Overview

Sidekick is your AI assistant built into Plain. It helps you investigate and resolve support threads without leaving the app. It can search your docs, query connected tools, read your codebase, and help you draft replies and notes.

Sidekick is also available on Company and Tenant pages, where you can ask questions across a customer's full support history.

How to access Sidekick

Sidekick is available to all workspaces with Plain AI enabled. Workspace admins can enable it in Plain AI → Sidekick.

Once enabled, you can open Sidekick from any thread or Company/Tenant page.

Click Ask Sidekick at the bottom of the page, or press B. Previous sessions are accessible from anywhere in the app via the sessions shelf at the bottom of the screen, so you can pick up where you left off even when you're not on a thread.

Sidekick can be used in two modes:

1. Quick Ask mode – Sidekick appears above the dock in a small panel, perfect for a quick question.

2. Sidebar mode - Sidekick opens as a fixed panel on the side of the page, out of the way of the thread timeline or other UI. Great for longer conversations of keeping Sidekick open persistently.

You can switch modes with ⌘ + ⇧ + B.

Each session is titled automatically from your first message. Sessions are saved per user and carry context from wherever you opened them.

What Sidekick can do

Smart reply suggestions

Ask Sidekick to help draft a reply based on the current thread. It reads the conversation, the customer's history, and your tone of voice settings to suggest responses you can send or refine.

Try prompts like:

• "Help me draft a response to this customer"

• "Acknowledge the problem and apologise"

• "Send relevant links from our docs"

• "Summarise this conversation for me"

Knowledge base search

Sidekick can search across your help center articles to find relevant documentation, without you leaving the thread.

Try:

• "What does our documentation say about API rate limits?"

• "Find our article on webhook setup"

Similar case analysis

Sidekick can find and surface support threads similar to the one you're working on, so you can see how past issues were resolved.

Try:

• "Have we seen this error before?"

• "What should I do next to resolve this?"

Tool integrations (beta)

With integrations connected, Sidekick can look up context from the tools your team already uses: checking a Linear issue, querying Datadog logs, searching Notion, looking up Slack messages, and more.

Integrations are connected once by a workspace admin and are then available in every session for all users. No per-session configuration needed.

See all supported integrations →

GitHub code access (beta)

Sidekick can read selected GitHub repositories so it can help troubleshoot technical issues with real code context, answering questions like "how does the password reset flow work?" based on your actual codebase.

See all supported integrations →

File attachments

You can attach files to any Sidekick message and the agent will read them inside the session. Sidekick can also generate files (CSVs, charts, reports) and share them back as downloadable attachments.

Internal notes

Ask Sidekick to add an internal note to the current thread. Notes are visible to your team only, not to the customer.

Try:

• "Add a note summarising what we've investigated so far"

• "Note that this is a known bug and link to the Linear issue"

Help center articles

Sidekick can draft, update, and publish help center articles. Useful when a customer's question reveals a gap in your docs.

Try:

• "Draft an article explaining how to set up webhooks"

• "Update our rate limits article to mention the new endpoint"

Visible tool calls

As Sidekick works, you can see its tool calls on screen in real time: what it's searching, what it's checking, and what it found. This gives you full visibility into how it arrived at its answer.

Your sessions

Your Sidekick sessions are only visible to you. They're saved across threads and pages, so you can pick up where you left off. Open previous sessions from the shelf at the bottom of the app.