Decision table
| Need | Pick | Price or limit (as listed 17 October 2026) | Verdict |
|---|---|---|---|
| Fastest full-featured AI inbox | Superhuman | Business USD 33 per member a month billed annually | Worth it if email is most of your day |
| AI help inside Gmail at the lowest cost | Gemini in Gmail | Workspace Business Starter USD 7 per user a month | Start here if you already use Workspace |
| Replies drafted before you open the inbox | Fyxer | Pro USD 37 per person a month billed annually | Good for executives and client work |
| Answers from years of email | Shortwave | Business USD 30 per seat a month; 5 years of AI search | Pick it for research-heavy inboxes |
| Outlook user wanting AI drafts | Fyxer | Pro USD 49 per person billed monthly | One of two picks here that supports Outlook |
The 4 tools on the same fields
Superhuman
- Best for: founders, sales leads and anyone answering hundreds of emails a week.
- Main limitation: the AI mail features sit in Business, so the cheaper Pro plan is a writing and docs plan rather than an email client.
- Price or plan limits: Free USD 0; Pro USD 12 per member billed annually; Business USD 33 billed annually or USD 40 monthly, as listed on 17 October 2026.
- Accounts supported: Gmail and Outlook.
Superhuman Business cost USD 33 per member a month billed annually, according to Superhuman's plans page checked 17 October 2026.
Gemini in Gmail
- Best for: small businesses already paying for Google Workspace.
- Main limitation: it needs an eligible Workspace or Google AI plan, and it lives in Gmail only.
- Price or plan limits: Google's Workspace pricing page lists the Gemini AI assistant in Gmail on Business Starter at USD 7 per user a month, with Standard at USD 14 adding Gemini in Docs, Meet and more.
- Accounts supported: Gmail. Google's Gemini in Gmail help page lists summarizing threads, drafting, organizing, search and scheduling.
Gemini in Gmail came with Google Workspace Business Starter at USD 7 per user a month, according to Google's pricing page checked 17 October 2026.
Fyxer
- Best for: consultants, executives and client-facing teams who want drafts prepared in advance.
- Main limitation: it is the most expensive per seat here, and usage is metered in credits after a launch offer.
- Price or plan limits: Fyxer's pricing page lists Pro at USD 37 per person a month billed annually (USD 49 monthly) and Team at USD 64 billed annually. After three months of unlimited credits, Pro includes 3,000 credits a month.
- Accounts supported: Gmail and Outlook, plus a meeting notetaker.
Fyxer Pro cost USD 37 per person a month billed annually, according to Fyxer's pricing page checked 17 October 2026.
Shortwave
- Best for: people who use email as a searchable archive of decisions and documents.
- Main limitation: the Business plan allows only 3 AI filters, and Shortwave describes its daily AI quota as roughly 150 to 300 standard requests.
- Price or plan limits: Shortwave's pricing page lists Business at USD 30 per seat a month, Premier at USD 45 and Max at USD 120, with a 14-day free trial.
- Accounts supported: built around Gmail, with AI search over 5 years of history on Business and unlimited on Premier.
Shortwave Business cost USD 30 per seat a month with 5 years of AI search history, according to Shortwave's pricing page checked 17 October 2026.
AI drafts still fall under CAN-SPAM
If an assistant writes a commercial email, the sender is still you, and so is the liability.
The FTC's CAN-SPAM compliance guide says each separate email that breaks the law can draw penalties of up to USD 53,088. The law covers all commercial messages, including business-to-business email, not just bulk sends. The guide sets out rules an AI draft can quietly break:
- No deceptive subject lines. An assistant that writes "Re:" on a cold pitch creates a problem.
- Identify ads and include a postal address in commercial messages.
- Honor opt-outs within 10 business days. An assistant that drafts a follow-up to someone who unsubscribed can still trigger a violation.
- You cannot contract away responsibility. The FTC says both the advertiser and the sender can be liable.
Keep auto-send off for anything that promotes a product. Use AI for drafts and sorting, and approve each commercial message yourself.
What to check before connecting your inbox
An email assistant reads everything: contracts, invoices, HR threads. Before you connect it:
- Read the data terms for training and retention on the exact plan you would buy.
- Limit who installs it. In a company, ask your admin to approve one tool rather than letting everyone connect a different one.
- Test tone on real threads. A draft that sounds like you on a sales email may sound wrong to a colleague.
For general writing beyond email, see our AI writing tool rankings. If you mainly want grammar and tone fixes, our Grammarly review covers that, and our Gemini review covers Google's assistant outside Gmail.
How to choose
- Note your provider. Gmail and Outlook narrow the field fast.
- Pick 20 real threads that needed replies last week.
- Run two assistants on trials for five working days.
- Count edits per draft and replies you sent unchanged.
- Check labels and summaries for anything misfiled or missed.
Teams that also want call notes turned into follow-ups should read our meeting assistant picks, and shared support inboxes are covered in our customer support AI rankings. Owners weighing all of this against budget can start with our small business AI guide.
How we rank
We compared drafting, sorting, summary and search features, supported email providers, AI usage limits, data terms and price per seat, as listed on each vendor's pricing and help pages on 17 October 2026. Our ranking method explains how documented features and limits shape each verdict.
Frequently asked questions
Is Superhuman free? Yes, there is a free tier, but the AI mail features such as Auto Drafts sit in Business at USD 33 per member a month billed annually.
Does Superhuman work with Outlook? Yes. Superhuman says its mail app is built for teams that use Gmail or Outlook.
Is Gemini in Gmail included with Google Workspace? Yes, on eligible plans. Google's pricing page lists the Gemini AI assistant in Gmail on Business Starter at USD 7 per user a month.
Which AI email assistant works with Outlook? Superhuman and Fyxer both list Outlook support. Gemini in Gmail works only in Gmail.
Can an AI email assistant send emails automatically? Some can draft and organize on their own, but keep sending manual for commercial email, since CAN-SPAM penalties apply to each email.
How much does Fyxer cost? Pro is USD 37 per person a month billed annually or USD 49 monthly. Fyxer's FAQ says its 14-day free trial starts on the Team plan.
What is the best AI email assistant for searching old emails? Shortwave, which offers AI search across 5 years of history on Business and unlimited history on Premier.