent's algorithm on timeout. Then state the deduplication horizon and justify it against that unique constraint.

Approach

Fix the per-item outcome taxonomy first, because the status code follows from it: accepted, duplicate, and rejected with a permanent code. A duplicate is a success; reporting it as an error makes the agent either re-send revenue it already delivered or drop it.
Allow only permanent failures per item. A transient per-item failure inside a 200 invites the agent to discard that event, so anything transient escalates to a 5xx for the entire batch. A 200 is then a promise that every event not marked rejected is committed and durable.
Return 200 with a results array aligned by index and carrying the event id, so the agent can retry precisely the subset that needs it and quarantine the ten malformed events instead of hard-looping a poison batch forever. Cap the batch at 1,000 items and a byte size, with 413 beyond it and 429 with Retry-After for backpressure.
Deduplicate per event, never per batch: the agent may split, merge or reorder a retried batch, so a batch-level key matches nothing on the second attempt. The key is (tenant_id, idempotency_key), and the tenant comes from the resolved credential; a tenant id present in the body is compared against it, never trusted.
Size the horizon as a correctness parameter. The unique index includes the partition key, so it deduplicates only within one day: a retry that crosses midnight, or a replay run a week later, passes straight through it. A separate dedup store keyed (tenant_id, idempotency_key) with a TTL exceeding the agent's maximum retry window plus the longest replay you intend to support is what actually enforces the invariant, which makes its retention a correctness setting rather than a cost knob.
Order the commit against the response and the acknowledgement: commit then respond at the endpoint, and downstream commit the fold then acknowledge the message. Acknowledging first turns a crash into silently lost revenue with no error raised anywhere.

Worked solution (40 min)

Write the request body schema with the batch envelope and one event, and state which fields the server assigns rather than accepts.
Write the 200 response for the 900/90/10 case, showing three result entries, one of each outcome, with the rejected one carrying a permanent code.
Write the rule separating per-item rejection from whole-batch failure, and list which conditions fall on each side.
Compute the dedup horizon from the agent's retry window plus the replay window you support, and say where the dedup state lives and how it ages out.
Write the agent's pseudocode for timeout, 5xx, 429 and 200-with-rejections, four branches, and mark which branch may drop an event.
Trace the crash between commit and response, and between fold and acknowledgement, and say what each produces.

Expected result: A 200 with an index-aligned results array where duplicates count as success and rejections are permanent-only, transient problems escalated to a whole-batch 5xx, per-event deduplication keyed on (tenant_id, idempotency_key), and a published horizon larger than retry plus replay because the partitioned unique index only covers one day.

Verify it yourself

The agent can distinguish 'already counted' from 'never counted' for every event in the batch.
Exactly one branch of the agent's algorithm ever discards an event, and it is the permanent-rejection branch.
A retry crossing midnight is still deduplicated, and the mechanism named is not the unique index.
No crash point in the pipeline both commits work and loses it without an error.

Follow-up

The agent times out at 30 seconds having received nothing. What exactly does it do next, and what in your design makes that safe?
Ten events are rejected every hour for a week and nobody notices. What does the endpoint owe the customer beyond a per-item 4xx code?
A replay pushes 40 million events through this endpoint in an hour. Which part of your design degrades first?

Webhook workers leak until OOM and drop in-flight deliveries

Medium · memory leak · eviction · leases

webhook-delivery workers grow from 400 MB to a 2 GB limit over about 36 hours, are OOM-killed, restart, and repeat. Each restart abandons in-flight attempts, so webhook_delivery rows sit in in_flight until their leases expire and the backlog spikes. The live set measured after a forced full collection also grows. The fleet serves tens of thousands of subscriptions, several thousand of which have been failing for weeks. Give an ordered checklist, the measurement separating retention from fragmentation, and the fix.

Approach

Separate the two failure shapes with one measurement: track resident set size against the live set after a forced full collection. A live set that climbs monotonically is retention; a flat live set under a rising RSS is fragmentation, off-heap or native allocation, or an allocator that never returns pages. The stated symptom puts this in the first category, which rules out allocator tuning as a fix.
Characterise the curve rather than the total. Growth linear in uptime implies an unbounded structure keyed by something that keeps arriving; step growth implies buffering a large object. Correlate the slope against event rate and separately against the count of distinct subscriptions seen, because those two diverge and only one of them will fit.
Diff two heap snapshots an hour apart by retained size grouped by dominant root, not by allocation count, which is dominated by short-lived objects and will point at the wrong thing.
Expect a per-subscription map with no eviction: circuit-breaker or backoff state created on first failure and never removed, so the retained set grows with endpoints that have ever failed, and the several thousand permanently dead endpoints hold theirs forever.
Fix in two places. Bound the in-memory structure with a size-capped LRU or a TTL keyed on last use, and move state that must survive a restart onto the subscription or webhook_delivery row, since the worker holding it in memory is exactly why a restart loses it.
Repair the second-order damage separately, because it will outlive the leak: workers claim by compare-and-set with leased_until, so a bounded lease returns in_flight rows to pending on a known schedule, and a graceful shutdown releases leases instead of waiting them out.

Follow-up

The backlog spike after a restart is itself a thundering herd against customer endpoints. What stops the recovery from becoming a second incident?
Suppose the live set had been flat while RSS still climbed. Name two causes and the measurement that separates them.
How would you size the LRU, and what does a miss on an evicted circuit-breaker entry cost a customer whose endpoint is down?

Suggested practice checklist

For someone who has spent the last few years shipping features and reading other people's code, and who has not solved a timed problem from a blank file in a long time. Five days rebuild the primitives and the patterns that sit on them, working from invariants rather than remembered solutions, and the last two attach that back to the rest of the loop.

Day 1 — Rebuild the primitives by implementing them

Implement a dynamic array with doubling growth and an operation counter, then change the growth rule to add a fixed sixteen slots instead, and time both for n of ten thousand, a hundred thousand and a million. The fixed-increment version resizes n/16 times at O(n) each, so its total work is quadratic; doubling is what makes append amortised constant.
Implement a hash map with separate chaining and a load-factor resize, then insert ten thousand keys engineered to land in one bucket and record what happens to lookup time, so that average-case O(1) becomes a claim with a stated precondition rather than a reflex.
For dynamic-array append and hash-map insert, write down which cost is amortised rather than worst-case, which single operation pays the whole bill, and what a system with a hard per-operation deadline would have to do instead.

Deliverable: Two working implementations plus a timing table showing the input at which each structure's advertised complexity stops holding.

Day 2 — Arrays under an invariant: two pointers, sliding window, binary search

Solve longest-subarray-with-sum-at-most-K using a sliding window, then run it on an input containing negative numbers and watch it return the wrong answer: extending the window only moves the sum monotonically when every element is non-negative, and that precondition is the whole reason the technique works.
Write the binary search that finds the first index satisfying a predicate rather than an exact value, put the loop invariant above the loop in a comment, and verify termination on the two inputs that break careless versions: the empty range, and a range where every element satisfies the predicate.
Compute the midpoint as lo + (hi - lo) / 2 and write one line on why the obvious (lo + hi) / 2 is a genuine defect in a fixed-width integer type and a non-issue in a language with arbitrary-precision integers.

Deliverable: Three solved problems, each with its invariant written above the loop, plus one recorded input on which the sliding window is provably wrong.

Day 3 — Sorting, heaps, and the greedy argument that has to be proved

Solve one top-k problem three ways, by full sort, by a size-k heap, and by quickselect, then write the values of n and k at which each becomes the right choice, along with quickselect's quadratic worst case and why a randomised pivot makes that unlikely rather than impossible.
Implement bottom-up heapify and count sift-down steps to confirm it does linear work rather than n log n, because most nodes sit near the bottom of the tree and therefore move only a short distance.
Take interval scheduling by earliest finishing time and write the exchange argument out in full: given any optimal schedule, swapping in the earliest-finishing interval keeps it feasible and no smaller. Then construct the weighted variant where that same greedy fails and name what has to replace it.

Deliverable: A three-way top-k comparison with measured crossover points, one written exchange argument, and one counterexample to a greedy rule that looks almost identical.

Day 4 — Recursion, memoisation, and the step to a table

Take one problem with overlapping subproblems, such as edit distance or coin change, instrument the plain recursion with a call counter to show the blow-up, then add memoisation and re-count.
Convert the memoised version to a bottom-up table and state the two properties you relied on: each subproblem's result depends only on its arguments, and the dependencies form a DAG you can enumerate in order.
Rewrite one deep recursion with an explicit stack, then find the input length at which the original hits the interpreter's frame limit, which defaults to about a thousand frames in CPython, so you know when the rewrite is required rather than decorative.

Deliverable: One problem in three forms, naive, memoised and tabulated, with call counts for each and the input length at which recursion depth becomes the binding constraint.

Day 5 — Graphs, where most of the work is choosing the traversal

Implement BFS and DFS over one adjacency list, then answer for each which finds a shortest path in an unweighted graph and which you would use to detect a cycle in a directed graph, including why the in-progress versus finished distinction matters for the second.
Implement topological sort by in-degree, feed it a graph containing a cycle, and confirm the failure signature is that fewer than V nodes come out rather than an exception, then note that the order it produces is one of several valid ones.
Run a shortest-path search on a graph with a single negative edge weight and show the wrong answer, then write the precondition Dijkstra actually needs, non-negative weights, because it finalises a node's distance the first time that node is popped, and name the algorithm you would switch to and its own limit.

Deliverable: A small graph library with BFS, DFS and topological sort, plus two inputs that produce documented wrong answers under the wrong algorithm choice.

Day 6 — One day for everything that is not an algorithm

Sketch one system only to the depth a coding-heavy loop tends to reach: the endpoints, what the service stores, and the single query pattern that decides the schema. Stop at twenty-five minutes.
Prepare the project answer for an interviewer who codes, which means rehearsing the two levels they push to: the specific thing you built, and why you chose that approach over the alternative they will name. Open with a number and be ready to say what it excludes.
Prepare the answer to what you would do differently, choosing a real technical mistake with a specific fix rather than a complaint about process or staffing.

Deliverable: One design sketch at endpoint-and-schema depth, plus a project answer rehearsed to two levels of follow-up.

Day 7 — Solve out loud, under time

Do three timed problems at twenty-five minutes each in a plain editor with no autocomplete and no execution until the end, then tally separately the failures that were syntax and the ones that were approach, because those two numbers call for different fixes.
Narrate one solution from the first sentence, stating the approach and its complexity before writing any code, and rehearse the sentence you will use when you realise mid-solution that the approach is wrong.
Re-solve from blank the two problems you were slowest on this week and compare the times against the day they first appeared.

Deliverable: A recording of one fully narrated solution and a tally that separates syntax failures from approach failures.

'We rewrote it in a better framework' is not a story

A migration is a cost you chose to pay, not an achievement. The story is what the old system made expensive, what you measured before committing, what kept serving traffic during the cutover, and what you would have done if the numbers had come back flat. Without those, a rewrite reads as taste.

Can you tell me about the specific challenges you faced during this project on your resume?

Medium · behavioural and engineering judgement

Approach

Name the disagreement and how you resolved it with evidence.
Close with what you would do differently, concretely.
Give the blast radius: what could have broken, and what you measured.

Follow-up

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

Resolve a review disagreement over a quota check

Easy · code review · isolation levels · write skew · disagreement

A colleague's pull request enforces a per-tenant quota by selecting the current count and then inserting when it is under the limit. You flag it as a race. They reply that the transaction already runs at repeatable read, so the snapshot makes it safe, and the tests pass. Walk through taking that disagreement to a resolution: what you write in the review, what you demonstrate rather than assert, which fix you propose and why, and what you do if they still disagree after all of it.

Approach

Answer the claim precisely instead of restating your objection, because they have made a specific technical argument. In PostgreSQL, repeatable read is snapshot isolation; this is write skew, which snapshot isolation permits by design. Both transactions read a count that is stable within their own snapshot, insert disjoint rows that the other cannot see, and both commit, so the limit is exceeded by exactly the concurrency.
Demonstrate rather than cite. Two psql sessions, both BEGIN ISOLATION LEVEL REPEATABLE READ, both select the count, both insert, both commit: it succeeds. Repeat at SERIALIZABLE and the second commit fails with serialization_failure, SQLSTATE 40001. That takes two minutes, ends the argument without anyone conceding a position, and leaves an artefact for the next reviewer.
Offer the options with their costs rather than a verdict. Serialisable plus a retry loop on 40001 is correct but obliges every caller to retry and degrades under contention. An increment-and-compare on a counter row — update tenant_quota set used = used + 1 where tenant_id = $1 and used < limit returning used — is safe even at read committed, because a blocked updater re-evaluates the WHERE clause against the row version it finally locks, and zero rows returned means full. A unique or exclusion constraint that makes the surplus write fail is the third.
Name the plausible non-fix explicitly, since it is what usually gets merged instead: folding the count into the insert as insert ... select ... where (select count(*) ...) < limit is still racy under read committed, because the subquery cannot see the other transaction's uncommitted rows. It looks atomic and is not.
Say what you do if they still disagree: escalate the decision rather than the disagreement. Attach the reproduction, hand it to the service owner or a third reviewer, and state that you will not block the merge if the owner accepts the risk knowingly — and that you want that acceptance written down.
Close with the general lesson worth leaving in the review thread: a passing suite is weak evidence for a concurrency claim because it runs one request at a time. Ask for a test that runs two.

Follow-up

Write the counter-row version. Does your answer change if the quota counts child rows rather than a column?
Under serialisable, who performs the retry, and what does the API client see if the retry also fails?
This is the third disagreement with the same reviewer this month. What changes in how you review?

Ship metered billing with a named deduplication horizon

Medium · technical debt · deduplication · deadline pressure · detectors

Metered billing must be on in three weeks. usage_event is partitioned daily, so its unique index must include the partition key and deduplicates only within a day: a producer retry that crosses midnight, or a replay run a week later, gets through. A cross-partition dedup store is two weeks you do not have. Describe shipping with debt you named in advance: what you shipped, what you wrote down, the detector you added, the trigger and date for paying it off, and what you would have refused to ship under the same pressure.

Approach

Show you can separate the two kinds of debt, because that distinction is what the question actually probes. Debt that costs engineering time later is shippable on a deadline. Debt that silently corrupts a number a customer gets charged for is not shippable unless the corruption is detectable, and detectability is the whole negotiation.
Make the exposure narrow and measured rather than gestural. The hole is duplicates whose occurrences straddle a UTC day boundary, plus any replay older than partition retention. Measure it before arguing about it: how often an idempotency_key recurs at all, and the distribution of the gap between first and last occurrence. If the ninety-ninth percentile of that gap is four minutes, the residual risk is a small band around midnight and you can say so numerically.
Add the detector before the feature, not after. A nightly job counting keys that appear in more than one partition is one grouped scan over recent partitions, and it converts a silent overcount into a page. State what it costs to run and what it fires on.
Buy the cheap half of the real fix immediately: extend partition retention so the dedup horizon exceeds the producer's maximum retry window plus the longest replay you intend to support. That reframes retention as a correctness parameter rather than a storage cost, which is the sentence you need on record before someone optimises the bill.
Make repayment mechanical instead of aspirational: a dated entry with a named owner, plus a threshold that pulls the date forward — first detector hit above N events, or first customer dispute. Debt with a trigger gets paid; debt with only a date does not.
Answer the second half honestly by naming what you would refuse under identical pressure: the sealing path, because a sealed row is frozen and a wrong number there stops being a bug and becomes an adjustment line, a dispute and an audit question.

Follow-up

The detector fires on forty duplicate events for one tenant, and two of their invoices have already sealed. What happens next?
Whom did you tell that the billing numbers had a known hole, and in what words?
Finance asks you to cut storage by shortening partition retention. What do you say, and to whom?