Last updated: August 5, 2026
Postail lives in a panel inside Outlook. Open a message, click Open Postail in the ribbon, and the panel appears beside it. Everything below happens in that panel.
Reads the message you have open and writes a reply in your voice, in first person, with no signature block (your Outlook signature gets added automatically, so a second one would be redundant). Pick a tone, hit Regenerate to rewrite in a different one, edit the text directly in the box, then Insert as Reply. That opens Outlook's own reply window with the draft in it. Nothing sends until you click send. Tick Reply All first if the whole thread should get it.
Turns a long thread into a few sentences: what it's about, who it's from, and what it needs from you. Useful on the ones you keep scrolling past.
Decides whether the open message is an invitation to bid, and if so pulls out the general contractor, project name, deadline, and scope. If it can resolve an exact date, Add to Calendar downloads a calendar file with a reminder the day before. If the email words the deadline vaguely ("end of next week"), that button stays greyed out rather than guessing a date at you.
Your license key, the mailbox connection, and links to these docs.
Everything above only runs when you click a button, which means it only helps with the email you already opened. The mailbox connection is what lets Postail help with the ones you didn't open.
In Settings → Automatic reminders, click Connect mailbox. You sign in with Microsoft, approve the permissions, and that's it. From then on Postail checks your mail on a schedule and emails you when:
Reminders arrive as ordinary emails from you, to you. No new app, no new inbox, no notification you have to remember to check. The strip at the top of the panel always says whether this is on.
Postail only ever emails you. Reminders go from your address to your own inbox, never to your contacts or clients. Replies you write go out only when you press send yourself. Microsoft's consent screen asks for permission to "send mail as you" because that is the permission reminders need; how Postail uses it is the commitment above.
Click Disconnect in the same place. The stored sign-in is deleted immediately. You can also revoke access from your Microsoft account's app permissions page.
Microsoft sign-ins expire — after a password change, or a long stretch of no activity. When that happens the panel says so and the fix is one click on Reconnect mailbox.
Reminders are a safety net, not a system of record. They can be mistimed, can miss a thread, and depend on services that occasionally go down. Keep tracking anything with real consequences the way you already do.
Each license has a daily cap and a short burst cap, so a runaway loop can't quietly rack up cost. Hit one and you get a plain message saying so, not a silent failure. If the cap is getting in the way of real work, email me and I'll raise it.
Outlook on the web and Outlook for Windows and Mac. Mobile Outlook is not supported — the API Postail uses to open a reply window doesn't exist there. Automatic reminders still reach your phone, because they're just email.
Email tgorman93@gmail.com. It's one person reading them, and it helps to include what you clicked and what the panel said.