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Azure DevOps Podcast

Message from Jeffrey Palermo: Howdy.  Welcome to my podcast.  I hope it helps you ship software more quickly and more reliably. Through the topics and guests, I hope your life is made easier. Let me know what topics would be helpful for you.

Podcast sponsor: Clear Measure We are a software architecture company that empowers our client's development teams to be self-sufficient: moving fast, delivering quality, and running their systems with confidence.

Sep 18, 2023

Jonathan, or J. as he’s known to friends, is a husband, a father, and the owner of Trailhead Technology Partners, a custom software consulting company with employees all around the world. He is also a Microsoft MVP in .NET and frequently speaks at software meetups and conferences. He doesn’t mind too much because he loves sharing what he’s learned, and it also gives him an excuse to visit any nearby National Parks, a passion of his, proven by the fact that he's currently made it to 56 of the 63 parks.


J. also has a passion for building community and has served on several non-profit boards over the years as a result. Currently, J. sits on the SoftwareGR board, a non-profit trade organization dedicated to building the software industry in West Michigan. He also runs Beer City Code, a software conference, and has served as president on that board for over a decade. J. loves hiking, reading, photography, and trying to see all the best picture nominees before the Oscars ceremony.


Topics of Discussion:

[4:18] J starting his own consulting company, Trailhead.

[4:55] The two categories that make up software architecture.

[5:54] J’s philosophy on when he would rewrite a legacy software system.

[10:52] The pros and cons of making small improvements over time.

[11:33] What is the strangler fig pattern, and how does that turn into a strategy for a software update?

[16:02] Bringing older ASP.NET applications up to .NET7.

[19:55] What is a reverse proxy?

[22:21] We reference the book Working Effectively with Legacy Code.

[25:08] In this process, do both of the applications just get access to everything, or do you have to do something specific?

[31:28] Architecturally, does this approach work in modernizing from older or other platform web applications?

[34:02] The concept of microfrontends.


Mentioned in this Episodes:

Clear Measure Way

Architect Forum

Software Engineer Forum

Programming with Palermo — New Video Podcast! Email us at

Clear Measure, Inc. (Sponsor)

.NET DevOps for Azure: A Developer’s Guide to DevOps Architecture the Right Way, by Jeffrey Palermo — Available on Amazon!

Jeffrey Palermo’s Twitter — Follow to stay informed about future events!

Architect Tips — Video podcast!

J. Tower on Twitter

J. Tower on LinkedIn


Basic YARP Sample

Strangler Fig Application


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