DEV Community: Otto Mail

Gmail and Outlook in one place

Otto Mail — Mon, 02 Nov 2026 09:59:17 +0000

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're running two inboxes, two calendars, two sets of shortcuts and two mental models, and the switching isn't what costs you. The mistakes are.

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 lands in the task list you only open on Thursdays.

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

One workspace, separate identities

Putting two accounts in one window doesn't merge them, and it shouldn't. You still need to know which address is sending, which calendar is getting the meeting and which list owns the task.

In Otto the selected account decides all three at once. Pick the work account and the mail, the calendar and the tasks are the work ones. Tasks follow the provider too: Google Tasks for a Google account, Microsoft To Do for a Microsoft one. It's a single rule, so you don't have to remember a set of per-feature exceptions while you're moving fast.

Before any AI action, that account is on the card you approve, and so is the recipient list. Checking takes a second, and it's the one habit worth building if you live across two providers.

Two accounts is also where a slow app hurts twice. Gmail and Outlook both push new mail into Otto instead of waiting to be polled, so either inbox can show a message as it arrives. Folder switches come from Otto’s up-to-date inbox list, not from a fresh request to whichever provider you just jumped to.

Check the providers before you fall for the AI

How clever an assistant is says nothing about whether it'll connect your accounts. Settle the connection question first, then compare the help.

Shortwave supports Gmail and Google Workspace. Spark supports Gmail and Outlook, plus Exchange, Microsoft 365, iCloud, Yahoo and IMAP. Otto supports Gmail and Outlook. That's three different answers to the same question, and the wrong one puts you back in two apps however good the drafting is.

We last looked at prices in September 2026. Shortwave listed Business at $30, Premier at $45 and Max at $120 per seat a month. Spark listed a Free tier, Plus at $10 a month or $99 a year, and Pro at $20 a month or $199 a year. They're different products with different billing shapes, so compare what's included before you compare the numbers.

Their own pages are Shortwave pricing and Spark pricing. We've also written up the Shortwave comparison and the Spark comparison. Otto is ours, so read our side of those with that in mind.

Move one workflow first

Don't 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 right, 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 too. Work and personal calendars often disagree about them, and a proposal that reads fine in one is an hour off in the other.

Then decide what to move

Once a whole workflow lands where you expect, move your daily triage. Leave anything that's truly provider-specific where it already works. You can make this switch in pieces.

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

First published on the Otto Mail blog.

Inbox overload for founders

Otto Mail — Mon, 02 Nov 2026 09:58:27 +0000

It isn't an email problem

You've got a queue of three hundred decisions that all arrived wearing the same font.

The customer who's about to churn looks exactly like the newsletter. The investor waiting on an update looks exactly like the recruiter spam. The inbox flattens it all to one size, and then you feel guilty about the count instead of dealing with the four things that change your week.

So stop treating unread as a to-do list. It never was one.

Find the four

Start each session by asking what actually needs you. Skip what's new and look for what's consequential: money, people, legal, customers about to leave.

If you use Otto, ask it straight out: what needs my attention today. It reads the mail you haven't and answers in a few lines. If you don't, search for your five most important senders by hand. Either way it takes two minutes and gets you the same thing, a short list of threads where something changes if you act and a much longer one where nothing does.

Deal with the short list first, every time. An empty inbox is a nice feeling, but it isn't a business outcome.

Every thread gets one of five outcomes

Reply. Book a meeting. Create a task. Wait on someone. Archive.

Pick one and move. Most of the pain in an overloaded inbox is re-reading. You open a message, feel the weight of it, decide nothing, and pay the same cost again tomorrow. Three passes over the same thread is worse than one imperfect decision.

If it needs a reply, settle what you're saying before you polish how you say it. If it needs work outside email, make it a task with a date you'd defend out loud. If you're waiting on somebody, pick when you'll chase them instead of trusting your memory.

Two of the five feel productive and mostly aren't. Archiving removes a message, and it doesn't answer it. Snoozing delays a thread, and the work stays the same size. Both are fine as decisions and bad as reflexes.

Do the pass on the keyboard if your app has one. In Otto it's J and K to move and a single key to archive, star or reply. The seconds saved matter less than your hands never leaving the decision.

Let the assistant take the tedious half

The drafting, the scheduling and the remembering are the parts that really do benefit from help.

Open a thread and say what you want to happen: accept the terms and ask for the contract by Friday. Otto drafts the reply in your voice, and you check the account, the recipients and any date before you approve it. Ask for a call on Thursday and it proposes the event on your connected calendar, with attendees and time zone visible. Ask to be reminded if nobody replies by Tuesday, and the thread comes back on Tuesday.

That's one thread, three pieces of work, one pass. An ordinary assistant send waits for your approval, so your judgement goes into the review and not the typing.

For the noise, go wide instead of working one message at a time. Ask for every newsletter from the last quarter to be archived, read the scope on the card, and approve it once. Ten minutes of clicking becomes one decision you can inspect.

End with a handoff to yourself

Before you close the tab, spend sixty seconds on three questions. What am I waiting on? What's on the calendar tomorrow? What did I promise someone today?

The answers belong in your task list, not in your head or the unread count. Tomorrow you start from commitments instead of scrolling from the top and hoping the important thing is still visible. Otto can write that handoff for you as a routine, such as a morning brief, on a schedule you set, so the day opens with a briefing and not a scroll. The morning brief is on every plan.

If the same conversation keeps coming back without a decision, the routine isn't the problem. That thread needs a call, or a no.

Try it on one bad morning

Core mail, calendar and tasks are free on one connected account, with an AI allowance. Run tomorrow through it before you decide anything about tiers.

The founder workflow shows where each step lives, and AI that waits for your approval covers what to check before you approve a send.

First published on the Otto Mail blog.

An AI email assistant that asks first

Otto Mail — Mon, 02 Nov 2026 09:57:37 +0000

Autopilot sounds great until the first wrong send

The pitch for fully automatic email is easy to like. Mail comes in, an AI answers it, you go and do something else. Nobody enjoys their inbox, so nobody argues.

We'd argue a little. The average reply isn't the problem, because models write a perfectly good average reply now. The problem is the one in a hundred that restates a price you never agreed, goes to the whole distribution list, or leaves from the wrong address. Once the other person has read a sent email, you can't unsend it in any way that matters.

So the question we'd ask of any AI email assistant isn't how well it writes. It's who decides when something leaves your mailbox. In Otto, by default, you do, every time.

Speed isn't the real prize anyway. The prize is skipping the boring part, and asking first keeps it. Drafting and finding are the boring parts, and so is getting things ready. Otto does those without waiting for you.

What asking first looks like

Ask Otto to reply, to delete, or to change a lot of mail at once and it prepares the work, then stops at a review card. The card shows the sending account and the recipients, plus the wording. For a bulk job it shows the scope too: which search, which mailbox, which action. Approve it, or edit it first, or throw it away.

Everything before that point moves freely. Otto reads threads and searches and summarizes without asking. It drafts and proposes without asking too, because none of that changes anything outside your own screen. The checkpoint sits where something becomes real: a send, a delete, a bulk change.

It's one narrow gate instead of a hundred small prompts. The fewer places you're asked, the more attention each one gets.

A walkthrough: invoice 2041

Say Maya at Studio Luma writes: "Can you confirm invoice 2041 goes out Friday? Priya needs it for month end."

You open the thread, press ⌘J and type: "Reply to Maya, confirm invoice 2041 goes out Friday, and thank her."

Otto drafts the reply in your voice and shows the card. Three things on it are worth reading, and we'd read only those.

The account. Is it going from your work address or your personal one? The text won't tell you, which is why this is the field that bites hardest.

The recipients. Priya was on the thread. If the draft is addressed to both of them and you meant to answer Maya alone, change it now. Reply and reply all read exactly the same in the body.

The facts. Invoice 2041 and Friday are what Maya will hold you to. If the draft says anything else, a different date or an amount you didn't mention, it came from somewhere in the thread, and that's worth tracking down.

Say Priya is on the card. You remove her and approve, and the reply goes. Then you glance at Sent to confirm. All of that takes about as long as rereading the subject line.

Or say the draft promised the invoice for Thursday. Type "make it Friday" and the draft changes before anything leaves. The card is a place to fix a draft, not only to accept or reject it.

Where automatic replies fit

Some replies you never want to see again. "Got it, thanks, I will look today" to the same supplier, every time. For those, Otto offers opt-in automatic replies, and opt-in means something specific here.

They're off until you accept a policy for one mailbox. You choose the allowed senders or domains and the topics. You set the active hours, a daily limit, and a cancellation delay of at least five minutes. Before you grant any permission to send, you can keep the policy draft-only and read samples of what it would have written.

A few more limits are built in. Replies go to the original sender, never to a group, and only for new incoming mail. Activity shows every candidate as queued, preparing, ready for review, sending, sent or uncertain, and you can cancel one before its window closes. Pausing the policy stops new candidates from starting.

That's the gap between this and autopilot. You pick the limits in advance, you can see them, and you can undo them, instead of finding out after something went wrong. Automatic replies are a Plus feature. The automatic replies guide has the full setup.

What asking first costs you

Attention. Approve every card without reading it and you've built autopilot with extra clicks. The safety was never there.

Two habits help. Shrink the request when you're unsure: "draft a reply" before "reply", "show me the messages" before "clean these up". And save your attention for the cards that touch a customer or a lot of mail, where a mistake is expensive.

Approval isn't completion either. It starts the work. A queued send still has to go out. A large bulk job runs in the background and can come back partial. Pausing an automatic-reply policy doesn't recall a send the provider already confirmed. If an outcome comes back uncertain, check Sent before you retry by hand, or you'll send the same email twice. AI that waits for your approval goes through those checks in detail.

Plenty of people will reasonably pick a more automatic tool, especially when most of their mail is routine and low stakes. The five questions in how to choose an AI email assistant will tell you whether one fits.

Try it on a reply you've been avoiding

Pick one low-stakes thread today. Ask for the reply, read the card, approve it, then look at Sent.

Free to start: one connected Gmail or Outlook account, with core mail, calendar and tasks and an AI allowance. Read the assistant guide or open Otto and try it on a real thread.

First published on the Otto Mail blog.

Build a Gmail filter you can check first

Otto Mail — Mon, 02 Nov 2026 09:56:40 +0000

Four tools that sound like one

People say "filter" when they mean any of four different things, then wonder why what they set up didn't do what they expected.

Labels and folders are where mail lives in your provider. They organize. Gmail labels can overlap, so one message can carry several. Outlook folders work differently.

Smart views save a search. You find the same messages again with one click, and nothing moves or changes.

Filters run on incoming mail, using the conditions and actions your provider supports. They're the "from now on" tool.

Rules, cleanups and automations are the rest. Otto rules act on incoming mail within one mailbox. A cleanup processes mail that's already there, using the bulk-action flow with visible progress. An automation runs a digest or cleanup on a schedule.

So pick by the question you're asking. Want to find the same mail again? Smart view. Want new mail sorted as it arrives? Filter. Want the old mail tidied? Cleanup. Want it on a calendar? Automation.

Why the preview matters

The classic filter mistake is a condition that's slightly too broad. You write "from the accountant" and discover it also caught the personal thread with the same accountant. You find out three weeks later.

Otto's filter builder shows what it would match while you build it. Set a condition and a count and a sample of real messages appear beside it, live, before you save anything. If the sample has something you didn't expect, tighten the condition and watch it change.

The conditions cover From, To, Subject, words it has and words it doesn't have, attachments and size. You can also exclude chats.

A walkthrough: invoices from Studio Luma

Say invoice mail from Studio Luma keeps landing in your inbox, and you want it labelled and out of the way.

Open Settings → Automations and start a new filter. Set From to the billing address and Has the words to invoice. Watch the preview. It reports a count and shows a sample, and you spot a thread from Maya that isn't an invoice at all. So you add a word to Doesn't have, and the count drops.

Now choose what to do. Apply the label Invoices. Tick Skip inbox, which archives it. You could also mark it read, star it, mark it important, or tell Gmail never to send it to spam. The list has Delete it too, and that's the one we'd think twice about.

One more checkbox deserves a pause: Also apply to existing emails. Without it, the filter only touches mail that arrives from now on. With it, the past gets tidied too. For a first filter we'd leave it off, save, and watch what happens to the next few messages. Turn it on once you trust the match.

Filters can also forward matching mail, but only to a verified address.

Before you save, read the preview one more time. It's the cheapest review you'll get: a list of real messages your filter is about to touch. Five messages when you expected five, you're done. Five hundred, and you've just saved yourself an afternoon.

Filter, saved view, or quiet the sender

If you want mail handled, use a filter. If you only want to look at it, use a saved view.

Say you want unread mail from finance in a single view, but you still want it in the inbox. A saved view does that. Otto can create one for you: "create a saved view for unread mail from finance". Or search, then pin the search as a Smart View in the sidebar.

Saved views are safe because they change nothing. Filters are powerful because they do.

For a new inbox we'd go in this order. Start with a saved view for anything you only want to look at, add filters for the senders you're certain about, and use a cleanup for the backlog. Add an automation once you catch yourself doing the cleanup every month.

Sometimes the answer is neither. Where sender screening is enabled on Plus, you can allow, quiet or Hide in Otto an exact sender. Hiding takes the mail out of Otto's primary inbox and its new-mail alerts, but it doesn't block delivery, archive, trash or mark anything read in Gmail or Outlook. All Mail and search still find it, and you can undo the choice.

For mail you're done with entirely, use the message's unsubscribe action when the sender provides one. That asks the sender to stop. It doesn't delete what has already arrived.

Limits

A filter is only as good as its conditions. The preview shows a sample, so read it, and keep an eye on the first few real matches.

Gmail and Outlook aren't the same. Gmail categories and Important markers aren't Outlook folders, and filter actions, label and folder management and search-wide actions depend on what each provider supports. Otto shouldn't offer a choice a provider can't carry out, and if an action is unavailable it says so.

Explicit rules stay in charge. Otto's learned memory doesn't silently replace a rule you wrote.

Large changes to existing mail go through the bulk-action flow. Read the scope on the card before you approve.

Build one filter today

Pick the sender that clutters your inbox most. Build the filter with the preview open, save it without touching existing mail, and check the next few arrivals.

Free to start, with filters and one-off rules included. The labels, saved views, filters and rules guide lays out the choices, the bulk actions guide covers cleanups, or open Otto and build the first one. To put a cleanup on a calendar, read inbox automations.

First published on the Otto Mail blog.

How to follow up on an email without annoying anyone

Otto Mail — Mon, 02 Nov 2026 09:56:35 +0000

The short answer

Reply on the same thread three to five working days after your first email. Add one thing they didn't have before and ask a single question they can answer in a line. If there's a real deadline, go a day or two before it instead, and say so.

That's most of it. The rest of this page is timing, wording and when to give up. (The timings are what we'd do ourselves. We haven't seen a study on this that we'd trust.)

Why it feels awkward, and mostly isn't

People put off following up because it feels pushy. We get it. But think about what usually happened on the other end: they opened your email between two meetings, thought "I'll answer that properly later", and later never came.

You're not interrupting a considered silence. You're picking the message back up off the floor.

What makes a follow-up annoying is how it's written. A third "just bumping this!" with nothing new in it is annoying. A short note with the date they need to know about isn't.

When to send it

For a routine request we'd wait three to five working days. Any sooner and it can read as if you didn't trust them to answer.

If you gave a deadline, follow up a day or two before it and mention the deadline again.

Sales and cold outreach are their own thing. Wait a week, maybe send one more a week or two after that, and then stop. Past two or three it starts to feel like a campaign.

After a meeting, send your own recap the same day. Then chase the open items on whatever dates you all agreed.

How to write it

Reply to your original email so the history sits right under your note. If you start a new thread with a new subject, they have to go digging, and digging is exactly what they didn't get round to the first time.

Then add something. A new fact, the attachment, a firmer date, or the ask cut down to one line. "Just checking in" doesn't count, because there's nothing in it to respond to.

Ask one thing. Ask two and you'll often get an answer to neither.

Make the answer cheap to give: yes or no, Tuesday or Thursday, this version or that one.

And give them a way out. Something like "If this isn't a priority right now, tell me and I'll close it on my side" works well on people who were stuck and didn't want to say so.

Four sentences is usually plenty. If yours runs longer, the first email probably did too.

Here's one we'd send:

Hi Maya, following up on Thursday's call. I've attached the two-page scope so you don't have to dig for it. Can you confirm by Friday that we're on for the 12th, or tell me what's in the way? If the timing's changed, a one-line reply is fine and I'll adjust.

A few common situations

After an interview or a pitch:

Thanks again for Tuesday. You mentioned you'd decide by the end of the month. Is there anything else I can send that would help?

When you need a document back:

Could you send the signed form by Thursday? I can't book the room without it. A photo of the signed page is fine if that's easier.

That last line does more than it looks like. People put forms off because finding a scanner is a chore.

For an unpaid invoice:

This invoice was due on the 3rd. I've attached a copy in case the first one got lost. Could you let me know when it'll be paid?

Attach the invoice every time, even if you sent it before.

For a colleague who owes you their part:

I'm sending the draft to the client on Friday at noon and I still need your section. Can you get it to me by Thursday evening, or tell me what's blocking it?

What we'd avoid

Sending the exact same text again. If it didn't work once, change something about it.

Copying their manager in to "help things along". Everyone can tell what that is, and it turns a reminder into an escalation.

Following up every day. Space them out, and decide before you start how many you'll send.

"Per my last email." You know what it means. So do they.

The real problem is remembering

Most follow-ups that go out late weren't held back on purpose. Somebody forgot. So decide when you send the first email, not later. Put it in your calendar, flag it, whatever you'll actually look at.

Plenty of mail apps will do this part for you. Superhuman says it brings a thread back if nobody replies by a time you pick, and SaneBox has reminders for messages that don't get a response. We haven't tested either for this page; that's how they describe it.

Otto does it too (it's our app, so weigh that). Set a follow-up on a thread and if a reply comes in, the reminder cancels itself. If nothing comes, the thread comes back to the top. You can also ask the assistant to set one for you. The snooze and follow-ups guide has the details.

When to stop

Two or three follow-ups over a few weeks, then let it go. We'd still send one last short note, so it isn't silence on your side as well:

I'll take this as a no for now. Happy to pick it up again whenever it suits you.

Oddly, that's often the one that gets a reply.

First published on the Otto Mail blog.

Best AI email assistants: how to choose

Otto Mail — Mon, 02 Nov 2026 09:56:00 +0000

The short answer

Three things narrow this down fast. Which email provider do you use? How much do you want the assistant to do without asking? Do you want a new app, or a layer on the one you have? On Gmail only? Then Shortwave and Gmail's own Gemini features are built for you. On Outlook, or both, check provider support first. It knocks out more options than any feature will. And if you want an assistant that prepares the work and then stops for your approval, that's the line Otto draws.

Otto is ours. This list isn't paid placement and has no affiliate links. We read each product's own pages on 9 October 2026 and didn't run a head-to-head test, so every entry links to its source. Plans and features change.

How we compared them

We asked six questions, roughly in the order they decide a choice. What can it change without asking? Drafts only, or can it also send mail and archive or delete it? Which providers does it support? What does it read and keep, whole message bodies or only headers? What's the cost shape: a free plan, a trial, a per-seat price, usage credits? Which platforms does it run on? And what job is it doing: a new mail app, a layer on yours, or an assistant?

If we couldn't find a claim on the product's own pages, we left it out. A price appears only where the vendor's page states it in US dollars.

The eight

Otto

Gmail and Outlook in one app, with a calendar and tasks alongside an assistant that drafts replies, finds mail, books meetings and files things away. It asks for your approval before it sends, books or edits anything, and automatic replies only run inside limits you set. Free covers one connected account. Plus is $6.99 a month and Pro is $19.99 a month. It runs on the web and on iPhone.

It's for people on Gmail or Outlook, or both, who want mail with a calendar and tasks alongside it. There's no native Mac or Windows app, and no meeting recording. The alternatives pages say more.

Superhuman Mail

A shortcut-first client that says it's built for teams that use Gmail or Outlook. Its Mail page lists Split Inbox, follow-up reminders, Send Later, snippets, read statuses and shared views. It describes AI that drafts and, if you want, sends for you. As of October 2026 its plans page lists Mail on the Business and Enterprise plans.

Good if your day lives in the inbox and you want speed. We didn't find a free Mail plan on the page we read. See Superhuman alternatives.

Shortwave

An AI mail client for Gmail. It has AI search and AI filters, bundles, delivery schedules and a free plan. Its docs say Microsoft 365 and Exchange accounts aren't supported at this time. Apps cover Mac and Windows, plus iOS and Android.

A good fit for Gmail and Google Workspace users who want AI inside the inbox. Outlook is out. See Shortwave alternatives.

Spark

Its Free plan lists a Smart Inbox and a calendar, with unlimited accounts. The AI features and team tools are on paid plans, and the pricing page marks Autopilot and Auto-Drafts as coming soon. Same four platforms as Shortwave.

Pick it if you've got lots of accounts and want a good free client. The AI is the paid part. See Spark alternatives.

Fyxer

Works inside Gmail and Outlook. It drafts replies in your tone, and it labels mail. It also records meetings for notes. Its pricing page says it drafts and you decide what's sent, and it describes monthly credits.

Best for a week that's mostly email and meetings. Usage is credit-based, and it's an add-on rather than a mail app. See Fyxer alternatives.

SaneBox

Works with every email client. It filters unimportant mail and has BlackHole for unwanted senders, a Daily Digest, follow-up reminders and snooze. It says it looks at the sender, the subject and the date, and doesn't store full emails or attachments.

If you're happy in your current client and just want it quieter, this fits. It sorts mail but doesn't write replies. See SaneBox alternatives.

Gmail with Gemini

Google's own AI inside Gmail, including thread summaries and Help me write. Which features you get depends on your plan and on your language and region. Google keeps the current list on its Gemini in Gmail help page.

No new app to learn, which is the appeal. It's Gmail only, and eligibility varies.

Outlook with Copilot

According to Microsoft's FAQ, Copilot in Outlook can prioritize your inbox, summarize a thread, draft with Copilot and coach on tone. Some features need a Copilot license.

It's aimed at Microsoft 365 organizations, and what you get depends on the license and the client.

What they cost

Otto Free costs nothing. The rest are the lowest paid plans, in USD on monthly billing, from each vendor's own pricing page.

Product	Lowest paid plan	Price	Notes
Otto	Plus	from $6.99/month	Pro $19.99/month; $55.99/year for Plus
Fyxer	Pro	from $49/month	per seat, $37/month billed yearly
Shortwave	Business	from $30/month	per seat
Spark	Plus	from $10/month	per seat, $8.25/month billed yearly
SaneBox	Snack	from $3.49/month	filtering for your current mail app, $2.42/month billed yearly

Superhuman's price depends on your region, and Gmail with Gemini and Outlook with Copilot depend on your plan or license, so we've listed no figure for them. Yearly billing is cheaper where a vendor offers it.

Which to pick

On Gmail only and want AI in the inbox? Shortwave, or Gmail with Gemini if not adding an app is the point.
On Outlook or Microsoft 365: Outlook with Copilot if you're licensed. Otherwise Otto, Superhuman or Spark, but not Shortwave.
On both Gmail and Outlook: one of Otto, Superhuman or Spark.
A free client for many accounts: Spark.
You like your client and want it calmer: SaneBox, or the filters and rules Gmail and Outlook already have.
Meetings eat your week: Fyxer.
You want to approve everything it does before it happens: Otto.

Whatever you pick, run one real week through it first. The side-by-side comparisons can narrow the field, and a trial does the rest.

First published on the Otto Mail blog.