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Feature Request: User-defined tags on sessions (searchable and filterable) #3970

Description

@RockNoggin

Describe the feature or problem you'd like to solve

As the number of active sessions grows, it becomes difficult to organize and find specific sessions. Currently there's no way to categorize sessions beyond their name. Users working across multiple features, repos, or workstreams need a lightweight way to group and locate sessions.

Proposed solution

Allow users to add custom tags to sessions. Tags should be:

  • User-defined: Free-form text labels (e.g., auth, frontend, bugfix, v2.1, urgent)
  • Displayed on session items: Shown as compact colored badges/chips on each session in the sidebar list
  • Searchable: A search/filter input in the session list that matches against tag names
  • Filterable: Ability to filter the session list to show only sessions with a specific tag (click-to-filter or dropdown)
  • Multi-tag support: A session can have multiple tags

Workflow:

  1. User right-clicks or uses a menu on a session → "Add tag"
  2. Autocomplete suggests previously-used tags, or user types a new one
  3. Tags appear as small chips on the session item in the sidebar
  4. User clicks a tag (or uses a filter bar) to narrow the session list to only matching sessions
  5. A search box matches against session names AND tags

Optional enhancements:

  • Tag color assignment (auto or manual)
  • Pinned/favorite tags for quick filtering
  • Tag management view (rename, merge, delete unused tags)
  • Keyboard shortcut to add/search tags

Example prompts or workflows

  1. User is working on a large project with sessions for auth, payments, and UI
  2. They tag sessions: auth, payments, ui
  3. Later, they click the payments tag filter → sidebar shows only the 3 payment-related sessions
  4. They search "bugfix" → shows all sessions tagged bugfix regardless of session name

Additional context

This is complementary to #3969 (plan status indicators). Together, tags + status indicators would give users powerful at-a-glance organization and progress visibility across many sessions.

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