Windows · Outlook Classic · Multiple accounts

One AI conversation across your Outlook accounts.

Use Claude, ChatGPT or another compatible AI assistant to search the Outlook Classic mailboxes you choose and create real drafts in the right account. No Outlook add-in. ReplyPort cannot send: you review and press Send in Outlook.

Get it from Microsoft Store Watch the 38-second film

Early access · US$29.99 one-time purchase

Works with the AI you already use
Real Outlook drafts
No send function
One-time purchase

Works with ChatGPT, ChatGPT Work, Codex, Claude, Claude Cowork and Claude Code.

Outlook Classic in dark mode with two accounts, a university account and a personal account, each with its own Drafts folder. An unsent draft with a PDF attached is open in the university account, marked Draft - Not Sent, with the Send button still waiting. — Real drafts. Correct mailbox. You press Send. Example accounts. Each draft waits, unsent, in the Drafts folder of the account it belongs to.

Who it is for

Built for people with more than one Outlook account.

Work, clients, projects and personal correspondence often live in different mailboxes. ReplyPort lets one AI conversation work across the accounts you choose and puts each draft back into the correct Outlook account for review.

Consultants and advisers

Consultancy, university and personal

Ask one question across every identity, while each reply still comes from the account and signature it belongs to.

Agencies and independent professionals

Your business and client accounts

Find what a client said, whichever mailbox it reached, and prepare the reply from the account that client expects.

Researchers, founders, small businesses

Several projects or brands

Prepare a batch of messages in one conversation. Each draft is created in the mailbox it should come from.

What you can do

Three jobs across your accounts.

Ask in ordinary language. The examples below use ChatGPT with a university account and a personal account; Claude works the same way.

01

Orient yourself across accounts

Ask what is happening on a project. Your AI searches every mailbox you have enabled, opens the relevant messages and tells you what matters and what to do next. Nothing is created in Outlook.

“Orient yourself to my Tiny Towns Atlas project. Search across all enabled mailboxes and identify the 3 most important recent items.”Example request

A ChatGPT conversation using ReplyPort. The AI searched the enabled mailboxes and lists the three most important recent items for the project, each with what it is about, who is involved, why it matters and what to do next. — ChatGPT, using ReplyPort. Open the full screenshot.

02

Find it, whichever account received it

You do not need to remember which mailbox a message went to. Your AI runs one search in each enabled account and reads the full message before it reports back. Ask for a reply and the draft is created in the account that received the original.

“Where’s Anton’s email about the podcast?”Shown in the film

Read what the film shows

Your work email isn’t always in one inbox. One inbox becomes three separate work accounts.
And Outlook add-ins aren’t always available. An add-in approaches the accounts but is not available.
But your accounts are already in Outlook. The accounts sit inside Outlook Classic on Windows.
ReplyPort connects Outlook to the AI you already use. ReplyPort runs on your Windows PC between Outlook and your AI, with a separate path to each account.
Ask a question, and your AI searches every mailbox you’ve enabled. “Where’s Anton’s email about the podcast?” is checked in each account. Two have no match; the University account has it, and the answer comes back from there.
Ask for a reply, and a real draft appears in the right Outlook account. The AI writes only the reply text. ReplyPort adds the recipient, subject and signature from Outlook and saves the draft in the University account’s Drafts.
Nothing sends automatically. The draft stays unsent.
You review. You send. The person reads the draft and presses Send in Outlook.

03

Prepare drafts in the right identities

Ask for several drafts at once. A reply is always created in the account that received the original message. A new message comes from the account you name, or that your AI chose and reported to you. Each draft carries that account’s signature, and nothing is sent.

“Identify 5 potential partners for the Tiny Towns Atlas project, prepare a tailored outreach draft for each and place it in the most appropriate mailbox. Do not send anything.”Example request

A ChatGPT conversation using ReplyPort. The AI lists five outreach targets; for each it gives the reason, the mailbox used (University or Personal) and Draft: created. It ends: All 5 drafts are ready in Outlook for review. — Each draft names the mailbox it was created in. Open the full screenshot.

How it works

Ask your AI. Review in Outlook. You send.

ReplyPort has no send function.

Every draft waits, unsent, in Outlook until you act on it.

01
Your accounts stay in Outlook.

Outlook Classic is already set up on your Windows PC. Nothing to migrate and no Outlook add-in.
02
You choose what to share.

ReplyPort copies recent mail from the mailboxes you approve into a ReplyPort folder in your Dropbox.
03
Ask your AI.

Your assistant reads that folder to search, summarise and write replies, then leaves a draft request there.
04
ReplyPort checks and creates the draft.

On your PC it checks the account, recipients, subject and conversation, then saves an unsent draft in that account.
05
You review and send.

Open the draft in Outlook. Edit it, discard it or press Send yourself.

Data flow

What runs on your PC, and what does not.

ReplyPort’s connection to Outlook runs on your PC. The mail your AI reads does not stay there: the current version copies it to your Dropbox so your AI can reach it.

On your Windows PC

ReplyPort works with Outlook Classic directly. No Outlook add-in, and you do not sign ReplyPort in through Microsoft Graph.
Every draft request is checked against the live mailbox before a draft is saved.
Account bindings and keys stay on the PC. Logs contain no subjects, bodies or addresses.
There is no ReplyPort server and no send function.

In your Dropbox

Copies of the last 90 days of mail, only from the mailboxes and folders you approve. Mail copying is off until you turn it on.
Attachments only if you turn them on for that mailbox.
Search and draft requests passing between your AI and the PC.
Dropbox’s terms and privacy policy apply.

With your AI

Your assistant reads the approved copies and writes requests. It never connects to Outlook or to your PC.
Messages marked Personal, Private or Confidential, and encrypted messages, are not copied.
Your AI provider’s terms and data policies apply.

Full details: Privacy policy · Documentation

ReplyPort Control Centre showing ReplyPort running, Outlook Classic connected and storage connected, with two example mailbox cards, University and Personal. Each card shows mail copying enabled, Include all mail folders and Include email attachments turned on, and both up to date. — Control Centre shows each connected mailbox, which folders are copied and whether attachments are included.

Requirements & fit

Check the fit before you buy.

ReplyPort is early-access Windows software. These are the requirements and limits of the current Microsoft Store release.

You need

Windows 11 on an x64 PC where you can install apps from the Microsoft Store.
Outlook Classic with your accounts already set up. It must be open for drafts to be created.
The Dropbox desktop app, signed in on the same PC.
An AI assistant that can read and create files in your Dropbox, such as ChatGPT, ChatGPT Work, Codex, Claude, Claude Cowork or Claude Code.

Accounts and mail

Tested with Microsoft 365 work or school accounts and personal Outlook.com accounts in Outlook Classic. IMAP, POP and on-premises Exchange accounts have not been verified.
Searches cover the last 90 days. For each mailbox you choose Inbox and Sent Items only, or all ordinary mail folders; individual folders cannot be selected. Deleted Items, Junk Email, Drafts, Outbox, shared mailboxes, PST files and Online Archive are never copied.
Shared or delegated mailboxes are not included unless they are set up as their own account.
Replies, Reply All and new messages, with files your AI chooses attached. No Forward.

Not a fit if

You use New Outlook, Outlook on the web, a Mac or a phone only.
You want email sent automatically.
You cannot install software on the PC, or may not use Dropbox or an external AI with this mail.
You need centrally managed deployment for a team.

ReplyPort does not need an Outlook add-in, and you do not authorise it through Microsoft Graph. Your organisation’s device, storage and AI-use policies still apply.

Early access · US$29.99 one-time purchase · Local prices shown in the Microsoft Store · Updates through the Microsoft Store

Install from Microsoft Store Setup guide

Questions

When ReplyPort is the right tool.

Already happy with Claude for Outlook, ChatGPT’s Outlook apps or Microsoft 365 Copilot? Keep using them where they support your accounts, your organisation permits the connection and they handle the work you need.

ReplyPort is for people who keep several accounts in Outlook Classic, want to use the AI they already prefer, do not want an Outlook add-in, and want drafts created through the Outlook accounts already on their PC.

Is ReplyPort a Claude or ChatGPT product?

No. ReplyPort is independent software and does not contain an AI model. It works with assistants that can read and create files in your Dropbox, including Claude and ChatGPT.

Does my email stay on my PC?

Not all of it. ReplyPort runs on your PC, but so that your AI can read mail it copies recent mail from the mailboxes you approve to your Dropbox. Dropbox and your AI provider process those copies under their own terms. See Data flow.

Can ReplyPort send email?

No. ReplyPort has no send function of any kind. It does not use Outlook’s Send, SMTP, Microsoft Graph or any other mail service. Every draft stays unsent until you send it in Outlook.

How does it choose the account for a draft?

A reply is always created in the account that received the original message. A new message is created in the account named in the request; if the account is unclear, your AI should ask you. ReplyPort never guesses an account from an address or domain.

Do I need another AI subscription?

No subscription comes from ReplyPort. You use your own assistant, on whatever plan lets it read and create files in Dropbox. ReplyPort is a one-time purchase.

Does it work with New Outlook or on a Mac?

No. ReplyPort works only with Outlook Classic on Windows. If New Outlook is active, draft requests are refused.

What does it cost?

US$29.99 as a one-time purchase in the Microsoft Store during early access. Outside the United States, the Store shows the price in your local currency.

Where can I read the details?

The documentation describes what the current release does and does not support. The Setup guide covers connecting your AI after installation.