An inbox is rarely a reading problem — it's a sorting problem, and most of the sorting is deciding what can wait. Pepper reads your mail so you don't have to open it to find that out: ask what's waiting and you get an answer, not a list of subject lines. When something needs a reply, you say what to say and Pepper writes it.
No filters to build, no labels to invent first. Connect Gmail (see Connecting your accounts) and ask.
What you can ask
- Search and triage: "Any important email from this week?", "What did Jenna send me?", "Did the contract come back?" Pepper searches your inbox and summarizes what's worth your attention rather than dumping every message.
- Summarize your email: "Summarize my email", or
/email. Pepper covers the last three days of mail Gmail marked important: unread first, then the ones you've already read, each message once. Recent mail Gmail didn't mark important is left out. The email line in your morning brief is picked the same way. Name a different window ("summarize this week's email") to change how far back it looks. - Narrow time windows: "Anything in the last half hour?", "What came in while I was on the call?" Windows shorter than a day work, which matters most for a recurring check you've set up to watch for something specific.
- Read a specific message: "Read me the latest from the school", "What's the gist of that thread?"
- Read what's attached: "What does the estimate in Dan's email say?", "Compare the two quotes the electricians sent." Pepper can open a PDF or a picture (PNG, JPEG, GIF or WebP) attached to an email and read it.
- Labels: Pepper can list your labels and use them to scope a search.
- Draft a reply: "Draft a reply telling them Thursday works." Pepper writes the draft and saves it to your Gmail drafts for you to review. On the web, the draft also appears in the conversation as a card you can read, edit and send without leaving the chat — see Working on a draft in the chat.
- Find everyone who's waiting on you: "Who's waiting on me?", "What do I need to reply to?" That's the Email reply assistant routine — it goes through your unread mail for the messages actually waiting on a reply from you and drafts each one. See Skills; it's also worth scheduling (see Reminders & scheduling).
- Send on your behalf: "Send Jenna a note saying Thursday works." Pepper drafts it, reads it back, and — once you confirm — sends it from your Gmail.
- Send as your assistant: "Email Sam to set up a meeting." Pepper can reach out to a third party as your assistant, from its own address, with you automatically copied so you see the thread.
Two ways Pepper can send
There are two distinct identities, and Pepper will be clear about which one it's using:
- As you, from your Gmail. Used when you're personally writing to someone (replying to a friend, sending a quick note). The message appears in your sent folder and the recipient sees it from your address.
- As your assistant, from Pepper's own address. Used when you're delegating outreach ("email Sam to set up a meeting"). Pepper writes as your assistant — not pretending to be you — and you're always CC'd so you can see and jump in on the reply. To write to Pepper, use the Pepper address shown in Settings — see Ways to reach Pepper for emailing Pepper directly and looping it into a thread.
Pepper confirms the recipient and the message before sending, and defaults to a draft if anything's ambiguous. For requests that happen automatically in the background (a scheduled task, say), sending from your Gmail is downgraded to a draft instead — there's no way to ask you mid-task, and an unintended send is the kind of mistake that can't be undone.
Working on a draft in the chat
When Pepper drafts an email for you on the web, the draft shows up in the conversation as a card rather than as a wall of quoted text. The card shows the subject, who it's going to, and the opening of the message; the rest is there too, just clipped, and Read more opens it in place.
Two things on the card are editable:
- The subject. Click it and type. It's the card's heading and its text field at the same time.
- Who it's from. If you've connected more than one Google account, the From line is a picker. Choosing a different account moves the draft to that account's Drafts folder — a draft belongs to one mailbox, so it can't be in both.
If you have only one account connected there's no From line, since there's nothing to choose.
Then there are two buttons:
- Save to drafts keeps your changes without sending. What lands in Gmail is what the card shows, so the draft you open later in your own mail app is the one you edited here.
- Send sends it, from the account named on the card. It saves your edits first, so what goes out is what you were looking at.
Sending from the card is a real send and can't be undone, the same as pressing send in Gmail. Replies stay in their original thread — the card sends the draft Pepper actually staged, so the threading it was written with is preserved rather than rebuilt.
Once a draft has gone, its card says Sent and its buttons are off — including when you come back to the conversation later — so the same draft can't go out twice.
Don't want it? The trash icon at the top right of the card discards the draft: it's deleted from your Gmail Drafts and the card disappears from the chat, for good — it doesn't come back when you return to the conversation. There's no confirmation step; if you change your mind, ask Pepper to draft it again. A card that has already been sent has no trash icon.
When a reply comes back that Pepper can't handle
When Pepper emails someone for you, it usually picks their reply up and carries on. Occasionally it can't — the reply arrives in a shape Pepper can't tie back to the conversation it started. Rather than let it vanish, Pepper adds a todo saying who replied and on what thread, so you can open your own inbox and answer. You'll get at most one of these per person per day, and it never quotes what they wrote — that's in your mail, which is the right place to read it.
Occasionally you may get one of these for a reply that turns out not to concern you — if you and a colleague have both had Pepper email the same person, a reply that doesn't say which thread it belongs to reaches both of you. Pepper would rather tell you both than guess and tell the wrong one.
Catching up on a stretch of mail
Beyond a single message, you can ask Pepper to read across recent mail and tell you what's there — "what's in my inbox?", "anything I need to deal with from this week?", "what did I miss while I was away?" It searches, reads what matters, and answers in prose rather than handing back a list of subject lines.
If what you want out of your mail is the action items, that's the Find todos skill: it sweeps unread mail (plus your calendar and, if connected, GitHub), checks against your existing list, and adds only what's genuinely new. See Skills and Todos.
Good to know
- If Gmail isn't connected, Pepper tells you rather than guessing — connect it under Settings → Accounts.
- Attachments: Pepper reads PDFs and pictures attached to your mail. Other files — Word documents, spreadsheets, zip archives, calendar invites — and very large ones it can't open, and it tells you so rather than guessing at what's inside. An attachment Pepper reads is kept for about two days so follow-up questions don't fetch it again, and it isn't added to your files. Ask Pepper to save it ("save that estimate") and a copy goes into your files to keep. You can also pull an image attachment out of Gmail into your Images app (see Images).
- Pepper can't attach a file when it sends or drafts an email on your behalf — a send or draft is text only, even if you asked for something attached. If your wording says "attach", Pepper tells you the file wasn't attached; ask a different way ("include the receipt") and it may not say so, so don't count on the attachment being there without checking. For a draft, you can add the file yourself in Gmail before you send it.
- Pepper doesn't delete messages or change folder structure for you.
Things to try
- Who's waiting on you. Monday morning, ask "who's waiting on me?" and Pepper goes through your inbox for the threads that need a reply and drafts each one. Nothing is sent until you send it.
Try it: "Who's waiting on me?" - Back from time off. Back from vacation, "what did I miss while I was away?" gets you an answer instead of a pile of subject lines.
Try it: "What did I miss while I was away?" - Did it come back? Waiting on something by email? "Did the contract come back?" checks your inbox and answers yes or no, with the message if it did.
Try it: "Did the contract come back?"