Inside new Natural Language Search for Outlook

Microsoft is hyping natural language searches in Outlook for Windows and Mac, so we dug down to see how it works and for whom.  There’s a lot of ‘gotchas’ overlooked in the boasting.

According to Microsoft, Outlook now has better searches:

“With Natural Language in search, you simply type the way you would ask a question/statement, no fancy syntax needed. We take the guess work out of choosing the right words and understand your intents expressed naturally. “

Sounds great but at Office Watch we don’t take Microsoft’s promises at face value. We did some testing of Natural Language searches and discovered there’s a lot of catches to get this feature.  Even then it might not work.

How Natural Language Outlook Search works

The concept is typing a more human like phrase which Microsoft’s systems will convert into a machine-understood search.

Here we’ve searched for ‘unread emails’ which Outlook has converted into a search for message with the read flag OFF. 

Example from Outlook for Mac.  The ‘original query’ offered is the non-natural search for those two words.

The old search would have looked for messages with the terms ‘unread’ and ‘emails’ like this, on the same mail folder:

To and From messages

The terms ‘To … ‘ or ‘From … ‘ work to find names that start with the name given.

For example:  ‘From ton’  will show message from ‘Tony’ ‘Jim Tonlin’ but not ‘Anton Readton’. That includes email addresses too.

With Attachments

Natural Search will find messages ‘with attachments’ just using that phrase.

‘with pdf attachments’ will find PDF’s attached to messages.

There’s some flexibility:

‘with doc attachments’ finds Word, Excel, PowerPoint and PDF files, perhaps other formats too.

‘with word attachments’ finds Word .docx .doc .dot .dotx etc.

But ‘with ppt attachments’ doesn’t work as a natural language search?

‘with jpeg attachments’ finds both .jpeg and .jpg files.

Searches can be combined for example “From Scott with pdf’ the ‘attachment’ term doesn’t seem necessary in this context.

More filters and saving

Click the inverted pyramid at right of the search box to see the usual collection of specific filters and ‘Save Search’.

Note that the Natural Language search is left in ‘keywords’.  The search hasn’t been converted into its machine equivalent with terms in the ‘From’ and attachments fields.


Here’s Microsoft’s list of natural language search examples.  They all should work but some are unnecessarily wordy.  ‘Emails with attachments’ can be just ‘with attachments’ if the search scope is the mailbox or a mail folder.

The terms mail, email, mails and emails all work in a natural language search but ‘message’ or ‘messages’ revert to a normal search.

ScenarioExample Queries
Find mail from someoneFrom John
Find email where someone is either on the To or CC list  To John
Find emails from someone  to someoneFrom John to Mary
Find email sent within a specific date range  From John last weekend
From John last month
Emails from previous week
From John on Monday
From John in June
From John between 8/5 and 8/15
From Mary after June and before July
Find email from/to someone with attachment  From John with ppt
Excel shared by Mary
To John with attachment
Attachment from Debra last week 
Find emails from someone about a keyword Emails from John about planning 
Find emails with attachmentsEmails with attachments
Find unread emailsUnread emails
Microsoft supplied examples of Outlook Natural Language search.

There are many limitations on Natural Language search.  Some will be lifted over time as the feature spreads to more languages and regions.  Others are there to stay.

Limitation: software

According to Microsoft, Outlook Natural Language Search is available in Outlook for Windows Insider v2102 build 13801.20084 (8 Feb 2021).  We’ve waited a few weeks but the feature hasn’t appeared.  You might have better luck.

The examples in this article are from Outlook 365 for Mac.  Even then, Natural Language search only appears in the ‘New Outlook’ interface with limited ribbon and simplistic options. 

Limitation: mailboxes

An Microsoft 365 hosted, Exchange Online or mailbox is required.

Limitation: language and region

For the moment, Natural Language search is only in English language and the Region setting is ‘United States’.

It’s possible the feature is currently limited to devices running in the USA.

Limitations: the usual cloud stuff

Lastly, this is a cloud feature so the usual limits apply. Each search you type is sent to Microsoft’s servers for interpretation. 

There has to be an internet connection, obviously.  Searches could be logged by Microsoft and shared with ‘the authorities’, a concern for any organization dealing with private data.

New Search bar in Outlook
Search Scope in Outlook
All mailbox limits (& how to find yours) in and Microsoft hosting

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