Connect Outlook
Updated 4 September 2026
The Short Answer
Open Extensions then Connectors and use the Outlook card. Microsoft signs you in, so there is no app password to find. Tick every permission on the Microsoft screen: PropKaki writes the message in your mailbox before it sends, and that is what matches a reply back to the right person.
This card covers Microsoft 365 work addresses too, not just @outlook.com. If your agency runs on Microsoft, this is your card even though the address does not say Outlook.
How do I connect Outlook?
- Open Extensions → Connectors and open the Outlook card.
- Press Sign in with Microsoft. A Microsoft window opens — sign in with the account you email clients from.
- Allow PropKaki to send mail as you and read your mail. It keeps only what is from someone in your list.
- Press Send Me a Test and watch it arrive from your own address.
There is no app password anywhere in this one. Microsoft signs you in, and PropKaki never sees the password.
Why does Microsoft ask to write in my mailbox as well as send?
Sending on its own is not enough. PropKaki writes the message in your mailbox and then sends it, and the identifier that write hands back is the only thing a reply can be matched by. Grant permission to send but not to write, and mail goes out while replies never find their way to anybody.
So tick every permission on the Microsoft screen. If your company manages the account, your IT admin may have to allow it for you.
If you connected Outlook before September 2026, sign in again — permission to write was not part of the older grant.
What if the Microsoft sign-in doesn't finish?
The card tells you the sign-in did not complete — it was cancelled, or your organisation has not allowed PropKaki yet. Try again, or ask your IT admin to allow it.
Nothing is lost while you sort that out. If you already send from another mailbox, PropKaki keeps using it until an Outlook sign-in has actually worked, and the card says which one it is before you start: you send from Gmail today. Signing in here switches your email to Outlook.
How do I check that sending and replies are both working?
A mailbox does two jobs and each is reported on its own. Open the Outlook card and press View Status: Sending says whether the last test worked, Replies says when the mailbox was last read. PropKaki checks for replies every 5 minutes.
One case worth knowing. If your Outlook was set up years ago with a password rather than Sign in with Microsoft, the card opens the three-field form instead — and that mailbox can send but cannot receive, so Replies reads Send only. Signing in with Microsoft is what fixes it.
Is there a size limit on attachments?
Microsoft will not carry a file over 3 MB on this route, so PropKaki asks you before it sends rather than letting the message fail at the far end. It names the file, so you know which one to swap.
The limit is Microsoft's and it applies to this mailbox only. Gmail, Zoho and Other Email have no such rule, and WhatsApp never carries the bytes at all — so the same brochure that is refused here goes through on another channel.