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Stonetusker Insights · Five-minute checklist

Developer Experience and Modernisation: 5-Minute Delivery Risk Checklist and Dates to Watch

Eight yes or no questions for teams whose pipelines and runtimes carry many products at once. Each one links to the page that explains it, and the dates below show which gaps carry a deadline.

For: Leaders of engineering and platform teams at cloud software companies, security vendors or enterprise internal systems groups.

By Subeesh Sivanandan, Founder, Stonetusker Systems · Updated 29 October 2026 · About 3 minutes to read · PDF version

The short version

  • Eight yes or no questions about delivery risk for developer experience and modernisation teams.
  • Ask your team to answer them in five minutes, from what they know today, with no checks run first.
  • A "no" marks a gap worth a closer look. The dates below show which gaps carry a deadline.

Eight questions for your team

  1. Have your own GitHub Actions, and the actions your workflows use, all moved off Node 20? Why it matters
  2. Have all build jobs moved off the macOS 14 runner image? Why it matters
  3. Does every service on .NET 8 or .NET 9 have an owner and a date for its move to .NET 10? Why it matters
  4. Has each CDK for Terraform stack been moved, or does it have a planned move? Why it matters
  5. Are most of your repositories built from shared pipeline templates? Why it matters
  6. Do fewer than one in ten pipeline runs need a rerun? Why it matters
  7. Do you know the median time from pull request opened to merged, for this quarter and for the same quarter last year? Why it matters
  8. Has someone compared the cost of hosted and self-hosted runners this year? Why it matters

Reading your answers

  • 7 or 8 yes: in good shape. Ask the questions again each quarter.
  • 4 to 6 yes: pick the first "no" that has a date attached, and give it an owner.
  • 3 or fewer yes: start with the dated items below, in date order.

Dates for your team

DateWhat changesDetails
10 December 2025 (passed)CDK for Terraform was archived, and HashiCorp ended its maintenance and development.1Radar: CDK for Terraform
1 January 2026GitHub reduced prices for GitHub-hosted runners by up to 39%. A planned platform charge for self-hosted runners was postponed, and it may return.2Radar: runner pricing
23 September 2026 (passed)GitHub removed Node 20 from its runners, which also ended the opt-out. Node 20 reached end of life on 30 April 2026.3,4Radar: Node 20
2 November 2026GitHub retires the macOS 14 runner image. The last two brownouts run on 29 and 30 October 2026, from 14:00 to 24:00 Coordinated Universal Time.5Radar: macOS 14 runner
10 November 2026Microsoft ends support for .NET 8 and .NET 9. .NET 10 is a long-term support release, supported until 14 November 2028.6Radar: .NET 8 and .NET 9

A note to forward to your team

Developer experience delivery risk checklist

Please answer the eight yes or no questions in this note from what you know today. It takes about five minutes.

Reply by [date] with:
1. The number of "yes" answers (out of 8)
2. The numbers of the questions answered "no"

Owner: [name]
Note: https://stonetusker.com/insights/checklist-developer-experience.html

Want a second opinion?

Answer the eight questions with your team first. If you would like a second opinion, reply with two things only: the number of "yes" answers and the numbers of the questions answered "no". Nothing else is needed. Within five working days you receive a short written note on what to do first. It is free and confidential, and a call is optional.

Ask for a second opinion

The button opens an email to subeesh@stonetusker.com with the subject and the numbers to fill in. You can also use the contact page, or reply to the email or LinkedIn message that brought you here.

Next page for your situation

Sources

  1. HashiCorp: CDK for Terraform repository (archived)
  2. GitHub: 2026 pricing changes for GitHub Actions
  3. GitHub: Node 20 is no longer available in GitHub Actions (23 September 2026)
  4. Node.js: Release schedule
  5. GitHub: macOS 14 runner image retirement
  6. Microsoft: .NET and .NET Core support policy

About the author

Subeesh Sivanandan is the Founder and CEO of Stonetusker Systems. He has worked for more than 27 years in release engineering, DevOps, platform engineering & embedded Linux. His career includes serving as the Principal Engineer & Manager of Release Engineering at Stryker, alongside earlier roles at Nokia, VeriSign, and IP Infusion. LinkedIn profile.

Revision history (recent 3 updates)

Version 1.0, 29 October 2026. Every fact on this page is checked against a minimum of two sources each month.

VersionDateChange
1.029 October 2026First edition