Chapter 1Estimating a login feature

How to estimate a login feature: the hidden scope (password reset, 2FA, federation, rate limiting, sessions) and the questions to land before anyone votes.

Chapter 2Estimating an SSO integration

How to estimate an SSO integration: the work lives outside your codebase, in the identity provider's quirks. The questions to answer before you vote a number.

Chapter 3Estimating a payment integration

How to estimate a payment integration: sandbox vs live, refunds, webhooks, idempotency, PCI scope. The conversation that has to happen before any number lands.

Chapter 4Estimating a search feature

How to estimate a search feature: relevance, ranking, faceting and who owns the index. The questions that turn 'add a search bar' into a real estimate.

Chapter 5Estimating a notifications system

How to estimate a notifications system: channels, preferences, deduplication and delivery guarantees. Why 'send an email' quietly becomes a six-week project.

Chapter 6Estimating a file upload

How to estimate a file upload: size limits, virus scanning, resumability, storage and retention. The drag-and-drop is the easy part; underneath is the ticket.

Chapter 7Estimating a dashboard

How to estimate a dashboard: data sources, refresh cadence, time zones, drill-down, permissions. The chart is easy; the data pipeline behind it is the work.

Chapter 8Estimating a flaky test

How to estimate a flaky test: why it's two estimates, not one, and why a time-box beats arguing about points when the answer depends on what you find.

Chapter 9Estimating a bug with no repro

How to estimate a bug with no repro: you can't size the fix, only the search. How to time-box the investigation instead of voting on a story nobody can see.

Chapter 10Estimating a performance regression

How to estimate a performance regression: the work is mostly diagnosis, not the fix. How to size it when the cause is unknown and an SLO is on the line.

Chapter 11Estimating a customer-reported bug

How to estimate a customer-reported bug: the account on the ticket decides the size. How to separate the one-line fix from the response that eats the sprint.

Chapter 12Estimating a database migration

How to estimate a database migration: backfill, lock duration, rollout and rollback. 'Add a column' is one line of SQL; the estimate is about the second clock.

Chapter 13Estimating a data migration

How to estimate a data migration: moving data between systems, reconciliation and cutover. The transform runs in an hour; the cleanup runs for a quarter.

Chapter 14Estimating a framework upgrade

How to estimate a framework upgrade: why a major version bump is a project, not a ticket, and how to break it into stories you can actually size.

Chapter 15Estimating a dependency upgrade

How to estimate a dependency upgrade: the long-tail bump that hides N spikes in one ticket. Read the changelogs first, then estimate what you found.

Chapter 16Estimating a CI/CD overhaul

How to estimate a CI/CD overhaul: pipeline work has no demo, so slice by what can be deleted. The quarter-long story that hides on the backlog as a refactor.

Chapter 17Estimating a third-party API swap

How to estimate a third-party API swap: semantic gaps, dual-running and the assumptions baked into the old vendor's quirks. The new API only looks identical.

Chapter 18Estimating a rate-limit rollout

How to estimate a rate-limit rollout: thresholds, dry-run periods, customer comms. The code is half a day; picking limits nobody complains about is the work.

Chapter 19Estimating a design-system change

How to estimate a design-system change: token rollouts, deprecation paths, codemod coverage and the 200 call-sites that use the old component. Size the downstream.

Chapter 20Estimating an accessibility fix

How to estimate an accessibility fix: a11y issues are features you didn't ship the first time. Why to size the class of problem, not the single instance.

Chapter 21Estimating a feature-flag rollout

How to estimate a feature-flag rollout: staged percentages, kill-switches, gating metrics and the cleanup nobody schedules. A flag is a small product, not a deploy.

Chapter 22Estimating a research spike

How to estimate a research spike: a spike is a time-box with a deliverable, not a story. How to keep it from quietly becoming the work it was meant to scope.

Chapter 23Estimating a prototype

How to estimate a prototype: it's a deliverable sized for learning, not for use. How to keep the throwaway from becoming the production code nobody planned for.

Chapter 24Estimating an ML experiment

How to estimate an ML experiment: it's research with engineering attached. The model is easy, the data is the work. How to size a budget, not a forecast.