diff --git a/app/assets/stylesheets/conversation.css b/app/assets/stylesheets/conversation.css
new file mode 100644
index 000000000..f6574ce1e
--- /dev/null
+++ b/app/assets/stylesheets/conversation.css
@@ -0,0 +1,89 @@
+@layer components {
+  .conversation {
+    --color-border: #fff;
+
+    display: flex;
+    flex-direction: column;
+    height: 100%;
+    margin-bottom: 0;
+
+    .conversation__messages {
+      display: flex;
+      flex-direction: column;
+      gap: 1.6rem;
+      height: 100%;
+      margin: 1rem;
+      overflow-x: hidden;
+      overflow-y: auto;
+    }
+
+    .conversation__composer {
+      border-top: 1px solid var(--color-border);
+      display: flex;
+      flex-direction: row;
+      gap: 1rem;
+      min-height: 6rem;
+      padding: 1rem;
+
+      .conversation__composer__submit {
+        display: flex;
+        flex-direction: column;
+        flex-grow: 0;
+      }
+
+      .conversation__composer__input {
+        flex-grow: 1;
+      }
+
+      .conversation__composer__input textarea {
+        border-radius: 0.5rem;
+        border: 1px solid var(--color-border);
+        height: 100%;
+        padding: 0.5rem;
+        resize: none;
+        width: 100%;
+      }
+    }
+
+    .conversation__message {
+    }
+
+    .conversation__message--user {
+      .action-text-content {
+        border-left: 1px solid var(--color-border);
+        border-radius: 0.5rem;
+        border-top: 1px solid var(--color-border);
+        margin-left: 15%;
+        padding: 1rem;
+        text-align: right;
+      }
+
+      details {
+        margin-top: 0.5rem;
+
+        summary {
+          text-align: right;
+        }
+      }
+    }
+
+    .conversation__message--assistant {
+      .action-text-content {
+        padding: 1rem;
+        text-align: left;
+        margin-right: 15%;
+        border-right: 1px solid var(--color-border);
+        border-top: 1px solid var(--color-border);
+        border-radius: 0.5rem;
+      }
+
+      details {
+        margin-top: 0.5rem;
+
+        summary {
+          text-align: left;
+        }
+      }
+    }
+  }
+}
diff --git a/app/assets/stylesheets/terminals.css b/app/assets/stylesheets/terminals.css
index a35fc0dda..b0c6be5d2 100644
--- a/app/assets/stylesheets/terminals.css
+++ b/app/assets/stylesheets/terminals.css
@@ -240,6 +240,17 @@
     }
   }
 
+  .terminal__modal {
+    position: fixed;
+    top: 0;
+    left: 0;
+    right: 0;
+    bottom: 0;
+    margin: auto 15rem;
+    margin-bottom: 3.55rem;
+    height: calc(100vh - 15rem);
+  }
+
   /* Lexical prompt insertions
   /* ------------------------------------------------------------------------ */
 
diff --git a/app/controllers/commands_controller.rb b/app/controllers/commands_controller.rb
index 65017df7a..060f7ae17 100644
--- a/app/controllers/commands_controller.rb
+++ b/app/controllers/commands_controller.rb
@@ -45,6 +45,8 @@ class CommandsController < ApplicationController
         respond_with_composite_response(result)
       when Command::Result::Redirection
         redirect_to result.url
+      when Command::Result::ShowModal
+        respond_with_turbo_frame_modal(result.turbo_frame, result.url)
       else
         redirect_back_or_to root_path
       end
@@ -68,6 +70,10 @@ class CommandsController < ApplicationController
       render json: { message: chat_response.content }, status: :accepted
     end
 
+    def respond_with_turbo_frame_modal(turbo_frame, url)
+      render json: { turbo_frame: turbo_frame, url: url }, status: :accepted
+    end
+
     def respond_with_error(command)
       error_message = command.error_messages.map { |msg| "- #{msg}\n" }.join
       render json: { error: error_message, context_url: command.context.url }, status: :unprocessable_entity
diff --git a/app/controllers/conversations/messages_controller.rb b/app/controllers/conversations/messages_controller.rb
new file mode 100644
index 000000000..ee0a6ce4d
--- /dev/null
+++ b/app/controllers/conversations/messages_controller.rb
@@ -0,0 +1,11 @@
+class Conversations::MessagesController < ApplicationController
+  def create
+    Current.user.resume_or_start_conversation(message_params[:content])
+    head :no_content
+  end
+
+  private
+    def message_params
+      params.require(:conversation_message).permit(:content)
+    end
+end
diff --git a/app/controllers/conversations_controller.rb b/app/controllers/conversations_controller.rb
new file mode 100644
index 000000000..09a7d5264
--- /dev/null
+++ b/app/controllers/conversations_controller.rb
@@ -0,0 +1,15 @@
+class ConversationsController < ApplicationController
+  def create
+    Current.user.resume_or_start_conversation(question_params[:conversation][:question])
+    redirect_to conversation_path, status: :see_other
+  end
+
+  def show
+    @conversation = Current.user.conversation
+  end
+
+  private
+    def conversation_params
+      params.require(:conversation).permit(:question)
+    end
+end
diff --git a/app/controllers/prompts/commands_controller.rb b/app/controllers/prompts/commands_controller.rb
index 3f9c75bf9..4073a716c 100644
--- a/app/controllers/prompts/commands_controller.rb
+++ b/app/controllers/prompts/commands_controller.rb
@@ -13,6 +13,7 @@ class Prompts::CommandsController < ApplicationController
       [ "/user", "Open user profile", "/user " ],
       [ "/tag", "Tag selected cards", "/tag #" ],
       [ "/stage", "Move cards to a Workflow Stage", "/stage " ],
+      [ "/ask", "Ask a question about cards", "/ask " ],
       [ "/help", "Show help menu", "/help" ]
     ]
 
diff --git a/app/javascript/controllers/terminal_controller.js b/app/javascript/controllers/terminal_controller.js
index 35681f97c..4a5ccc39d 100644
--- a/app/javascript/controllers/terminal_controller.js
+++ b/app/javascript/controllers/terminal_controller.js
@@ -5,9 +5,10 @@ import { marked } from "marked"
 import { nextFrame } from "helpers/timing_helpers";
 
 export default class extends Controller {
-  static targets = [ "input", "form", "output", "confirmation", "recentCommands" ]
+  static targets = [ "input", "form", "output", "confirmation", "recentCommands", "modalTurboFrame" ]
   static classes = [ "error", "confirmation", "help", "output", "busy" ]
   static values = { originalInput: String, waitingForConfirmation: Boolean }
+  static outlets = [ "dialog" ]
 
   connect() {
     if (this.waitingForConfirmationValue) { this.focus() }
@@ -141,7 +142,7 @@ export default class extends Controller {
   }
 
   #handleJsonResponse(responseJson) {
-    const { confirmation, message, redirect_to } = responseJson
+    const { confirmation, message, redirect_to, turbo_frame, url } = responseJson
 
     if (message) {
       this.#showOutput(message)
@@ -154,6 +155,10 @@ export default class extends Controller {
     if (redirect_to) {
       Turbo.visit(redirect_to)
     }
+
+    if (turbo_frame && url) {
+      this.#showTurboFrameModal(turbo_frame, url)
+    }
   }
 
   async #requestConfirmation(confirmationPrompt) {
@@ -204,4 +209,11 @@ export default class extends Controller {
   #hideOutput(html) {
     this.element.classList.remove(this.outputClass)
   }
+
+  #showTurboFrameModal(name, url) {
+    this.inputTarget.blur()
+    this.modalTurboFrameTarget.id = name
+    this.modalTurboFrameTarget.src = url
+    this.dialogOutlet.open()
+  }
 }
diff --git a/app/jobs/conversation/response_generator_job.rb b/app/jobs/conversation/response_generator_job.rb
new file mode 100644
index 000000000..5f2ce7f7d
--- /dev/null
+++ b/app/jobs/conversation/response_generator_job.rb
@@ -0,0 +1,5 @@
+class Conversation::ResponseGeneratorJob < ApplicationJob
+  def perform(message)
+    message.generate_response
+  end
+end
diff --git a/app/models/ai/tool/list_cards.rb b/app/models/ai/tool/list_cards.rb
new file mode 100644
index 000000000..cae800912
--- /dev/null
+++ b/app/models/ai/tool/list_cards.rb
@@ -0,0 +1,117 @@
+class Ai::Tool::ListCards < RubyLLM::Tool
+  description <<-MD
+    Lists all cards accessible by the current user.
+    The response is paginated so you may need to iterate through multiple pages to get the full list.
+    A next page exists if the `pagination.next_page` field is present in the response.
+    Responses are JSON objects that look like this:
+    ```
+    {
+      "cards": [
+        { "id": 3 },
+        { "id": 4 }
+      ],
+      "pagination": {
+        "next_page": "e3c2gh75e4..."
+      }
+    }
+    ```
+    Each collection object has the following fields:
+    - id [Integer, not null]
+    - title [String, not null] - The title of the card
+    - status [String, not null] - Enum of "creating", "draft" and "published"
+    - last_active_at [DateTime, not null] - The last time the card was updated
+    - collection_id [Integer, not null] - The ID of the collection this card belongs to
+    - stage [Object, not null] - The stage this card is in, with fields:
+      - id [Integer, not null]
+      - name [String, not null]
+    - creator [Object, not null] - The user who created the card, with fields:
+      - id [Integer, not null]
+      - name [String, not null]
+    - assignees [Array of Objects, not null] - The users assigned to the card, each with fields:
+      - id [Integer, not null]
+      - name [String, not null]
+  MD
+
+  param :query,
+    type: :string,
+    desc: "If provided, will perform a semantinc search by embeddings and return only matching cards",
+    required: false
+  param :page,
+    type: :string,
+    desc: "Which page to return. Leave balnk to get the first page",
+    required: false
+  param :collection_id,
+    type: :integer,
+    desc: "If provided, will return only cards for the specified collection",
+    required: false
+  param :golden,
+    type: :boolean,
+    desc: "If provided, will return only golden cards",
+    required: false
+  param :created_at_gte,
+    type: :string,
+    desc: "If provided, will return only card created on or after after the given ISO timestamp",
+    required: false
+  param :created_at_lte,
+    type: :string,
+    desc: "If provided, will return only card created on or before the given ISO timestamp",
+    required: false
+  param :last_active_at_gte,
+    type: :string,
+    desc: "If provided, will return only card that were last active on or after after the given ISO timestamp",
+    required: false
+  param :last_active_at_lte,
+    type: :string,
+    desc: "If provided, will return only card that were last active on or before the given ISO timestamp",
+    required: false
+
+  def execute(**params)
+    cards = Card.all.includes(:stage, :creator, :assignees, :goldness)
+
+    cards = cards.search(params[:query]) if params[:query].present?
+    cards = cards.golden if params[:golden].present?
+    cards = cards.where(collection_id: params[:collection_id]) if params[:collection_id].present?
+
+    if params[:last_active_at_gte].present?
+      timestamp = Time.iso8601(params[:last_active_at_gte])
+      cards = cards.where(last_active_at: timestamp..)
+    end
+
+    if params[:last_active_at_lte].present?
+      timestamp = Time.iso8601(params[:last_active_at_lte])
+      cards = cards.where(last_active_at: ..timestamp)
+    end
+
+    if params[:created_at_gte].present?
+      timestamp = Time.iso8601(params[:created_at_gte])
+      cards = cards.where(created_at: timestamp..)
+    end
+
+    if params[:created_at_lte].present?
+      timestamp = Time.iso8601(params[:created_at_lte])
+      cards = cards.where(created_at: ..timestamp)
+    end
+
+    page = GearedPagination::Recordset.new(cards, ordered_by: { id: :desc }).page(page)
+
+    {
+      cards: page.records.map do |card|
+        {
+          id: card.id,
+          title: card.title,
+          status: card.status,
+          last_active_at: card.last_active_at,
+          collection_id: card.collection_id,
+          golden: card.golden?,
+          stage: card.stage.as_json(only: [ :id, :name ]),
+          creator: card.creator.as_json(only: [ :id, :name ]),
+          assignees: card.assignees.as_json(only: [ :id, :name ]),
+          description: card.description.to_plain_text.truncate(1000)
+        }
+      end,
+      pagination: {
+        next_page: page.next_param
+      }
+    }.to_json
+  end
+end
diff --git a/app/models/ai/tool/list_collections.rb b/app/models/ai/tool/list_collections.rb
new file mode 100644
index 000000000..73fff94d7
--- /dev/null
+++ b/app/models/ai/tool/list_collections.rb
@@ -0,0 +1,47 @@
+class Ai::Tool::ListCollections < RubyLLM::Tool
+  description <<-MD
+    Lists all collections accessible by the current user.
+    The response is paginated so you may need to iterate through multiple pages to get the full list.
+    Responses are JSON objects that look like this:
+    ```
+    {
+      "collections": [
+        { "id": 3, "name": "Foo" },
+        { "id": 4, "name": "Bar" }
+      ],
+      "pagination": {
+        "next_page": "e3c2gh75e4..."
+      }
+    }
+    ```
+    Each collection object has the following fields:
+    - id [Integer, not null]
+    - name [String, not null]
+  MD
+
+  param :page,
+    type: :string,
+    desc: "Which page to return. Leave balnk to get the first page",
+    required: false
+
+  def execute(page: nil)
+    puts "= TOOL CALL: ListCollections"
+
+    page = GearedPagination::Recordset.new(
+      Collection.all,
+      ordered_by: { name: :asc, id: :desc }
+    ).page(page)
+
+    {
+      collections: page.records.map do |collection|
+        {
+          id: collection.id,
+          name: collection.name
+        }
+      end,
+      pagination: {
+        next_page: page.next_param
+      }
+    }.to_json
+  end
+end
diff --git a/app/models/ai/tool/list_comments.rb b/app/models/ai/tool/list_comments.rb
new file mode 100644
index 000000000..04c703e3b
--- /dev/null
+++ b/app/models/ai/tool/list_comments.rb
@@ -0,0 +1,61 @@
+class Ai::Tool::ListComments < RubyLLM::Tool
+  description <<-MD
+    Lists all comments accessible by the current user.
+    The response is paginated so you may need to iterate through multiple pages to get the full list.
+    Responses are JSON objects that look like this:
+    ```
+    {
+      "collections": [
+        {
+          "id": 3,
+          "card_id": 5,
+          "body": "This is a comment",
+          "created_at": "2023-10-01T12:00:00Z",
+          "creator": { "id": 1, "name": "John Doe" },
+          "reactions": [
+            { "content": "👍", "reacter": { "id": 2, "name": "Jane Doe" } }
+          ]
+      ],
+      "pagination": {
+        "next_page": "e3c2gh75e4..."
+      }
+    }
+    ```
+    Each collection object has the following fields:
+    - id [Integer, not null]
+    - name [String, not null]
+  MD
+
+  param :page,
+    type: :string,
+    desc: "Which page to return. Leave balnk to get the first page",
+    required: false
+
+  def execute(page: nil)
+    page = GearedPagination::Recordset.new(
+      Comment.all.preload(:card, :creator, reactions: [ :reacter ]),
+      ordered_by: { created_at: :asc, id: :desc }
+    ).page(page)
+
+    {
+      collections: page.records.map do |comment|
+        {
+          id: comment.id,
+          card_id: comment.card_id,
+          body: comment.body.to_plain_text,
+          created_at: comment.created_at.iso8601,
+          creator: comment.creator.as_json(only: [ :id, :name ]),
+          reactions: comment.reactions.map do |reaction|
+            {
+              content: reaction.content,
+              reacter: reaction.reacter.as_json(only: [ :id, :name ])
+            }
+          end
+        }
+      end,
+      pagination: {
+        next_page: page.next_param
+      }
+    }.to_json
+  end
+end
diff --git a/app/models/ai/tool/list_users.rb b/app/models/ai/tool/list_users.rb
new file mode 100644
index 000000000..0c4fc3e85
--- /dev/null
+++ b/app/models/ai/tool/list_users.rb
@@ -0,0 +1,45 @@
+class Ai::Tool::ListUsers < RubyLLM::Tool
+  description <<-MD
+    Lists all users accessible by the current user.
+    The response is paginated so you may need to iterate through multiple pages to get the full list.
+    Responses are JSON objects that look like this:
+    ```
+    {
+      "collections": [
+        { "id": 3, "name": "John Doe" },
+        { "id": 4, "name": "Johanna Doe" }
+      ],
+      "pagination": {
+        "next_page": "e3c2gh75e4..."
+      }
+    }
+    ```
+    Each collection object has the following fields:
+    - id [Integer, not null]
+    - name [String, not null]
+  MD
+
+  param :page,
+    type: :string,
+    desc: "Which page to return. Leave balnk to get the first page",
+    required: false
+
+  def execute(page: nil)
+    page = GearedPagination::Recordset.new(
+      User.all,
+      ordered_by: { name: :asc, id: :desc }
+    ).page(page)
+
+    {
+      collections: page.records.map do |user|
+        {
+          id: user.id,
+          name: user.name
+        }
+      end,
+      pagination: {
+        next_page: page.next_param
+      }
+    }.to_json
+  end
+end
diff --git a/app/models/command/ask.rb b/app/models/command/ask.rb
new file mode 100644
index 000000000..8712c5bb4
--- /dev/null
+++ b/app/models/command/ask.rb
@@ -0,0 +1,12 @@
+class Command::Ask < Command
+  store_accessor :data, :question, :card_ids
+
+  def title
+    "Ask '#{question}'"
+  end
+
+  def execute
+    Current.user.resume_or_start_conversation(question)
+    Command::Result::ShowModal.new(turbo_frame: "conversation", url: conversation_path)
+  end
+end
diff --git a/app/models/command/parser.rb b/app/models/command/parser.rb
index 3a1ca9f71..cba13ded4 100644
--- a/app/models/command/parser.rb
+++ b/app/models/command/parser.rb
@@ -67,6 +67,8 @@ class Command::Parser
         Command::VisitUrl.new(url: command_arguments.first)
       when "/tag"
         Command::Tag.new(tag_title: tag_title_from(combined_arguments), card_ids: cards.ids)
+      when "/ask"
+        Command::Ask.new(question: combined_arguments, card_ids: cards.ids)
       when /^gid:\/\//
         parse_gid command_name
       else
diff --git a/app/models/command/result/show_modal.rb b/app/models/command/result/show_modal.rb
new file mode 100644
index 000000000..19922ab5f
--- /dev/null
+++ b/app/models/command/result/show_modal.rb
@@ -0,0 +1,12 @@
+class Command::Result::ShowModal
+  attr_reader :url, :turbo_frame
+
+  def initialize(url:, turbo_frame:)
+    @url = url
+    @turbo_frame = turbo_frame
+  end
+
+  def as_json
+    { turbo_frame: turbo_frame, url: url }
+  end
+end
diff --git a/app/models/conversation.rb b/app/models/conversation.rb
new file mode 100644
index 000000000..1bdc4ca13
--- /dev/null
+++ b/app/models/conversation.rb
@@ -0,0 +1,39 @@
+class Conversation < ApplicationRecord
+  broadcasts_refreshes
+
+  belongs_to :user
+  has_many :messages, dependent: :destroy
+
+  enum :state, %w[ ready thinking ].index_by(&:itself), default: :ready
+
+  def price
+    messages.pluck(:price_microcents).compact.sum.to_d / 100_000
+  end
+
+  def clear
+    messages.delete_all
+    touch
+  end
+
+  def ask(question)
+    raise ArgumentError, "Question cannot be blank" if question.blank?
+
+    with_lock do
+      return false if thinking?
+
+      thinking!
+      messages.create!(role: :user, content: question)
+    end
+  end
+
+  def respond(answer, **attributes)
+    raise ArgumentError, "Answer cannot be blank" if answer.blank?
+
+    with_lock do
+      return false unless thinking?
+
+      messages.create!(**attributes, role: :assistant, content: answer)
+      ready!
+    end
+  end
+end
diff --git a/app/models/conversation/message.rb b/app/models/conversation/message.rb
new file mode 100644
index 000000000..1d5db9748
--- /dev/null
+++ b/app/models/conversation/message.rb
@@ -0,0 +1,40 @@
+class Conversation::Message < ApplicationRecord
+  has_rich_text :content
+
+  belongs_to :conversation, inverse_of: :messages
+
+  enum :role, %w[ user assistant ].index_by(&:itself)
+
+  after_create_commit :generate_response_later, if: :user?
+
+  def generate_response_later
+    Conversation::ResponseGeneratorJob.perform_later(self)
+  end
+
+  def generate_response
+    response = Conversation::ResponseGenerator.new(self).generate
+
+    message_attributes = {
+      model_id: response.model_id,
+      input_tokens: response.input_tokens,
+      output_tokens: response.output_tokens,
+      input_cost_microcents: response.input_cost_microcents,
+      output_cost_microcents: response.output_cost_microcents,
+      cost_microcents: response.cost_microcents
+    }
+
+    conversation.respond(response.answer, **message_attributes)
+  end
+
+  def to_llm
+    RubyLLM::Message.new(
+      role: role.to_sym,
+      content: content.to_plain_text,
+      tool_calls: nil,
+      tool_call_id: nil,
+      input_tokens: input_tokens,
+      output_tokens: output_tokens,
+      model_id: model_id
+    )
+  end
+end
diff --git a/app/models/conversation/response_generator.rb b/app/models/conversation/response_generator.rb
new file mode 100644
index 000000000..651ccdb6d
--- /dev/null
+++ b/app/models/conversation/response_generator.rb
@@ -0,0 +1,88 @@
+class Conversation::ResponseGenerator
+  SYSTEM_PROMPT = <<~PROMPT
+    You are **Fizzy**, a helpful assistant for the Fizzy app by 37signals.
+    Fizz helps users track projects, manage tasks, and collaborate with their teams.
+
+    ### 🗂 App Structure
+    - An account can have multiple **collections**
+    - Each collection contains **cards**
+    - Cards go through various **stages** and have a **creator** and one or more **assignees**
+
+    ### 🧠 Your Role
+    You help users with anything related to their Fizz data — tasks, projects, trends, and team activity.
+
+    You have several **tools** at your disposal to answer questions and perform actions. Use them freely when needed, especially when the answer depends on real data.
+
+    ### ✅ Guidelines
+    - Be **concise**, **accurate**, and **friendly**
+    - Speak naturally — no corporate tone or robotic phrasing
+    - **Never suggest follow-up questions, extra details, or further actions** unless the user explicitly asks
+    - Do **not** include phrases like “If you want more…” or “Let me know if…” — just answer the question as asked
+    - Stick strictly to the user's intent — no speculation, hedging, or filler
+    - If you're unsure what they mean, ask a clarifying question — but only if you truly cannot infer it from context
+    - Always assume questions are about **their own Fizz data** — cards, collections, or team activity
+    - If a question isn’t related to Fizz, respond politely with “I don’t know” or “I’m not sure” and explain that you can only answer questions related to Fizzy
+    - Don’t explain concepts or go off-topic — answer only what was asked
+    - Respond in **Markdown**
+
+    When in doubt, examine their cards, collections, or team activity to figure out the answer.
+
+    You're here to help — not to anticipate.
+  PROMPT
+
+  attr_reader :message
+
+  delegate :conversation, to: :message
+
+  def initialize(message)
+    @message = message
+  end
+
+  def generate
+    response = llm.ask(message.content.to_plain_text)
+    answer = markdown_to_html(response.content)
+
+    Response.new(
+      answer: answer,
+      input_tokens: response.input_tokens,
+      output_tokens: response.output_tokens,
+      model_id: response.model_id
+    )
+  end
+
+  private
+    def llm
+      RubyLLM.chat.tap do |chat|
+        chat.with_tool(Ai::Tool::ListCards.new)
+        chat.with_tool(Ai::Tool::ListCollections.new)
+        chat.with_tool(Ai::Tool::ListComments.new)
+        chat.with_tool(Ai::Tool::ListUsers.new)
+
+        chat.reset_messages!
+
+        previous_messages.each do |message|
+          chat.add_message(message.to_llm)
+        end
+
+        chat.with_instructions(instructions)
+      end
+    end
+
+    def previous_messages
+      conversation.messages.order(id: :asc).where(id: ...message.id).limit(50).with_rich_text_content
+    end
+
+    def instructions
+      [ SYSTEM_PROMPT, user_context ].compact.join("\n\n").strip
+    end
+
+    def user_context
+      "You are talking to “#{conversation.user.name}”, their Fizzy User ID is #{conversation.user.id}"
+    end
+
+    def markdown_to_html(markdown)
+      renderer = Redcarpet::Render::HTML.new
+      markdowner = Redcarpet::Markdown.new(renderer, autolink: true, tables: true, fenced_code_blocks: true, strikethrough: true, superscript: true)
+      markdowner.render(markdown).html_safe
+    end
+end
diff --git a/app/models/conversation/response_generator/response.rb b/app/models/conversation/response_generator/response.rb
new file mode 100644
index 000000000..bd9b4cf16
--- /dev/null
+++ b/app/models/conversation/response_generator/response.rb
@@ -0,0 +1,54 @@
+class Conversation::ResponseGenerator::Response
+  MICROCENTS_PER_DOLLAR = 100_000
+
+  attr_reader :answer, :input_tokens, :output_tokens, :model_id, :tool_calls, :tool_call_id
+
+  def initialize(answer:, input_tokens:, output_tokens:, model_id:)
+    @answer = answer
+    @input_tokens = input_tokens
+    @output_tokens = output_tokens
+    @model_id = model_id
+  end
+
+  def cost
+    cost_microcents.to_d / MICROCENTS_PER_DOLLAR
+  end
+
+  def cost_microcents
+    input_cost_microcents + output_cost_microcents
+  end
+
+  def input_cost_microcents
+    return unless token_price = input_token_price_microcents
+
+    (input_tokens * token_price).to_i
+  end
+
+  def input_token_price_microcents
+    return unless model_info
+
+    price_per_million_tokens_to_microcents(model_info.input_price_per_million)
+  end
+
+  def output_cost_microcents
+    return unless token_price = output_token_price_microcents
+
+    (output_tokens * token_price).to_i
+  end
+
+  def output_token_price_microcents
+    return unless model_info
+
+    price_per_million_tokens_to_microcents(model_info.output_price_per_million)
+  end
+
+  def model_info
+    @model_info ||= RubyLLM.models.find(model_id)
+  end
+
+  private
+    def price_per_million_tokens_to_microcents(price)
+      single_token_price = price.to_d / 1_000_000
+      single_token_price * MICROCENTS_PER_DOLLAR
+    end
+end
diff --git a/app/models/user.rb b/app/models/user.rb
index dcc3ba9b8..bd8cf990d 100644
--- a/app/models/user.rb
+++ b/app/models/user.rb
@@ -1,6 +1,6 @@
 class User < ApplicationRecord
   include Accessor, Attachable, Assignee, Mentionable, Named, Role, Searcher,
-    SignalUser, Staff, Transferable
+    SignalUser, Staff, Transferable, Conversational
   include Timelined # Depends on Accessor
 
   has_one_attached :avatar
diff --git a/app/models/user/conversational.rb b/app/models/user/conversational.rb
new file mode 100644
index 000000000..503351652
--- /dev/null
+++ b/app/models/user/conversational.rb
@@ -0,0 +1,13 @@
+module User::Conversational
+  extend ActiveSupport::Concern
+
+  included do
+    has_one :conversation, dependent: :destroy
+  end
+
+  def resume_or_start_conversation(question = nil)
+    (conversation || create_conversation).tap do |conversation|
+      conversation.ask(question) if question.present?
+    end
+  end
+end
diff --git a/app/views/commands/_terminal.html.erb b/app/views/commands/_terminal.html.erb
index b649e7c1e..444fab807 100644
--- a/app/views/commands/_terminal.html.erb
+++ b/app/views/commands/_terminal.html.erb
@@ -1,8 +1,11 @@
+<%= turbo_stream_from Current.user.resume_or_start_conversation %>
+
 <%= tag.div \
       id: "command-terminal",
       class: "terminal full-width flex flex-column justify-end",
       data: {
         controller: "toggle-class terminal navigable-list",
+        terminal_dialog_outlet: "#terminal-modal",
         terminal_error_class: "terminal--error",
         terminal_confirmation_class: "terminal--confirmation",
         terminal_help_class: "terminal--showing-help",
@@ -13,6 +16,16 @@
         action: "keydown->terminal#handleKeyPress keydown->navigable-list#navigate focusin->navigable-list#select keydown.esc->toggle-class#remove:stop keydown.esc->terminal#focus keydown.esc->navigable-list#selectLast keydown.esc@document->terminal#hideMenus" } do %>
   <%= turbo_frame_tag :recent_commands, src: commands_path, data: { terminal_target: "recentCommands" } %>
   <div class="terminal__output" data-terminal-target="output"></div>
+  <%= tag.dialog \
+    id: "terminal-modal",
+    class: "terminal__modal",
+    data: {
+      controller: "dialog",
+      dialog_target: "dialog",
+      dialog_modal_value: "true",
+      action: "keydown.esc->dialog#close click@document->dialog#closeOnClickOutside" } do %>
+    <%= turbo_frame_tag nil, refresh: :morph, data: { terminal_target: "modalTurboFrame" } %>
+  <% end %>
 
   <%= render "commands/form" %>
 <% end %>
diff --git a/app/views/conversations/_message.html.erb b/app/views/conversations/_message.html.erb
new file mode 100644
index 000000000..5cd354b42
--- /dev/null
+++ b/app/views/conversations/_message.html.erb
@@ -0,0 +1,5 @@
+<div id="<%= dom_id(message) %>" class="conversation__message conversation__message--<%= message.role %>">
+  <div>
+    <%= message.content %>
+  </div>
+</div>
diff --git a/app/views/conversations/show.html.erb b/app/views/conversations/show.html.erb
new file mode 100644
index 000000000..f9dd6b39b
--- /dev/null
+++ b/app/views/conversations/show.html.erb
@@ -0,0 +1,19 @@
+<%= turbo_stream_from @conversation %>
+
+<%= turbo_frame_tag "conversation", target: "_top" do %>
+  <div class="conversation" id="<%= dom_id(@conversation) %>">
+    <div class="conversation__messages">
+      <%= render collection: @conversation.messages, partial: "conversations/message" %>
+    </div>
+
+    <%= form_with(model: Conversation::Message.new, local: true, html: { class: "conversation__composer" }) do |form| %>
+      <div class="conversation__composer__input">
+        <%= form.text_area :content, placeholder: "Type your message here...", rows: 3, class: "form-control" %>
+      </div>
+      <div class="conversation__composer__submit">
+        <%= form.submit "Send", class: "btn" %>
+      </div>
+    <% end %>
+  </div>
+<% end %>
+
diff --git a/config/routes.rb b/config/routes.rb
index 9ea3825a8..4ee497259 100644
--- a/config/routes.rb
+++ b/config/routes.rb
@@ -115,6 +115,12 @@ Rails.application.routes.draw do
     end
   end
 
+  resource :conversation, only: %i[ show create ] do
+    scope module: :conversations do
+      resource :messages, only: %i[ create ]
+    end
+  end
+
   namespace :my do
     resources :pins
   end
@@ -175,6 +181,10 @@ Rails.application.routes.draw do
     polymorphic_path(event.target, options)
   end
 
+  # resolve "Conversation::Message" do |message, options|
+  #   polymorphic_path([ :conversations, :messages ], options)
+  # end
+  #
   get "up", to: "rails/health#show", as: :rails_health_check
   get "manifest" => "rails/pwa#manifest", as: :pwa_manifest
   get "service-worker" => "pwa#service_worker"
diff --git a/db/migrate/20250728131423_create_conversations.rb b/db/migrate/20250728131423_create_conversations.rb
new file mode 100644
index 000000000..f5c7db613
--- /dev/null
+++ b/db/migrate/20250728131423_create_conversations.rb
@@ -0,0 +1,10 @@
+class CreateConversations < ActiveRecord::Migration[8.1]
+  def change
+    create_table :conversations do |t|
+      t.belongs_to :user, null: false, foreign_key: true, index: { unique: true }
+      t.string :state, :string
+
+      t.timestamps
+    end
+  end
+end
diff --git a/db/migrate/20250728131624_create_conversation_messages.rb b/db/migrate/20250728131624_create_conversation_messages.rb
new file mode 100644
index 000000000..89771306b
--- /dev/null
+++ b/db/migrate/20250728131624_create_conversation_messages.rb
@@ -0,0 +1,16 @@
+class CreateConversationMessages < ActiveRecord::Migration[8.1]
+  def change
+    create_table :conversation_messages do |t|
+      t.belongs_to :conversation, null: false, foreign_key: true
+      t.string :role
+      t.string :model_id
+      t.bigint :input_tokens
+      t.bigint :output_tokens
+      t.bigint :input_cost_microcents
+      t.bigint :output_cost_microcents
+      t.bigint :cost_microcents
+
+      t.timestamps
+    end
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index b4721da26..7e05051f5 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -208,6 +208,30 @@ ActiveRecord::Schema[8.1].define(version: 2025_08_12_195130) do
     t.index ["card_id"], name: "index_comments_on_card_id"
   end
 
+  create_table "conversation_messages", force: :cascade do |t|
+    t.string "client_message_id", null: false
+    t.integer "conversation_id", null: false
+    t.bigint "cost_microcents"
+    t.datetime "created_at", null: false
+    t.bigint "input_cost_microcents"
+    t.bigint "input_tokens"
+    t.string "model_id"
+    t.bigint "output_cost_microcents"
+    t.bigint "output_tokens"
+    t.string "role", null: false
+    t.datetime "updated_at", null: false
+    t.index ["conversation_id"], name: "index_conversation_messages_on_conversation_id"
+  end
+
+  create_table "conversations", force: :cascade do |t|
+    t.datetime "created_at", null: false
+    t.string "state"
+    t.string "string"
+    t.datetime "updated_at", null: false
+    t.integer "user_id", null: false
+    t.index ["user_id"], name: "index_conversations_on_user_id", unique: true
+  end
+
   create_table "creators_filters", id: false, force: :cascade do |t|
     t.integer "creator_id", null: false
     t.integer "filter_id", null: false
@@ -438,6 +462,8 @@ ActiveRecord::Schema[8.1].define(version: 2025_08_12_195130) do
   add_foreign_key "commands", "commands", column: "parent_id"
   add_foreign_key "commands", "users"
   add_foreign_key "comments", "cards"
+  add_foreign_key "conversation_messages", "conversations"
+  add_foreign_key "conversations", "users"
   add_foreign_key "events", "collections"
   add_foreign_key "mentions", "users", column: "mentionee_id"
   add_foreign_key "mentions", "users", column: "mentioner_id"
diff --git a/db/schema_cache.yml b/db/schema_cache.yml
index 3398114f4..ccbc42f82 100644
--- a/db/schema_cache.yml
+++ b/db/schema_cache.yml
@@ -634,6 +634,125 @@ columns:
   - *24
   - *6
   - *9
+  conversation_messages:
+  - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+    auto_increment:
+    name: client_message_id
+    cast_type: *7
+    sql_type_metadata: *8
+    'null': false
+    default:
+    default_function:
+    collation:
+    comment:
+  - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+    auto_increment:
+    name: conversation_id
+    cast_type: *3
+    sql_type_metadata: *4
+    'null': false
+    default:
+    default_function:
+    collation:
+    comment:
+  - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+    auto_increment:
+    name: cost_microcents
+    cast_type: *11
+    sql_type_metadata: *12
+    'null': true
+    default:
+    default_function:
+    collation:
+    comment:
+  - *5
+  - *6
+  - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+    auto_increment:
+    name: input_cost_microcents
+    cast_type: *11
+    sql_type_metadata: *12
+    'null': true
+    default:
+    default_function:
+    collation:
+    comment:
+  - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+    auto_increment:
+    name: input_tokens
+    cast_type: *11
+    sql_type_metadata: *12
+    'null': true
+    default:
+    default_function:
+    collation:
+    comment:
+  - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+    auto_increment:
+    name: model_id
+    cast_type: *7
+    sql_type_metadata: *8
+    'null': true
+    default:
+    default_function:
+    collation:
+    comment:
+  - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+    auto_increment:
+    name: output_cost_microcents
+    cast_type: *11
+    sql_type_metadata: *12
+    'null': true
+    default:
+    default_function:
+    collation:
+    comment:
+  - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+    auto_increment:
+    name: output_tokens
+    cast_type: *11
+    sql_type_metadata: *12
+    'null': true
+    default:
+    default_function:
+    collation:
+    comment:
+  - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+    auto_increment:
+    name: role
+    cast_type: *7
+    sql_type_metadata: *8
+    'null': false
+    default:
+    default_function:
+    collation:
+    comment:
+  - *9
+  conversations:
+  - *5
+  - *6
+  - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+    auto_increment:
+    name: state
+    cast_type: *7
+    sql_type_metadata: *8
+    'null': true
+    default:
+    default_function:
+    collation:
+    comment:
+  - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+    auto_increment:
+    name: string
+    cast_type: *7
+    sql_type_metadata: *8
+    'null': true
+    default:
+    default_function:
+    collation:
+    comment:
+  - *9
+  - *25
   creators_filters:
   - *24
   - *19
@@ -1201,6 +1320,8 @@ primary_keys:
   collections_filters:
   commands: id
   comments: id
+  conversation_messages: id
+  conversations: id
   creators_filters:
   entropy_configurations: id
   event_activity_summaries: id
@@ -1248,6 +1369,8 @@ data_sources:
   collections_filters: true
   commands: true
   comments: true
+  conversation_messages: true
+  conversations: true
   creators_filters: true
   entropy_configurations: true
   event_activity_summaries: true
@@ -1948,6 +2071,40 @@ indexes:
     nulls_not_distinct:
     comment:
     valid: true
+  conversation_messages:
+  - !ruby/object:ActiveRecord::ConnectionAdapters::IndexDefinition
+    table: conversation_messages
+    name: index_conversation_messages_on_conversation_id
+    unique: false
+    columns:
+    - conversation_id
+    lengths: {}
+    orders: {}
+    opclasses: {}
+    where:
+    type:
+    using:
+    include:
+    nulls_not_distinct:
+    comment:
+    valid: true
+  conversations:
+  - !ruby/object:ActiveRecord::ConnectionAdapters::IndexDefinition
+    table: conversations
+    name: index_conversations_on_user_id
+    unique: true
+    columns:
+    - user_id
+    lengths: {}
+    orders: {}
+    opclasses: {}
+    where:
+    type:
+    using:
+    include:
+    nulls_not_distinct:
+    comment:
+    valid: true
   creators_filters:
   - !ruby/object:ActiveRecord::ConnectionAdapters::IndexDefinition
     table: creators_filters
diff --git a/test/fixtures/conversation/messages.yml b/test/fixtures/conversation/messages.yml
new file mode 100644
index 000000000..7cdb27dd0
--- /dev/null
+++ b/test/fixtures/conversation/messages.yml
@@ -0,0 +1,9 @@
+# Read about fixtures at https://api.rubyonrails.org/classes/ActiveRecord/FixtureSet.html
+
+one:
+  conversation: one
+  role: MyString
+
+two:
+  conversation: two
+  role: MyString
diff --git a/test/fixtures/conversations.yml b/test/fixtures/conversations.yml
new file mode 100644
index 000000000..6dc1ab362
--- /dev/null
+++ b/test/fixtures/conversations.yml
@@ -0,0 +1,7 @@
+# Read about fixtures at https://api.rubyonrails.org/classes/ActiveRecord/FixtureSet.html
+
+one:
+  user: one
+
+two:
+  user: two
diff --git a/test/models/conversation/message_test.rb b/test/models/conversation/message_test.rb
new file mode 100644
index 000000000..f233d579b
--- /dev/null
+++ b/test/models/conversation/message_test.rb
@@ -0,0 +1,7 @@
+require "test_helper"
+
+class Conversation::MessageTest < ActiveSupport::TestCase
+  # test "the truth" do
+  #   assert true
+  # end
+end
diff --git a/test/models/conversation_test.rb b/test/models/conversation_test.rb
new file mode 100644
index 000000000..0c0d00ac7
--- /dev/null
+++ b/test/models/conversation_test.rb
@@ -0,0 +1,7 @@
+require "test_helper"
+
+class ConversationTest < ActiveSupport::TestCase
+  # test "the truth" do
+  #   assert true
+  # end
+end