Ways to use AI with Outlook
There are three broad approaches. Which one suits you depends on your accounts, your AI and what your organisation allows.
- An integration from Microsoft or your AI provider. Microsoft 365 Copilot, Claude for Outlook and ChatGPT’s Outlook apps each connect to Outlook in their own way. What they can do depends on your plan, your account type and your organisation’s settings. If one of them supports your accounts and your organisation permits it, it may be all you need.
- A different email client with AI built in. These replace Outlook as the place where you read and write mail.
- A bridge to the Outlook you already have. ReplyPort takes this approach. Outlook Classic and its accounts stay as they are. Your AI works with copies, in your Dropbox, of the mail you approve, and ReplyPort turns its replies into ordinary Outlook drafts.
When ReplyPort fits
- You use Outlook Classic on a Windows PC you control.
- You keep two or more accounts there, such as work, clients, a university or personal mail, and want one AI conversation across them. See AI across multiple Outlook accounts.
- You already use Claude, ChatGPT or another assistant that can read and create files in Dropbox, and would rather not add another AI subscription.
- You do not want an Outlook add-in, and want every draft to wait in Outlook until you send it.
It is not a fit if you use New Outlook, Outlook on the web, a Mac or a phone only, if you want email sent automatically, or if you need centrally managed deployment for a team.
What your AI can do with ReplyPort
- Search and read recent mail across the accounts you enable, and open full messages before reporting on them.
- Summarise and triage: “What needs my attention?” or “What changed on this project this week?”
- Reply and reply all to a message, using Outlook’s own reply in the account that received it.
- Write new messages from the account you name, to exact addresses.
- Attach exact files to drafts, such as a PDF or an Office document. ReplyPort checks each file and confirms the attachment in Outlook.
- Prepare several drafts in one request, each reported separately.
What it cannot do
- Send email. ReplyPort has no send function of any kind; you send from Outlook.
- Forward messages. Forward is planned but not available.
- Search mail older than 90 days, or Deleted Items, Junk Email, shared mailboxes, PST files and Online Archive.
- Format draft text. Your AI writes plain text; the account’s signature keeps its own formatting.
The feature status table in the documentation lists what the current release supports.
Where your mail goes
ReplyPort’s connection to Outlook runs on your PC and does not use an Outlook add-in or Microsoft Graph. To let your AI read mail, the current version copies recent mail from the accounts you approve into a ReplyPort folder in your Dropbox. Your AI reads those copies and leaves draft requests there; ReplyPort checks each request on your PC before creating the draft.
Dropbox and your AI provider process the copied mail under their own terms. Messages marked Personal, Private or Confidential, and encrypted messages, are not copied. Details are in the Privacy policy.
Requirements
- Windows 11 on an x64 PC where you can install apps from the Microsoft Store.
- Outlook Classic with your accounts already set up, open while drafts are created.
- The Dropbox desktop app, signed in on the same PC.
- An AI assistant connected to that same Dropbox account, with permission to read and create files there, such as ChatGPT, ChatGPT Work, Codex, Claude, Claude Cowork or Claude Code.
Use ReplyPort only if your organisation permits copying this mail to Dropbox and using it with your AI service. ReplyPort does not need an Outlook add-in, but your organisation’s device, Dropbox and AI-use policies still apply.
After installing, the Setup guide connects your AI in three steps.