When I think about Microsoft Outlook, and especially trying to find an email, I feel it's like I'm in the realms of impossibility.
No matter what keyword I type, no matter what phrase I try to search for, it seems that Outlook puts everything in its path to stop me trying to find the correct email.
It's perfectly fine if the email had been sent or received the same day, or even the same week. You at least have a small possibility of retrieving the blasted thing. But leave it one, two, or heaven forbid, six months, then I simply wouldn't even bother. I'd have a better chance of scraping the email from my memory.
So I'm going to give Copilot a go to help find an email that a client sent me last month. The trouble is that I can't remember exactly what the email was about or when I received it. All I know is that it was regarding Excel training. Let's see if Copilot can help me track this little elusive thing down.
The Challenge:
- Find an email about Excel training
- Received roughly a month ago
- Can't remember the sender
- Can't remember the exact wording
- Outlook search versus Copilot: who wins?
The Search
Let's see if we can find that email. So, I open Outlook and, as I look at the top, I can see a search box that says "Search or ask Copilot". Let's give that a go, shall we?
I click on the box at the top. I type "Last week". Press Enter. Absolutely nothing.
However, when I click on the Search with Copilot button that has magically appeared at the top, I have Copilot on the right-hand side saying I have 42 emails of activity from last week. This is far less than I've actually received. I mean, who receives only 42 emails in a week?
However, now I can use Copilot on the right, and I use it to type in, "Which emails are enquiries?" I'm eager to hear which ones. Of course, enquiries.
Now this seems to work a little better. I have a list of genuine enquiries this week. I can see who they're from, and I can see if they're high priority or not, so Copilot genuinely has helped with this.
What Worked:
- Found genuine enquiries quickly
- Highlighted priorities
- Didn't require me to remember Outlook's mysterious search syntax
What Didn't:
- The original Outlook search returned absolutely nothing useful
- Copilot's email count didn't seem accurate
🏆 Round Score: Copilot 1 - Outlook 0
Outlook gets pinned to the mat.
The Calendar Appointment
Now, this is where things get a bit difficult, because I have other people managing my calendar and I'm the only one in the organisation, at the moment, who has Copilot Premium.
Let's see if it can find appointments, not just my own, but others'. I click on the Calendar button with a little bit of trepidation, and I'm going to try the normal search at the top, which has helped me in a limited way, but not really when it comes to time.
So, clicking on the Calendar, I go to the search bit at the top and I type in "next week". If the appointment has "next week" or "next" in it, then it would work, but I'm looking at appointments in November 2025.
This is anything but next week.
So that magic button, Search with Copilot, has appeared. Let me click on it and see what happens.
Now, I'll give Copilot its due. It does find appointments. It's not fast about it, but on the right-hand side I have my schedule for next week, giving appointments and so on.
I don't know about you, but no matter how often I try to type in the search at the top, and it used to be that in the old Classic Outlook you could do greater than or equal to today, etc., and it would work.
But this time, absolutely nothing.
So it looks, with the new Outlook, that Microsoft really foresaw the need to work with Copilot.
Which basically means you'll need to have a premium version of Copilot, or at least a basic version of Copilot, to use the search facility properly in the new Outlook.
I never really held up much hope for this anyway, but needs must.
What Worked:
- Copilot eventually found appointments
- Displayed my schedule clearly
- Understood natural language better than Outlook search
What Didn't:
- It wasn't particularly quick
- Standard Outlook search struggled again
- Date searches still felt unnecessarily difficult
🏆 Round Score: Copilot 2 - Outlook 0
Outlook is looking increasingly worried in the corner.
Contacts I Contacted in the Last Month
Now, moving on to Contacts, it seems that, with the search in this new Outlook, things are OK. I can click at the top and type in a name, and it comes up with the name. I type in a domain name such as @computertutoring.co.uk and it seems to find all the people with that domain name. No problem.
This is something basic. I can't believe that I'm actually trying it out in Outlook. It's absolutely crazy. However, the real challenge comes next.
I click in the search and type "last month" and, lo and behold, I get nothing back, and it's hardly surprising.
But let me try Copilot on the right. If I tell it to list all the contacts I dealt with in the last two months, and...
Yes, it hasn't given me the context within the Contacts list itself. However, Copilot has given me a list of all of the contacts that I've dealt with, or had emails with.
Now for the real test, because I don't think any of those people appear in my Contacts list. It would be great if Copilot could automatically add them into our Contacts list within Microsoft Outlook. Am I asking too much?
And it seems that I am asking too much.
It can't do this automatically, but I have a series of options to copy a list into Excel, save the list, and then import it.
Let's give it a go.
So, I'm OK with Excel. Let's see if we can copy and paste that list into Excel.
Not a good start.
The list is pasted all into one cell. Fortunately, I can use Copilot in Excel to tidy that up.
A quick prompt, which was:
"Format the text, or separate the text in cell A1 separated by commas so that first name, last name, and email are column headers, and then the subsequent data is below it."
...resulted in my data being converted into an Excel table that I thought I could now import into Outlook.
Let's give it a go.
The first obstacle: the file I created was an Excel file, and I can only import a CSV file. Making sure I got the correct CSV format, who knew there were multiple CSV options with different text encodings?
Eventually, Outlook said "Contacts imported".
Let me have a look to see where they are.
And yes, they're imported.
So Copilot did help by extracting the names, but I had to manually put them into an Excel spreadsheet. Then Copilot came to the rescue again.
What Worked:
- Copilot identified people I'd recently dealt with
- Excel Copilot transformed the mess into a usable table
- The contacts did eventually import successfully
What Didn't:
- Copilot couldn't add contacts directly into Outlook
- The export/import process felt unnecessarily manual
- CSV formats and text encodings nearly defeated me
🏆 Round Score: Copilot 3 - Outlook 1
Copilot gets the points, but Excel deserves an honourable mention for the assist.
To Do or Not To Do, With Copilot
Now, with To Do, or not To Do, I really expect Copilot to help extract the key tasks that are assigned to me.
The search in the To Do list is just like any of the searches in Outlook. Pretty pathetic, but let's give it a go anyway, so we can do a little comparison before and afterwards.
Just when I think Outlook couldn't get any more pathetic with its search, I click on To Do, I click at the top where it says "Search To Do", and I'm going to type in the name of a colleague who is pretty much the only colleague I work with all the time.
So I type her name in and...
"We searched high and low but couldn't find what you're looking for."
Ah, my mistake.
I need to make sure I click on "All", and it has found the name of my colleague, which is great.
Let's just try something else.
Let's type the word "urgent".
Apparently, there's nothing urgent.
I'm having to look for an exact word or an exact keyword, and to remember that?
Really?
Can I believe we're living in 2026 with Outlook?
I don't think so.
Let's see if Copilot will fight with us, on our side or against us.
But you know what?
When I'm hunting or searching high and low, I can't see Copilot as a list or a help at all within To Do in Microsoft Outlook.
But, not one to be deterred, let's see if we can find it in Copilot Chat.
The prompt that I used was:
"Find To Do items that I added this week."
And...
Just waiting for the results.
Still waiting.
Nothing.
It looked at basically all my To Do items and could not find anything that I had added this week.
Seeing as I use To Do on a daily basis, I find that hard to believe.
So I feel Copilot, on all parts of To Do, hasn't really helped.
I should call these tasks because I call them tasks in Outlook.
Let's give that one more go, shall we?
Still with a little hint of optimism.
I enter the prompt:
"Find all the tasks that I have to do today."
It is able to find my emails, but it is not looking at any actual tasks.
Shame, really.
What Worked:
- Outlook eventually found a colleague's name once I changed the filter
What Didn't:
- Copilot wasn't integrated into To Do in any meaningful way
- Natural language prompts failed repeatedly
- Task searches returned emails instead of tasks
- The whole experience felt surprisingly old-fashioned
🏆 Round Score: Copilot 3 - Outlook 2
Outlook claws one back simply because Copilot forgot to turn up for the match.
Conclusion
After each and every science experiment, there is a conclusion. After you've gone about your method, gathered your apparatus, and actually carried out the experiments, you then get the results and come up with the conclusion.
Well, I've included the results basically within the text above. However, my conclusion is that yes, Copilot can help you with Outlook.
In fact, I find it a lot easier to work with than typical searches within Outlook. I don't have to remember lots of long search strings, especially with the new version of Outlook.
However, on certain items, just when you think that it's on your side in a tag-team wrestling match, occasionally Copilot can turn and slap you in the face.
So, are we there yet with Copilot in Outlook?
Not yet.
But as long as your knowledge of other apps is good, then it can certainly help.
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Until next time, may your searches be accurate, your CSV files import first time, and your Copilot stay firmly on your side of the ring.