Find what you half remember
“When does my flight to Lisbon leave?”
It searches your mail, reads the confirmation, and answers with the time.
An AI assistant can find the mail you mean, sum up a thread and draft the reply. Here’s what Gmail’s own Gemini does, the apps built around AI, and how Ask AI works in Dodosend, where nothing changes until you say so.
Free for one Gmail mailbox, on macOS, Windows, and Linux.
Ask the way you’d ask a colleague. These work in Dodosend’s Ask AI as written.
“When does my flight to Lisbon leave?”
It searches your mail, reads the confirmation, and answers with the time.
“Sum up this conversation”
With a conversation open, it reads it and tells you where things stand.
“Draft a reply to Dana: Tuesday works, and ask for the agenda”
The draft waits in your Drafts for you to read, change and send.
“Fill this in for Priya at Northwind: Hi [name], great to meet the [company] team today.”
It finds Priya’s address in your mail, fills in the blanks, and leaves the mail in your Drafts.
“Archive everything from Medium Daily Digest”
It finds those conversations, and asks before it archives a single one.
“Make me a tab for this year’s invoices”
It writes the search, picks an icon, and adds the tab to your sidebar if you accept it.
Gmail has Gemini built in, and other mail apps bring their own. Features and prices come from each one’s own site, checked in November 2026.
| Assistant | What it does with your mail | Before it acts | Where it runs | Price |
|---|---|---|---|---|
| Gemini in Gmail | Gmail’s search answers questions from your mail, Gemini sums up threads and helps you write, and its side panel can archive, label, star and mark read. | The side panel changes nothing until you confirm it. | Gmail on the web, iPhone and Android | Summaries and Help me write are free in the US; inbox questions and the side panel need a paid Google AI plan (Pro is $19.99 a month) or Workspace |
| Shortwave | Its AI Assistant answers questions about your mail, writes drafts in your style, and archives, labels and deletes. | Waits for you to confirm before it organizes your inbox. | Web, Mac, Windows, iPhone and Android; on Linux, the browser app | Free with a limited AI quota; paid plans from $18 a month (Pro) to $120 a seat (Max) |
| Superhuman | Ask AI finds mail from a question, without senders or keywords, and drafts emails and events. | Its help page describes answers and drafts, not changes to your mail. | Mac, Windows, web, iPhone and Android | Ask AI comes with the Business plan: $40 a member a month, or $33 billed yearly |
| Dodosend | Ask AI answers questions about your mail and uses the app’s own features for you: drafts and replies, reminders, tabs, archive and the Trash. | Changes nothing until you approve it, and can’t send mail or delete it for good. | Its own desktop app, for macOS, Windows and Linux | A few questions a day free, for one Gmail mailbox; more with the Multi-mailbox plan |
Mailspring and Thunderbird have no assistant of their own. Mailspring can instead let an AI app on your computer, such as Claude or ChatGPT, work with your mail through its MCP server.
A panel beside your mail. It answers from the mail on your computer, works through the app’s own reminders, tabs and drafts, and asks before it changes anything.
Press CtrlL anywhere in the app, or click Ask AI at the top of the window, and type your question.
Each search it runs and each conversation it reads shows as a step above the answer, so you can tell where the answer came from.
It can archive, move to the Inbox, star, mark read or unread, move to the Trash, set a reminder, or suggest a tab for a search. Nothing changes until you press the button, and Don’t leaves everything as it was.
A mail or a reply it writes goes to your Drafts, and the panel says so: “In your Drafts. Nothing was sent.” The AI can’t send mail.
Did Northwind pay the October invoice?
Yes. Priya at Northwind wrote on Monday that the payment went out, with the receipt attached. Two of your reminders about it are still in the Inbox.
The AI wants to
archive 2 conversations
The AI needs to read mail to answer about it. Here’s what that means, in short; the privacy policy names every company involved.
Yes, Gemini. On a free personal account in the US, it sums up threads, suggests replies and helps you write. Asking questions about your whole inbox, and the Gemini side panel that can archive or label mail for you, need a paid Google AI plan or a Google Workspace plan, and inbox questions aren’t offered in the EU, the UK, Switzerland or Japan. Gemini works in Gmail on the web and on phones; Google has no Gmail desktop app.
It works through the app’s own features. It searches and reads your mail; archives, moves to the Inbox or the Trash, stars, and marks read or unread; sets reminders; writes mails and replies, from a template or a few notes if you give it one; and adds a search as a tab. It doesn’t apply labels, use the calendar, schedule a send or unsubscribe.
Not in Dodosend. Ask AI writes drafts, and they wait in your Drafts until you send them. It can’t send mail, and it can’t delete mail for good.
No. The model runs with zero data retention: it doesn’t keep your question, the answer or your mail, and doesn’t learn from them. Dodosend’s server doesn’t keep them either. The privacy policy lists exactly what goes where.
No. It sees an attachment’s name, not what’s in it.
Yes, for a few questions a day on the Free plan, for one Gmail mailbox. The Multi-mailbox plan gives more AI each month, along with more mailboxes.
It’s off until you turn it on, on its first screen in the app. Settings, Privacy turns it off again.
Shortwave builds the inbox around its assistant. Dodosend builds it around the keyboard: every action has a key, and Ask AI is a panel you open when you want it. The full comparison has the rest.
Ask AI, the command palette and a key for everything, on your own Gmail. Free for one mailbox, with a few questions a day.
Free for one Gmail mailbox, on macOS, Windows, and Linux.