What people actually ask for.

A file moved between messages without passing through the model

Nothing else on this market does this the same way, and the mechanism is why. The assistant never has to see the file. It reads the message, gets a handle to the attachment, and passes that handle to the send.

The bytes go from your mailbox to the outgoing message on our side. The model only ever holds a filename and a size, unless you ask it what the file says.

So the only ceiling left is the message itself: 20 MB in total, which is our limit rather than the provider's. A 6 MB PDF costs no more in the conversation than a 6 KB one, which is the part that was impossible before.

Compare Anthropic's Microsoft 365 connector. Its own security guide says attachments are not supported in any write tool, and that sending, forwarding and drafting all reject a message carrying one.

A file off your own computer, without opening the panel

The file isn't in the mailbox and has no web address, so there's nothing to hand the send. The assistant asks for a one-off upload link, then takes whichever of 2 routes it can.

If it can run commands or make requests, it uploads the file itself and you do nothing at all. If it can't, it gives you the link, you open it and choose your files, and it carries on. Either way you never sign in anywhere.

What arrives goes into your own Drafts folder as a draft, which you can open, keep or delete in Outlook like any other. Nothing is stored on our side, and the link stops working after half an hour.

From there it works like the case above. The assistant gets a handle rather than the bytes, so a 6 MB file costs no more in the conversation than a 6 KB one, and the only ceiling is the ordinary 20 MB on the whole message.

A real draft, in the real Drafts folder

It's APPENDed to the mailbox's own Drafts folder, so it appears in Outlook, in webmail and on your phone, and you can edit it, send it or delete it there. A draft you can only see in a chat window is a record of a draft rather than a draft.

You can also ask for another go, which is the part most assistants get wrong. Say the second paragraph is too stiff and it rewrites that draft. It doesn't save a second one, and it doesn't put the first in your bin.

So a wording you worked through 5 times leaves exactly one message in Drafts. Anything already attached stays attached.

When you do send from here instead, exactly one copy is filed in the real Sent folder. Not none, which leaves you with no record, and not 2, which is what happens when a server files a copy and the mail host files another.

A reply that stays in its own thread

It replies inside the original conversation and quotes the original below the new text, the way a mail client does. It files the copy in Sent and marks the original as answered, so your own client shows the little reply arrow next to it.

One safety rule worth knowing: a Reply-To header pointing somewhere the message didn't come from is refused until the caller names that address explicitly. That header is how a redirected reply ends up somewhere you didn't intend, and it's set by the sender, not by you.

A forward that carries its attachments

The original's attachments and inline images travel with it, under the forwarded-message block a real mail client produces.

If a carried file won't fit inside the message ceiling, it's reported as skipped, by name, rather than dropped quietly. So you find out at the point where you can still do something about it.

Recipients are exactly the addresses supplied. Nothing is inferred, and nothing is added.

A search across folders, with the vagueness intact

One call searches up to 25 folders, by sender, recipient, subject, body, date range, read state, flag state and whether a message has been answered. The assistant turns "some time last spring" into a date range and a set of folders; you don't have to.

Results are capped, and this is the part worth trusting. The response reports the total found, the number returned, and whether it capped. So an answer built from the first 50 of 400 results says so, rather than reading like the whole story.

An address resolved from your own history, or your own address book

It looks the person up in the mailbox's own correspondence, and in your own address book where you've connected one. A person in the book comes first, with every address, the phone numbers and the employer on the card.

Among the mail, an address you've sent to outranks one that merely arrived from somebody using that name, because a display name on inbound mail can say anything at all.

That ranking rule is a small anti-phishing measure hiding in a convenience feature. The address you put in your own contacts, or have actually written to, is the one you trusted before.

A thread in one call, oldest first

From any single message in it. You don't have to find the first one, and the assistant doesn't have to make 12 calls to walk the chain.

A long thread is capped and the result says so, rather than quietly returning the newest few and letting a summary be built from the wrong half of a conversation.

The file read, not just the message around it

It opens the message, then reads the attachment itself. A PDF or a Word document comes back as text, a spreadsheet as rows with the formulas already worked out and every sheet reachable, a slide deck slide by slide, and a photo as a picture it can look at.

A scanned letter is a PDF with no text behind the picture. It comes back as pictures of its pages, so it's read the way you would read it.

However many files are on the message, one call reads them, and a long document comes back in windows it can page through. Nothing is kept afterwards, and the message isn't marked read.

If the file is a zip, an RTF or an old .doc, it says so, and the download link is still there for you.

A time everybody can make, found and booked in one ask

It reads everybody's free and busy blocks and picks an hour inside all 3 working days, not one that is merely empty at 7 in the evening. Then it creates the meeting with an online link and sends the invitations.

Watch what it does when it can't see somebody. That person comes back as unknown rather than free, and it says so instead of booking over an afternoon it couldn't read.

This one needs a Microsoft 365 mailbox with calendar access approved. It's also the case that most clearly beats doing it yourself, because the manual version is 4 calendars open in 4 tabs and a message that starts "does anyone mind if".

A day read back in your own timezone, repeats included

It reads the window you asked about and reports each event with who organises it and how many people are on it, so a block of your own time is never read back as a meeting.

A weekly meeting appears on the date it actually falls on, the way it does in Outlook, rather than as a rule somebody has to interpret.

Every time comes back in the mailbox's own timezone and is stated with it. That sounds pedantic until the first time somebody answers "three o'clock" from a laptop in a different country. Works on any connected calendar, whoever hosts it.

A decline that carries an alternative, not just a no

It declines the invitation and proposes the new time in the same action, with a note to the organiser. That's the answer a person actually wants to give.

Most integrations can't express it at all: they can accept and they can decline, and the useful third option is missing. Where the organiser has switched proposals off, it says so rather than trying and failing.

Microsoft 365 mailboxes only. The organiser sees exactly what they would see if you had done it in Outlook, because it's the same request.

Out of office set for a period, and the meeting moved

It writes the out-of-office reply for the exact date range, with a different message for people outside your organisation. Then it reschedules the meeting and tells everybody who was on it.

The reply is the same setting Outlook writes, so it shows in Outlook and switches itself off at the end of the period.

Nothing of ours runs while you're away to make that happen. Microsoft applies the setting at the time, exactly as it would if you had ticked the box yourself. Microsoft 365 mailboxes only.