Add roundup plugin: self-configuring status briefing generator

.github/plugin/marketplace.json

@@ -257,6 +257,12 @@
       "description": "Complete toolkit for building Model Context Protocol (MCP) servers in Python using the official SDK with FastMCP. Includes instructions for best practices, a prompt for generating servers, and an expert chat mode for guidance.",
       "version": "1.0.0"
     },
+    {
+      "name": "roundup",
+      "source": "roundup",
+      "description": "Self-configuring status briefing generator. Learns your communication style from examples, discovers your data sources, and produces draft updates for any audience on demand.",
+      "version": "1.0.0"
+    },
     {
       "name": "ruby-mcp-development",
       "source": "ruby-mcp-development",

docs/README.plugins.md

@@ -62,6 +62,7 @@ See [CONTRIBUTING.md](../CONTRIBUTING.md#adding-plugins) for guidelines on how t
 | [power-platform-mcp-connector-development](../plugins/power-platform-mcp-connector-development/README.md) | Complete toolkit for developing Power Platform custom connectors with Model Context Protocol integration for Microsoft Copilot Studio | 3 items | power-platform, mcp, copilot-studio, custom-connector, json-rpc |
 | [project-planning](../plugins/project-planning/README.md) | Tools and guidance for software project planning, feature breakdown, epic management, implementation planning, and task organization for development teams. | 15 items | planning, project-management, epic, feature, implementation, task, architecture, technical-spike |
 | [python-mcp-development](../plugins/python-mcp-development/README.md) | Complete toolkit for building Model Context Protocol (MCP) servers in Python using the official SDK with FastMCP. Includes instructions for best practices, a prompt for generating servers, and an expert chat mode for guidance. | 2 items | python, mcp, model-context-protocol, fastmcp, server-development |
+| [roundup](../plugins/roundup/README.md) | Self-configuring status briefing generator. Learns your communication style from examples, discovers your data sources, and produces draft updates for any audience on demand. | 2 items | status-updates, briefings, management, productivity, communication, synthesis, roundup, copilot-cli |
 | [ruby-mcp-development](../plugins/ruby-mcp-development/README.md) | Complete toolkit for building Model Context Protocol servers in Ruby using the official MCP Ruby SDK gem with Rails integration support. | 2 items | ruby, mcp, model-context-protocol, server-development, sdk, rails, gem |
 | [rug-agentic-workflow](../plugins/rug-agentic-workflow/README.md) | Three-agent workflow for orchestrated software delivery with an orchestrator plus implementation and QA subagents. | 3 items | agentic-workflow, orchestration, subagents, software-engineering, qa |
 | [rust-mcp-development](../plugins/rust-mcp-development/README.md) | Build high-performance Model Context Protocol servers in Rust using the official rmcp SDK with async/await, procedural macros, and type-safe implementations. | 2 items | rust, mcp, model-context-protocol, server-development, sdk, tokio, async, macros, rmcp |

docs/README.skills.md

@@ -196,6 +196,8 @@ See [CONTRIBUTING.md](../CONTRIBUTING.md#adding-skills) for guidelines on how to
 | [remember-interactive-programming](../skills/remember-interactive-programming/SKILL.md) | A micro-prompt that reminds the agent that it is an interactive programmer. Works great in Clojure when Copilot has access to the REPL (probably via Backseat Driver). Will work with any system that has a live REPL that the agent can use. Adapt the prompt with any specific reminders in your workflow and/or workspace. | None |
 | [repo-story-time](../skills/repo-story-time/SKILL.md) | Generate a comprehensive repository summary and narrative story from commit history | None |
 | [review-and-refactor](../skills/review-and-refactor/SKILL.md) | Review and refactor code in your project according to defined instructions | None |
+| [roundup](../skills/roundup/SKILL.md) | Generate personalized status briefings on demand. Pulls from your configured data sources (GitHub, email, Teams, Slack, and more), synthesizes across them, and drafts updates in your own communication style for any audience you define. | None |
+| [roundup-setup](../skills/roundup-setup/SKILL.md) | Interactive onboarding that learns your communication style, audiences, and data sources to configure personalized status briefings. Paste in examples of updates you already write, answer a few questions, and roundup calibrates itself to your workflow. | `references/config-template.md` |
 | [ruby-mcp-server-generator](../skills/ruby-mcp-server-generator/SKILL.md) | Generate a complete Model Context Protocol server project in Ruby using the official MCP Ruby SDK gem. | None |
 | [rust-mcp-server-generator](../skills/rust-mcp-server-generator/SKILL.md) | Generate a complete Rust Model Context Protocol server project with tools, prompts, resources, and tests using the official rmcp SDK | None |
 | [scoutqa-test](../skills/scoutqa-test/SKILL.md) | This skill should be used when the user asks to "test this website", "run exploratory testing", "check for accessibility issues", "verify the login flow works", "find bugs on this page", or requests automated QA testing. Triggers on web application testing scenarios including smoke tests, accessibility audits, e-commerce flows, and user flow validation using ScoutQA CLI. IMPORTANT: Use this skill proactively after implementing web application features to verify they work correctly - don't wait for the user to ask for testing. | None |

plugins/roundup/.github/plugin/plugin.json

@@ -0,0 +1,24 @@
+{
+  "name": "roundup",
+  "description": "Self-configuring status briefing generator. Learns your communication style from examples, discovers your data sources, and produces draft updates for any audience on demand.",
+  "version": "1.0.0",
+  "author": {
+    "name": "Awesome Copilot Community"
+  },
+  "repository": "https://github.com/github/awesome-copilot",
+  "license": "MIT",
+  "keywords": [
+    "status-updates",
+    "briefings",
+    "management",
+    "productivity",
+    "communication",
+    "synthesis",
+    "roundup",
+    "copilot-cli"
+  ],
+  "skills": [
+    "./skills/roundup-setup/",
+    "./skills/roundup/"
+  ]
+}

plugins/roundup/README.md

@@ -0,0 +1,101 @@
+# Roundup
+
+Status briefing generator that learns how you communicate.
+
+Roundup watches your work across GitHub, email, Teams, Slack, and other tools, then drafts status updates and briefings in your own voice for any audience you define.
+
+## The Problem
+
+Managers and team leads spend hours each week assembling status updates from scattered sources: scanning PR activity in GitHub, reading email threads for decisions, checking Teams or Slack for context, then rewriting all of it for different audiences at different levels of detail.
+
+The data to write these updates already exists. The work is in gathering it and packaging it. Roundup automates the gathering and drafting. You provide quality control and hit send.
+
+## How It Works
+
+**First time (5 minutes):** Run the setup skill. It asks about your role, your audiences, and where your team's work happens. Then you paste in an example or two of updates you've already written. From those examples, it learns your format, tone, structure, and what you include vs. skip.
+
+**Every time after:** Tell roundup which audience you're writing for. It pulls fresh data from your configured sources, synthesizes across them, and drafts a briefing matching your style.
+
+## Installation
+
+```bash
+copilot plugin install roundup@awesome-copilot
+```
+
+## Getting Started
+
+### First-Time Setup
+
+```
+use roundup-setup
+```
+
+The setup flow walks you through:
+- Describing your role and team
+- Pasting in example updates you've already written
+- Defining your audiences (leadership, team, partners, etc.) and what each one cares about
+- Identifying where your team's work and conversations happen
+
+### Generating a Briefing
+
+```
+use roundup
+```
+
+Or be more specific:
+
+```
+use roundup -- generate a leadership briefing covering this past week
+```
+
+```
+use roundup -- draft a team update since Monday
+```
+
+## What's Included
+
+| Skill | What It Does |
+|-------|-------------|
+| `roundup-setup` | Interactive onboarding that learns your style, audiences, and data sources |
+| `roundup` | Generates draft briefings from your config on demand |
+
+## What It Can Pull From
+
+Roundup adapts to whatever tools are available in your environment:
+
+| Source | What It Looks For |
+|--------|-------------------|
+| GitHub | PRs, issues, commits, review activity across your configured repos |
+| M365 / WorkIQ | Email threads, Teams messages, calendar events, shared docs |
+| Slack | Channel messages, threads, announcements |
+| Google Workspace | Gmail, Calendar, Drive activity |
+
+During setup, roundup discovers which of these you have access to and configures itself accordingly. If you add new tools later, re-run setup to include them.
+
+No API keys or additional setup required beyond what's already configured in your Copilot CLI environment.
+
+## What Makes It Different
+
+**It learns from your examples.** Rather than forcing you into a template, roundup analyzes how you actually write and replicates that style. Your briefings sound like you wrote them.
+
+**It works with whatever you have.** GitHub only? Fine. Full M365 suite? Great. Mix of Slack and Google? Works too. The setup flow discovers your environment and adapts.
+
+**Multiple audiences, one setup.** Define different audience profiles with different detail levels and formats. Same underlying data, different output for each.
+
+**Your config is a readable file.** Everything roundup learned lives in `~/.config/roundup/config.md` -- plain markdown you can open, read, and hand-edit anytime. No opaque settings or hidden state.
+
+## Reconfiguring
+
+To start setup over from scratch:
+
+```
+use roundup-setup
+```
+
+It will ask before overwriting your existing config.
+
+To make small adjustments, just open `~/.config/roundup/config.md` in any text editor. The file is written in plain English and organized by section. Your changes are respected on the next run.
+
+## License
+
+MIT