AI email assistant for sole practitioners in Australia: what to look for

Usually yes, through an add-in, which is a small app that opens beside your email. Microsoft's page on using add-ins in Outlook shows how to find one in new Outlook: select More apps, then Add apps, then search the store.

Three things to check first:

• Who installs it. Microsoft says some add-ins are installed by your email administrator. If an IT provider set up your Microsoft 365, you may need them for this step.
• Your account type. If your email is a personal Outlook.com address, check the listing to see what account the add-in needs.
• What it can see. Microsoft says most add-ins only have access to the email you are working in, that an add-in might send data to its own service, but only to complete the task you asked for, and that you are asked for consent the first time an add-in needs your data. A tool that sorts your whole inbox has to see more than one email, so read the consent screen properly.

Microsoft has its own option too. Its Copilot Business page says Copilot is built into Outlook and sells it as an add-on to a qualifying Microsoft 365 plan, or in a bundle. Microsoft also says people with an eligible business subscription can use Copilot Chat in Outlook without the add-on, with more limited access to data. Our guide to Microsoft Copilot in Outlook vs a legal AI add-in sets out the differences.

You are the whole IT committee, so ask these before you connect a client mailbox. Get the answers in writing and keep them on file.

• Where is the app and its database hosted?
• Where is the AI processing done, and is anything kept there afterwards?
• Is client correspondence used to train AI models?
• Can the tool send an email without me?
• Is there a record of what it did?
• What happens to my data if I cancel?

1. Write down which email job takes the most time: sorting, drafting or chasing.
2. Confirm it runs on the Outlook you use, whether that is Windows, Mac or the web.
3. Confirm replies wait for you, and that it can't send by itself.
4. Get the data answers above in writing.
5. Check it works with your practice management system, or works without one if you don't have one.
6. Check whether the price is per practitioner, whether it includes GST, and whether there is a minimum term.
7. Trial it for a week on real email, and include your busiest day.
8. Count how many drafts you send with light edits and how many you rewrite. That number tells you more than the feature list.
9. Find out how to cancel before you start.

An assistant works better on top of a few habits. These are tips, so keep what suits you.

• Set two or three inbox times a day. An affidavit due Friday won't get drafted between notification sounds.
• Finish at night, send in the morning. Microsoft's page on delaying or scheduling email says that in new Outlook you select the dropdown next to Send, then Schedule send. The message waits in Drafts until the time you pick. It isn't available for IMAP or POP accounts.
• Use automatic replies when you are in court or away. Microsoft's steps for new Outlook are View, View settings, Accounts, then Automatic Replies, where you can set a start and end time. Microsoft suggests choosing "Send replies only to contacts" so newsletters and junk don't get a reply. The catch is that a new client who isn't in your Contacts won't get one either. Automatic replies aren't supported for POP or IMAP accounts. Say when you will next read email.
• Flag anything you are waiting on. In classic Outlook, Follow Up sets a flag and a reminder, and flagged messages show in the To-Do Bar and Tasks. It suits the client who still owes you ID.
• Record the time when you finish the reply. For a rough idea of what unrecorded email costs you, try the unbilled time calculator.

Our guide on managing a law firm inbox in Outlook has more on folders, rules and routines.

AI Legal Toolbox is an Outlook add-in made in Queensland for Australian legal practices, including sole practitioners. Its AI paralegal, Nova, triages the inbox, drafts replies into your drafts folder (it has no send function) and reviews contracts and documents. With Smokeball it files emails and records time after you confirm. Without Smokeball it does everything except those two. It needs a Microsoft 365 work or school account. It is hosted in Sydney, with AI text processing by OpenAI in the United States, not retained there. Client correspondence is never used to train AI models. It starts with a 7 day free trial (card needed, nothing charged until day 8), then $149 AUD per practitioner per month including GST. See the facts page.

Microsoft changes Outlook menus and features regularly, so check the Microsoft pages linked above for current details. Last checked 10 November 2026.

This guide is general information, not legal advice.

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