AI email assistant: a guide

What an AI email assistant is

An AI email assistant is software that works on your mailbox and not beside it. It reads the thread, drafts the reply, sorts what arrived, proposes the meeting and keeps track of what you're waiting on.

How well it writes isn't the thing to look at, because every model writes well now. Look at whether it can change anything: send, archive, delete, move four thousand messages, put an event on your calendar. A chat window that summarizes an email you pasted into it is a different product. It's useful, but it isn't touching your mail, so it can't send the wrong thing either.

AI email, AI mail, AI inbox

People search for this a dozen ways. AI email. AI mail. AI inbox. Email AI. AI email assistant. Underneath all of them is the same question: can something take the tedious half of my inbox off me without making a new kind of mess?

The answer depends far more on the boundaries a product sets than on the model behind it. So here are the five things to find out, in the order they'll decide your choice.

What it can change without asking you

Find this out before you read the feature list. Some assistants only ever write a draft into your drafts folder, which is safe and limited. Some can archive and send mail and delete it, all on their own. Some sit in between and don't document where the line is.

Ask what it does on its own, what it shows you before it acts, and what it tells you afterwards. If the help pages don't answer that, try it on a message that doesn't matter and watch what happens.

Where you approve

A review step is what makes handing over a mailbox reasonable, because a sent message can't be unsent and a deleted thread is gone. A useful one shows the sending account and the recipients, plus the wording, and for a bulk job the scope it will touch. A draft button on its own answers none of that.

AI that waits for your approval walks through the six seconds of checking, including the part people skip. Approving starts the work, and it doesn't finish it.

Where your mail is stored

Every product in this category says it takes privacy seriously. Far fewer say which bytes land in whose database. Read for specifics. Does it keep message bodies? Does it keep attachments? What happens to the text when you ask an AI about a message, and is any of it used to train a model?

Which providers it supports

This settles your shortlist faster than anything else, and most people get to it last. Several well-known AI email tools are Gmail and Google Workspace only. If one address in your day ends in Microsoft 365, a Gmail-only tool leaves you running two apps, which is the thing you were trying to stop doing.

What it costs, and whether you can test it properly

Several tools in this field start around $30 a seat a month behind a one or two week trial. Fourteen days is enough to judge an interface. It isn't enough to know whether an assistant helps in a bad week, and a bad week is what you're buying for.

How Otto answers those five

Otto is ours, so take this section with that in mind.

On what it can change: Otto reads and searches, and it summarizes and prepares work on its own. Sends and deletes don't happen on their own, and neither do bulk changes. Each of those comes back as a card with the sending account, the recipients, the wording and, for a bulk job, the scope. You can approve it, or change it first, or throw it away.

On where your mail is stored, Otto keeps an inbox list with message details so folders load quickly. Selected content may be retained when you save a chat or a note, a draft or prepared work. What Otto stores explains the categories.

On providers, it's Gmail and Outlook in one app, with the same assistant and the same shortcuts. The selected account supplies the mail, and the calendar and task list come with it, so a work reply can't slip out from a personal address.

On cost, Free connects one account with core mail and a calendar and tasks, plus an AI allowance, with no clock on it. Plus is $6.99 a month and Pro is $19.99. Pricing has the current tiers.

Two more things decide how the first week feels. Otto is one app for mail with a calendar and tasks, so a single thread can become a reply and an event and a task in one pass, on the web and on iPhone. And it's built to stay out of your way. Gmail and Outlook push new mail to it, folder switches come off Otto's up-to-date inbox list, and you can drive the whole inbox from the keyboard.

Under that sit the unglamorous parts that decide whether a week survives: snooze and follow-up nudges, scheduled send and undo send, filters and rules, bulk actions across a whole search, and saved snippets. There's a shared inbox for teams too, and a memory of your preferences so drafts sound like you by the second week. Otto AI is the short version of all this.

A short tour of the alternatives

The comparison hub has the full field, each one with prices and a verdict, and the alternatives pages cover who each one suits and why people switch.

Superhuman is the keyboard-speed inbox, with Mail on its paid plans and a native Windows app that Otto doesn't have. Shortwave has strong AI help inside the thread, and it's for Gmail and Google Workspace only. Spark has the most generous free tier here, with unlimited accounts across iCloud and Yahoo and IMAP, and no task list. SaneBox isn't a client at all. It sorts mail in the app you already use and reads headers only, which is the smallest data footprint in this list. Missive is built for teams working one shared queue, from $14 a user, and it also handles WhatsApp and SMS. Gmail with Gemini is free for summaries and Help me write, and it's Gmail only.

None of those are wrong choices. They answer different questions.

Which one are you?

If you run a company, the problem is finding the four threads that matter inside three hundred: Otto for founders. If you're moving forty candidates through interviews, it's scheduling and follow-ups: for recruiters. If client threads pass between people, it's the handoff: for agencies. If you're the whole back office, it's one client email that's really three jobs: for freelancers.

Where to start

Connect one real account and not a test one, and run an ordinary morning through it. Ask for a reply you've been putting off, accept a meeting, set one follow-up, then look at where each of the three landed.

The glossary covers the vocabulary if any of it is new, and if you run both providers, Gmail and Outlook together is worth reading first.