Tag: Troubleshooting the New Outlook: Fix Common Issues

New Outlook Book for Technicians

| August 13, 2025

New Outlook Book for Technicians

Introduction

If you’re searching for a book about New Outlook for just technicians, you’re in the right place!

This Patreon is where I’m publishing each chapter as I write it. Once the book is complete, I’ll release it as a downloadable eBook (PDF) here and on my business website www.callthatgirl.biz and publish it on Amazon.

Why I Wrote This Book

Last April, I was answering a question on LinkedIn about New Outlook. Halfway through my response, it hit me: I should write a book.

New Outlook is here to stay, and the questions about it are going to keep coming for years. The people who will need this book the most are:

  • Break/fix technicians

  • Computer techs (in-store or remote)

  • IT consultants and MSPs

  • Tech-savvy end users

My goal is to give you everything I know about manual migrations from Outlook Classic to New Outlook. Some “basic IT knowledge” won’t be included, simply because it’s assumed for this audience or it changes too quickly to keep up with in print.

What This Book Covers and What It Doesn’t

  • Most of the steps you’ll learn here are completed in Outlook Classic before the migration.
    Once all data is moved to an Exchange account, adding it to New Outlook is straightforward. Customization options in New Outlook are limited, so most of the work happens in the setup phase.
  • This book focuses only on manual migrations using Outlook Classic.
    If you want instructions on migration software, this book won’t cover it. Most Microsoft 365 vendors offer migration services for a fee, or software vendors provide tech support for their own tools.
  • Why manual migrations? Because while moving the data itself is often simple, managing the migration and finishing without pulling your hair out is the real challenge.

Why This Matters

  • Microsoft 365 changes almost daily, and New Outlook is still a teenager in tech years. With Outlook Classic reaching end-of-life in Q2 2029, the demand for migrations is going to outpace the number of available technicians.
  • Millions of users still run older versions of Outlook. Once New Outlook becomes the only option, many small businesses and PST file users will want to move to Exchange for better performance and full access to 365 features.
  • I saw this coming back in 2022 when one of my clients suddenly had New Outlook replace Outlook Classic without warning. Now, New Outlook is starting to allow PST files for some users (and soon, for all). But PST users won’t get the same smooth experience they’re used to and in some cases, you can’t even add a PST without a paid Microsoft license. I’ve seen it twice this month alone.

Real-World Challenges

The request for migration help doesn’t always come in the form of “Can you migrate my email?”
It’s more often:

  • “My calendar isn’t syncing with my phone.”

  • “I can’t do something I used to do in Outlook.”

Moving clients to Exchange is now my number one recommendation because:

  • It works better with New Outlook

  • It’s part of the Microsoft 365 “mothership”

  • It avoids many compatibility headaches

For example, just last month I had a client with a paid New Outlook license and an IMAP mailbox. His CRM wouldn’t integrate in New Outlook but it worked fine in Outlook Classic. We eventually had to roll him back. I’m discovering new limitations like this all the time.

A Bit of History

This isn’t my first Outlook migration book. Over a decade ago, I wrote one for Outlook Classic.
The core data migration process hasn’t changed much since 2010, but the tech world around it has and this new book reflects today’s challenges, cloud tools, and client expectations.

With New Outlook rolling out to most computers (unless blocked by admins), I’m already hearing:

  • “Nope, not loving it. I miss my old Outlook.”

  • “I like it, but… where’s my calendar?”

How to Read This Book

The chapters I’ve completed so far are free to read here on Patreon.
When the final version is ready, it will be fully edited, downloadable, and packed with real-world migration stories. I’ve always written in my own voice, mixing technical steps with field experiences and this book will be no different.

I am using some AI assistance for step-by-step clarity, but all stories, insights, and troubleshooting tips are my own.

About the Author

Lisa Hendrickson is a Microsoft Outlook and Office 365 expert with over 30 years of hands-on experience helping clients worldwide solve complex email, calendar, and contact challenges. Since 1996, she has specialized in guiding technicians, MSPs, IT professionals, and savvy end users through smooth migrations and custom configurations. Known for her clear teaching style, real-world tips, and deep technical knowledge, Lisa is the go-to resource for those making the leap from Outlook Classic to New Outlook. When she’s not troubleshooting or writing, you’ll find her sharing advice with her global tech community and empowering others to master their digital tools.

Contact: Lisa@callthatgirl.biz
Website: www.callthatgirl.biz

New Outlook Book

| August 10, 2025

New Outlook Book

Hi readers of my articles and posts here on my website. I’m Lisa Hendrickson, the owner of this site and Microsoft Outlook Expert & 365 Consultant. I decided to open this page up on my navigation bar for those curious about what a New Outlook Book would be about. In all my years of being a technician, I have also had a flare for writing, storytelling and how-to articles. In fact, it’s how I have done my marketing since 2009 on this website. You most likely searched something in Google, found content and maybe explored the banner and navigation tabs. All the content I publish is either about Outlook, New Outlook or another tech issue. Many times, I have full blown how-to and sometimes just a bit of an answer, due to the complications of the fix.

Since 2022, I have been diving into New Outlook learning as much as I could about the technical side of it. My clients will need me to help them migrate their data, help with contacts, phones and a variety of 365 issues that are now happening faster. In the spring of this year, I decided I had enough information to write a book about New Outlook. Not your ordinary book about how to use the product, but an in-depth tutorial of every step a technician will need to learn to help clients prepare for New Outlook.

I opened up a Patreon account and have been writing the chapters on that site. I started last March and am up to Chapter 8. I have two chapters left and after that, I will do all the step-by-step tutorials and then close and publish. The full eBook should be ready before Christmas. It will be available for $9.99 on Amazon and you can read the chapters now for free if you like.

Read below more about the book to give you an idea. My Patreon site requires no membership to read but if you want to show support and create a free account, I’d appreciate that.

https://www.patreon.com/c/NewOutlookForTechnicians

More about the book!

Introduction

If you’re searching for a book about New Outlook, you’re in the right place.

This Patreon is where I’m publishing each chapter as I write it. https://www.patreon.com/c/NewOutlookForTechnicians

Once the book is complete, I’ll release it as a downloadable eBook (PDF) here and on my business website www.callthatgirl.biz and publish it on Amazon.

Why I Wrote This Book

Last April, I was answering a question on LinkedIn about New Outlook. Halfway through my response, it hit me: I should write a book.

New Outlook is here to stay, and the questions about it are going to keep coming for years. The people who will need this book the most are:

  • Break/fix technicians

  • Computer techs (in-store or remote)

  • IT consultants and MSPs

  • Tech-savvy end users

My goal is to give you everything I know about manual migrations from Outlook Classic to New Outlook. Some “basic IT knowledge” won’t be included, simply because it’s assumed for this audience or it changes too quickly to keep up with in print.

What This Book Covers and What It Doesn’t

  • Most of the steps you’ll learn here are completed in Outlook Classic before the migration.
  • Once all data is moved to an Exchange account, adding it to New Outlook is straightforward. Customization options in New Outlook are limited, so most of the work happens in the setup phase.
  • This book focuses only on manual migrations using Outlook Classic.
  • If you want instructions on migration software, this book won’t cover it. Most Microsoft 365 vendors offer migration services for a fee, or software vendors provide tech support for their own tools.
  • Why manual migrations? Because while moving the data itself is often simple, managing the migration and finishing without pulling your hair out is the real challenge.

Why This Matters

  • Microsoft 365 changes almost daily, and New Outlook is still a teenager in tech years. With Outlook Classic reaching end-of-life in Q2 2029, the demand for migrations is going to outpace the number of available technicians.
  • Millions of users still run older versions of Outlook. Once New Outlook becomes the only option, many small businesses and PST file users will want to move to Exchange for better performance and full access to 365 features.
  • I saw this coming back in 2022 when one of my clients suddenly had New Outlook replace Outlook Classic without warning. Now, New Outlook is starting to allow PST files for some users (and soon, for all). But PST users won’t get the same smooth experience they’re used to and in some cases, you can’t even add a PST without a paid Microsoft license. I’ve seen it twice this month alone.

Real-World Challenges

The request for migration help doesn’t always come in the form of “Can you migrate my email?”
It’s more often:

  • “My calendar isn’t syncing with my phone.”

  • “I can’t do something I used to do in Outlook.”

Moving clients to Exchange is now my number one recommendation because:

  • It works better with New Outlook

  • It’s part of the Microsoft 365 “mothership”

  • It avoids many compatibility headaches

For example, just last month I had a client with a paid New Outlook license and an IMAP mailbox. His CRM wouldn’t integrate in New Outlook but it worked fine in Outlook Classic. We eventually had to roll him back. I’m discovering new limitations like this all the time.

A Bit of History

This isn’t my first Outlook migration book. Over a decade ago, I wrote one for Outlook Classic.
The core data migration process hasn’t changed much since 2010, but the tech world around it has and this new book reflects today’s challenges, cloud tools, and client expectations.

With New Outlook rolling out to most computers (unless blocked by admins), I’m already hearing:

  • “Nope, not loving it. I miss my old Outlook.”

  • “I like it, but… where’s my calendar?”

About the Author

Lisa Hendrickson is a Microsoft Outlook and Office 365 expert with over 30 years of hands-on experience helping clients worldwide solve complex email, calendar, and contact challenges. Since 1996, she has specialized in guiding technicians, MSPs, IT professionals, and savvy end users through smooth migrations and custom configurations. Known for her clear teaching style, real-world tips, and deep technical knowledge, Lisa is the go-to resource for those making the leap from Outlook Classic to New Outlook. When she’s not troubleshooting or writing, you’ll find her sharing advice with her global tech community and empowering others to master their digital tools.

Contact: Lisa@callthatgirl.biz
Website: www.callthatgirl.biz