---
name: outlook-emails-waiting-on-reply
description: "Weekday afternoons: Outlook conversations where the last message is from someone else and over 24 hours old, with an offer to draft replies. Use when the user asks for this, or when it runs on a schedule."
---

# Outlook emails waiting on your reply

Weekday afternoons: Outlook conversations where the last message is from someone else and over 24 hours old, with an offer to draft replies.

Outlook's flags and Focused Inbox help only if you use them every time, and the message that slips is always the one you read on your phone between meetings. A day later the sender is still waiting, and nothing in the inbox says so.

This skill compares what arrived with what you sent in the same conversation. When the last word belongs to a real person and it is more than a day old, the conversation goes on the list, oldest first. It then asks which ones to draft; drafts land in each conversation and nothing is sent.

## Two ways to get the data

Use the API or MCP route when you have an MCP server, a CLI or an API token for the app. Otherwise, if you can drive a browser the user is signed in to (Claude in Chrome, a Playwright or Chrome DevTools MCP server), use the browser route. Say which one you used.

## Route A: API or MCP server

### What you need

- Claude's Microsoft 365 connector (work or school accounts on a Microsoft Entra tenant), whose Outlook tools search your mail, or a Microsoft Graph app with delegated `Mail.ReadBasic`, enough to read senders, subjects and conversations.
- `Mail.ReadWrite` as well, only if the agent should create reply drafts.

If something is missing, say what and stop; do not invent numbers.

### Steps

1. **Read the inbox** (Outlook): `GET /me/mailFolders/inbox/messages?$filter=receivedDateTime ge <14 days ago>&$orderby=receivedDateTime desc&$select=id,conversationId,from,subject,receivedDateTime,toRecipients,ccRecipients,inferenceClassification&$top=200`, following `@odata.nextLink`. Graph requires the `$orderby` field to appear first in `$filter`.
2. **Read what you sent** (Outlook): `GET /me/mailFolders/sentitems/messages?$filter=sentDateTime ge <14 days ago>&$orderby=sentDateTime desc&$select=conversationId,sentDateTime&$top=200`.
3. **Find who wrote last**: Per `conversationId`, compare the newest inbox message with your newest sent message. The conversation waits on you when the inbox message is newer, from someone else, and more than 24 hours old.
4. **Drop what is not a person**: Skip senders like `noreply@` and `notifications@`, meeting requests and responses, messages where you are only in Cc, and messages Focused Inbox put in Other (`inferenceClassification: other`).
5. **Rank and ask** (Outlook): Order by hours waiting and ask which to draft. Drafts are made with `POST /me/messages/{id}/createReply`, which saves a reply in Drafts for you to edit; nothing is sent.

## Route B: the browser

### What you need

- Signed in to Outlook on the web as the mailbox owner (or with full access to a shared mailbox), with any 2FA prompt already done.

If something is missing, say what and stop; do not invent numbers.

### Steps

Start at https://outlook.office.com/mail/. The user is signed in already; never type passwords or codes, and ask if a sign-in page appears.

1. **Open the inbox in conversation view**: For a work or school account open outlook.office.com/mail; a personal account uses outlook.live.com/mail. Under **Settings > Mail > Layout**, make sure **Message organization** is set to show email grouped by conversation, so each thread shows who wrote last.
2. **Filter to the last two weeks**: Search `received>=<date 14 days ago>` in the search box, with **Focused** selected if Focused Inbox is on. Sort by **Date** with oldest first so the longest waits come up first.
3. **Find the threads where someone else wrote last**: Open each conversation. It waits on you when the newest message is from a person, you are in To rather than Cc, and it arrived more than 24 hours ago with no reply from you after it. Skip `noreply@` and `notifications@` senders and meeting invitations or responses.
4. **Rank and ask before drafting**: List the conversations by hours waiting with sender and subject. Ask which to draft; for each one chosen, click **Reply** in the conversation, write the draft, and close it so it stays in **Drafts**. Never click Send.

Note: Conversation view hides your own replies inside the thread, so the agent opens each one; with more than about 50 conversations in two weeks this is slow and the API route is better. The web Sent Items folder shows the same conversations from your side if you want a cross-check.

## The report

- **Count** of conversations waiting on you, and the oldest.
- **Per conversation**: sender, subject and how long they have waited.
- The ask: which conversations to draft replies for, if any.

## Post it to Briefkin

When `BRIEFKIN_TOKEN` is set, or `~/.config/briefkin/env` exists (the installer from https://briefkin.dev/docs writes it), also send the result to the user's Briefkin board as one card. Keep the `item_key` the same on every run so the card updates in place, use a new `event_id` per run, and put today's real numbers in place of the example ones. If the request fails, say so once and carry on.

```bash
[ -n "${BRIEFKIN_TOKEN:-}" ] || . ~/.config/briefkin/env
curl -sS -X POST "${BRIEFKIN_URL:-https://briefkin.dev}/v1/events" \
  -H "authorization: Bearer $BRIEFKIN_TOKEN" \
  -H "content-type: application/json" \
  -d @- <<'JSON'
{
  "v": 1,
  "event_id": "outlook-emails-waiting-on-reply/<date of this run, e.g. 2026-10-16>",
  "item_key": "outlook-emails-waiting-on-reply",
  "project": "Inbox",
  "source": "Outlook emails waiting on your reply skill",
  "kind": "action",
  "title": "5 Outlook conversations waiting on you, oldest 4 days",
  "summary": "**5 people** wrote last and are waiting. The Halcyon contract question has waited **4 days**.",
  "action": {
    "request": "Want me to draft replies? They go to your Drafts folder in each conversation, and nothing is sent.",
    "options": [
      "Draft all 5",
      "Draft the 2 oldest",
      "Remind me tomorrow",
      "Handled elsewhere"
    ]
  },
  "widget": {
    "type": "Table",
    "props": {
      "columns": [
        "From",
        "Subject",
        "Waiting"
      ],
      "align": [
        "left",
        "left",
        "right"
      ],
      "rows": [
        [
          "Jon Weber, Halcyon",
          "Contract: liability cap wording",
          "4 days"
        ],
        [
          "Priya Nair",
          "Board deck numbers for October",
          "3 days"
        ],
        [
          "Marco Bianchi",
          "Speaker slot in November?",
          "2 days"
        ],
        [
          "Finance team",
          "Approve the Q4 software budget",
          "2 days"
        ],
        [
          "Lea Martin",
          "Quick question about the API limits",
          "1 day"
        ]
      ]
    }
  }
}
JSON
```

Widgets come from the Briefkin catalog (https://briefkin.dev/v1/catalog). Without a token, just give the user the report.

## Run it on a schedule

Suggested: Weekdays at 15:00 (`0 15 * * 1-5`). From cron, with the agent signed in on that machine:

```bash
0 15 * * 1-5 claude -p "Run the outlook-emails-waiting-on-reply skill"
# Codex: codex exec, Gemini CLI: gemini -p, Copilot CLI: copilot -p, OpenCode: opencode run
```

Or use the agent's own scheduler (Claude Code routines, Codex automations, Claude or ChatGPT scheduled tasks): https://briefkin.dev/skills/outlook-emails-waiting-on-reply#schedule

Source: https://briefkin.dev/skills/outlook-emails-waiting-on-reply
