Otto drafts from the wrong email: running several inboxes and personas at the same time

You connected a second inbox, ran a batch of outreach, and the drafts came out under the wrong name. People write in about this three ways: "can I use two Gmail accounts", "Otto keeps drafting from the wrong email", and "wrong From address on my drafts". They are all the same question. One performer laid the whole thing out like this: "I need the ability to connect, draft, and deploy from multiple email accounts at the same time. Right now, the system only allows me to draft and place into one email account at a time. To use a second email, I have to manually disconnect the first account and enable the second one. This creates a bottleneck because I run themed outreach campaigns representing different personas (for example, one for a magician persona, one for a speaker persona, and one for a Santa persona)." That is exactly the case this article is about, and it works now. It did not always.

Start here: this needs version 1.11.0 or newer

Running several inboxes at once arrived in 1.11.0. On anything older, nothing in this article works, and no amount of careful setup will make it work. So check your version before you change a single setting.

1. Click Check for updates next to the logo in the top bar and install whatever it offers.
2. Or download a fresh build from booked.kivimedia.co/download. That page always serves the newest build for your computer.

If you are already on 1.11.0 or newer, skip ahead to What works now.

What it was like before 1.11.0, and why you were not doing it wrong

Worth saying plainly, because people on older builds still land here and assume they misconfigured something. Before 1.11.0, Otto's email connection bound to one inbox at a time. Adding a second inbox under Connections > Mail & calendars did not help: Otto kept drafting from the first inbox he had, and the only way to point him at another was to remove the current inbox and add the next one. It was genuinely one persona per campaign run, swapped between runs. That was a limit on our side, not a switch you missed.

If you are stuck on an old build for the moment

Run one persona at a time. Set up that persona's inbox, run its outreach batch, then swap to the next persona's inbox and run that batch. It is not simultaneous and it is not enjoyable, but it keeps each persona's outreach cleanly separated and it stops a wrong From address slipping onto a draft while you get the update installed.

What works now

• Add every persona's inbox under Connections > Mail & calendars, each with its own Google app password. Magician, speaker, Santa, as many as you actually run.
• Otto reads replies across all connected accounts inside one campaign run. You do not pick an inbox for the run and you do not swap anything mid-campaign.
• Every draft is placed in the right account's own Drafts folder, from the right address.
• When more than one account is connected, Otto has to name the account before he reads a message or places a draft. He is not allowed to fall back on a default and guess. That is the guardrail that keeps a magician draft out of the Santa inbox.
• Each account has its own on and off switch, so a seasonal persona can be parked without being deleted.
• Saving a new inbox switches its tools on for Otto by itself. There is no hidden second switch to go hunting for.
• Adding, editing, switching off, or removing an account reaches Otto the moment you save it. There is no restart step.

Add one inbox per persona

1. Open the Connections tab and scroll to the Mail & calendars section.
2. Click Add an email account.
3. Give it a name you will recognise at a glance, like "Magician bookings" or "Santa bookings". You will be reading these labels when Otto tells you which inbox he worked in, so make them obvious.
4. Pick its purpose tag: bookings, personal, support, or business. Be clear about what this tag does and does not do. On a mail account it tells Otto what the address is for, so he writes from the one that matches the message. It is not what routes a persona, and it is not what powers the date clash check either: that check runs on the purpose tags of your calendars. The detail is in Purpose tags on mail and calendars: bookings vs personal, and the clash check.
5. Leave the method on Any email (IMAP), which is the form's default and the path that works with a Google app password. Do not switch it to Gmail (linked account): that is the browser sign-in that rides your Claude account, and it is the one that expires on you. Enter that persona's address and paste that account's own Google app password.
6. Click Check it. It has to come back green before you go any further, because green means Gmail itself accepted the login. Red means keep fixing this account before you add the next one.
7. Click Save, then repeat the whole sequence for the next persona.

Here is the mistake that catches almost everyone running several personas: an app password generated while you happened to be signed into a different Google account. Google issues app passwords per account, and one made under your magician account will never sign in your Santa account. Generate each one while signed in as that exact address. The full walkthrough, including custom-domain Google accounts (which need imap.gmail.com as the mail server), is in Connect your Gmail with an app password (step by step).

Park a persona without taking it apart

Seasonal personas are the reason the on and off switch exists. Every account row has a Turn off button, a switched-off account carries an Off badge, and one tap of Turn on brings it back.

• The app password stays saved. You never retype it to bring an account back.
• A switched-off inbox drops out of Otto's email tools and out of the background inbox checks until you switch it back on. The same switch on a calendar takes it out of the date clash check.
• The change applies immediately. No remove-and-re-enter, no restart.

So a Santa inbox can sit switched off from January through October, and come back in one tap in November with its credentials intact.

The one ceiling that did not move: drafts only

Otto drafts. You review and send from Gmail. There is deliberately no send tool on this connection at all, which is also why a message can never leave under the wrong persona while your back is turned. That line does not move at any automation level, including Autopilot and Fully Autonomous Booking. How the outreach plays are built, and what the app deliberately does not do, is covered in Cold outreach in Booked Solid: what's built in (and what isn't).

What is still one at a time: the Microsoft 365 sign-in

Being straight about the edge that did not change. Everything above applies to inboxes added as Any email (IMAP), which is the path Gmail and most other providers use. The Microsoft 365 connection is a different mechanism: it holds a single Microsoft sign-in, and signing in again replaces the one before it. There is no multi-persona mode on that path today, so if all your personas live on Microsoft 365 mailboxes you are still swapping.

The nearest real alternative is to add those mailboxes as Any email (IMAP) instead, using your provider's own mail server and that mailbox's password, since IMAP accounts are the ones that run several at once. Whether your mailboxes accept that kind of sign-in depends on how your Microsoft tenant is configured, so treat it as worth testing with Check it rather than as a promise. What the Microsoft path can and cannot do is in Microsoft 365 by device code: what Otto can and cannot do in Outlook.

If every Gmail account stops authenticating right after you update

This is a known follow-on and it is worth recognising before you take everything apart. The performer whose request built this feature updated, and both of his inboxes stopped authenticating at once. He deleted both accounts and added them back, generated fresh app passwords for both, confirmed 2-Step Verification, and reconnected everything from scratch. None of it changed anything, and it cost him days. Do not spend your evening the same way.

Two messages usually turn up together here, and they are two different things:

• "The mail server refused that sign-in. For Gmail/iCloud use an app-specific password." This is the direct connection, your address plus an app password, being turned away by the mail server at login. This is the one actually blocking you.
• "authorization error: invalid_grant" This is the older Gmail link that rides your Claude account. Otto only falls back to it because the direct connection above is failing, and its Google token has gone stale. It is a symptom, not the cause. Fix the first one and this one stops on its own.

So everything hinges on getting Check it to go green, one account at a time. Deleting and re-adding all your accounts is the thing almost everyone tries first, and it is a dead end: it adds variables without removing any, and it makes you retype credentials that were probably fine. Skip it. Every account card has an Edit button that opens the account pre-filled, so you can change one field and re-test. Leaving the password box blank keeps the password already saved.

One thing that used to break this and no longer does: Google displays an app password as four blocks with spaces. On builds before 1.11.5 pasting it that way failed the sign-in every time, identically on every account, which is exactly what "all my inboxes broke at once" looks like. From 1.11.5 the password box strips the spaces for you, so paste it exactly as Google shows it. If you are below 1.11.5, update before you troubleshoot anything else.

Then work through Connect your Gmail with an app password (step by step) on one account until it is green, and only then move to the next.

If it still does not work

Open a ticket rather than starting another round of removing and re-adding. Tell us four things and we can usually name the cause in one reply: your app version, how many inboxes are connected and whether each one's Check it is green or red, whether these are personal @gmail.com addresses or addresses on your own domain, and the exact red text you are getting. If a draft came out of the wrong account, say which address it came from and which one you expected.

Still stuck? Email bookedsolid@kivimedia.freshdesk.com and a person will help.