# Connecting your mail

Connect Gmail or iCloud mail with an app password.

ASIST connects directly to your mail server over IMAP and SMTP. It works with Gmail, iCloud and any other service that offers IMAP and SMTP. Instead of your account password, it uses an "app password", which you create for mail apps.

> [!WARNING]
> Outlook.com and Microsoft 365 do not accept IMAP connections with a password, so they cannot be used at the moment.

1. **Create an app password**

   **Gmail**

   1. Turn on 2-Step Verification under "Security" in your Google Account. You can create app passwords only for accounts that have 2-Step Verification turned on.
   2. Open [myaccount.google.com/apppasswords](https://myaccount.google.com/apppasswords), enter "ASIST" as the app name and click "Create".
   3. Write down the 16-character password that appears. It is never shown again once you close the screen; if that happens, create a new one.

   For Google Workspace accounts, the administrator may not allow app passwords. If the screen for creating one does not appear, ask your administrator.

   **iCloud**

   1. Sign in at [account.apple.com](https://account.apple.com/) and open "App-Specific Passwords" under "Sign-In and Security".
   2. Create a password with a name such as "ASIST", and write it down.

2. **Add the account to ASIST**

   In the settings, open "Calendar and mail" and click "Add" under "Mail". Choose Gmail or iCloud under "Type", and the server details are filled in. For other services, enter the IMAP and SMTP hosts and ports (for most services, IMAP uses 993 and SMTP uses 465 or 587). Enter a display name (such as "Work" or "Personal"), the email address, the sender name and the app password.

3. **Check the connection and save**

   Click "Check the connection", and ASIST connects to the server and looks for the Sent, Archive and Trash folders. It does not guess folders it cannot find; they show "None", and you can set them later for each account. Click "Add", and ASIST encrypts and saves the password and starts fetching your mail.

   ![A Gmail account entered and its connection checked](https://asist-agent.com/screens/en/mail-add-account.webp)

4. **Check it**

   Say "Do I have any unread mail?" and check that the inbox card appears.

## If you also send from other addresses

If you also send from other addresses, such as a work address added under "Send mail as" in Gmail, write them down in ASIST. In the settings, open "Calendar and mail", click "Other addresses you send from" for that account, write the addresses one per line and click "Save".

![An account's "Other addresses you send from", opened](https://asist-agent.com/screens/en/mail-other-addresses.webp)

ASIST takes these addresses as yours, just like the account's own address. A reply to a message you sent from one of them goes to the people you sent it to, not to you. "Reply all" leaves your addresses out as well. The conversation takes them as yours too. Replies and new messages are always sent from the account's own address; ASIST cannot send from the addresses you list here.

ASIST does not guess your addresses from the senders in your Sent folder, since you may have sent a message from your manager's address on their behalf.

## What ASIST fetches

| Item | Details |
|---|---|
| Period | "Days to fetch" in the settings (30 days by default). Older mail does not appear in the list. |
| Folders | Inbox, Sent and Archive. Trash and spam are not fetched. |
| New mail | ASIST waits on the inbox with IMAP IDLE and fetches new mail as soon as it arrives. Everything is fetched again every 5 minutes and when your computer wakes from sleep. After sleep, ASIST first checks that the server still answers on the connection it had, and connects again if nothing arrives from it within 10 seconds. |
| Attachments | Only the file name and size are shown; the contents are not fetched. |

## If it does not connect

- If you see "Invalid credentials", the app password is wrong or 2-Step Verification is turned off. Create a new app password and enter it again for that account.
- If an account says its folders are not set, the server did not report which folders serve as Sent, Archive and Trash. In that account's folder settings, enter the folder names used on the server (for Gmail, something like `[Gmail]/All Mail`).
- When the connection drops, ASIST reconnects, waiting longer between each try. The reason appears in the settings and in the mail screen.
- If ASIST says it does not know whether a message was sent, check the Sent folder before you send the same message again. ASIST does not resend automatically.

## How ASIST handles your mail

The password is encrypted before it is saved, with a key from the keychain on a Mac and with a key tied to your Windows user account (DPAPI) on Windows. The settings file holds each account's display name, email addresses, sender name, server details and folder names, but not its password. Fetched mail is kept on your computer and can be rebuilt from the server. Removing an account removes that account's fetched mail and its password. The mail on the server stays as it is.

Mail read in the conversation is sent to the provider of the conversation model you chose, so that it can write a reply. It may also stay in the conversation history and be used in memory curation.