Gmail and Outlook in one place

Two inboxes, two calendars, two sets of habits

A Gmail address for the company you started and a Microsoft 365 address for the one that acquired you. Or work on Outlook and life on Gmail. Either way you are running two inboxes, two calendars, two sets of shortcuts and two mental models, and the cost is not the switching. It is the mistakes.

The wrong calendar gets the client call. The reply goes out from the address that makes you look like a freelancer to your own board. The follow-up goes into the task list you only open on Thursdays.

One app fixes the switching. What you actually want is one app that keeps the identities straight.

One workspace, separate identities

Putting two accounts in one window does not merge them, and it should not. You still need to know which address is sending, which calendar is receiving the meeting and which list owns the task.

In Otto the selected account decides all three at once. Choose the work account and the mail, the calendar and the tasks are the work ones. The task service follows the provider too: Google Tasks for a Google account, Microsoft To Do for a Microsoft account. It is one rule rather than a set of per-feature exceptions you have to remember at speed.

Before any AI action, that account is on the card you approve. So is the recipient list. Checking it takes a second and it is the one habit worth building for a two-provider life.

Running two accounts is also where a slow app hurts twice. Both Gmail and Outlook push new mail into Otto rather than waiting to be polled, so either inbox can surface a message as it arrives, and folder switches come off Otto’s up-to-date inbox list rather than a fresh request to whichever provider you just jumped to.

Check the providers before you fall in love with the AI

An assistant being clever tells you nothing about whether it will connect your accounts. Work out the connection question first, then compare the help.

Shortwave supports Gmail and Google Workspace. Spark supports Gmail and Outlook among other providers, including Exchange, Microsoft 365, iCloud, Yahoo and IMAP. Otto supports Gmail and Outlook. Those are three different answers to the same question, and the wrong one leaves you back in two apps no matter how good the drafting is.

As of Sept 2026, Shortwave lists Business at $30, Premier at $45 and Max at $120 per seat/month. Spark lists a Free tier, Plus at $10/month or $99/year, and Pro at $20/month or $199/year. Different products, different billing shapes: compare what is included before you compare the numbers.

See Shortwave pricing and Spark pricing, alongside the Shortwave comparison and the Spark comparison.

Move one workflow, not your whole life

Do not migrate on a Monday morning. Take one thread that needs an answer, a meeting and a follow-up, and run it end to end in the new app.

Then go and look. Is the sent message in the right Sent folder. Is the event on the calendar you meant. Is the task in the list you actually check on your phone. If all three landed correctly, add the second account and repeat the test there, because similar folder names and overlapping contacts make two accounts feel interchangeable long before they are.

Watch the time zones as well. Work and personal calendars often disagree about them, and a proposal that reads fine in one is an hour wrong in the other.

Then decide what to move

Once a full workflow lands where you expect, move the daily triage. Keep anything genuinely provider-specific where it already works. This is a switch you can make in pieces.

Otto Free includes one connected account with core mail, calendar and tasks, and an AI allowance; paid tiers add accounts and capacity. The multiple accounts guide explains how account context works, and pricing has the current tiers.