Interview guides · Character.AI

Character.AI Software Engineer Interview Guide

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

The 60-second brief

As a Software Engineer at Character AI, you are at the forefront of the generative AI revolution. You will be building the infrastructure and algorithmic foundations that allow millions of users to interact with sophisticated, human-like personas. Your work directly impacts the latency, quality, and scalability of the Character AI platform, requiring you to balance cutting-edge research implementation with high-performance production engineering.

The title spans product, platform and infrastructure work, and which of those the seat actually is decides whether design or algorithms carries more weight in your preparation. The posting rarely settles it; what the team is on call for usually does.

Focus areas

Make every write idempotent under client retries
Scope every query and cache key by tenant
Keep money in integer minor units

Overview

This role is both technically demanding and strategically significant. You will tackle complex challenges in data structures, state management, and algorithmic efficiency to ensure a seamless experience for a global user base. Success in this position requires a passion for pushing the boundaries of what is possible in conversational AI, coupled with the discipline to write clean, maintainable, and highly efficient code that operates at scale.

Where to focus your preparation

Treat the sections below as preparation areas and confirm the format with your recruiter.

Preparation focus

No round sequence has been reported for this company, so work the categories below and confirm the format with your recruiter.

What to demonstrate

Breadth across SQL, experimentation and product reasoning
Ability to state assumptions before choosing a method

How to prepare

Drill the practice exercises below and time yourself
Prepare three quantified stories about decisions you drove

Where candidates lose points

Checking a quota with a select and then writing

Under read-committed isolation, two concurrent transactions both observe a count below the limit and both insert, so the limit is exceeded by exactly the concurrency. Repeatable read does not rescue it either: it provides a stable snapshot, and this is write skew, which snapshot isolation permits by design. The options are serialisable isolation, which detects the conflict and aborts one transaction with a serialisation failure and therefore obliges the caller to retry; a single statement with the predicate inside the write; or a constraint that makes the surplus insert fail outright. The reason this pattern survives review is that it is correct in every test that runs one request at a time.

Paginating a growing table with limit and offset

Two unrelated defects share the idiom. Correctness: rows inserted or deleted between page requests shift the window, so a consumer walking an export skips rows and sees others twice, which for a customer-facing sync is silent data loss rather than an error anyone notices. Cost: the database still produces and discards the skipped rows, so page N costs time proportional to N times the page size and a deep page on a large table degrades from milliseconds to seconds. Keyset pagination over a stable, unique, indexed ordering -- where (created_at, id) < ($1, $2) order by created_at desc, id desc limit $3 -- is constant-cost per page and immune to shifting, on the precondition that the cursor columns never change value for a row, which disqualifies updated_at as a cursor.

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

Given a list of 6-letter strings, implement a function to guess a secret word from the list.

Medium · data structures and algorithms

Approach

Restate the input: its shape, its size, and what is guaranteed about it.
Walk one small example through your approach before writing the whole thing.
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?
Which test case would catch an off-by-one here?

Design a map-like class that supports insertion with timestamps and retrieval based on a key and a timestamp threshold.

Medium · data structures and algorithms

Approach

Walk one small example through your approach before writing the whole thing.
Name the brute-force solution and its complexity before improving on it.
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?
Which test case would catch an off-by-one here?

Implement a function to provide feedback (e.g., correct letters/positions) when comparing a guess to a secret word.

Medium · data structures and algorithms

Approach

State the target complexity and say which constraint rules the naive version out.
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.

Follow-up

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

How would you modify your data structure to handle unordered timestamps during insertion?

Medium · data structures and algorithms

Approach

Restate the input: its shape, its size, and what is guaranteed about it.
Choose the data structure from the access pattern, not from familiarity.
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?

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

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.
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.
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.
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).
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)

Write the null policy as three lines of prose first, one per case, and keep them beside the output.
Emit 2n endpoint tuples (timestamp, delta, run_id) and sort on the key (timestamp, delta) so -1 precedes +1.
Sweep, tracking cur, peak, peak_at updated only on a strict increase, and the first run_id whose +1 takes cur to C+1.
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.
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?

Paginate a tenant's delivery export without skipping rows

Easy · keyset pagination · indexing · multi-tenancy

A customer exports webhook_delivery: delivery_id (bigint identity), subscription_id, tenant_id, event_id, status, attempt_count, next_attempt_at, created_at, delivered_at, updated_at. The endpoint runs select ... where tenant_id = $1 order by created_at desc limit 100 offset $2, and customers report rows missing from exports taken while new deliveries are being inserted. Write the replacement query and the index that supports it, paging a tenant's deliveries newest first at constant cost per page. State why updated_at cannot be the cursor column.

Approach

Name the defect precisely. OFFSET is a position in a result set that is recomputed on every request, so a row inserted ahead of the window shifts everything back by one and the next page starts after a row the client never received. Nothing errors and no identifier gap appears, so the loss is silent.
Replace the position with a value predicate over a stable, unique, indexed ordering: where tenant_id = $1 and (created_at, delivery_id) < ($2, $3) order by created_at desc, delivery_id desc limit 100. The row comparison is load-bearing: created_at alone is not unique, so ties straddling a page boundary are dropped or repeated, which is the same bug in a smaller window.
Index (tenant_id, created_at, delivery_id). PostgreSQL scans a btree in either direction, so an all-DESC ORDER BY is served by an ASC index read backwards and no DESC modifiers are needed; they only matter when the ORDER BY mixes directions. Confirm the plan has no Sort node above the index scan, or the LIMIT stops being an early exit.
Price both forms: keyset is one index descent plus 100 adjacent leaf entries per page, constant regardless of depth, while OFFSET still produces and discards every skipped row, so page N costs time proportional to N times the page size and a deep page on a large table goes from milliseconds to seconds.
Rule out updated_at as the cursor from the precondition, not from taste: a cursor column must never change value for a row already paged past. updated_at moves on every delivery attempt, so a row the client already emitted re-enters a later page and is exported twice. created_at and delivery_id are immutable, which is the whole qualification.

Follow-up

The client wants a snapshot as of one instant rather than a live tail. Compare a repeatable-read transaction held open, an added created_at <= $snapshot bound, and a materialised export table.
A retention job deletes deliveries older than 90 days. What does a client mid-walk see, and does keyset pagination help at all?
The customer wants to resume an export from yesterday's last cursor. What must be true of the cursor for that to be safe?

Model credential revocation so history survives the delete

Easy · soft delete · partial indexes · check constraints · audit history

tenant_api_key stores key_id, tenant_id, workspace_id, name, key_prefix, secret_hash, scopes text[], status (active, revoked, expired, compromised), auth_version, created_at, expires_at, last_used_at, revoked_at, revoked_reason. Rotation inserts a new row and revocation never deletes, because an incident review asks which credential served a request last quarter. Write the constraints that enforce: a label is unique only among a tenant's live keys, revoked_at and status can never disagree, and scopes is never empty. Then write the authentication lookup predicate, and name one column in this table that must stay out of it.

Approach

Reach for a partial unique index rather than a plain UNIQUE: create unique index on tenant_api_key (tenant_id, name) where revoked_at is null. Any number of revoked rows may share a label, the live namespace stays unique per tenant, and the revoked majority is not in the index at all, so it stays small on a table that only grows.
Tie the nullable timestamp to the enum so the two cannot drift: check ((revoked_at is not null) = (status in ('revoked','compromised'))) and check ((revoked_at is null) = (revoked_reason is null)). A revocation that records no reason is the one an incident review cannot use.
Write the emptiness check as check (cardinality(scopes) > 0), not array_length(scopes, 1) > 0. array_length returns NULL for an empty array, a CHECK constraint passes when its expression is NULL, so the array_length version accepts exactly the value it was written to reject.
Make the lookup a single index probe with every liveness condition inside it: where secret_hash = $1 and revoked_at is null and (expires_at is null or expires_at > now()) and auth_version = $2, backed by a unique index on secret_hash. Nothing is filtered in application code, so there is no path that forgets a clause.
Keep last_used_at out of that predicate. It is written asynchronously and is allowed to lag by a minute, so it is a usage signal; feeding it into an authorisation decision makes the decision depend on a write that may be late, batched away or lost.
Flag the modelling smell while you are here: expired is derivable from expires_at < now(), so storing it as a status obliges a job to keep it true and guarantees the column is wrong between the expiry instant and that job's next run. Derive it in the predicate; keep the stored status for states that are decisions rather than clock readings.

Worked solution (20 min)

Create the table with all three constraints on a scratch database and insert two revoked rows sharing (tenant_id, name); the partial index should accept both.
Insert a second live row with that same name and confirm the violation names the partial index.
Run update tenant_api_key set revoked_at = now() leaving status = 'active' and confirm the CHECK rejects it; then try insert ... scopes = '{}' against both the cardinality and the array_length forms and note that only one rejects it.
Run explain (analyze, buffers) on the lookup predicate for a live key and confirm an index scan on secret_hash with rows removed by filter equal to zero.

Expected result: A partial unique index on (tenant_id, name) where revoked_at is null; check ((revoked_at is not null) = (status in ('revoked','compromised'))); check ((revoked_at is null) = (revoked_reason is null)); check (cardinality(scopes) > 0); a single-probe lookup on secret_hash plus revoked_at, expires_at and auth_version; last_used_at excluded, with a note that 'expired' should be derived rather than stored.

Verify it yourself

Two revoked keys with the same name insert cleanly; a second live one does not.
The array_length form of the emptiness check accepts an empty array and the cardinality form rejects it.
No statement anywhere in the design deletes or updates a revoked row.
Revoking a key touches exactly one row and takes effect on the next lookup with no application-side filtering.

Follow-up

Rotation issues a replacement while the old key stays live for a 30-day overlap. What does the uniqueness rule become, and what does the UI show to tell two same-named keys apart?
A password reset bumps the principal's auth_version. No row in this table changed. How does the next request fail, and what query counts how many keys that bump just killed?
A key turns up in a public repository. Which columns let you find it, and what do you write to the row?

Ship three breaking-looking changes without breaking pinned SDKs

Hard · versioning · backward compatibility · deprecation

GET /v1/runs/{id} returns status from the set queued, leased, running, succeeded, failed, timed_out, cancelled. You must add the terminal state lost, add an optional billable_seconds field, and start rejecting name values over 64 characters that were previously accepted. Clients are generated SDKs pinned inside customer build pipelines you cannot redeploy or reliably contact, some with strict deserialisers. Classify each change as compatible or breaking and justify it mechanically, then give the rollout: the versioning scheme, the transform old clients receive, the telemetry, and the sunset process.

Approach

Classify against a deserialiser rather than against intuition. A new enum value breaks a generated client that validates the enum or switches exhaustively; a new optional field breaks one generated with additionalProperties false; tightening validation breaks every caller already sending an 80-character name even though no field moved. All three are breaking for some real client, and that is the answer, not a technicality.
Choose the versioning axis on maintenance cost. A path version forks the handler, and each subsequent change multiplies the fork. A date-pinned version header, defaulted per credential at first use and pinned thereafter, keeps one internal model and a chain of ordered response transforms, so the handler stays single and the transforms compose.
Write the downgrade honestly. Older versions have no lost, so the transform maps it to the least-wrong existing value and the changelog says which; mapping it to failed asserts an outcome nobody observed, so pair it with a reason field the old version already exposes rather than inventing a field, and keep the mapping in one documented table instead of a conditional inside the serialiser.
Sequence the validation tightening separately from the payload changes: first measure how many tenants send names over 64 characters, then warn for a stated window with a Deprecation header and a non-fatal warning code, then reject only for versions dated after the change, never retroactively for a pinned client.
Deprecate from evidence, not from announcement: per-version, per-tenant, per-credential request counts from the gateway, a Sunset header carrying the date, direct contact for the handful of accounts that make up most of the tail, and short scheduled brownouts before the cutoff so the clients nobody can reach fail on your calendar rather than during their release.

Worked solution (40 min)

Write the three-row classification table with the client-side mechanism that breaks in each case, not just a verdict.
Pick the versioning scheme and write the header, the default-and-pin rule for a new credential, and where the transform chain sits relative to the handler.
Write the lost mapping for pre-change versions as an explicit table entry plus the changelog sentence a customer reads.
Write the validation timeline with four dated steps, and mark which one is visible to clients that never change their version.
Write the deprecation plan: the telemetry query by version and tenant, the headers, the brownout schedule, and the fallback for the largest holdout.

Expected result: All three changes classified breaking with the mechanism named, a date-pinned version header with one internal model and ordered downgrade transforms, a documented lost mapping, validation tightened only for versions after the change, and a sunset driven by per-version traffic with brownouts.

Verify it yourself

No change is called additive without naming the client behaviour that makes it safe.
A client that never changes its version header sees no behaviour change from any of the three.
The plan names a measurement that tells you when sunset is safe.
The lost mapping is stated once, in a table, not implied by serialiser branches.

Follow-up

Which step of your rollout cannot be rolled back cleanly once a client has depended on it?
A tenant pinned to a sunset version breaks their build the morning after the cutoff. What in your plan already lets you resolve it within an hour?
Your transform chain is now six versions deep. What stops it becoming the fork you were avoiding?

Build a resumable usage export the customer can reconcile against

Medium · pagination · cursors · late data

Customers reconcile invoices against usage_event (event_id uuid, tenant_id, workspace_id, environment, sku, quantity numeric(20,6), idempotency_key, occurred_at, ingested_at, source_service, request_id), partitioned daily on ingested_at. The current export is ?page=N&per_page=1000 ordered by occurred_at, and a customer syncing hourly reports rows that never appear in their export but do appear on their invoice. Design the replacement: the ordering, the cursor's contents, the index it requires, and the rule deciding where a page stops. State what the client does on a timeout and on a cursor older than retention.

Approach

Separate the two defects in the current shape. Offset makes the database produce and discard N * per_page rows, so page cost grows linearly and a deep page degrades from milliseconds to seconds. Concurrent inserts also shift the window between requests, so a walker skips rows with no error raised anywhere, which for a customer sync is silent data loss.
Order by ingestion, not by occurrence. During a replay events arrive hours out of occurred_at order, so a consumer holding an occurred_at high-water mark can never see a late event that falls below it; (ingested_at, event_id) is the only ordering under which 'everything after my cursor' is a complete statement.
Page with a row comparison: where tenant_id = $1 and (ingested_at, event_id) > ($2, $3) order by ingested_at, event_id limit $4, backed by an index on (tenant_id, ingested_at, event_id). That seeks directly to the resume point, so every page costs the same regardless of depth.
Trail the head of the table. With ingested_at defaulting to now(), which is transaction start time, a long insert transaction receives an earlier timestamp and becomes visible after a reader has already passed it. Cap each page at ingested_at <= now() - delta, with delta larger than the longest write transaction as bounded by statement_timeout and idle_in_transaction_session_timeout, or the export skips exactly the rows written under load.
Make the cursor opaque and self-describing: base64 of the timestamp, the event id and a fingerprint of the filters, rejected when the filters differ from the current request. Return 410 with a cursor_expired code once the cursor's partition has been dropped, so the client restarts from a known time instead of resuming into a hole.
Keep a page a pure GET with no server-side consumption, so a timeout is resolved by retrying the identical cursor.

Follow-up

The customer asks for a total count alongside the first page. What do you offer instead, and why is an exact count both expensive here and wrong by the time it is read?
How would you let a customer re-read a window they have already consumed without giving up the forward-only cursor?

Hourly rollups merge one hour and lose another

Easy · timezone · rollups · reconciliation

Reconciliation flags one tenant on one day. Summing usage_event.quantity by hour of occurred_at gives 24 non-empty hours, but usage_rollup_hourly holds 23 rows for that tenant, workspace and SKU, one of which carries roughly the sum of two adjacent hours. Other days reconcile exactly, and the affected date matches a civil-time transition. hour_start is documented as truncated to the hour in UTC. You have both tables, the rollup job source, and its runtime environment. Give an ordered checklist, the mechanism, and the correction path for a day that may already be sealed.

Approach

Bisect by dimension until one cell explains the whole difference: tenant, then day, then SKU, then hour. A defect confined to a single transition date already rules out deduplication and late arrival, both of which are indifferent to which hour an event lands in.
Read the truncation with its precondition stated: date_trunc on a timestamptz value is evaluated in the session TimeZone, not in UTC. If the job connects without pinning that setting, it inherits the server or container default.
Follow that to the collision: in a zone that observes daylight saving, two distinct UTC hours map to the same local wall-clock label at the autumn transition, so both fold into one key under the unique constraint on (tenant_id, workspace_id, sku, hour_start) and their quantities sum into one row. At the spring transition a label never occurs and the row is simply absent.
Confirm from data rather than from reading code: run the same aggregate twice, once with the session pinned to UTC and once with the job host zone, and check that the second reproduces the stored rollup exactly.
Fix at the source by pinning the connection to UTC explicitly, or by truncating on occurred_at AT TIME ZONE 'UTC', rather than relying on a default that differs between a developer machine, CI and production.
Correct according to status, not convenience: an open hour is recomputed with revision incremented, a sealed hour is frozen and the difference becomes an adjustment line on the next invoice with voided_by_line_id pointing at the line it reverses.

Follow-up

The same job also emits a daily figure for a dashboard. Why can a correct hourly rollup still produce a wrong day, and what does the tenant's billing timezone have to do with it?
How would you detect this class automatically rather than waiting for reconciliation, given that it only manifests twice a year per zone?

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.

Risky changes and the reversal path

For anything that touched live traffic, be ready to say how you would have undone it: a flag, a staged rollout, dual writes with the old path still authoritative. Once the old column is dropped or the source rows are overwritten there is no reverse, so name what you kept a copy of and for how long.

Reverse a webhook ordering decision after measuring its cost

Medium · reversing decisions · head-of-line blocking · at-least-once · api contracts

You argued for strict per-subscription ordering in webhook-delivery, which means one in-flight attempt per subscription. It shipped. Three months later a single unresponsive endpoint holds one subscription's queue at a six-hour backlog, and two customers report events arriving out of order anyway once their own retries are counted. Describe a decision you reversed: what you originally optimised for, the measurement that changed your mind, what the reversal cost in engineering time and customer change, and how you told the people who had already built on the original guarantee.

Approach

State the original decision as a trade you made knowingly. Ordering across a network requires a single in-flight attempt per subscription, and its price is head-of-line blocking whenever one endpoint is slow. 'We priced it wrong' is a much stronger opening than 'we did not realise', and it is usually the true one.
Bring the measurement that flipped it, not the anecdote: backlog age at the ninety-ninth percentile per subscription, the share of subscriptions where one slow endpoint gated an otherwise healthy queue, and the delivery throughput lost to serialisation. A reversal justified by complaints is indistinguishable from a reversal justified by fatigue.
Name what you learned about the guarantee itself, which is the engineering content of this story. At-least-once delivery means a retried event already arrives after newer ones and the consumer already must be idempotent, so a guarantee the customer has to defend against anyway was never worth what it cost to provide.
Describe the migration, because reversing a published contract is the hard half and the part candidates skip. Parallel attempts behind a per-subscription flag, a monotonically increasing sequence number added to the envelope so order-sensitive consumers can sort or discard, documentation that states at-least-once and unordered in those words, and a deprecation measured in quarters because the client is a pinned SDK inside a build pipeline you cannot see or redeploy.
Give the cost in the two currencies that matter: engineer-weeks, and how many customers had to change code. Then say who you told before it shipped rather than in a changelog afterwards, and which large customer you left on the old behaviour and for how long.
Close with the signal you now weight differently, stated as something you would do earlier next time: measuring the blocking cost on the slowest decile of endpoints before committing to the guarantee, rather than after a customer noticed.

Follow-up

A customer insists they need ordering. What do you offer them that is not global serialisation?
How did you choose the deprecation window given that you cannot see or redeploy the clients?
What would have to be true for you to reverse back?

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?

Unblock an engineer on a job run that finished twice

Easy · mentoring · fencing tokens · lease expiry · debugging method

An engineer two weeks into the team brings you a job_run row showing status succeeded with an exit_code written by a worker declared dead ten minutes earlier; the retry attempt also shows succeeded. They have spent a day adding logging and are no closer. You have twenty minutes and you do not want to take the keyboard. Describe how you unblock someone: the question you ask first, what you let them find themselves, the concept you name and when, and how you check the next day that they own the fix rather than having watched you produce it.

Approach

Ask what they expect rather than what they see: which statement set status to succeeded, and what did it check before writing? That question points directly at the update's WHERE clause, which is where the answer lives, and it costs them nothing to answer, so it does not read as a test.
Let them build the timeline themselves from the row: queued_at, started_at, leased_until, finished_at and worker_id, on both the original run and the retry. Two different worker_ids with a lease expiry between them tells the whole story, and they will see it before you say it.
Name the concept once the evidence has earned it. A lease bounds time; it does not prevent a write. The store has to reject a stale writer, which means the update carries a fencing token the row compares — update job_run set status = 'succeeded' where run_id = $1 and lease_token = $2 and status = 'running' — and a long garbage-collection pause or a brief partition is enough to produce what they are looking at.
Point at the second, less obvious half and let them decide it: 'lost' exists in the status enum precisely so a run whose worker vanished is not recorded as failed, because failed asserts an outcome nobody observed and the system then bills and retries on that assertion. Ask them what these two rows should have said.
Leave them with the next step rather than the patch — a test that kills the first worker after the sandbox exits and before the row is written — and say when you are available again, so the offer is real rather than polite.
Check ownership the next day by what they produced, not by asking if it went well: a test that reproduces the window proves they understood it; a test that only asserts the new WHERE clause proves they copied it. Ask them to explain it to a third person and listen for whether the explanation is theirs.

Follow-up

They propose a longer lease instead of a token. What do you say, and what breaks when legitimate runs last thirty minutes?
How can you tell whether your explanation landed or they simply deferred to you?
The same engineer hits a variant of this next month. What did you fail to teach the first time?