Outlook on the web
Outlook comes up less often than Gmail in what people ask dassi to do, but when it does, the jobs are nearly identical. The one thing to know up front is that dassi works inside your browser, so this means Outlook on the web (outlook.office.com for Microsoft 365 work mail, outlook.live.com for a personal account) and not the desktop program. Same mailbox, though. It’s probably signed in already.
What people hand off here is what they hand off in Gmail. They want the morning’s mail sorted, replies drafted in their own voice, and invoice and receipt details copied out of email into a spreadsheet (that last one tends to eat Friday afternoons). Outlook’s answer to labels is a mix of categories, flags and folders, plus the Focused/Other split, and dassi uses whichever of those you already use. If you only ever look at Focused, tell it to check Other as well, because that’s where newsletters go and sometimes a supplier invoice goes with them.
The morning routine is written out in full in the Gmail inbox triage job. It talks about labels; read those as categories.
Worked example: the Friday invoice sweep
Invoices arrive all week from a dozen vendors and somebody has to log them before the weekend. Taught once, in plain English, the workflow goes:
- Search the past seven days for “invoice” in the subject, or anything from a vendor on your list.
- Open each one and read the vendor, invoice number, amount and due date.
- Check the invoice log (a Google Sheet, or a workbook in Excel for the web) so nothing is entered twice.
- Add the new rows and flag any invoice due in the next seven days.
- Move the logged emails into Invoices/2026.
- Draft a short reply to any vendor whose invoice is missing your PO number, and list those drafts at the end.
If I could only teach one step it would be the sixth, since a missing PO number is the thing that tends to hold up payment for a week or more while emails go back and forth with the vendor’s accounts people. When an amount only shows up in an attached PDF it couldn’t read, the row stays blank and the email goes on the list for you. Excel for the web works as the log too, a little slower than Sheets because the page is heavier.
Approvals
Which actions need your yes is your call. For email I’d flag sending, deleting, bulk moves and anything addressed to a customer, and let categories and flags run on their own since they undo in a click. dassi also stops without being told when a message needs judgment. The vendor who writes in to say their bank details have changed is the textbook one (it’s also a textbook invoice scam), and that email gets put in front of you untouched.
Sign-in, sending caps and the rest
Work accounts usually come with Microsoft’s own sign-in rules, Authenticator prompts and conditional access among them, and dassi goes through them the way you do. If Outlook wants you to sign in again, it uses what your browser’s password manager autofills and you tap approve on your phone. Your password stays in the password manager; you never paste it into a chat or into dassi’s settings.
Some companies lock the browser down so tightly that none of this will run. I can’t predict which ones. Try it on one inbox before planning anything around it, and talk to IT if the account belongs to your employer.
Exchange Online allows 30 messages a minute and 10,000 recipients a day per mailbox, which is far more than a person working an inbox will use. The mail dassi reads goes to the AI model you chose, directly with your own key or through dassi’s relay on included credits. Scheduled runs happen in your own browser, too, so a laptop that’s shut at 4pm on Friday means no sweep at 4pm on Friday.