Understand the current message
Summarize a thread, pull out action items, and stay oriented without digging through long email chains or losing the current Outlook context.
Built for classic Windows Outlook
AI for people who live in Outlook.
Skipper Agent helps Outlook-heavy users reply, forward, search mailbox history, read attachment content, speak requests into the side panel, and take real Outlook actions without leaving Outlook. Use your own API key for OpenAI, Anthropic, Gemini, or Qwen, and if you already use Codex, you can use your Codex subscription too.
- Reply, forward, and revise open drafts inside Outlook
- Bring your own OpenAI, Anthropic, Gemini, or Qwen API key, and optionally use your Codex subscription too
- You choose the model, the cost, and the tradeoff instead of taking whatever someone else picked
- Learn how you write and what you work on from Sent Items
- Run workflows that prepare replies and surface workflow-suggested next actions
- Use microphone instead of the keyboard
- Search local mailbox memory, inspect attachments, and work from the actual message
- Open native Outlook commands, create Outlook items, run scripts, and handle local-file work
Classic Outlook only
Side panel inside Outlook
Reply, forward, and draft revision
Contacts, meetings, tasks, scripts, and local-file work
What It Does
Focused on real Outlook work.
Skipper Agent helps with the Outlook tasks people repeat every day, while staying closer to an Outlook operator than a generic summary panel.
Create and refine native Outlook drafts
Generate a reply, forward, or new draft, revise the Skipper-generated portion of an open unsent draft, and send the current draft when it is ready without disturbing the quoted thread or signature.
Search Outlook mail with natural language
Ask for the messages you need in plain English, use semantic mailbox memory for related prior mail, show the search in Outlook, or inspect returned matches when the answer depends on exact messages.
Ground replies in prior Sent Items
Before drafting a mailbox-grounded reply or forward, Skipper can search your local sent-mail memory and Sent Items cache for similar prior answers, then draft from the wording, facts, and technical context you used before instead of generic model memory alone.
Speak instead of type
Use the microphone in the Skipper pane to dictate requests when speaking is faster than typing, or attach the captured voice message to a reply as an MP3.
Inspect attachments and message context
Read the text inside common Office, PDF, HTML, ZIP, and other supported attachment types when the answer depends on the file, not just the email body.
Drive built-in Outlook UI by asking
Open native Outlook dialogs, panes, and compose commands such as Rules and Alerts, attach-file flows, recurrence, Scheduling Assistant, or formatting controls when the fastest path is to use Outlook's own UI.
Go beyond Outlook when the task demands it
When the job involves your local files or a utility step outside Outlook, Skipper can use local PowerShell-backed work instead of stopping at the edge of the mailbox.
Use advanced Outlook automation when built-ins are too small
For tasks that outgrow the small built-in actions, Skipper can generate and run C# automation against Outlook and related local .NET APIs.
Create Outlook items right from the message
Turn the current email into a contact, an appointment draft, or a task draft without manually copying names, dates, or summary details into a separate Outlook form.
Run inbox workflows in the background
Turn on workflows for newly received Inbox messages so Skipper can prepare reply actions, surface workflow-suggested next steps, and handle recurring inbox work without waiting for you to start from scratch each time.
See suggested next actions on the message
Workflows can figure out which next actions fit a message, such as reply, create meeting, create task, create contact, or delete, instead of treating every message the same.
Why It Goes Beyond Basic Outlook AI
More than summaries and canned replies.
Skipper is not just another paragraph generator. It stays aware of Outlook context and can do real mailbox work around the message instead of acting like a floating chatbot.
Revise an open draft in place
When an unsent draft is already open, Skipper Agent can refine the generated draft content inside that draft instead of creating another disconnected version. It can also make exact replacements in the generated draft range for small wording changes.
Search memory before drafting
For reply and forward drafts, Skipper can search local sent-mail precedent and exact Sent Items matches first, wait for those results, then create the native Outlook draft from the evidence it found.
Use semantic retrieval when keywords are too small
Mailbox-memory search can combine exact text signals with local semantic matching, so a prior technical reply can still surface when the new request uses different wording.
Talk to it naturally
For many users the fastest workflow is voice. Skipper supports microphone input in the side panel, so you can speak the request, review the result, attach the recording to a reply when voice is the message, and keep moving without stopping to type every prompt.
Check your calendar before promising a time
Skipper can inspect your calendar and free/busy availability before it confirms a proposed meeting time, and it uses that schedule context when preparing appointment drafts.
Read the file before answering
When the important detail is inside the attachment, Skipper can read supported files and respond from the actual document instead of guessing from the email body alone.
Do the Outlook work, not just the writing
Set categories, apply follow-up flags, mark messages read, open the found item, move or archive mail, and keep those actions in the same Outlook-side workflow.
Use Outlook's own commands when that is the right move
Skipper can open built-in Outlook UI such as Rules and Alerts, Reading Pane options, attach-file flows, recurrence, Scheduling Assistant, or native compose formatting instead of forcing everything through a text-only answer.
Work with local files too
Ask about your Documents or Downloads folders, search local text, inspect archives, or handle other file-system utility tasks through local PowerShell execution when the answer is not only in Outlook.
Escalate to real Outlook scripting
If the built-in tools are not enough, Skipper can generate and execute more complex Outlook-aware C# scripts instead of giving up at the first hard case or falling back to a shallow text-only answer.
Draft emails that feel like you wrote them
Skipper can build and update both a writing profile and an expertise profile from your Sent Items. Drafts can reflect not only how you write, but also how you previously answered similar questions and what product, technical, or business knowledge those answers relied on.
Turn one email into the next Outlook object
Pull a contact, a meeting draft, or a task draft out of the current message when the conversation should become something you act on, not just something you reply to.
Author workflows in chat, then test them
Describe the workflow in a dedicated editor chat, review the compiled plan with scope, decision rules, and allowed actions, then test it against selected messages before you rely on it for incoming mail.
Specific Capabilities
What it can do today.
These are product capabilities, not vague "AI assistance" claims: Outlook-aware tools mapped to real mail, attachment, file, and automation tasks.
Draft tools
Create a new message, reply, or forward. Then rewrite the open draft, make exact text substitutions, or send the current draft without rebuilding the whole message.
Search and follow-up on results
Search the current folder, subfolders, store, or local MailMemory cache, then use the exact found Outlook item as the source for the next draft or action. Semantic memory search helps find related precedent when exact keywords are not enough.
Open native Outlook UI on demand
Open Outlook's own dialogs, panes, and compose commands for things like Reading Pane settings, Rules and Alerts, attach-file flows, recurrence, Scheduling Assistant, or formatting changes.
Calendar-aware meeting help
List calendar events, inspect free/busy availability, and use that schedule context when creating meeting drafts or replying about proposed times.
Mailbox-aware item actions
Apply a category, flag an item, clear a flag, mark mail as read, open an already-found message, navigate to a folder, or prepare move and archive actions inside Outlook.
Voice input in the side panel
Dictate prompts through the built-in microphone control when speaking is faster than typing, then continue with the same message, draft, and Outlook context on screen. After recording, Skipper can also attach the latest voice capture to a reply draft as an MP3. If your main chat provider is text-only, Skipper can use another configured speech-capable provider for voice input.
Attachment-aware help
Read the contents of supported attachments when the important answer is inside the file rather than in the message preview.
Local file and folder work
Search local folders, inspect text files, work with archives, and handle utility tasks through local PowerShell-backed execution when Outlook is only part of the job.
Personal guidance, not just generic prompts
Tell Skipper about yourself, keep known facts and preferences close at hand, and use writing plus expertise profiles built from your guidance and Sent Items so the product understands both your voice and the work you actually do.
Create contacts, meetings, and tasks from email
Build a contact draft from the sender or another person in the thread, create an appointment draft from the message, or turn the email into an Outlook task draft with extracted timing and summary details.
Incoming-mail workflows
Create and manage workflows for newly received Inbox messages, including categorization, spam detection, draft-reply preparation, inline reply-draft preparation, and suggested next actions on the message.
How It Works
Ask for the result you want, then stay in control.
Prepared by AI. Confirmed by you. Skipper can line up the work, but the final decision on meaningful actions stays with the user.
Open Skipper inside Outlook
The product lives where the work already happens, with Outlook context and the selected message visible.
Ask for an outcome
Summarize the thread, draft a reply, search related mail, inspect an attachment, or request a specific Outlook action.
Review what happens next
Tool activity stays visible, and higher-trust actions like move, delete, archive, sending, or script-driven changes can remain approval-aware instead of disappearing into background automation.
Trust And Privacy
Designed to feel understandable.
Prepared by AI. Confirmed by you. Skipper does the preparation work, while meaningful actions stay visible and approval-aware so the final decision remains with the user.
No embarrassing surprises
Skipper can draft the reply, prepare the meeting, organize the message, and line up the next step, but it is designed so important actions do not happen behind your back.
Provider choice stays with the user
Bring your own API key, choose your provider, and pick the model you want to pay for. Skipper supports OpenAI, Anthropic, Gemini, and Qwen, and if you already use Codex, it can use that setup too.
Outlook remains the visible workspace
The message, the draft, and the side panel all stay in view so users can see what the product is acting on.
Actions stay inspectable
Status, progress, and results stay legible instead of hiding the work behind a single vague answer bubble, especially for more meaningful Outlook changes that deserve a final human review.
It can be personal to you
Skipper is not limited to a generic prompt every time. You can tell it about yourself, keep stable preferences, and use profile guidance plus Sent Items learning to build both writing and expertise profiles, so drafting feels like it was written by you and shaped by the work you actually do.
Built for classic Outlook
Skipper Agent is for classic Windows Outlook because that is where it can do deeper, more useful work for you. The result is more capability where Outlook power users already live, not a watered-down feature set stretched across every Outlook surface.
Local desktop install
Skipper installs locally for your Windows user. There is no server component to stand up and no Microsoft 365 admin deployment step just to try it in classic Outlook.
Download
Get the current Windows installer.
Download the per-user MSI build for classic Windows Outlook. This is a local desktop install, so you can run it for your Windows user without a server setup or Microsoft 365 admin rollout.
Installer: SkipperAgentInstaller.msi
Download MSI
Per-user installer for native desktop Outlook on Windows.
FAQ
Questions a serious Outlook user will ask first.
Which Outlook does this support?
Skipper Agent supports classic Windows Outlook.
Does it work inside Outlook?
Yes. It runs in an Outlook side panel that stays next to the message and draft workflow.
Will it send, delete, or change things on its own?
Skipper is designed to do the preparation work while keeping meaningful actions visible and approval-aware. It can draft, organize, and line things up for you, but the final decision on risky or embarrassing actions stays with the user.
Do I need admin setup or a server deployment?
No server component or Microsoft 365 admin rollout is required for the standard per-user install. In a normal desktop setup, you can install and remove it locally for your Windows user. For technical readers, this is a native desktop Outlook add-in delivered as a per-user MSI rather than a web add-in that depends on tenant deployment.
Do I bring my own API key and choose the model?
Yes. Skipper is built around your own provider account, so you choose the provider, the model, and the spending level that fits you. If you want to use a smaller cheaper model, you can. If you want the latest stronger model from OpenAI, Anthropic, Gemini, or Qwen, you can do that too. If you already use Codex, Skipper can also use your existing Codex setup.
Can I use my Codex subscription?
Yes. If Codex is already set up on your machine, Skipper can use that existing Codex setup instead of asking for a separate OpenAI API key.
Can I talk to it instead of typing?
Yes. Skipper supports microphone input in the side panel, so you can speak a request instead of typing it. Voice input works directly with OpenAI, Qwen, and Gemini. Anthropic and Codex can still use voice input by borrowing another configured speech-capable provider.
Can I send a voice message in a reply?
Yes. After recording, Skipper can attach the latest voice capture to the active reply draft as an MP3, or create a reply draft and attach it there.
Can it open Outlook dialogs and built-in commands for me?
Yes. Skipper can open a curated set of native Outlook UI flows when that is the right next step, including things like Rules and Alerts, Reading Pane options, attach-file flows, recurrence, Scheduling Assistant, and native compose formatting controls.
Can it suggest the next action on a message?
Yes. Workflows can suggest actions for the current message, such as reply, create meeting, create task, create contact, or delete, when the message strongly points to one of those next steps.
Can it run workflows on incoming mail?
Yes. Skipper supports opt-in workflows for newly received Inbox messages. Built-in workflow patterns include categorization, spam detection, draft-reply preparation, inline reply-draft preparation, and suggested message actions. You can also author workflows in the workflow editor chat, review the compiled plan, and test a workflow against selected Outlook messages.
Can it check my calendar before proposing or confirming a meeting?
Yes. Skipper can inspect your calendar events and free/busy availability before it confirms a proposed time, and it uses that schedule context when preparing appointment drafts and meeting-related replies.
What kinds of tasks does it handle?
Message understanding, native Outlook drafting, open-draft revision, mail search, attachment-aware help, local file work, create-from-message flows for contacts, meetings, and tasks, and concrete Outlook actions like categories, flags, read-state changes, archive, move, and delete are all part of what it handles today.
Does Skipper search mailbox memory or only the current email?
Skipper can use a local MailMemory cache for searchable received and sent mail. Reply and forward drafting can search prior sent-mail precedent before drafting, while exact email search still returns concrete Outlook message rows when the task needs exact messages or entry IDs.
Why not just use Outlook Copilot?
The value here is not just summary text. Skipper is for users who want native draft revision, mailbox-aware search, attachment reading, local file work, Sent Items style learning, and concrete Outlook actions in the same side-panel flow.
Can it work with local files and more advanced automation?
Yes. Skipper can do local PowerShell-backed file and utility work, plus generated C# automation for Outlook-heavy tasks that are more complex than the small built-in actions.
Does it adapt to me personally?
Yes. You can provide self-description, known facts, preferences, and drafting guidance so Skipper feels more personal than a generic assistant. It can also analyze Sent Items to build both a writing profile and an expertise profile, then search prior replies for similar situations. That helps it reuse the way you explained the issue, the facts you considered important, and the domains or responsibilities that show up in your mail.
What gets stored locally, and what goes to the AI provider?
Skipper stores your settings, API key, learnings, writing profile, and local mailbox-memory search data on your machine. API keys are encrypted locally before they are written to the local database. When you ask it to help with a message, attachment, Sent Items style analysis, or another task that needs AI processing, the relevant content goes only to the provider you selected for that work. The resulting profile and product state stay local to your Outlook setup.