Can Otto write a draft inside Gmail using browser control? No - here's where your drafts actually go

You asked for something like this: "I tried getting Otto to write a draft email in my Gmail account in the browser using browser control, and it keeps failing on the newest update. How do I get Otto to draft an email in Gmail via the browser?" You tried it again, you went hunting through the settings, and you are now at "I still can't figure this out". Here is the honest answer in one line: Otto will not open Gmail in a browser window and build a draft there, and there is no setting that turns that on. What he can do is put a real draft email in Gmail for you, sitting in your own Gmail Drafts folder, ready to send. That happens through a mail connection, not through the browser.

Nothing regressed in the newest update

Before you spend another evening on it: do not roll back a version, do not reinstall, and do not reset the app. Otto has never created drafts by driving the Gmail web page. This is a deliberate guardrail that has been in the product the whole time, so an older build will behave exactly the same way. The update you installed is not what broke this, because it was never working.

There is one genuinely update-related Gmail failure, and it looks different: your app password tested green, and Otto still says reconnect Gmail or invalid grant. That one is covered further down.

Why Otto will not drive the Gmail page

Otto's rule is that everything outgoing stays a draft inside Booked Solid, where you read it, edit it and approve it. In the product's own words, chat "produces drafts and answers only. No email, message, or reply goes out from a chat conversation without you approving it." That rule does not relax at the top end either: even in Fully Autonomous Booking, cold outreach, quotes and contracts always stay drafts.

Browser control sits on the other side of that line. Otto is told, in his own operating instructions, that browser control is not required for Gmail work and is not a substitute for it. Email work runs through the account you added under Connections > Mail & calendars, whether or not browsing is switched on. Adding a browser never fixes an email problem.

What browser control can do with Chrome

• Open and read ordinary web pages.
• Keep sign-ins between runs. Otto browses in a dedicated Chrome window that holds its own logins, so you sign in there once for each site you want him to read.
• Research lead sites, venue pages, your own site, a company before you reply.
• Reach a form. But as the Web browsing (Chrome) row itself says, anything that submits, uploads or posts always waits for you.

What browser control can do with Safari

Safari is stricter still. There is no click, type, form or upload tool at all. It can read what is already open and open a new address, and that is the whole surface. A Gmail compose window is out of reach by construction, not by configuration.

Almost everyone goes looking for a permission that unlocks this, and that is the dead end. There is no switch, hidden or otherwise, that lets browsing write into Gmail. Turning on Web tasks use my own browser together with Control this computer changes which browser Otto works in. It does not change the email rule. Skip that hunt.

The path that does put a draft in your Gmail

Connect the mailbox properly instead. When Gmail is connected the direct way, as an IMAP account secured with a Google App Password, Otto gets real Gmail tools: he can search your mail, read a message, and create a draft that lands in your own Gmail Drafts folder. Sending still stays with you in Gmail. This is the thing you were trying to get browser control to do, and it works in background runs too.

1. Turn on 2-Step Verification for the Google account if it is not on already, at myaccount.google.com/security. Google only issues app passwords to accounts that have it.
2. Go to myaccount.google.com/apppasswords, name the app password something you will recognize, and click Create. Google shows a 16-letter code. Copy it.
3. In Booked Solid, open the Connections tab and scroll to Mail & calendars.
4. Click Add an email account. Leave the method on Any email (IMAP).
5. Enter your Gmail address and paste the 16-letter app password. The spaces Google displays are stripped for you.
6. Fill in the mail server yourself. The field starts empty, and the answer is imap.gmail.com for every Google address: a plain @gmail.com one and a custom-domain Google Workspace one (you@yourband.com) alike. The two outgoing fields are optional; if you do fill them, use smtp.gmail.com and port 465.
7. Click Save. The inbox now has its own row under Mail & calendars, with a Check it button on it. Click Check it and wait for it to confirm the sign-in works.

That is the whole setup. Saving the inbox switches the Gmail (app password) tool on for Otto automatically, so there is no second switch to find and no restart step. The full walkthrough, including several inboxes at once, is in Connect your Gmail with an app password (step by step).

Now ask Otto for the same email again. He names which inbox he acted in, so you can see the right address doing the work, and the draft appears in Gmail under Drafts.

Three traps on the way in

• Do not use the Gmail (linked account) method through claude.ai for drafting. The badge can read Linked while drafting still fails, and relinking it on claude.ai will not fix it. Once the app password inbox is saved, the claude.ai Gmail connector can stay disconnected entirely.
• Check it failed with "The mail server refused that sign-in". That is almost always your normal Gmail password pasted in instead of an app password, or an app password that was revoked. Generate a fresh one and paste that.
• The password checked green but Otto still says "reconnect Gmail" or "invalid grant". On app versions before 1.11.5 there was a packaging bug: the Gmail tool programs were missing from every installed build. Update to 1.11.5 or newer, then use Start fresh so a clean conversation picks up the fixed tools.

Where do my drafts go in the meantime

Until the mailbox is connected, Otto's written work is not lost. It is waiting on three surfaces inside the app, which is the part people cannot find:

• The Inbox tab holds drafted replies to inbound conversations, grouped by what needs you. Anything ready to go sits under Reply ready, and you send it yourself.
• The Activity board holds outreach as a gate card, with To, Fee and Date laid out on the card. Your options are Approve, Edit, Not now, or dismiss it.
• The Tasks tab, under Needs your decision, lists everything Otto stopped on rather than acting alone, under the line Stopped safely until you choose. Those same items are the decision cards in Activity, and the Watch live work in Activity button at the top of the tab takes you there.

If it still does not work

• If you connected the inbox during a conversation that was already open, that conversation does not have the Gmail tools. Use Start fresh, or quit and reopen the app, and ask again.
• If a single draft attempt fails in the first hours after creating a new app password, ask once more. Each call opens its own short connection to Gmail and a momentary refusal clears on its own. There is nothing to re-approve.
• Open Settings > Permissions and find the Gmail tool under What each connected tool may do. If its reach was narrowed to Read-only, Otto can search your mail but cannot create a draft. Set it back to Read & write.
• Confirm the account was saved with the method left on Any email (IMAP), not linked through claude.ai.

Still stuck? Email bookedsolid@kivimedia.freshdesk.com and a person will help. Tell us the exact wording Otto came back with and which of the steps above you have already done, and we can go straight to the cause.