Merge branch 'develop' into fix/agent-bot-assignment-webhook

app/javascript/dashboard/api/captain/customTools.js

@@ -31,6 +31,12 @@ class CaptainCustomTools extends ApiClient {
   delete(id) {
     return axios.delete(`${this.url}/${id}`);
   }
+
+  test(data = {}) {
+    return axios.post(`${this.url}/test`, {
+      custom_tool: data,
+    });
+  }
 }
 
 export default new CaptainCustomTools();

app/javascript/dashboard/components-next/captain/pageComponents/customTool/CustomToolCard.vue

@@ -101,12 +101,9 @@ const authTypeLabel = computed(() => {
         </Policy>
       </div>
     </div>
-    <div class="flex items-center justify-between w-full gap-4">
-      <div class="flex items-center gap-3 flex-1">
-        <span
-          v-if="description"
-          class="text-sm truncate text-n-slate-11 flex-1"
-        >
+    <div class="flex items-center justify-between w-full gap-4 min-w-0">
+      <div class="flex items-center gap-3 flex-1 min-w-0">
+        <span v-if="description" class="text-sm truncate text-n-slate-11">
           {{ description }}
         </span>
         <span

app/javascript/dashboard/components-next/captain/pageComponents/customTool/CustomToolForm.vue

@@ -1,9 +1,10 @@
 <script setup>
-import { reactive, computed, useTemplateRef, watch } from 'vue';
+import { reactive, computed, ref, useTemplateRef, watch } from 'vue';
 import { useI18n } from 'vue-i18n';
 import { useVuelidate } from '@vuelidate/core';
-import { required } from '@vuelidate/validators';
+import { required, maxLength } from '@vuelidate/validators';
 import { useMapGetter } from 'dashboard/composables/store';
+import CustomToolsAPI from 'dashboard/api/captain/customTools';
 
 import Input from 'dashboard/components-next/input/Input.vue';
 import TextArea from 'dashboard/components-next/textarea/TextArea.vue';
@@ -72,8 +73,12 @@ const DEFAULT_PARAM = {
   required: false,
 };
 
+// OpenAI enforces a 64-char limit on function names. The backend slug is
+// "custom_" (7 chars) + parameterized title, so cap the title conservatively.
+const MAX_TOOL_NAME_LENGTH = 55;
+
 const validationRules = {
-  title: { required },
+  title: { required, maxLength: maxLength(MAX_TOOL_NAME_LENGTH) },
   endpoint_url: { required },
   http_method: { required },
   auth_type: { required },
@@ -103,9 +108,15 @@ const isLoading = computed(() =>
 );
 
 const getErrorMessage = (field, errorKey) => {
-  return v$.value[field].$error
-    ? t(`CAPTAIN.CUSTOM_TOOLS.FORM.${errorKey}.ERROR`)
-    : '';
+  if (!v$.value[field].$error) return '';
+
+  const failedRule = v$.value[field].$errors[0]?.$validator;
+  if (failedRule === 'maxLength') {
+    return t(`CAPTAIN.CUSTOM_TOOLS.FORM.${errorKey}.MAX_LENGTH_ERROR`, {
+      max: MAX_TOOL_NAME_LENGTH,
+    });
+  }
+  return t(`CAPTAIN.CUSTOM_TOOLS.FORM.${errorKey}.ERROR`);
 };
 
 const formErrors = computed(() => ({
@@ -140,6 +151,30 @@ const handleSubmit = async () => {
 
   emit('submit', state);
 };
+
+const isTesting = ref(false);
+const testResult = ref(null);
+const isTestDisabled = computed(
+  () => state.endpoint_url.includes('{{') || !!state.request_template
+);
+
+const handleTest = async () => {
+  if (!state.endpoint_url) return;
+
+  isTesting.value = true;
+  testResult.value = null;
+  try {
+    const { data } = await CustomToolsAPI.test(state);
+    const isOk = data.status >= 200 && data.status < 300;
+    testResult.value = { success: isOk, status: data.status };
+  } catch (e) {
+    const message =
+      e.response?.data?.error || t('CAPTAIN.CUSTOM_TOOLS.TEST.ERROR');
+    testResult.value = { success: false, message };
+  } finally {
+    isTesting.value = false;
+  }
+};
 </script>
 
 <template>
@@ -248,6 +283,45 @@ const handleSubmit = async () => {
       class="[&_textarea]:font-mono"
     />
 
+    <div class="flex flex-col gap-2">
+      <Button
+        type="button"
+        variant="faded"
+        color="slate"
+        icon="i-lucide-play"
+        :label="t('CAPTAIN.CUSTOM_TOOLS.TEST.BUTTON')"
+        :is-loading="isTesting"
+        :disabled="isTesting || !state.endpoint_url || isTestDisabled"
+        @click="handleTest"
+      />
+      <p v-if="isTestDisabled" class="text-xs text-n-slate-11">
+        {{ t('CAPTAIN.CUSTOM_TOOLS.TEST.DISABLED_HINT') }}
+      </p>
+      <div
+        v-if="testResult"
+        class="flex items-center gap-2 px-3 py-2 text-xs rounded-lg"
+        :class="
+          testResult.success
+            ? 'bg-n-teal-2 text-n-teal-11'
+            : 'bg-n-ruby-2 text-n-ruby-11'
+        "
+      >
+        <span
+          :class="
+            testResult.success ? 'i-lucide-check-circle' : 'i-lucide-x-circle'
+          "
+          class="size-3.5 shrink-0"
+        />
+        {{
+          testResult.status
+            ? t('CAPTAIN.CUSTOM_TOOLS.TEST.SUCCESS', {
+                status: testResult.status,
+              })
+            : testResult.message
+        }}
+      </div>
+    </div>
+
     <div class="flex gap-3 justify-between items-center w-full">
       <Button
         type="button"

app/javascript/dashboard/components-next/captain/pageComponents/emptyStates/CustomToolsPageEmptyState.vue

@@ -1,8 +1,11 @@
 <script setup>
+import { useAccount } from 'dashboard/composables/useAccount';
 import EmptyStateLayout from 'dashboard/components-next/EmptyStateLayout.vue';
+import FeatureSpotlight from 'dashboard/components-next/feature-spotlight/FeatureSpotlight.vue';
 import Button from 'dashboard/components-next/button/Button.vue';
 
 const emit = defineEmits(['click']);
+const { isOnChatwootCloud } = useAccount();
 
 const onClick = () => {
   emit('click');
@@ -10,6 +13,15 @@ const onClick = () => {
 </script>
 
 <template>
+  <FeatureSpotlight
+    :title="$t('CAPTAIN.CUSTOM_TOOLS.EMPTY_STATE.FEATURE_SPOTLIGHT.TITLE')"
+    :note="$t('CAPTAIN.CUSTOM_TOOLS.EMPTY_STATE.FEATURE_SPOTLIGHT.NOTE')"
+    fallback-thumbnail="/assets/images/dashboard/captain/assistant-light.svg"
+    fallback-thumbnail-dark="/assets/images/dashboard/captain/assistant-dark.svg"
+    learn-more-url="https://chwt.app/hc/captain-tools"
+    class="mb-8"
+    :hide-actions="!isOnChatwootCloud"
+  />
   <EmptyStateLayout
     :title="$t('CAPTAIN.CUSTOM_TOOLS.EMPTY_STATE.TITLE')"
     :subtitle="$t('CAPTAIN.CUSTOM_TOOLS.EMPTY_STATE.SUBTITLE')"

app/javascript/dashboard/components-next/sidebar/Sidebar.vue

@@ -63,6 +63,16 @@ const hasAdvancedAssignment = computed(() => {
   );
 });
 
+const hasCustomTools = computed(() => {
+  return (
+    isFeatureEnabledonAccount.value(
+      accountId.value,
+      FEATURE_FLAGS.CAPTAIN_CUSTOM_TOOLS
+    ) ||
+    isFeatureEnabledonAccount.value(accountId.value, FEATURE_FLAGS.CAPTAIN_V2)
+  );
+});
+
 const toggleShortcutModalFn = show => {
   if (show) {
     emit('openKeyShortcutModal');
@@ -364,14 +374,18 @@ const menuItems = computed(() => {
             navigationPath: 'captain_assistants_inboxes_index',
           }),
         },
-        {
-          name: 'Tools',
-          label: t('SIDEBAR.CAPTAIN_TOOLS'),
-          activeOn: ['captain_tools_index'],
-          to: accountScopedRoute('captain_assistants_index', {
-            navigationPath: 'captain_tools_index',
-          }),
-        },
+        ...(hasCustomTools.value
+          ? [
+              {
+                name: 'Tools',
+                label: t('SIDEBAR.CAPTAIN_TOOLS'),
+                activeOn: ['captain_tools_index'],
+                to: accountScopedRoute('captain_assistants_index', {
+                  navigationPath: 'captain_tools_index',
+                }),
+              },
+            ]
+          : []),
         {
           name: 'Settings',
           label: t('SIDEBAR.CAPTAIN_SETTINGS'),

app/javascript/dashboard/featureFlags.js

@@ -37,6 +37,7 @@ export const FEATURE_FLAGS = {
   CHANNEL_INSTAGRAM: 'channel_instagram',
   CHANNEL_TIKTOK: 'channel_tiktok',
   CONTACT_CHATWOOT_SUPPORT_TEAM: 'contact_chatwoot_support_team',
+  CAPTAIN_CUSTOM_TOOLS: 'custom_tools',
   CAPTAIN_V2: 'captain_integration_v2',
   CAPTAIN_TASKS: 'captain_tasks',
   SAML: 'saml',

app/javascript/dashboard/i18n/locale/en/integrations.json

@@ -807,6 +807,7 @@
     "CUSTOM_TOOLS": {
       "HEADER": "Tools",
       "ADD_NEW": "Create a new tool",
+      "SOFT_LIMIT_WARNING": "Having more than 10 tools may reduce the assistant's reliability in selecting the right tool. Consider removing unused tools for better results.",
       "EMPTY_STATE": {
         "TITLE": "No custom tools available",
         "SUBTITLE": "Create custom tools to connect your assistant with external APIs and services, enabling it to fetch data and perform actions on your behalf.",
@@ -837,11 +838,18 @@
         "SUCCESS_MESSAGE": "Custom tool deleted successfully",
         "ERROR_MESSAGE": "Failed to delete custom tool"
       },
+      "TEST": {
+        "BUTTON": "Test connection",
+        "SUCCESS": "Endpoint returned HTTP {status}",
+        "ERROR": "Connection failed",
+        "DISABLED_HINT": "Testing is only available for endpoints without templates or request bodies."
+      },
       "FORM": {
         "TITLE": {
           "LABEL": "Tool Name",
           "PLACEHOLDER": "Order Lookup",
-          "ERROR": "Tool name is required"
+          "ERROR": "Tool name is required",
+          "MAX_LENGTH_ERROR": "Tool name must be {max} characters or fewer"
         },
         "DESCRIPTION": {
           "LABEL": "Description",

app/javascript/dashboard/routes/dashboard/captain/captain.routes.js

@@ -46,7 +46,7 @@ const assistantRoutes = [
     path: frontendURL('accounts/:accountId/captain/:assistantId/tools'),
     component: CustomToolsIndex,
     name: 'captain_tools_index',
-    meta: metaV2,
+    meta,
   },
   {
     path: frontendURL('accounts/:accountId/captain/:assistantId/scenarios'),

app/javascript/dashboard/routes/dashboard/captain/tools/Index.vue

@@ -2,21 +2,29 @@
 import { computed, onMounted, ref, nextTick } from 'vue';
 import { useMapGetter, useStore } from 'dashboard/composables/store';
 import { FEATURE_FLAGS } from 'dashboard/featureFlags';
+import { usePolicy } from 'dashboard/composables/usePolicy';
 
 import PageLayout from 'dashboard/components-next/captain/PageLayout.vue';
-import CaptainPaywall from 'dashboard/components-next/captain/pageComponents/Paywall.vue';
 import CustomToolsPageEmptyState from 'dashboard/components-next/captain/pageComponents/emptyStates/CustomToolsPageEmptyState.vue';
 import CreateCustomToolDialog from 'dashboard/components-next/captain/pageComponents/customTool/CreateCustomToolDialog.vue';
 import CustomToolCard from 'dashboard/components-next/captain/pageComponents/customTool/CustomToolCard.vue';
 import DeleteDialog from 'dashboard/components-next/captain/pageComponents/DeleteDialog.vue';
 
 const store = useStore();
+const { isFeatureFlagEnabled } = usePolicy();
+
+const SOFT_LIMIT = 10;
+const isV2 = computed(() => isFeatureFlagEnabled(FEATURE_FLAGS.CAPTAIN_V2));
 
 const uiFlags = useMapGetter('captainCustomTools/getUIFlags');
 const customTools = useMapGetter('captainCustomTools/getRecords');
 const isFetching = computed(() => uiFlags.value.fetchingList);
 const customToolsMeta = useMapGetter('captainCustomTools/getMeta');
 
+const showSoftLimitWarning = computed(
+  () => !isV2.value && customToolsMeta.value.totalCount > SOFT_LIMIT
+);
+
 const createDialogRef = ref(null);
 const deleteDialogRef = ref(null);
 const selectedTool = ref(null);
@@ -86,21 +94,23 @@ onMounted(() => {
     :show-pagination-footer="!isFetching && !!customTools.length"
     :is-fetching="isFetching"
     :is-empty="!customTools.length"
-    :feature-flag="FEATURE_FLAGS.CAPTAIN_V2"
     :show-know-more="false"
     @update:current-page="onPageChange"
     @click="openCreateDialog"
   >
-    <template #paywall>
-      <CaptainPaywall />
-    </template>
-
     <template #emptyState>
       <CustomToolsPageEmptyState @click="openCreateDialog" />
     </template>
 
     <template #body>
       <div class="flex flex-col gap-4">
+        <div
+          v-if="showSoftLimitWarning"
+          class="flex items-center gap-2 px-4 py-3 text-sm rounded-lg bg-n-amber-2 text-n-amber-11"
+        >
+          <span class="i-lucide-triangle-alert size-4 shrink-0" />
+          {{ $t('CAPTAIN.CUSTOM_TOOLS.SOFT_LIMIT_WARNING') }}
+        </div>
         <CustomToolCard
           v-for="tool in customTools"
           :id="tool.id"

app/models/attachment.rb

@@ -37,6 +37,7 @@ class Attachment < ApplicationRecord
   belongs_to :account
   belongs_to :message
   has_one_attached :file
+  before_save :set_extension
   validate :acceptable_file
   validates :external_url, length: { maximum: Limits::URL_LENGTH_LIMIT }
   enum file_type: { :image => 0, :audio => 1, :video => 2, :file => 3, :location => 4, :fallback => 5, :share => 6, :story_mention => 7,
@@ -111,6 +112,7 @@ class Attachment < ApplicationRecord
   def file_metadata
     metadata = {
       extension: extension,
+      content_type: file.content_type,
       data_url: file_url,
       thumb_url: thumb_url,
       file_size: file.byte_size,
@@ -154,6 +156,13 @@ class Attachment < ApplicationRecord
     }
   end
 
+  def set_extension
+    return unless file.attached?
+    return if extension.present?
+
+    self.extension = File.extname(file.filename.to_s).delete_prefix('.').presence
+  end
+
   def should_validate_file?
     return unless file.attached?
     # we are only limiting attachment types in case of website widget

config/locales/en.yml

@@ -387,6 +387,7 @@ en:
       page_processing_error: 'Error processing pages %{start}-%{end}: %{error}'
     custom_tool:
       slug_generation_failed: 'Unable to generate unique slug after 5 attempts'
+      limit_exceeded: 'You can create a maximum of %{limit} custom tools per account'
   public_portal:
     search:
       search_placeholder: Search for article by title or body...

config/routes.rb

@@ -72,7 +72,9 @@ Rails.application.routes.draw do
             resources :copilot_threads, only: [:index, :create] do
               resources :copilot_messages, only: [:index, :create]
             end
-            resources :custom_tools
+            resources :custom_tools do
+              post :test, on: :collection
+            end
             resources :documents, only: [:index, :show, :create, :destroy]
             resource :tasks, only: [], controller: 'tasks' do
               post :rewrite

enterprise/app/controllers/api/v1/accounts/captain/custom_tools_controller.rb

@@ -1,16 +1,19 @@
 class Api::V1::Accounts::Captain::CustomToolsController < Api::V1::Accounts::BaseController
   before_action :current_account
+  before_action :ensure_custom_tools_enabled
   before_action -> { check_authorization(Captain::CustomTool) }
   before_action :set_custom_tool, only: [:show, :update, :destroy]
 
   def index
-    @custom_tools = account_custom_tools.enabled
+    @custom_tools = account_custom_tools
   end
 
   def show; end
 
   def create
     @custom_tool = account_custom_tools.create!(custom_tool_params)
+  rescue Captain::CustomTool::LimitExceededError => e
+    render_could_not_create_error(e.message)
   end
 
   def update
@@ -22,8 +25,22 @@ class Api::V1::Accounts::Captain::CustomToolsController < Api::V1::Accounts::Bas
     head :no_content
   end
 
+  def test
+    tool = account_custom_tools.new(custom_tool_params)
+    result = execute_test_request(tool)
+    render json: { status: result.code.to_i, body: result.body.to_s.truncate(500) }
+  rescue StandardError => e
+    render json: { error: e.message }, status: :unprocessable_content
+  end
+
   private
 
+  def ensure_custom_tools_enabled
+    return if Current.account.feature_enabled?('custom_tools') || Current.account.feature_enabled?('captain_integration_v2')
+
+    render json: { error: 'Custom tools are not enabled for this account' }, status: :forbidden
+  end
+
   def set_custom_tool
     @custom_tool = account_custom_tools.find(params[:id])
   end
@@ -32,6 +49,11 @@ class Api::V1::Accounts::Captain::CustomToolsController < Api::V1::Accounts::Bas
     @account_custom_tools ||= Current.account.captain_custom_tools
   end
 
+  def execute_test_request(tool)
+    http_tool = Captain::Tools::HttpTool.new(nil, tool)
+    http_tool.send(:execute_http_request, tool.endpoint_url, nil, nil)
+  end
+
   def custom_tool_params
     params.require(:custom_tool).permit(
       :title,

enterprise/app/models/captain/custom_tool.rb

@@ -24,6 +24,10 @@
 #  index_captain_custom_tools_on_account_id_and_slug  (account_id,slug) UNIQUE
 #
 class Captain::CustomTool < ApplicationRecord
+  class LimitExceededError < StandardError; end
+
+  MAX_PER_ACCOUNT = 15
+
   include Concerns::Toolable
   include Concerns::SafeEndpointValidatable
 
@@ -31,6 +35,10 @@ class Captain::CustomTool < ApplicationRecord
 
   NAME_PREFIX = 'custom'.freeze
   NAME_SEPARATOR = '_'.freeze
+  # OpenAI enforces a 64-char limit on function names. The slug is used
+  # verbatim as the tool name in LLM requests, so it must fit within this limit.
+  MAX_SLUG_LENGTH = 64
+  COLLISION_SUFFIX_LENGTH = 7 # "_" + 6 random alphanumeric chars
   PARAM_SCHEMA_VALIDATION = {
     'type': 'array',
     'items': {
@@ -52,8 +60,9 @@ class Captain::CustomTool < ApplicationRecord
   enum :auth_type, %w[none bearer basic api_key].index_by(&:itself), default: :none, validate: true, prefix: :auth
 
   before_validation :generate_slug
+  before_create :ensure_within_limit
 
-  validates :slug, presence: true, uniqueness: { scope: :account_id }
+  validates :slug, presence: true, uniqueness: { scope: :account_id }, length: { maximum: MAX_SLUG_LENGTH }
   validates :title, presence: true
   validates :endpoint_url, presence: true
   validates_with JsonSchemaValidator,
@@ -73,21 +82,29 @@ class Captain::CustomTool < ApplicationRecord
 
   private
 
+  def ensure_within_limit
+    # Lock the account row to serialize concurrent creates and prevent exceeding the cap
+    Account.lock.find(account_id)
+    return if account.captain_custom_tools.count < MAX_PER_ACCOUNT
+
+    raise LimitExceededError, I18n.t('captain.custom_tool.limit_exceeded', limit: MAX_PER_ACCOUNT)
+  end
+
   def generate_slug
     return if slug.present?
     return if title.blank?
 
-    paramterized_title = title.parameterize(separator: NAME_SEPARATOR)
-
-    base_slug = "#{NAME_PREFIX}#{NAME_SEPARATOR}#{paramterized_title}"
+    parameterized_title = title.parameterize(separator: NAME_SEPARATOR)
+    base_slug = "#{NAME_PREFIX}#{NAME_SEPARATOR}#{parameterized_title}".truncate(MAX_SLUG_LENGTH, omission: '')
     self.slug = find_unique_slug(base_slug)
   end
 
   def find_unique_slug(base_slug)
     return base_slug unless slug_exists?(base_slug)
 
+    truncated = base_slug.truncate(MAX_SLUG_LENGTH - COLLISION_SUFFIX_LENGTH, omission: '')
     5.times do
-      slug_candidate = "#{base_slug}#{NAME_SEPARATOR}#{SecureRandom.alphanumeric(6).downcase}"
+      slug_candidate = "#{truncated}#{NAME_SEPARATOR}#{SecureRandom.alphanumeric(6).downcase}"
       return slug_candidate unless slug_exists?(slug_candidate)
     end
 

enterprise/app/models/concerns/toolable.rb

@@ -1,15 +1,23 @@
 module Concerns::Toolable
   extend ActiveSupport::Concern
 
-  def tool(assistant)
+  # Isolated namespace for user-defined custom tool classes.
+  # Keeps them separate from built-in classes in Captain::Tools (e.g., HttpTool, CustomHttpTool).
+  module CustomTools; end
+
+  def tool(assistant, base_class: Captain::Tools::HttpTool, **)
     custom_tool_record = self
-    # Convert slug to valid Ruby constant name (replace hyphens with underscores, then camelize)
     class_name = custom_tool_record.slug.underscore.camelize
 
     # Always create a fresh class to reflect current metadata
-    tool_class = Class.new(Captain::Tools::HttpTool) do
+    tool_slug = custom_tool_record.slug
+    tool_class = Class.new(base_class) do
       description custom_tool_record.description
 
+      # Override name to use the slug directly, avoiding the namespace prefix
+      # that RubyLLM's default normalization would produce (e.g., "captain--tools--custom_dog_facts").
+      define_method(:name) { tool_slug }
+
       custom_tool_record.param_schema.each do |param_def|
         param param_def['name'].to_sym,
               type: param_def['type'],
@@ -18,17 +26,14 @@ module Concerns::Toolable
       end
     end
 
-    # Register the dynamically created class as a constant in the Captain::Tools namespace.
-    # This is required because RubyLLM's Tool base class derives the tool name from the class name
-    # (via Class#name). Anonymous classes created with Class.new have no name and return empty strings,
-    # which causes "Invalid 'tools[].function.name': empty string" errors from the LLM API.
-    # By setting it as a constant, the class gets a proper name (e.g., "Captain::Tools::CatFactLookup")
-    # which RubyLLM extracts and normalizes to "cat-fact-lookup" for the LLM API.
-    # We refresh the constant on each call to ensure tool metadata changes are reflected.
-    Captain::Tools.send(:remove_const, class_name) if Captain::Tools.const_defined?(class_name, false)
-    Captain::Tools.const_set(class_name, tool_class)
+    # Register as a constant so the class gets a proper name (Class#name).
+    # Anonymous classes return nil for #name, which causes "Invalid 'tools[].function.name':
+    # empty string" errors from the LLM API. We use CustomTools as the namespace to avoid
+    # collisions with real classes in Captain::Tools.
+    CustomTools.send(:remove_const, class_name) if CustomTools.const_defined?(class_name, false)
+    CustomTools.const_set(class_name, tool_class)
 
-    tool_class.new(assistant, self)
+    tool_class.new(assistant, self, **)
   end
 
   def build_request_url(params)

enterprise/app/policies/captain/custom_tool_policy.rb

@@ -11,6 +11,10 @@ class Captain::CustomToolPolicy < ApplicationPolicy
     @account_user.administrator?
   end
 
+  def test?
+    @account_user.administrator?
+  end
+
   def update?
     @account_user.administrator?
   end

enterprise/app/services/captain/llm/assistant_chat_service.rb

@@ -30,7 +30,12 @@ class Captain::Llm::AssistantChatService < Llm::BaseAiService
   private
 
   def build_tools
-    [Captain::Tools::SearchDocumentationService.new(@assistant, user: nil)]
+    tools = [Captain::Tools::SearchDocumentationService.new(@assistant, user: nil)]
+    return tools unless custom_tools_enabled?
+
+    tools + @assistant.account.captain_custom_tools.enabled.map do |ct|
+      ct.tool(@assistant, base_class: Captain::Tools::CustomHttpTool, conversation: @conversation)
+    end
   end
 
   def system_message
@@ -38,11 +43,24 @@ class Captain::Llm::AssistantChatService < Llm::BaseAiService
       role: 'system',
       content: Captain::Llm::SystemPromptsService.assistant_response_generator(
         @assistant.name, @assistant.config['product_name'], @assistant.config,
-        contact: contact_attributes
+        contact: contact_attributes,
+        custom_tools: custom_tools_metadata
       )
     }
   end
 
+  def custom_tools_metadata
+    return [] unless custom_tools_enabled?
+
+    @assistant.account.captain_custom_tools.enabled.map do |ct|
+      { name: ct.slug, description: ct.description }
+    end
+  end
+
+  def custom_tools_enabled?
+    @assistant.account.feature_enabled?('custom_tools')
+  end
+
   def contact_attributes
     return nil unless @conversation&.contact
     return nil unless @assistant&.feature_contact_attributes

enterprise/app/services/captain/llm/system_prompts_service.rb

@@ -152,7 +152,7 @@ class Captain::Llm::SystemPromptsService
     # rubocop:enable Metrics/MethodLength
 
     # rubocop:disable Metrics/MethodLength
-    def assistant_response_generator(assistant_name, product_name, config = {}, contact: nil)
+    def assistant_response_generator(assistant_name, product_name, config = {}, contact: nil, custom_tools: [])
       assistant_citation_guidelines = if config['feature_citation']
                                         <<~CITATION_TEXT
                                           - Always include citations for any information provided, referencing the specific source (document only - skip if it was derived from a conversation).
@@ -187,7 +187,7 @@ class Captain::Llm::SystemPromptsService
         #{assistant_citation_guidelines}
 
         #{build_contact_context(contact)}[Task]
-        Start by introducing yourself. Then, ask the user to share their question. When they answer, call the search_documentation function. Give a helpful response based on the steps written below.
+        Start by introducing yourself. Then, ask the user to share their question. When they answer, use the most appropriate tool to find information. Give a helpful response based on the steps written below.
 
         - Provide the user with the steps required to complete the action one by one.
         - Do not return list numbers in the steps, just the plain text is enough.
@@ -203,6 +203,8 @@ class Captain::Llm::SystemPromptsService
         ```
         - If the answer is not provided in context sections, Respond to the customer and ask whether they want to talk to another support agent . If they ask to Chat with another agent, return `conversation_handoff' as the response in JSON response
         #{'- You MUST provide numbered citations at the appropriate places in the text.' if config['feature_citation']}
+
+        #{build_tools_section(custom_tools)}
       SYSTEM_PROMPT_MESSAGE
     end
 
@@ -291,6 +293,15 @@ class Captain::Llm::SystemPromptsService
 
     private
 
+    def build_tools_section(custom_tools)
+      tools_list = custom_tools.map { |t| "- #{t[:name]}: #{t[:description]}" }.join("\n")
+      <<~TOOLS.strip
+        [Available Tools]
+        - search_documentation: Search and retrieve documentation from knowledge base
+        #{tools_list}
+      TOOLS
+    end
+
     def build_contact_context(contact)
       return '' if contact.nil?
 

enterprise/app/services/captain/tools/custom_http_tool.rb

@@ -0,0 +1,47 @@
+# V1-compatible wrapper for custom HTTP tools.
+#
+# V2's HttpTool inherits from Agents::Tool which overrides execute(tool_context, **params),
+# making it incompatible with V1's RubyLLM pipeline that calls execute(**keyword_args).
+#
+# This class bridges the gap: it inherits from BaseTool (RubyLLM::Tool) for V1 compatibility
+# and delegates the actual HTTP execution to HttpTool#perform.
+class Captain::Tools::CustomHttpTool < Captain::Tools::BaseTool
+  # BaseTool prepends Instrumentation, but our execute() shadows it in the MRO.
+  # Re-prepend so Langfuse captures tool call input/output/timing.
+  prepend Captain::Tools::Instrumentation
+
+  attr_reader :custom_tool
+
+  def initialize(assistant, custom_tool, conversation: nil)
+    @custom_tool = custom_tool
+    @conversation = conversation
+    super(assistant)
+  end
+
+  def active?
+    @custom_tool.enabled?
+  end
+
+  def execute(**params)
+    http_tool = Captain::Tools::HttpTool.new(assistant, @custom_tool)
+    http_tool.perform(build_tool_context, **params)
+  end
+
+  private
+
+  def build_tool_context
+    state = { account_id: assistant.account_id, assistant_id: assistant.id }
+    add_conversation_state(state) if @conversation
+    OpenStruct.new(state: state)
+  end
+
+  def add_conversation_state(state)
+    state[:conversation] = { id: @conversation.id, display_id: @conversation.display_id }
+    state[:contact] = slice_record_attrs(@conversation.contact, :id, :email, :phone_number)
+    state[:contact_inbox] = slice_record_attrs(@conversation.contact_inbox, :id, :hmac_verified)
+  end
+
+  def slice_record_attrs(record, *keys)
+    record&.attributes&.symbolize_keys&.slice(*keys)
+  end
+end

enterprise/app/services/enterprise/billing/reconcile_plan_features_service.rb

@@ -17,7 +17,7 @@ class Enterprise::Billing::ReconcilePlanFeaturesService
     linear_integration
   ].freeze
 
-  BUSINESS_PLAN_FEATURES = %w[sla custom_roles csat_review_notes conversation_required_attributes advanced_assignment].freeze
+  BUSINESS_PLAN_FEATURES = %w[sla custom_roles csat_review_notes conversation_required_attributes advanced_assignment custom_tools].freeze
   ENTERPRISE_PLAN_FEATURES = %w[audit_logs disable_branding saml].freeze
   PREMIUM_PLAN_FEATURES = (STARTUP_PLAN_FEATURES + BUSINESS_PLAN_FEATURES + ENTERPRISE_PLAN_FEATURES).freeze
 

enterprise/app/views/api/v1/models/captain/_custom_tool.json.jbuilder

@@ -7,7 +7,7 @@ json.http_method custom_tool.http_method
 json.request_template custom_tool.request_template
 json.response_template custom_tool.response_template
 json.auth_type custom_tool.auth_type
-json.auth_config custom_tool.auth_config
+json.auth_config custom_tool.auth_config if Current.user&.administrator?
 json.param_schema custom_tool.param_schema
 json.enabled custom_tool.enabled
 json.account_id custom_tool.account_id

spec/enterprise/controllers/api/v1/accounts/captain/custom_tools_controller_spec.rb

@@ -5,6 +5,8 @@ RSpec.describe 'Api::V1::Accounts::Captain::CustomTools', type: :request do
   let(:admin) { create(:user, account: account, role: :administrator) }
   let(:agent) { create(:user, account: account, role: :agent) }
 
+  before { account.enable_features!('custom_tools') }
+
   def json_response
     JSON.parse(response.body, symbolize_names: true)
   end
@@ -40,7 +42,7 @@ RSpec.describe 'Api::V1::Accounts::Captain::CustomTools', type: :request do
         expect(json_response[:payload].length).to eq(5)
       end
 
-      it 'returns only enabled custom tools' do
+      it 'returns all custom tools including disabled' do
         create(:captain_custom_tool, account: account, enabled: true)
         create(:captain_custom_tool, account: account, enabled: false)
         get "/api/v1/accounts/#{account.id}/captain/custom_tools",
@@ -48,8 +50,7 @@ RSpec.describe 'Api::V1::Accounts::Captain::CustomTools', type: :request do
             as: :json
 
         expect(response).to have_http_status(:success)
-        expect(json_response[:payload].length).to eq(1)
-        expect(json_response[:payload].first[:enabled]).to be(true)
+        expect(json_response[:payload].length).to eq(2)
       end
     end
   end

spec/models/attachment_spec.rb

@@ -187,6 +187,44 @@ RSpec.describe Attachment do
     end
   end
 
+  describe 'set_extension' do
+    it 'sets extension from filename on save' do
+      attachment = message.attachments.new(account_id: message.account_id, file_type: :file)
+      attachment.file.attach(io: StringIO.new('fake pdf'), filename: 'test.pdf', content_type: 'application/pdf')
+      attachment.save!
+
+      expect(attachment.extension).to eq('pdf')
+    end
+
+    it 'does not overwrite extension if already set' do
+      attachment = message.attachments.new(account_id: message.account_id, file_type: :file, extension: 'doc')
+      attachment.file.attach(io: StringIO.new('fake pdf'), filename: 'test.pdf', content_type: 'application/pdf')
+      attachment.save!
+
+      expect(attachment.extension).to eq('doc')
+    end
+
+    it 'handles filenames without extension' do
+      attachment = message.attachments.new(account_id: message.account_id, file_type: :file)
+      attachment.file.attach(io: StringIO.new('fake data'), filename: 'README', content_type: 'text/plain')
+      attachment.save!
+
+      expect(attachment.extension).to be_nil
+    end
+  end
+
+  describe 'push_event_data includes extension and content_type' do
+    it 'returns extension and content_type for file attachments' do
+      attachment = message.attachments.new(account_id: message.account_id, file_type: :file)
+      attachment.file.attach(io: StringIO.new('fake pdf'), filename: 'test.pdf', content_type: 'application/pdf')
+      attachment.save!
+
+      event_data = attachment.push_event_data
+      expect(event_data[:extension]).to eq('pdf')
+      expect(event_data[:content_type]).to eq('application/pdf')
+    end
+  end
+
   describe 'file size validation' do
     let(:attachment) { message.attachments.new(account_id: message.account_id, file_type: :image) }