diff --git a/Gemfile b/Gemfile
index 87a4a1367..933cb4e61 100644
--- a/Gemfile
+++ b/Gemfile
@@ -27,7 +27,7 @@ gem "rqrcode"
 gem "redcarpet"
 gem "rouge"
 gem "jbuilder"
-gem "actiontext-lexical", bc: "actiontext-lexical"
+gem "lexxy", bc: "lexxy"
 gem "image_processing", "~> 1.14"
 gem "platform_agent"
 gem "aws-sdk-s3", require: false
diff --git a/Gemfile.lock b/Gemfile.lock
index 76292e489..dbb76fd31 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -1,10 +1,3 @@
-GIT
-  remote: https://github.com/basecamp/actiontext-lexical
-  revision: 36c86dfd59406c853cb791adfd19a650f781d824
-  specs:
-    actiontext-lexical (0.1.0)
-      rails (>= 8.0.2)
-
 GIT
   remote: https://github.com/basecamp/active_record-tenanted
   revision: f7bf7c2ba5602ed6ad842b54da7355d281d52b21
@@ -38,6 +31,13 @@ GIT
       thor (~> 1.3)
       zeitwerk (>= 2.6.18, < 3.0)
 
+GIT
+  remote: https://github.com/basecamp/lexxy
+  revision: a3a06435302637a3c384f288a093946eefd37ff9
+  specs:
+    lexxy (0.1.0)
+      rails (>= 8.0.2)
+
 GIT
   remote: https://github.com/basecamp/portfolio
   revision: 86411a53d19a42ce44705a50ebe7c22828597991
@@ -596,7 +596,6 @@ PLATFORMS
   x86_64-mingw32
 
 DEPENDENCIES
-  actiontext-lexical!
   active_record-tenanted!
   activeresource
   aws-sdk-s3
@@ -612,6 +611,7 @@ DEPENDENCIES
   importmap-rails
   jbuilder
   kamal!
+  lexxy!
   mission_control-jobs
   mocha
   mysql2!
diff --git a/app/assets/stylesheets/bar.css b/app/assets/stylesheets/bar.css
index de71dbbb4..8370ef900 100644
--- a/app/assets/stylesheets/bar.css
+++ b/app/assets/stylesheets/bar.css
@@ -41,12 +41,18 @@
   }
 
   .bar__placeholder {
+    color: var(--color-ink-medium);
     font-weight: 500;
-    opacity: 0.66;
 
     .btn--plain {
-      font-weight: 500;
+      color: inherit;
+      font-weight: inherit;
+      padding-inline: 1ch;
       white-space: nowrap;
+
+      &:hover {
+        color: oklch(var(--lch-blue-dark));
+      }
     }
   }
 }
diff --git a/app/assets/stylesheets/cards.css b/app/assets/stylesheets/cards.css
index 7bedc3334..3183168f8 100644
--- a/app/assets/stylesheets/cards.css
+++ b/app/assets/stylesheets/cards.css
@@ -176,7 +176,7 @@
   }
 
   .card-field__description {
-    lexical-toolbar {
+    lexxy-toolbar {
       border-block-start: 1px solid var(--color-ink-light);
       margin-block-start: var(--block-margin) !important;
     }
diff --git a/app/assets/stylesheets/conversation.css b/app/assets/stylesheets/conversation.css
index 0ee03fa59..f5b0bbe8a 100644
--- a/app/assets/stylesheets/conversation.css
+++ b/app/assets/stylesheets/conversation.css
@@ -20,6 +20,7 @@
 
   .conversation__message {
     display: flex;
+    flex-direction: column;
 
     .action-text-content {
       border-radius: 0.5rem;
@@ -51,7 +52,7 @@
   }
 
   .conversation__message--assistant {
-    justify-content: flex-start;
+    align-items: flex-start;
 
     .action-text-content {
       margin-inline-end: 15%;
@@ -67,8 +68,15 @@
     color: var(--color-negative);
   }
 
+  .conversation__message--failed[data-error]::after {
+    color: var(--color-negative);
+    content: attr(data-error);
+    display: block;
+    padding: var(--inline-space);
+  }
+
   .conversation__message--user {
-    justify-content: flex-end;
+    align-items: flex-end;
 
     .action-text-content {
       background-color: var(--color-selected);
@@ -96,6 +104,7 @@
     display: flex;
     flex-direction: column;
     gap: var(--block-space);
+    inline-size: 100%;
     margin-inline: auto;
     max-inline-size: 67ch;
   }
diff --git a/app/assets/stylesheets/filters.css b/app/assets/stylesheets/filters.css
index 45be28002..da68a576c 100644
--- a/app/assets/stylesheets/filters.css
+++ b/app/assets/stylesheets/filters.css
@@ -10,6 +10,7 @@
 
     .btn {
       --btn-border-color: var(--color-ink-medium);
+      --input-background: var(--color-canvas);
     }
   }
 
diff --git a/app/assets/stylesheets/actiontext-lexical.css b/app/assets/stylesheets/lexxy.css
similarity index 85%
rename from app/assets/stylesheets/actiontext-lexical.css
rename to app/assets/stylesheets/lexxy.css
index c6ac46217..eb19c788a 100644
--- a/app/assets/stylesheets/actiontext-lexical.css
+++ b/app/assets/stylesheets/lexxy.css
@@ -1,5 +1,5 @@
 @layer components {
-  lexical-editor {
+  lexxy-editor {
     display: block;
     position: relative;
     overflow: visible;
@@ -18,11 +18,11 @@
       }
     }
 
-    /* Lexical still uses the `lexical-editor--empty` class if you have a list
+    /* Lexical still uses the `lexxy-editor--empty` class if you have a list
        started with no other characters. Here, we won't show the placeholder if
        you've clicked the List button in the toolbar. */
-    &.lexical-editor--empty {
-      .lexical-editor__content:not(:has(ul, ol))::before {
+    &.lexxy-editor--empty {
+      .lexxy-editor__content:not(:has(ul, ol))::before {
         content: attr(placeholder);
         color: currentColor;
         cursor: text;
@@ -40,7 +40,7 @@
     }
   }
 
-  .lexical-dialog-actions {
+  .lexxy-dialog-actions {
     display: flex;
     font-size: var(--text-x-small);
     flex: 1 1 0%;
@@ -65,7 +65,7 @@
     }
   }
 
-  .lexical-editor__content {
+  .lexxy-editor__content {
     margin: var(--block-space-half) 0;
     min-block-size: calc(7lh + var(--block-space));
     outline: 0;
@@ -81,13 +81,13 @@
     }
   }
 
-  .lexical-editor--drag-over {
+  .lexxy-editor--drag-over {
     background-color: var(--color-selected);
     border-radius: 4px;
     outline: 2px dashed var(--color-selected-dark);
   }
 
-  lexical-toolbar {
+  lexxy-toolbar {
     background-color: inherit;
     border-block-end: 1px solid var(--color-ink-light);
     color: currentColor;
@@ -152,7 +152,7 @@
     }
   }
 
-  .lexical-code-language-picker {
+  .lexxy-code-language-picker {
     /* Based on .input, .input--select */
     -webkit-appearance: none;
     appearance: none;
@@ -185,21 +185,21 @@
   /* Prompt
   /* ------------------------------------------------------------------------ */
 
-  .lexical-prompt-menu {
-    --lexical-prompt-avatar-size: 24px;
-    --lexical-prompt-min-width: 20ch;
-    --lexical-prompt-padding: 0.5ch;
+  .lexxy-prompt-menu {
+    --lexxy-prompt-avatar-size: 24px;
+    --lexxy-prompt-min-width: 20ch;
+    --lexxy-prompt-padding: 0.5ch;
 
     background-color: var(--color-canvas);
-    border-radius: calc(var(--lexical-prompt-padding) * 2);
+    border-radius: calc(var(--lexxy-prompt-padding) * 2);
     box-shadow: var(--shadow);
     color: var(--color-ink);
     font-family: var(--font-sans);
     font-size: var(--text-small);
     list-style: none;
     margin: 0;
-    min-inline-size: var(--lexical-prompt-min-width);
-    padding: var(--lexical-prompt-padding);
+    min-inline-size: var(--lexxy-prompt-min-width);
+    padding: var(--lexxy-prompt-padding);
     visibility: hidden;
     z-index: var(--z-popup);
 
@@ -207,17 +207,17 @@
     overflow: scroll;
   }
 
-  .lexical-prompt-menu--visible {
+  .lexxy-prompt-menu--visible {
     visibility: initial;
   }
 
-  .lexical-prompt-menu__item {
+  .lexxy-prompt-menu__item {
     align-items: center;
     border-radius: 0.5ch;
     cursor: pointer;
     display: flex;
-    gap: var(--lexical-prompt-padding);
-    padding: var(--lexical-prompt-padding);
+    gap: var(--lexxy-prompt-padding);
+    padding: var(--lexxy-prompt-padding);
     white-space: nowrap;
 
     &:hover {
@@ -229,10 +229,10 @@
     }
 
     img {
-      block-size: var(--lexical-prompt-avatar-size);
+      block-size: var(--lexxy-prompt-avatar-size);
       border-radius: 50%;
       flex-shrink: 0;
-      inline-size: var(--lexical-prompt-avatar-size);
+      inline-size: var(--lexxy-prompt-avatar-size);
       margin: 0;
     }
 
@@ -249,8 +249,8 @@
   }
 
   /* Empty state */
-  .lexical-prompt-menu__item--empty {
+  .lexxy-prompt-menu__item--empty {
     color: var(--color-ink-medium);
-    padding: var(--lexical-prompt-padding);
+    padding: var(--lexxy-prompt-padding);
   }
 }
diff --git a/app/assets/stylesheets/rich-text-content.css b/app/assets/stylesheets/rich-text-content.css
index b7d525c6d..118d3d77e 100644
--- a/app/assets/stylesheets/rich-text-content.css
+++ b/app/assets/stylesheets/rich-text-content.css
@@ -21,9 +21,9 @@
     :where(h6) { font-size: 0.67em; }
 
     :where(p, ul, ol, dl, blockquote, figure, .attachment) {
-      margin-block: var(--block-margin);
+      margin-block: 0 var(--block-margin);
 
-      &:not(lexical-editor &) {
+      &:not(lexxy-editor &) {
         overflow-wrap: break-word;
         text-wrap: pretty;
       }
@@ -171,13 +171,22 @@
     margin-inline: 0;
     max-inline-size: 100%;
 
-    &:is(figure) img,
-    &:is(figure) video {
-      block-size: auto;
-      display: block;
+    &:is(figure) {
+      inline-size: fit-content;
       margin-inline: auto;
-      max-inline-size: 100%;
-      user-select: none;
+      display: block;
+
+      img, video {
+        block-size: auto;
+        display: block;
+        margin-inline: auto;
+        max-inline-size: 100%;
+        user-select: none;
+      }
+
+      > a {
+        display: block;
+      }
     }
 
     :where(progress) {
@@ -362,7 +371,7 @@
        0.5ch 0 0 var(--attachment-bg-color);
     border-radius: 99rem;
 
-    lexical-editor & {
+    lexxy-editor & {
       cursor: pointer;
     }
 
diff --git a/app/assets/stylesheets/search.css b/app/assets/stylesheets/search.css
index d0fad3d64..49e466b39 100644
--- a/app/assets/stylesheets/search.css
+++ b/app/assets/stylesheets/search.css
@@ -25,9 +25,10 @@
 
     border-width: 0 0 1px;
     max-inline-size: 50ch;
+    position: relative;
 
     &::-webkit-search-cancel-button {
-      --clear-icon-size: 0.75rem;
+      --clear-icon-size: 0.66rem;
 
       -webkit-appearance: none;
       appearance: none;
@@ -37,7 +38,7 @@
       block-size: var(--clear-icon-size);
       cursor: pointer;
       inline-size: var(--clear-icon-size);
-      inset: 50% 1ch auto auto;
+      inset: 50% 0 auto auto;
       position: absolute;
       translate: 0 -50%;
 
diff --git a/app/assets/stylesheets/utilities.css b/app/assets/stylesheets/utilities.css
index 44e6a3afb..1691a36eb 100644
--- a/app/assets/stylesheets/utilities.css
+++ b/app/assets/stylesheets/utilities.css
@@ -79,6 +79,7 @@
   .half-width { inline-size: 50%; }
   .max-width { max-inline-size: 100%; }
   .min-content { inline-size: min-content; }
+  .fit-content { inline-size: fit-content; }
   .max-inline-size { max-inline-size: 100%; }
 
   /* Overflow */
diff --git a/app/controllers/conversations/messages_controller.rb b/app/controllers/conversations/messages_controller.rb
index 0a6ec8b31..b7585ac72 100644
--- a/app/controllers/conversations/messages_controller.rb
+++ b/app/controllers/conversations/messages_controller.rb
@@ -7,6 +7,10 @@ class Conversations::MessagesController < ApplicationController
 
   def create
     @conversation.ask(question, **message_params)
+  rescue Ai::Quota::UsageExceedsQuotaError
+    render json: { error: "You've depleted your quota" }, status: :too_many_requests
+  rescue Conversation::InvalidStateError
+    render json: { error: "Fizzy is still working on an answer to your last question" }, status: :conflict
   end
 
   private
diff --git a/app/helpers/hotkeys_helper.rb b/app/helpers/hotkeys_helper.rb
index a1894104c..7bd0424d1 100644
--- a/app/helpers/hotkeys_helper.rb
+++ b/app/helpers/hotkeys_helper.rb
@@ -11,7 +11,7 @@ module HotkeysHelper
         else
           key
         end
-      }.join("+")
+      }.join()
     else
       hotkey.split(",").first if hotkey
     end
diff --git a/app/helpers/rich_text_helper.rb b/app/helpers/rich_text_helper.rb
index 47941a6a7..752af1075 100644
--- a/app/helpers/rich_text_helper.rb
+++ b/app/helpers/rich_text_helper.rb
@@ -1,22 +1,22 @@
 module RichTextHelper
   def mentions_prompt(collection)
-    content_tag "lexical-prompt", "", trigger: "@", src: prompts_collection_users_path(collection), name: "mention"
+    content_tag "lexxy-prompt", "", trigger: "@", src: prompts_collection_users_path(collection), name: "mention"
   end
 
   def global_mentions_prompt
-    content_tag "lexical-prompt", "", trigger: "@", src: prompts_users_path, name: "mention"
+    content_tag "lexxy-prompt", "", trigger: "@", src: prompts_users_path, name: "mention"
   end
 
   def tags_prompt
-    content_tag "lexical-prompt", "", trigger: "#", src: prompts_tags_path, name: "tag"
+    content_tag "lexxy-prompt", "", trigger: "#", src: prompts_tags_path, name: "tag"
   end
 
   def cards_prompt
-    content_tag "lexical-prompt", "", trigger: "#", src: prompts_cards_path, name: "card", "insert-editable-text": true, "remote-filtering": true, "supports-space-in-searches": true
+    content_tag "lexxy-prompt", "", trigger: "#", src: prompts_cards_path, name: "card", "insert-editable-text": true, "remote-filtering": true, "supports-space-in-searches": true
   end
 
   def code_language_picker
-    content_tag "lexical-code-language-picker"
+    content_tag "lexxy-code-language-picker"
   end
 
   def general_prompts(collection)
diff --git a/app/javascript/application.js b/app/javascript/application.js
index 725acdc82..dbac91d0a 100644
--- a/app/javascript/application.js
+++ b/app/javascript/application.js
@@ -3,7 +3,7 @@ import "@hotwired/turbo-rails"
 import "initializers"
 import "controllers"
 
-import "actiontext-lexical"
+import "lexxy"
 import "@rails/actiontext"
 
 window.fetch = Turbo.fetch // TODO: We need to make @rails/request.js use Turbo's fetch when it's present.
diff --git a/app/javascript/controllers/conversation/composer_controller.js b/app/javascript/controllers/conversation/composer_controller.js
index 368716846..0f7e83223 100644
--- a/app/javascript/controllers/conversation/composer_controller.js
+++ b/app/javascript/controllers/conversation/composer_controller.js
@@ -27,7 +27,10 @@ export default class extends Controller {
     if (event.detail.success) {
       this.#reset()
     } else {
-      this.conversationMessagesOutlet.failPendingMessage(this.clientMessageIdInputTarget.value)
+      this.#failPendingMessage(
+        this.clientMessageIdInputTarget.value, 
+        event.detail.fetchResponse
+      )
     }
   }
 
@@ -60,4 +63,18 @@ export default class extends Controller {
     this.textInputTarget.value = ""
     this.clientMessageIdInputTarget.value = ""
   }
+
+  async #failPendingMessage(clientMessageId, response) {
+    let errorMessage = null
+
+    if (response?.contentType?.includes('application/json')) {
+      const error = JSON.parse(await response.responseText)
+      errorMessage = error.error
+    }
+
+    this.conversationMessagesOutlet.failPendingMessage(
+      this.clientMessageIdInputTarget.value,
+      errorMessage
+    )
+  }
 }
diff --git a/app/javascript/controllers/conversation/messages_controller.js b/app/javascript/controllers/conversation/messages_controller.js
index 4d484ee2d..32e3e58e9 100644
--- a/app/javascript/controllers/conversation/messages_controller.js
+++ b/app/javascript/controllers/conversation/messages_controller.js
@@ -12,11 +12,15 @@ export default class extends Controller {
     this.scrollToBottom()
   }
 
-  failPendingMessage(clientMessageId) {
+  failPendingMessage(clientMessageId, errorMessage) {
     const message = this.element.querySelector(`#message_${clientMessageId}`)
 
     if (message) {
       message.classList.add(this.failedMessageClass)
+
+      if (errorMessage) {
+        message.dataset.error = errorMessage
+      }
     }
   }
 
diff --git a/app/javascript/controllers/hotkey_controller.js b/app/javascript/controllers/hotkey_controller.js
index 1c85d69e8..a6b8192c9 100644
--- a/app/javascript/controllers/hotkey_controller.js
+++ b/app/javascript/controllers/hotkey_controller.js
@@ -9,7 +9,7 @@ export default class extends Controller {
   }
 
   #shouldIgnore(event) {
-    return event.defaultPrevented || event.target.closest("input, textarea, lexical-editor")
+    return event.defaultPrevented || event.target.closest("input, textarea, lexxy-editor")
   }
 
   get #isClickable() {
diff --git a/app/javascript/controllers/local_save_controller.js b/app/javascript/controllers/local_save_controller.js
index 5f9fc83a3..b7c2f5302 100644
--- a/app/javascript/controllers/local_save_controller.js
+++ b/app/javascript/controllers/local_save_controller.js
@@ -46,8 +46,8 @@ export default class extends Controller {
   }
 
   #triggerChangeEvent(newValue) {
-    if (this.inputTarget.tagName === "LEXICAL-EDITOR") {
-      this.inputTarget.dispatchEvent(new CustomEvent('actiontext:change', {
+    if (this.inputTarget.tagName === "LEXXY-EDITOR") {
+      this.inputTarget.dispatchEvent(new CustomEvent('lexxy:change', {
         bubbles: true,
         detail: {
           previousContent: '',
diff --git a/app/javascript/controllers/syntax_highlight_controller.js b/app/javascript/controllers/syntax_highlight_controller.js
index 02b66a0f7..cfaf93ba1 100644
--- a/app/javascript/controllers/syntax_highlight_controller.js
+++ b/app/javascript/controllers/syntax_highlight_controller.js
@@ -1,5 +1,5 @@
 import { Controller } from "@hotwired/stimulus"
-import { highlightAll } from "actiontext-lexical"
+import { highlightAll } from "lexxy"
 
 export default class extends Controller {
   connect() {
diff --git a/app/models/ai.rb b/app/models/ai.rb
new file mode 100644
index 000000000..4b4c17743
--- /dev/null
+++ b/app/models/ai.rb
@@ -0,0 +1,5 @@
+module Ai
+  def self.table_name_prefix
+    "ai_"
+  end
+end
diff --git a/app/models/ai/list_cards_tool.rb b/app/models/ai/list_cards_tool.rb
index 531f67d2d..ec105ba73 100644
--- a/app/models/ai/list_cards_tool.rb
+++ b/app/models/ai/list_cards_tool.rb
@@ -70,6 +70,7 @@ class Ai::ListCardsTool < Ai::Tool
   def execute(**params)
     cards = Card
       .where(collection: user.collections)
+      .published
       .with_rich_text_description
       .includes(:stage, :creator, :assignees, :goldness, :collection)
 
diff --git a/app/models/ai/quota.rb b/app/models/ai/quota.rb
new file mode 100644
index 000000000..955a855af
--- /dev/null
+++ b/app/models/ai/quota.rb
@@ -0,0 +1,50 @@
+class Ai::Quota < ApplicationRecord
+  class UsageExceedsQuotaError < StandardError; end
+
+  belongs_to :user
+
+  before_create -> { reset }
+
+  validates :limit, presence: true, numericality: { only_integer: true, greater_than_or_equal_to: 0 }
+  validates :used, presence: true, numericality: { only_integer: true, greater_than_or_equal_to: 0 }
+
+  def spend(cost)
+    cost = Money.wrap(cost)
+
+    transaction do
+      reset_if_due
+      increment!(:used, cost.in_microcents)
+    end
+  end
+
+  def ensure_not_depleted
+    reset_if_due
+
+    if depleted?
+      raise UsageExceedsQuotaError
+    end
+  end
+
+  private
+    def reset_if_due
+      reset if due_for_reset?
+    end
+
+    def reset
+      attributes = { used: 0, reset_at: 7.days.from_now }
+
+      if persisted?
+        update(**attributes)
+      else
+        assign_attributes(**attributes)
+      end
+    end
+
+    def due_for_reset?
+      reset_at.before?(Time.current)
+    end
+
+    def depleted?
+      used >= limit
+    end
+end
diff --git a/app/models/ai/quota/money.rb b/app/models/ai/quota/money.rb
new file mode 100644
index 000000000..f229c8def
--- /dev/null
+++ b/app/models/ai/quota/money.rb
@@ -0,0 +1,42 @@
+class Ai::Quota::Money < Data.define(:value)
+  CENTS_PER_DOLLAR = 100
+  MICROCENTS_PER_CENT = 1_000_000
+  MICROCENTS_PER_DOLLAR = CENTS_PER_DOLLAR * MICROCENTS_PER_CENT
+  NUMBER_REGEX = /\d+(\.\d+)?/
+
+  class << self
+    def wrap(value)
+      microcents = case value
+      when nil
+        raise ArgumentError, "#{self} can't wrap nil"
+      when self
+        value.value
+      when Integer
+        value
+      when String
+        convert_dollars_to_microcents(BigDecimal(value[NUMBER_REGEX]))
+      else
+        convert_dollars_to_microcents(value)
+      end
+
+      new(microcents)
+    end
+
+    private
+      def convert_dollars_to_microcents(dollars)
+        (dollars.to_d * MICROCENTS_PER_DOLLAR).round.to_i
+      end
+  end
+
+  def to_i
+    in_microcents
+  end
+
+  def in_microcents
+    value
+  end
+
+  def in_dollars
+    in_microcents.to_d / MICROCENTS_PER_DOLLAR
+  end
+end
diff --git a/app/models/conversation.rb b/app/models/conversation.rb
index 184394fb1..bf3a4a0ab 100644
--- a/app/models/conversation.rb
+++ b/app/models/conversation.rb
@@ -8,16 +8,9 @@ class Conversation < ApplicationRecord
 
   enum :state, %w[ ready thinking ].index_by(&:itself), default: :ready
 
-  def cost
-    messages.where.not(cost_microcents: nil).sum(:cost_microcents).to_d / 100_000
-  end
-
-  def clear
-    messages.delete_all
-    touch
-  end
-
   def ask(question, **attributes)
+    user.ensure_ai_quota_not_depleted
+
     create_message_with_state_change(**attributes, role: :user, content: question) do
       raise(InvalidStateError, "Can't ask questions while thinking") if thinking?
       thinking!
@@ -25,10 +18,14 @@ class Conversation < ApplicationRecord
   end
 
   def respond(answer, **attributes)
-    create_message_with_state_change(**attributes, role: :assistant, content: answer) do
+    message = create_message_with_state_change(**attributes, role: :assistant, content: answer) do
       raise(InvalidStateError, "Can't respond when not thinking") unless thinking?
       ready!
     end
+
+    user.spend_ai_quota(message.cost) if message.cost
+
+    message
   end
 
   private
diff --git a/app/models/conversation/message.rb b/app/models/conversation/message.rb
index dc817c500..72ea37b26 100644
--- a/app/models/conversation/message.rb
+++ b/app/models/conversation/message.rb
@@ -13,6 +13,10 @@ class Conversation::Message < ApplicationRecord
 
   scope :ordered, -> { order(created_at: :asc, id: :asc) }
 
+  def cost
+    cost_microcents && Ai::Quota::Money.new(cost_microcents)
+  end
+
   def all_emoji?
     content.to_plain_text.all_emoji?
   end
diff --git a/app/models/conversation/message/response_generator.rb b/app/models/conversation/message/response_generator.rb
index 032d2a0d8..365f9090d 100644
--- a/app/models/conversation/message/response_generator.rb
+++ b/app/models/conversation/message/response_generator.rb
@@ -12,13 +12,13 @@ class Conversation::Message::ResponseGenerator
     You are **Fizzy**, a helpful assistant for the Fizzy app by 37signals.
     Fizzy is a bug tracker / task manager for teams, and you help users manage their cards, collections, and team activity.
 
-    ### 🧠 Your Role
+    ### Your Role
     You help users with anything related to Fizzy — their cards, collections, 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
+    ### 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
@@ -31,6 +31,16 @@ class Conversation::Message::ResponseGenerator
     - Don’t explain concepts or go off-topic — answer only what was asked
     - Respond in **Markdown**
     - Always include links to cards, collections, comments, or users
+    - Always respond with a nicely formatted markdown link; NEVER respond with URLs or URL paths
+    - You are allowed to tell the user about themselves, the current time, their account, cards, collections, and comments
+
+    ### IMPORTANT: URL Handling
+    - **NEVER modify URLs in any way** - use them exactly as provided
+    - Always respond with markdown links, never bare URLs or paths
+    - If a URL starts with `/`, keep it as a relative path - do NOT add any domain
+    - Example: `{ "url": "/cards/123" }` becomes `[Card #123](/cards/123)
+    - `[/foo/bar]` isn't a valid Markdown link
+    - If a link doesn't have a title (e.g. `[](https://example.com)`) then use "Link" as the title (e.g. `[Link](https://example.com)`)
 
     You're here to help — not to anticipate.
   PROMPT
@@ -80,7 +90,7 @@ class Conversation::Message::ResponseGenerator
           chat.add_message(message.to_llm)
         end
 
-        chat.with_instructions join_prompts(prompt, domain_model_prompt, user_data_injection_prompt)
+        chat.with_instructions join_prompts(prompt, domain_model_prompt, user_data_injection_prompt, user_info_prompt)
 
         track_token_usage_of_intermediate_messages(chat)
       end
@@ -90,6 +100,12 @@ class Conversation::Message::ResponseGenerator
       conversation.messages.order(id: :asc).where(id: ...message.id).limit(50).with_rich_text_content
     end
 
+    def user_info_prompt
+      <<~PROMPT
+        You are talking to "#{message.owner.name}" who's User ID is #{message.owner.id}
+      PROMPT
+    end
+
     def track_token_usage_of_intermediate_messages(chat)
       chat.on_end_message do |response|
         @input_tokens = response.input_tokens
diff --git a/app/models/conversation/message/response_generator/response.rb b/app/models/conversation/message/response_generator/response.rb
index f404835a3..4d782bffd 100644
--- a/app/models/conversation/message/response_generator/response.rb
+++ b/app/models/conversation/message/response_generator/response.rb
@@ -1,6 +1,4 @@
 class Conversation::Message::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:)
@@ -10,10 +8,6 @@ class Conversation::Message::ResponseGenerator::Response
     @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
@@ -27,7 +21,7 @@ class Conversation::Message::ResponseGenerator::Response
   def input_token_price_microcents
     return unless model_info
 
-    price_per_million_tokens_to_microcents(model_info.input_price_per_million)
+    price_per_million_tokens_in_microcents(model_info.input_price_per_million)
   end
 
   def output_cost_microcents
@@ -39,7 +33,7 @@ class Conversation::Message::ResponseGenerator::Response
   def output_token_price_microcents
     return unless model_info
 
-    price_per_million_tokens_to_microcents(model_info.output_price_per_million)
+    price_per_million_tokens_in_microcents(model_info.output_price_per_million)
   end
 
   def model_info
@@ -47,8 +41,8 @@ class Conversation::Message::ResponseGenerator::Response
   end
 
   private
-    def price_per_million_tokens_to_microcents(price)
+    def price_per_million_tokens_in_microcents(price)
       single_token_price = price.to_d / 1_000_000
-      single_token_price * MICROCENTS_PER_DOLLAR
+      Ai::Quota::Money.wrap(single_token_price).in_microcents
     end
 end
diff --git a/app/models/user.rb b/app/models/user.rb
index bd8cf990d..af3ff9315 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, Conversational
+    SignalUser, Staff, Transferable, Conversational, AiQuota
   include Timelined # Depends on Accessor
 
   has_one_attached :avatar
diff --git a/app/models/user/ai_quota.rb b/app/models/user/ai_quota.rb
new file mode 100644
index 000000000..b34879fb9
--- /dev/null
+++ b/app/models/user/ai_quota.rb
@@ -0,0 +1,22 @@
+module User::AiQuota
+  extend ActiveSupport::Concern
+
+  DEFAULT_QUOTA = Ai::Quota::Money.wrap("$100").in_microcents
+
+  included do
+    has_one :ai_quota, class_name: "Ai::Quota"
+  end
+
+  def spend_ai_quota(cost)
+    fetch_or_create_ai_quota.spend(cost)
+  end
+
+  def ensure_ai_quota_not_depleted
+    fetch_or_create_ai_quota.ensure_not_depleted
+  end
+
+  private
+    def fetch_or_create_ai_quota
+      ai_quota || create_ai_quota!(limit: DEFAULT_QUOTA)
+    end
+end
diff --git a/app/views/bar/_bar.html.erb b/app/views/bar/_bar.html.erb
index 87c133be6..377348a04 100644
--- a/app/views/bar/_bar.html.erb
+++ b/app/views/bar/_bar.html.erb
@@ -6,7 +6,7 @@
         bar_search_url_value: search_path,
         bar_ask_url_value: conversation_path
       } do %>
-  <div class="flex justify-center gap bar__placeholder" data-bar-target="buttonsContainer">
+  <div class="flex justify-center bar__placeholder" data-bar-target="buttonsContainer">
     <%= tag.button \
           class: "btn btn--plain",
           data: {
@@ -14,7 +14,7 @@
             action: "
             bar#search
             keydown.meta+k@document->hotkey#click keydown.ctrl+k@document->hotkey#click" } do %>
-      <span>Search [<%= hotkey_label(["ctrl", "K"]) %>]</span>
+      <span>Search (<%= hotkey_label(["ctrl", "K"]) %>)</span>
     <% end %>
     <span>or</span>
     <%= tag.button \
@@ -24,7 +24,7 @@
             action: "
             bar#ask
             keydown.meta+a@document->hotkey#click keydown.ctrl+a@document->hotkey#click" } do %>
-      <span>Ask [<%= hotkey_label(["ctrl", "A"]) %>]</span>
+      <span>Ask (<%= hotkey_label(["ctrl", "A"]) %>)</span>
     <% end %>
   </div>
 
@@ -42,7 +42,7 @@
     data: {
       controller: "dialog",
       dialog_target: "dialog",
-      action: "keydown.esc->bar#reset:stop" } do %>
+      action: "keydown.esc@document->bar#reset:stop" } do %>
     <%= turbo_frame_tag "bar-content", data: { bar_target: "turboFrame" } %>
   <% end %>
 <% end %>
diff --git a/app/views/cards/comments/_new.html.erb b/app/views/cards/comments/_new.html.erb
index 14fb50a4a..6309e8536 100644
--- a/app/views/cards/comments/_new.html.erb
+++ b/app/views/cards/comments/_new.html.erb
@@ -10,7 +10,7 @@
                   local_save_key_value: "comment-#{card.id}",
                   action: "turbo:submit-end->local-save#submit keydown.ctrl+enter->form#submit:prevent keydown.meta+enter->form#submit:prevent keydown.esc->form#cancel:stop" } do |form| %>
         <%= form.rich_textarea :body, required: true, placeholder: new_comment_placeholder(card),
-              data: { local_save_target: "input", action: "actiontext:change->local-save#save turbo:morph-element->local-save#restoreContent" } do %>
+              data: { local_save_target: "input", action: "lexxy:change->local-save#save turbo:morph-element->local-save#restoreContent" } do %>
           <%= general_prompts(@card.collection) %>
         <% end %>
         <%= form.button class: "comment__submit btn btn--reversed flex-item-justify-start" do %>
diff --git a/app/views/cards/container/_title.html.erb b/app/views/cards/container/_title.html.erb
index 0521f52d0..248267dd2 100644
--- a/app/views/cards/container/_title.html.erb
+++ b/app/views/cards/container/_title.html.erb
@@ -17,7 +17,7 @@
     </h1>
     <%= form.rich_textarea :description, class: "card-field__description margin-block-start-half margin-block-end",
           placeholder: "Add some notes, context, pictures, or video about this…",
-          data: { action: "actiontext:change->auto-save#change focusout->auto-save#submit keydown.ctrl+enter->form#submit:prevent keydown.meta+enter->form#submit:prevent keydown.esc->form#cancel:stop" } do %>
+          data: { action: "lexxy:change->auto-save#change focusout->auto-save#submit keydown.ctrl+enter->form#submit:prevent keydown.meta+enter->form#submit:prevent keydown.esc->form#cancel:stop" } do %>
       <%= general_prompts(card.collection) %>
     <% end %>
   <% end %>
diff --git a/app/views/cards/edit.html.erb b/app/views/cards/edit.html.erb
index 5775947fe..e1b2a01bb 100644
--- a/app/views/cards/edit.html.erb
+++ b/app/views/cards/edit.html.erb
@@ -14,7 +14,7 @@
       <%= general_prompts(@card.collection) %>
     <% end %>
 
-    <%= form.button "Save changes", type: :submit, class: "btn btn--reversed", style: "--btn-background: #{@card.color}" %>
+    <%= form.button "Save changes", type: :submit, class: "btn btn--reversed fit-content", style: "--btn-background: #{@card.color}" %>
     <%= link_to "Close editor and discard changes", collection_card_path(@card.collection, @card), data: { form_target: "cancel" }, hidden: true %>
   <% end %>
 <% end %>
diff --git a/app/views/cards/index.html.erb b/app/views/cards/index.html.erb
index 079141ed3..7909a7bfa 100644
--- a/app/views/cards/index.html.erb
+++ b/app/views/cards/index.html.erb
@@ -13,8 +13,7 @@
 <% end %>
 
 <header class="header" style="--header-actions-width: 7rem;">
-  <%= render "filters/menu/add_card_button", user_filtering: @user_filtering %>
-
+  <div class="header__actions header__actions--start"></div>
   <h1 class="header__title overflow-ellipsis" style="view-transistion-name: card-collection-title">
     <%= @user_filtering.selected_collections_label %>
   </h1>
diff --git a/app/views/cards/index/_add_card_button.html.erb b/app/views/cards/index/_add_card_button.html.erb
new file mode 100644
index 000000000..a8b8d8caf
--- /dev/null
+++ b/app/views/cards/index/_add_card_button.html.erb
@@ -0,0 +1,8 @@
+<% if collection = user_filtering.collections.first %>
+  <div class="card card--new">
+    <%= button_to collection_cards_path(collection), method: :post, class: "btn" do %>
+      <%= icon_tag "add" %>
+      <span>Add a card</span>
+    <% end %>
+  </div>
+<% end %>
diff --git a/app/views/cards/index/engagement/_considering.html.erb b/app/views/cards/index/engagement/_considering.html.erb
index 7217fc74c..f445c1836 100644
--- a/app/views/cards/index/engagement/_considering.html.erb
+++ b/app/views/cards/index/engagement/_considering.html.erb
@@ -1,13 +1,6 @@
 <section id="considering-cards" class="cards cards--considering" data-drag-and-drop-target="container"  data-drop-target="considering">
   <div class="cards__decoration"></div>
-  <% if collection = @filter.single_collection || Current.user.collections.first %>
-    <div class="card card--new">
-      <%= button_to collection_cards_path(collection), method: :post, class: "btn" do %>
-        <%= icon_tag "add" %>
-        <span>Add a card</span>
-    </div>
-    <% end %>
-  <% end %>
+  <%= render "cards/index/add_card_button", user_filtering: @user_filtering %>
   <% if page.used? %>
     <%= render partial: "cards/display/preview", collection: page.records, as: :card, locals: { draggable: true }, cached: true %>
 
diff --git a/app/views/filters/menu/_add_card_button.html.erb b/app/views/filters/menu/_add_card_button.html.erb
index 0341b08c3..e49868993 100644
--- a/app/views/filters/menu/_add_card_button.html.erb
+++ b/app/views/filters/menu/_add_card_button.html.erb
@@ -5,4 +5,4 @@
       <span>Add a card</span>
     <% end %>
   <% end %>
-</div>
+</div>
\ No newline at end of file
diff --git a/app/views/prompts/cards/_card.html.erb b/app/views/prompts/cards/_card.html.erb
index ebecb20a6..3f45c6213 100644
--- a/app/views/prompts/cards/_card.html.erb
+++ b/app/views/prompts/cards/_card.html.erb
@@ -1,8 +1,8 @@
-<lexical-prompt-item>
+<lexxy-prompt-item>
   <template type="menu">
     #<%= card.id %> <%= card.title %>
   </template>
   <template type="editor">
     <%= link_to "##{card.id} #{card.title}", collection_card_url(card.collection, card) %>
   </template>
-</lexical-prompt-item>
+</lexxy-prompt-item>
diff --git a/app/views/prompts/collections/users/_user.html.erb b/app/views/prompts/collections/users/_user.html.erb
index ad4b917b2..3224f30a0 100644
--- a/app/views/prompts/collections/users/_user.html.erb
+++ b/app/views/prompts/collections/users/_user.html.erb
@@ -1,4 +1,4 @@
-<lexical-prompt-item search="<%= "#{user.name} #{user.initials} #{"me" if user == Current.user}" %>" sgid="<%= user.attachable_sgid %>">
+<lexxy-prompt-item search="<%= "#{user.name} #{user.initials} #{"me" if user == Current.user}" %>" sgid="<%= user.attachable_sgid %>">
   <template type="menu">
     <%= avatar_image_tag user %>
     <%= user.name %>
@@ -7,4 +7,4 @@
     <%= avatar_image_tag user %>
     <%= user.first_name %>
   </template>
-</lexical-prompt-item>
+</lexxy-prompt-item>
diff --git a/app/views/prompts/commands/_command.html.erb b/app/views/prompts/commands/_command.html.erb
index d9fc0f799..634483f58 100644
--- a/app/views/prompts/commands/_command.html.erb
+++ b/app/views/prompts/commands/_command.html.erb
@@ -1,10 +1,10 @@
 <% command, description, editor_version = command %>
 
-<lexical-prompt-item search="<%= description %> <%= command %>">
+<lexxy-prompt-item search="<%= description %> <%= command %>">
   <template type="menu">
     <code><%= command %></code> <%= description %>
   </template>
   <template type="editor">
     <%= editor_version.gsub(/ +$/, "&nbsp;").html_safe %>
   </template>
-</lexical-prompt-item>
+</lexxy-prompt-item>
diff --git a/app/views/prompts/tags/_tag.html.erb b/app/views/prompts/tags/_tag.html.erb
index 904484f5d..3be999a8e 100644
--- a/app/views/prompts/tags/_tag.html.erb
+++ b/app/views/prompts/tags/_tag.html.erb
@@ -1,8 +1,8 @@
-<lexical-prompt-item search="<%= tag.title %>" sgid="<%= tag.attachable_sgid %>">
+<lexxy-prompt-item search="<%= tag.title %>" sgid="<%= tag.attachable_sgid %>">
   <template type="menu">
     #<%= tag.title %>
   </template>
   <template type="editor">
     #<%= tag.title %>
   </template>
-</lexical-prompt-item>
+</lexxy-prompt-item>
diff --git a/app/views/searches/show.html.erb b/app/views/searches/show.html.erb
index b3be862d8..905afa257 100644
--- a/app/views/searches/show.html.erb
+++ b/app/views/searches/show.html.erb
@@ -10,7 +10,7 @@
     <div class="search__results">
       <% if @search_results.none? %>
         <div class="search__empty">
-          Not matches
+          No matches
         </div>
       <% end %>
 
diff --git a/config/importmap.rb b/config/importmap.rb
index 2abe3a805..f1da52737 100644
--- a/config/importmap.rb
+++ b/config/importmap.rb
@@ -10,6 +10,6 @@ pin_all_from "app/javascript/controllers", under: "controllers"
 pin_all_from "app/javascript/helpers", under: "helpers"
 pin_all_from "app/javascript/initializers", under: "initializers"
 pin "marked" # @15.0.11
-pin "actiontext-lexical"
+pin "lexxy"
 pin "@rails/activestorage", to: "activestorage.esm.js"
 pin "@rails/actiontext", to: "actiontext.esm.js"
diff --git a/config/initializers/inflections.rb b/config/initializers/inflections.rb
index 3d2359e52..62ffe294f 100644
--- a/config/initializers/inflections.rb
+++ b/config/initializers/inflections.rb
@@ -13,4 +13,7 @@
 # These inflection rules are supported but not enabled by default:
 ActiveSupport::Inflector.inflections(:en) do |inflect|
   inflect.acronym "SQLite"
+
+  inflect.singular "quotas", "quota"
+  inflect.plural "quota", "quotas"
 end
diff --git a/db/migrate/20250819101032_create_ai_quotas.rb b/db/migrate/20250819101032_create_ai_quotas.rb
new file mode 100644
index 000000000..6b4d9a4af
--- /dev/null
+++ b/db/migrate/20250819101032_create_ai_quotas.rb
@@ -0,0 +1,12 @@
+class CreateAiQuotas < ActiveRecord::Migration[8.1]
+  def change
+    create_table :ai_quotas do |t|
+      t.belongs_to :user, null: false, foreign_key: true
+      t.integer :limit, null: false
+      t.integer :used, null: false, default: 0
+      t.datetime :reset_at, null: false, index: true
+
+      t.timestamps
+    end
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index b31a7dc51..93533668e 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -73,6 +73,17 @@ ActiveRecord::Schema[8.1].define(version: 2025_08_19_105245) do
     t.index ["blob_id", "variation_digest"], name: "index_active_storage_variant_records_uniqueness", unique: true
   end
 
+  create_table "ai_quotas", force: :cascade do |t|
+    t.datetime "created_at", null: false
+    t.integer "limit", null: false
+    t.datetime "reset_at", null: false
+    t.datetime "updated_at", null: false
+    t.integer "used", default: 0, null: false
+    t.integer "user_id", null: false
+    t.index ["reset_at"], name: "index_ai_quotas_on_reset_at"
+    t.index ["user_id"], name: "index_ai_quotas_on_user_id"
+  end
+
   create_table "assignees_filters", id: false, force: :cascade do |t|
     t.integer "assignee_id", null: false
     t.integer "filter_id", null: false
@@ -438,6 +449,7 @@ ActiveRecord::Schema[8.1].define(version: 2025_08_19_105245) do
 
   add_foreign_key "active_storage_attachments", "active_storage_blobs", column: "blob_id"
   add_foreign_key "active_storage_variant_records", "active_storage_blobs", column: "blob_id"
+  add_foreign_key "ai_quotas", "users"
   add_foreign_key "card_activity_spikes", "cards"
   add_foreign_key "card_goldnesses", "cards"
   add_foreign_key "cards", "workflow_stages", column: "stage_id"
diff --git a/db/schema_cache.yml b/db/schema_cache.yml
index 58f3518f3..3f0d88ec2 100644
--- a/db/schema_cache.yml
+++ b/db/schema_cache.yml
@@ -20,7 +20,7 @@ columns:
     default_function:
     collation:
     comment:
-  - &23 !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+  - &24 !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
     auto_increment:
     name: collection_id
     cast_type: &3 !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3Adapter::SQLite3Integer
@@ -90,7 +90,7 @@ columns:
     default_function:
     collation:
     comment:
-  - &25 !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+  - &18 !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
     auto_increment:
     name: user_id
     cast_type: *3
@@ -258,7 +258,7 @@ columns:
     collation:
     comment:
   - *6
-  - &18 !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+  - &19 !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
     auto_increment:
     name: key
     cast_type: *7
@@ -301,9 +301,44 @@ columns:
     default_function:
     collation:
     comment:
+  ai_quotas:
+  - *5
+  - *6
+  - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+    auto_increment:
+    name: limit
+    cast_type: *3
+    sql_type_metadata: *4
+    'null': false
+    default:
+    default_function:
+    collation:
+    comment:
+  - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+    auto_increment:
+    name: reset_at
+    cast_type: *1
+    sql_type_metadata: *2
+    'null': false
+    default:
+    default_function:
+    collation:
+    comment:
+  - *9
+  - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+    auto_increment:
+    name: used
+    cast_type: *3
+    sql_type_metadata: *4
+    'null': false
+    default: 0
+    default_function:
+    collation:
+    comment:
+  - *18
   ar_internal_metadata:
   - *5
-  - *18
+  - *19
   - *9
   - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
     auto_increment:
@@ -316,7 +351,7 @@ columns:
     collation:
     comment:
   assignees_filters:
-  - &20 !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+  - &21 !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
     auto_increment:
     name: assignee_id
     cast_type: *3
@@ -326,7 +361,7 @@ columns:
     default_function:
     collation:
     comment:
-  - &19 !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+  - &20 !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
     auto_increment:
     name: filter_id
     cast_type: *3
@@ -337,7 +372,7 @@ columns:
     collation:
     comment:
   assigners_filters:
-  - &21 !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+  - &22 !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
     auto_increment:
     name: assigner_id
     cast_type: *3
@@ -347,11 +382,11 @@ columns:
     default_function:
     collation:
     comment:
-  - *19
-  assignments:
   - *20
+  assignments:
   - *21
-  - &22 !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+  - *22
+  - &23 !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
     auto_increment:
     name: card_id
     cast_type: *3
@@ -365,7 +400,7 @@ columns:
   - *6
   - *9
   card_activity_spikes:
-  - *22
+  - *23
   - *5
   - *6
   - *9
@@ -394,14 +429,14 @@ columns:
     comment:
   - *9
   card_goldnesses:
-  - *22
+  - *23
   - *5
   - *6
   - *9
   cards:
-  - *23
+  - *24
   - *5
-  - &24 !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
+  - &25 !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
     auto_increment:
     name: creator_id
     cast_type: *3
@@ -483,7 +518,7 @@ columns:
     default_function:
     collation:
     comment:
-  - *19
+  - *20
   closure_reasons:
   - *5
   - *6
@@ -499,7 +534,7 @@ columns:
     comment:
   - *9
   closures:
-  - *22
+  - *23
   - *5
   - *6
   - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
@@ -524,7 +559,7 @@ columns:
     collation:
     comment:
   collection_publications:
-  - *23
+  - *24
   - *5
   - *6
   - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
@@ -558,7 +593,7 @@ columns:
     collation:
     comment:
   - *5
-  - *24
+  - *25
   - *6
   - *10
   - *9
@@ -573,12 +608,12 @@ columns:
     collation:
     comment:
   collections_filters:
-  - *23
-  - *19
-  comments:
-  - *22
-  - *5
   - *24
+  - *20
+  comments:
+  - *23
+  - *5
+  - *25
   - *6
   - *9
   conversation_messages:
@@ -699,10 +734,10 @@ columns:
     collation:
     comment:
   - *9
-  - *25
+  - *18
   creators_filters:
-  - *24
-  - *19
+  - *25
+  - *20
   entropy_configurations:
   - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
     auto_increment:
@@ -760,7 +795,7 @@ columns:
     comment:
   - *5
   - *6
-  - *18
+  - *19
   - *9
   events:
   - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
@@ -773,9 +808,9 @@ columns:
     default_function:
     collation:
     comment:
-  - *23
-  - *5
   - *24
+  - *5
+  - *25
   - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
     auto_increment:
     name: eventable_id
@@ -818,7 +853,7 @@ columns:
   - *9
   filters:
   - *5
-  - *24
+  - *25
   - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
     auto_increment:
     name: fields
@@ -842,7 +877,7 @@ columns:
     comment:
   - *9
   filters_stages:
-  - *19
+  - *20
   - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
     auto_increment:
     name: stage_id
@@ -854,7 +889,7 @@ columns:
     collation:
     comment:
   filters_tags:
-  - *19
+  - *20
   - &34 !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
     auto_increment:
     name: tag_id
@@ -935,13 +970,13 @@ columns:
   - *28
   - *29
   - *9
-  - *25
+  - *18
   pins:
-  - *22
+  - *23
   - *5
   - *6
   - *9
-  - *25
+  - *18
   push_subscriptions:
   - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
     auto_increment:
@@ -986,7 +1021,7 @@ columns:
     default_function:
     collation:
     comment:
-  - *25
+  - *18
   reactions:
   - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
     auto_increment:
@@ -1103,7 +1138,7 @@ columns:
     collation:
     comment:
   - *9
-  - *25
+  - *18
   search_results:
   - *5
   - *6
@@ -1123,9 +1158,9 @@ columns:
     comment:
   - *9
   - *30
-  - *25
+  - *18
   steps:
-  - *22
+  - *23
   - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
     auto_increment:
     name: completed
@@ -1141,7 +1176,7 @@ columns:
   - *6
   - *9
   taggings:
-  - *22
+  - *23
   - *5
   - *6
   - *34
@@ -1207,11 +1242,11 @@ columns:
     comment:
   - *9
   watches:
-  - *22
+  - *23
   - *5
   - *6
   - *9
-  - *25
+  - *18
   - !ruby/object:ActiveRecord::ConnectionAdapters::SQLite3::Column
     auto_increment:
     name: watching
@@ -1259,6 +1294,7 @@ primary_keys:
   active_storage_attachments: id
   active_storage_blobs: id
   active_storage_variant_records: id
+  ai_quotas: id
   ar_internal_metadata: key
   assignees_filters:
   assigners_filters:
@@ -1307,6 +1343,7 @@ data_sources:
   active_storage_attachments: true
   active_storage_blobs: true
   active_storage_variant_records: true
+  ai_quotas: true
   ar_internal_metadata: true
   assignees_filters: true
   assigners_filters: true
@@ -1538,6 +1575,39 @@ indexes:
     nulls_not_distinct:
     comment:
     valid: true
+  ai_quotas:
+  - !ruby/object:ActiveRecord::ConnectionAdapters::IndexDefinition
+    table: ai_quotas
+    name: index_ai_quotas_on_reset_at
+    unique: false
+    columns:
+    - reset_at
+    lengths: {}
+    orders: {}
+    opclasses: {}
+    where:
+    type:
+    using:
+    include:
+    nulls_not_distinct:
+    comment:
+    valid: true
+  - !ruby/object:ActiveRecord::ConnectionAdapters::IndexDefinition
+    table: ai_quotas
+    name: index_ai_quotas_on_user_id
+    unique: false
+    columns:
+    - user_id
+    lengths: {}
+    orders: {}
+    opclasses: {}
+    where:
+    type:
+    using:
+    include:
+    nulls_not_distinct:
+    comment:
+    valid: true
   ar_internal_metadata: []
   assignees_filters:
   - !ruby/object:ActiveRecord::ConnectionAdapters::IndexDefinition
diff --git a/test/fixtures/ai/quotas.yml b/test/fixtures/ai/quotas.yml
new file mode 100644
index 000000000..66657f117
--- /dev/null
+++ b/test/fixtures/ai/quotas.yml
@@ -0,0 +1,11 @@
+kevin:
+  user: kevin
+  limit: 100_00_000_000
+  used: 1053
+  reset_at: <%= 7.days.from_now %>
+
+david:
+  user: david
+  limit: 20_00_000_000
+  used: 0
+  reset_at: <%= 3.days.from_now %>
diff --git a/test/models/ai/list_cards_tool_test.rb b/test/models/ai/list_cards_tool_test.rb
index dad13fb13..6cf9e5f54 100644
--- a/test/models/ai/list_cards_tool_test.rb
+++ b/test/models/ai/list_cards_tool_test.rb
@@ -33,15 +33,19 @@ class Ai::ListCardsToolTest < ActiveSupport::TestCase
   end
 
   test "execute when filtering by ids" do
+    creating_card = collections(:writebook).cards.create! creator: users(:kevin), status: :creating
+    drafted_card = collections(:writebook).cards.create! creator: users(:kevin), status: :drafted
+
     cards = cards(:shipping, :logo)
-    card_ids = cards.pluck(:id)
+    visible_card_ids = cards.pluck(:id)
+    card_ids = visible_card_ids + [ creating_card.id, drafted_card.id ]
 
     response = @tool.execute(ids: card_ids.join(", "))
     page = parse_paginated_response(response)
     record_ids = page[:records].map { |card| card["id"].to_i }
 
-    assert_equal 2, record_ids.count
-    assert_equal card_ids.sort, record_ids.sort
+    assert_equal visible_card_ids.count, record_ids.count
+    assert_equal visible_card_ids.sort, record_ids.sort
   end
 
   test "execute when filtering by collection_ids" do
diff --git a/test/models/ai/quota/money_test.rb b/test/models/ai/quota/money_test.rb
new file mode 100644
index 000000000..01498a30c
--- /dev/null
+++ b/test/models/ai/quota/money_test.rb
@@ -0,0 +1,40 @@
+require "test_helper"
+
+class Ai::Quota::MoneyTest < ActiveSupport::TestCase
+  test "wrapping" do
+    money = Ai::Quota::Money.wrap("$5.42")
+    assert_equal 5_42_000_000, money.in_microcents, "Strings with numbers are treated as dollars"
+
+    assert_raises TypeError do
+      Ai::Quota::Money.wrap("foobar")
+    end
+
+    money = Ai::Quota::Money.wrap(5.42)
+    assert_equal 5_42_000_000, money.in_microcents, "Decimals are treated as dollars"
+
+    money = Ai::Quota::Money.wrap(5)
+    assert_equal 5, money.in_microcents, "Integers are treated as microcents"
+
+    money1 = Ai::Quota::Money.wrap("$5")
+    money2 = Ai::Quota::Money.wrap(money1)
+    assert_equal money1, money2, "Money can wrap itself"
+
+    assert_raises ArgumentError do
+      Ai::Quota::Money.wrap(nil)
+    end
+  end
+
+  test "conversions" do
+    money = Ai::Quota::Money.wrap("$0")
+    assert_equal 0.0, money.in_dollars
+    assert_equal 0, money.in_microcents
+
+    money = Ai::Quota::Money.wrap("$1")
+    assert_equal 1, money.in_dollars
+    assert_equal 1_00_000_000, money.in_microcents
+
+    money = Ai::Quota::Money.wrap("$5.42")
+    assert_equal 5.42, money.in_dollars
+    assert_equal 5_42_000_000, money.in_microcents
+  end
+end
diff --git a/test/models/ai/quota_test.rb b/test/models/ai/quota_test.rb
new file mode 100644
index 000000000..b37e60ee9
--- /dev/null
+++ b/test/models/ai/quota_test.rb
@@ -0,0 +1,63 @@
+require "test_helper"
+
+class Ai::QuotaTest < ActiveSupport::TestCase
+  setup do
+    @quota = Ai::Quota.new(user: users(:jz), limit: Ai::Quota::Money.wrap("$100").in_microcents)
+  end
+
+  test "create" do
+    assert @quota.save
+
+    assert_in_delta 7.days.from_now, @quota.reset_at, 1.minute
+    assert_equal 0, @quota.used
+    assert_equal Ai::Quota::Money.wrap("$100").in_microcents, @quota.limit
+  end
+
+  test "increment usage" do
+    @quota.save
+
+    @quota.spend("$100")
+    assert_equal Ai::Quota::Money.wrap("$100").in_microcents, @quota.used
+    @quota.spend("$500")
+    assert_equal Ai::Quota::Money.wrap("$600").in_microcents, @quota.used
+    @quota.spend("$1000")
+    assert_equal Ai::Quota::Money.wrap("$1600").in_microcents, @quota.used
+    @quota.spend("$5000")
+    assert_equal Ai::Quota::Money.wrap("$6600").in_microcents, @quota.used
+    @quota.spend("$10000")
+    assert_equal Ai::Quota::Money.wrap("$16600").in_microcents, @quota.used
+
+    @quota.used = 0
+
+    @quota.spend("$10")
+    assert_equal Ai::Quota::Money.wrap("$10").in_microcents, @quota.used
+    assert_in_delta 7.days.from_now, @quota.reset_at, 1.minute
+
+    travel 2.days
+
+    @quota.spend("$5")
+    assert_equal Ai::Quota::Money.wrap("$15").in_microcents, @quota.used
+    assert_in_delta 5.days.from_now, @quota.reset_at, 1.minute
+
+    travel 8.days
+
+    @quota.spend("$5")
+    assert_equal Ai::Quota::Money.wrap("$5").in_microcents, @quota.used
+    assert_in_delta 7.days.from_now, @quota.reset_at, 1.minute
+  end
+
+  test "limit checks" do
+    @quota.save
+
+    @quota.used = 0
+    @quota.ensure_not_depleted
+
+    @quota.used = Ai::Quota::Money.wrap("$300").in_microcents
+    assert_raises Ai::Quota::UsageExceedsQuotaError do
+      @quota.ensure_not_depleted
+    end
+
+    travel 10.days
+    @quota.ensure_not_depleted
+  end
+end
diff --git a/test/models/conversation/response_generator/response_test.rb b/test/models/conversation/response_generator/response_test.rb
index c33798b63..40b4c287b 100644
--- a/test/models/conversation/response_generator/response_test.rb
+++ b/test/models/conversation/response_generator/response_test.rb
@@ -13,23 +13,20 @@ class Conversation::Message::ResponseGenerator::ResponseTest < ActiveSupport::Te
     # and 60 USD per million output tokens
     # That's 0.00003 cents per input token and 0.00006 cents
     # per output token
-    # Which is 3 micro-cents per input token and 6 micro-cents
+    # Which is 3000 micro-cents per input token and 6000 micro-cents
     # per output token
-    assert_equal "3.0".to_d, response.input_token_price_microcents
-    assert_equal "6.0".to_d, response.output_token_price_microcents
+    assert_equal "3000.0".to_d, response.input_token_price_microcents
+    assert_equal "6000.0".to_d, response.output_token_price_microcents
 
     # We've got 198 input tokens, so that's
-    # 193 * 3 = 594
-    assert_equal 594, response.input_cost_microcents
+    # 198 * 3000 = 594000
+    assert_equal 594000, response.input_cost_microcents
 
     # We've got 2 output tokens, so that's
-    # 2 * 6 = 12
-    assert_equal 12, response.output_cost_microcents
+    # 2 * 6000 = 12
+    assert_equal 12000, response.output_cost_microcents
 
-    # So the total is 594 + 12 micro-cents
-    assert_equal 606, response.cost_microcents
-
-    # If we convert that to a decimal value we get 0.00606 cents
-    assert_equal "0.00606".to_d, response.cost
+    # So the total is 594000 + 12000 micro-cents
+    assert_equal 606000, response.cost_microcents
   end
 end
diff --git a/test/models/conversation_test.rb b/test/models/conversation_test.rb
index 5691e7363..2f1e108d7 100644
--- a/test/models/conversation_test.rb
+++ b/test/models/conversation_test.rb
@@ -61,21 +61,25 @@ class ConversationTest < ActiveSupport::TestCase
     assert conversation.ready?, "The conversation should switch back to ready after a response is made"
   end
 
-  test "clearing conversation messages" do
+  test "cost limits" do
     conversation = conversations(:kevin)
 
-    assert conversation.messages.any?, "The conversation should have messages before clearing"
+    conversation.ask("Where does the planning office keep demolition notices?")
+    conversation.respond(
+      "In a locked filing cabinet in a disused lavatory",
+      cost_microcents: Ai::Quota::Money.wrap("$3").in_microcents
+    )
 
-    original_updated_at = conversation.updated_at
-    conversation.clear
-    assert conversation.updated_at > original_updated_at, "The conversation's updated_at timestamp should change after clearing messages"
+    conversation.ask("What's the meaning of life?")
+    conversation.respond("42", cost_microcents: Ai::Quota::Money.wrap("$120").in_microcents)
 
-    assert conversation.messages.empty?, "All messages should be deleted when clearing the conversation"
-  end
+    assert_raises Ai::Quota::UsageExceedsQuotaError do
+      conversation.ask("Should you leave a house without a towel?")
+    end
 
-  test "cost calculation" do
-    conversation = conversations(:kevin)
+    travel 1.month
 
-    assert_equal "0.01053".to_d, conversation.cost
+    conversation.ask("Should you leave a house without a towel?")
+    conversation.respond("Never", cost_microcents: Ai::Quota::Money.wrap("$0.01").in_microcents)
   end
 end
diff --git a/test/vcr_cassettes/conversation/message_test-test_response_generation.yml b/test/vcr_cassettes/conversation/message_test-test_response_generation.yml
index 6a87664c2..813b7cf4b 100644
--- a/test/vcr_cassettes/conversation/message_test-test_response_generation.yml
+++ b/test/vcr_cassettes/conversation/message_test-test_response_generation.yml
@@ -1245,4 +1245,317 @@ http_interactions:
         c2VydmljZV90aWVyIjogImRlZmF1bHQiLAogICJzeXN0ZW1fZmluZ2VycHJp
         bnQiOiAiZnBfM2Y1OGQxMTJmNyIKfQo=
   recorded_at: Mon, 18 Aug 2025 14:58:21 GMT
+- request:
+    method: post
+    uri: https://api.openai.com/v1/chat/completions
+    body:
+      encoding: UTF-8
+      base64_string: |
+        eyJtb2RlbCI6ImdwdC00LjEtbWluaSIsIm1lc3NhZ2VzIjpbeyJyb2xlIjoi
+        ZGV2ZWxvcGVyIiwiY29udGVudCI6IllvdSBhcmUgKipGaXp6eSoqLCBhIGhl
+        bHBmdWwgYXNzaXN0YW50IGZvciB0aGUgRml6enkgYXBwIGJ5IDM3c2lnbmFs
+        cy5cbkZpenp5IGlzIGEgYnVnIHRyYWNrZXIgLyB0YXNrIG1hbmFnZXIgZm9y
+        IHRlYW1zLCBhbmQgeW91IGhlbHAgdXNlcnMgbWFuYWdlIHRoZWlyIGNhcmRz
+        LCBjb2xsZWN0aW9ucywgYW5kIHRlYW0gYWN0aXZpdHkuXG5cbiMjIyBZb3Vy
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+    headers:
+      User-Agent:
+      - Faraday v2.13.4
+      Authorization:
+      - Bearer <OPEN_API_KEY>
+      Content-Type:
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