Microsoft Copilot – Outlook vs Bing Enterprise Chat

Please note that since the writing of this post in January 2024 that Microsoft has changed the name of the Copilot products and also the licensing. See this post in February for updated licensing information. Copilot: Which are which? (

Microsoft has allowed its MVPs access to Microsoft Copilot in a sandbox environment. Which means that it doesn’t have access to my data unless I upload it into that temporary tenant. However, it does afford me the opportunity to look at how Copilot has been implemented in each application and see how that contrasts with what I have available to me, today, as a small business.

For this comparison, I’m using an email that I created with my own brain this morning. I’ll put in into both Copilot for Outlook and later into Copilot with Bing Chat Enterprise to see how each performs as my assistant.

Copilot for Outlook

When creating an email, I get a new option. Instead of / to control my email editing options, now I have Draft with Copilot. To get started I click that option.

Draft with Copilot

I’m presented with a very small box in which to ask my Copilot to draft an email for me. The box does grow larger as I type or paste in content. Here I’m pasting in the email that I wrote this morning and I’m asking Copilot to draft a more professional sounding version.

Asking Copilot to improve an email for me

I have a few options where I can choose the length and tone of the response that I would like Copilot to generate.

Now I hit generate. It takes a few moments for it to generate a draft for me. Maybe 10 seconds in this case, but the time will vary depending on the complexity of the task I’m asking me assistant to do.

When it done the content is provided and we’re given a friendly reminded that what it has generated might be wrong and also a decision button set.

AI-generated content may be incorrect

In this case, since I provided the content, it’s very likely to be correct or at least as correct as I am. Below is the “improved version” generated by AI. And below that is the original content that I provided.


How did Copilot for Outlook do?

This was pretty simple test. Make my writing better was all that was asked. How do you think it did? Do you like the AI generated text better or less well than mine? Share your thoughts in the comments.

Bing Enterprise Chat

Today small businesses have access to Bing Enterprise Chat and since what you have today for free is much better than what you might have access to someday for a price, I want to see how well that Bing’s Copilot does as my assistant. I’m going to give it the exact save request and use the exact some content to see how different it is.

The first thing to know is that Bing Enterprise Chat isn’t built into your applications like Copilot for Microsoft 365 is. Instead, it operates outside of the apps in a single column. To launch Bing Enterprise Chat, I click the Copilot logo on the desktop near the time.

Click the Copilot logo to launch a new chat

Once it is open, I am free to start asking Bing Copilot to assist me. Below is what it looks like. Notice the green shield and word Protected. This means that Copilot is operating in my user context and is not sharing the information I upload outside of my tenant. Everything remains with the permissions that I have to access and save data. Companies might be surprised what the extent of that really is, because historically permissions have not been that tightly controlled.

Notice that instead of Formal, Casual, Short, Long, etc I have different options. Here, it’s just Creative, Balanced or Precise. Next, I’m going to make the exact same request in that Ask me anything…box at the bottom and we’ll see how this well this version of Copilot does at helping me edit my email.

Below is the text that was generated by Bing Enterprise Chat. Note that it starts off my reminding me that this information is private. Then because this is chat, it says Sure, I can help you improve this email. This version of Copilot is considerably more personality filled.

Your personal and company data are protected in this chat

Sure, I can help you improve this email. Here is a possible version that uses a more professional tone and structure:

Subject: Intune Learning Group – Course Details and Preparation

Dear Intune Learning Group Participants,

We are delighted to welcome you to the Intune Learning Group, a six-month course that will teach you how to use Microsoft Intune to manage your devices and applications. Your instructor for this course is Dave Shackelford, a certified Intune expert and trainer.

The course will start on January 17th and run until July 4th. It will consist of 12 biweekly sessions, each lasting two hours. The sessions will be held online via Microsoft Teams and will include lectures, demonstrations, and hands-on exercises.

To accommodate different time zones and preferences, we have created two groups for this course:

  • Group A: 3-5 pm Eastern Time (US and Canada)
  • Group B: 6-8 pm Eastern Time (US and Canada)

Participants from Australia and New Zealand will be automatically assigned to Group B. Participants from other regions can choose their preferred group, subject to availability. We aim to have no more than 12 participants in each group and to keep colleagues from the same company together.

Please reply to this email by January 10th and let us know which group you would like to join. If you do not have a preference or do not reply by the deadline, we will assign you to a group based on the criteria mentioned above.

Before the course begins, you will need to obtain the textbook for the course: Learning Microsoft Intune by Scott Duffy. This book is written by the project manager for Intune and covers all the topics and features that you will learn in the course. You can purchase the book online from this link and have it delivered to your address before the first session.

We will also create a Teams chat for each group, where you can communicate with your instructor and fellow participants, ask questions, share feedback, and access course materials. We will use the email address that you have provided for this course (the one this email was sent to) to add you to the chat and to send you the Teams meeting invites for the sessions. If you use a different email for Teams, please let us know as soon as possible.

To summarize, here are the steps you need to take to prepare for the course:

  • Reply to this email by January 10th and indicate your preferred group (A or B)
  • Purchase the textbook from this link and have it delivered before January 17th
  • Check your email for the Teams chat invitation and the meeting invites for the sessions

We look forward to seeing you in the Intune Learning Group and helping you master this powerful tool. If you have any questions or concerns, please do not hesitate to contact us.


Your name Your role Your contact details

How did Bing Enterprise Chat do?

I’m going to note that this version of Copilot took a lot more liberty with the content I provided it. Some of the content is no longer true. That’s one of the risks of using an AI. As humans we’ll have to get a lot better at proof reading (a skill I don’t have) and also be aware of how our different AI tools behave. AI’s are not all alike.

How do you think Bing Enterprise Chat Copilot did? Share your thoughts in the comments.

All we do is support IT professionals. Security communityMSP Legislation communityEndPoint, Defender and Lighthouse communityPeer groupscoursespapersBusiness consulting and more.

Leave a comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.