diff --git a/.circleci/config.yml b/.circleci/config.yml
index bc7053130..99795db91 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -73,15 +73,15 @@ jobs:
               libvips
 
       - run:
-          name: Install RVM and Ruby 3.3.3
+          name: Install RVM and Ruby 3.4.4
           command: |
             sudo apt-get install -y gpg
             gpg --keyserver hkp://keyserver.ubuntu.com --recv-keys 409B6B1796C275462A1703113804BB82D39DC0E3 7D2BAF1CF37B13E2069D6956105BD0E739499BDB
             \curl -sSL https://get.rvm.io | bash -s stable
             echo 'source ~/.rvm/scripts/rvm' >> $BASH_ENV
             source ~/.rvm/scripts/rvm
-            rvm install "3.3.3"
-            rvm use 3.3.3 --default
+            rvm install "3.4.4"
+            rvm use 3.4.4 --default
             gem install bundler -v 2.5.16
 
       - run:
diff --git a/.devcontainer/docker-compose.yml b/.devcontainer/docker-compose.yml
index c5530ac17..21a9fe909 100644
--- a/.devcontainer/docker-compose.yml
+++ b/.devcontainer/docker-compose.yml
@@ -12,7 +12,7 @@ services:
       args:
         VARIANT: 'ubuntu-22.04'
         NODE_VERSION: '23.7.0'
-        RUBY_VERSION: '3.3.3'
+        RUBY_VERSION: '3.4.4'
         # On Linux, you may need to update USER_UID and USER_GID below if not your local UID is not 1000.
         USER_UID: '1000'
         USER_GID: '1000'
@@ -25,7 +25,7 @@ services:
       args:
         VARIANT: 'ubuntu-22.04'
         NODE_VERSION: '23.7.0'
-        RUBY_VERSION: '3.3.3'
+        RUBY_VERSION: '3.4.4'
         # On Linux, you may need to update USER_UID and USER_GID below if not your local UID is not 1000.
         USER_UID: '1000'
         USER_GID: '1000'
diff --git a/.rubocop.yml b/.rubocop.yml
index dffd2283c..d1e1726a9 100644
--- a/.rubocop.yml
+++ b/.rubocop.yml
@@ -85,6 +85,10 @@ Metrics/ModuleLength:
     - lib/seeders/message_seeder.rb
     - spec/support/slack_stubs.rb
 
+Rails/HelperInstanceVariable:
+  Exclude:
+    - enterprise/app/helpers/captain/chat_helper.rb
+
 Rails/ApplicationController:
   Exclude:
     - 'app/controllers/api/v1/widget/messages_controller.rb'
@@ -112,6 +116,20 @@ Rails/TimeZoneAssignment:
 Rails/RedundantPresenceValidationOnBelongsTo:
   Enabled: false
 
+Rails/InverseOf:
+  Exclude:
+    - enterprise/app/models/captain/assistant.rb
+
+Rails/UniqueValidationWithoutIndex:
+  Exclude:
+    - 'app/models/canned_response.rb'
+    - 'app/models/telegram_bot.rb'
+    - 'enterprise/app/models/captain_inbox.rb'
+    - 'app/models/channel/twitter_profile.rb'
+    - 'app/models/webhook.rb'
+    - 'app/models/contact.rb'
+    - 'app/models/integrations/hook.rb'
+
 Style/ClassAndModuleChildren:
   EnforcedStyle: compact
   Exclude:
@@ -154,15 +172,6 @@ Metrics/AbcSize:
   Exclude:
     - 'app/controllers/concerns/auth_helper.rb'
 
-Rails/UniqueValidationWithoutIndex:
-  Exclude:
-    - 'app/models/channel/twitter_profile.rb'
-    - 'app/models/webhook.rb'
-    - 'app/models/contact.rb'
-    - 'app/models/integrations/hook.rb'
-    - 'app/models/canned_response.rb'
-    - 'app/models/telegram_bot.rb'
-
 Rails/RenderInline:
   Exclude:
     - 'app/controllers/swagger_controller.rb'
diff --git a/.ruby-version b/.ruby-version
index 619b53766..f9892605c 100644
--- a/.ruby-version
+++ b/.ruby-version
@@ -1 +1 @@
-3.3.3
+3.4.4
diff --git a/Gemfile b/Gemfile
index fe180439f..71d511ace 100644
--- a/Gemfile
+++ b/Gemfile
@@ -1,10 +1,12 @@
 source 'https://rubygems.org'
 
-ruby '3.3.3'
+ruby '3.4.4'
 
 ##-- base gems for rails --##
+
 gem 'rack-cors', require: 'rack/cors'
 gem 'rails', '~> 7.2.0'
+
 # Reduces boot times through caching; required in config/boot.rb
 gem 'bootsnap', require: false
 
diff --git a/Gemfile.lock b/Gemfile.lock
index cb2d6df68..a1d03a122 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -1069,4 +1069,4 @@ RUBY VERSION
    ruby 3.3.3p89
 
 BUNDLED WITH
-   2.5.16
+   2.5.16
\ No newline at end of file
diff --git a/app/builders/contact_inbox_builder.rb b/app/builders/contact_inbox_builder.rb
index ffa45db2e..788ae39d1 100644
--- a/app/builders/contact_inbox_builder.rb
+++ b/app/builders/contact_inbox_builder.rb
@@ -59,11 +59,13 @@ class ContactInboxBuilder
   end
 
   def create_contact_inbox
-    ::ContactInbox.create_with(hmac_verified: hmac_verified || false).find_or_create_by!(
+    attrs = {
       contact_id: @contact.id,
       inbox_id: @inbox.id,
       source_id: @source_id
-    )
+    }
+
+    ::ContactInbox.where(attrs).first_or_create!(hmac_verified: hmac_verified || false)
   rescue ActiveRecord::RecordNotUnique
     Rails.logger.info("[ContactInboxBuilder] RecordNotUnique #{@source_id} #{@contact.id} #{@inbox.id}")
     update_old_contact_inbox
diff --git a/app/javascript/dashboard/components-next/copilot/CopilotAgentMessage.vue b/app/javascript/dashboard/components-next/copilot/CopilotAgentMessage.vue
index ef8c2faf4..f1ad2afc1 100644
--- a/app/javascript/dashboard/components-next/copilot/CopilotAgentMessage.vue
+++ b/app/javascript/dashboard/components-next/copilot/CopilotAgentMessage.vue
@@ -1,31 +1,17 @@
 <script setup>
-import Avatar from '../avatar/Avatar.vue';
-
 defineProps({
   message: {
     type: Object,
     required: true,
   },
-  supportAgent: {
-    type: Object,
-    required: true,
-  },
 });
 </script>
 
 <template>
-  <div class="flex flex-row gap-2">
-    <Avatar
-      :name="supportAgent.available_name"
-      :src="supportAgent.avatar_url"
-      :size="24"
-      rounded-full
-    />
-    <div class="space-y-1 text-n-slate-12">
-      <div class="font-medium">{{ $t('CAPTAIN.COPILOT.YOU') }}</div>
-      <div class="break-words">
-        {{ message.content }}
-      </div>
+  <div class="space-y-1 text-n-slate-12">
+    <div class="font-medium">{{ $t('CAPTAIN.COPILOT.YOU') }}</div>
+    <div class="break-words">
+      {{ message.content }}
     </div>
   </div>
 </template>
diff --git a/app/javascript/dashboard/components-next/copilot/CopilotAssistantMessage.vue b/app/javascript/dashboard/components-next/copilot/CopilotAssistantMessage.vue
index 1877e1630..0a37600bf 100644
--- a/app/javascript/dashboard/components-next/copilot/CopilotAssistantMessage.vue
+++ b/app/javascript/dashboard/components-next/copilot/CopilotAssistantMessage.vue
@@ -9,7 +9,6 @@ import { COPILOT_EVENTS } from 'dashboard/helper/AnalyticsHelper/events';
 import MessageFormatter from 'shared/helpers/MessageFormatter.js';
 
 import Button from 'dashboard/components-next/button/Button.vue';
-import Avatar from '../avatar/Avatar.vue';
 
 const props = defineProps({
   message: {
@@ -46,33 +45,25 @@ const useCopilotResponse = () => {
 </script>
 
 <template>
-  <div class="flex flex-row gap-2">
-    <Avatar
-      name="Captain Copilot"
-      icon-name="i-woot-captain"
-      :size="24"
-      rounded-full
+  <div class="flex flex-col gap-1 text-n-slate-12">
+    <div class="font-medium">{{ $t('CAPTAIN.NAME') }}</div>
+    <span v-if="hasEmptyMessageContent" class="text-n-ruby-11">
+      {{ $t('CAPTAIN.COPILOT.EMPTY_MESSAGE') }}
+    </span>
+    <div
+      v-else
+      v-dompurify-html="messageContent"
+      class="prose-sm break-words"
     />
-    <div class="flex flex-col gap-1 text-n-slate-12">
-      <div class="font-medium">{{ $t('CAPTAIN.NAME') }}</div>
-      <span v-if="hasEmptyMessageContent" class="text-n-ruby-11">
-        {{ $t('CAPTAIN.COPILOT.EMPTY_MESSAGE') }}
-      </span>
-      <div
-        v-else
-        v-dompurify-html="messageContent"
-        class="prose-sm break-words"
+    <div class="flex flex-row mt-1">
+      <Button
+        v-if="!hasEmptyMessageContent"
+        :label="$t('CAPTAIN.COPILOT.USE')"
+        faded
+        sm
+        slate
+        @click="useCopilotResponse"
       />
-      <div class="flex flex-row mt-1">
-        <Button
-          v-if="!hasEmptyMessageContent"
-          :label="$t('CAPTAIN.COPILOT.USE')"
-          faded
-          sm
-          slate
-          @click="useCopilotResponse"
-        />
-      </div>
     </div>
   </div>
 </template>
diff --git a/app/mailboxes/application_mailbox.rb b/app/mailboxes/application_mailbox.rb
index 4fe931b9f..9fc7a435d 100644
--- a/app/mailboxes/application_mailbox.rb
+++ b/app/mailboxes/application_mailbox.rb
@@ -31,7 +31,7 @@ class ApplicationMailbox < ActionMailbox::Base
     end
 
     def in_reply_to_matches?(in_reply_to)
-      Array.wrap(in_reply_to).any? { _1.match?(CONVERSATION_MESSAGE_ID_PATTERN) }
+      Array.wrap(in_reply_to).any? { it.match?(CONVERSATION_MESSAGE_ID_PATTERN) }
     end
 
     # checks if follow this pattern  send it to reply_mailbox
diff --git a/app/models/conversation.rb b/app/models/conversation.rb
index bcb79c05b..3f1a20037 100644
--- a/app/models/conversation.rb
+++ b/app/models/conversation.rb
@@ -128,6 +128,12 @@ class Conversation < ApplicationRecord
     additional_attributes&.dig('conversation_language')
   end
 
+  # Be aware: The precision of created_at and last_activity_at may differ from Ruby's Time precision.
+  # Our DB column (see schema) stores timestamps with second-level precision (no microseconds), so
+  # if you assign a Ruby Time with microseconds, the DB will truncate it. This may cause subtle differences
+  # if you compare or copy these values in Ruby, also in our specs
+  # So in specs rely on to be_with(1.second) instead of to eq()
+  # TODO: Migrate to use a timestamp with microsecond precision
   def last_activity_at
     self[:last_activity_at] || created_at
   end
diff --git a/app/services/message_templates/template/csat_survey.rb b/app/services/message_templates/template/csat_survey.rb
index 3a7ca2605..dd9cf3bd6 100644
--- a/app/services/message_templates/template/csat_survey.rb
+++ b/app/services/message_templates/template/csat_survey.rb
@@ -12,7 +12,6 @@ class MessageTemplates::Template::CsatSurvey
   private
 
   delegate :contact, :account, :inbox, to: :conversation
-  delegate :csat_config, to: :inbox
 
   def should_send_csat_survey?
     return true unless survey_rules_configured?
diff --git a/app/services/twilio/incoming_message_service.rb b/app/services/twilio/incoming_message_service.rb
index 7a335c87d..c38577599 100644
--- a/app/services/twilio/incoming_message_service.rb
+++ b/app/services/twilio/incoming_message_service.rb
@@ -137,14 +137,19 @@ class Twilio::IncomingMessageService
   end
 
   def download_with_auth(media_url)
-    Down.download(
-      media_url,
-      http_basic_authentication: [twilio_channel.account_sid, twilio_channel.auth_token || twilio_channel.api_key_sid]
-    )
+    auth_credentials = if twilio_channel.api_key_sid.present?
+                         # When using api_key_sid, the auth token should be the api_secret_key
+                         [twilio_channel.api_key_sid, twilio_channel.auth_token]
+                       else
+                         # When using account_sid, the auth token is the account's auth token
+                         [twilio_channel.account_sid, twilio_channel.auth_token]
+                       end
+
+    Down.download(media_url, http_basic_authentication: auth_credentials)
   end
 
   def handle_download_attachment_error(error, media_url)
-    Rails.logger.info "Error downloading attachment from Twilio: #{error.message}: Retrying"
+    Rails.logger.info "Error downloading attachment from Twilio: #{error.message}: Retrying without auth"
     Down.download(media_url)
   rescue StandardError => e
     Rails.logger.info "Error downloading attachment from Twilio: #{e.message}: Skipping"
diff --git a/config/initializers/01_redis.rb b/config/initializers/01_redis.rb
index 664dcd435..93c12fce7 100644
--- a/config/initializers/01_redis.rb
+++ b/config/initializers/01_redis.rb
@@ -1,3 +1,7 @@
+# TODO: Phase out the custom ConnectionPool wrappers ($alfred / $velma),
+# switch to plain Redis clients here and let Rails 7.1+ handle pooling
+# via `pool:` in RedisCacheStore (see rack_attack initializer).
+
 # Alfred
 # Add here as you use it for more features
 # Used for Round Robin, Conversation Emails & Online Presence
diff --git a/config/initializers/rack_attack.rb b/config/initializers/rack_attack.rb
index fdbd47008..fe3f6c554 100644
--- a/config/initializers/rack_attack.rb
+++ b/config/initializers/rack_attack.rb
@@ -11,7 +11,12 @@ class Rack::Attack
   # Rack::Attack.cache.store = ActiveSupport::Cache::MemoryStore.new
 
   # https://github.com/rack/rack-attack/issues/102
-  Rack::Attack.cache.store = ActiveSupport::Cache::RedisCacheStore.new(redis: $velma)
+  # Rails 7.1 automatically adds its own ConnectionPool around RedisCacheStore.
+  # Because `$velma` is *already* a ConnectionPool, double-wrapping causes
+  # Redis calls like `get` to hit the outer wrapper and explode.
+  # `pool: false` tells Rails to skip its internal pool and use ours directly.
+  # TODO: We can use build in connection pool in future upgrade
+  Rack::Attack.cache.store = ActiveSupport::Cache::RedisCacheStore.new(redis: $velma, pool: false)
 
   class Request < ::Rack::Request
     # You many need to specify a method to fetch the correct remote IP address
diff --git a/deployment/chatwoot-web.1.service b/deployment/chatwoot-web.1.service
index 049ec85db..0d1d33804 100644
--- a/deployment/chatwoot-web.1.service
+++ b/deployment/chatwoot-web.1.service
@@ -16,10 +16,10 @@ KillMode=mixed
 StandardInput=null
 SyslogIdentifier=%p
 
-Environment="PATH=/home/chatwoot/.rvm/gems/ruby-3.3.3/bin:/home/chatwoot/.rvm/gems/ruby-3.3.3@global/bin:/home/chatwoot/.rvm/rubies/ruby-3.3.3/bin:/home/chatwoot/.rvm/bin:/usr/local/sbin:/usr/local/bin:/usr/sbin:/usr/bin:/sbin:/bin:/snap/bin:/home/chatwoot/.rvm/bin:/home/chatwoot/.rvm/bin"
+Environment="PATH=/home/chatwoot/.rvm/gems/ruby-3.4.4/bin:/home/chatwoot/.rvm/gems/ruby-3.4.4@global/bin:/home/chatwoot/.rvm/rubies/ruby-3.4.4/bin:/home/chatwoot/.rvm/bin:/usr/local/sbin:/usr/local/bin:/usr/sbin:/usr/bin:/sbin:/bin:/snap/bin:/home/chatwoot/.rvm/bin:/home/chatwoot/.rvm/bin"
 Environment="PORT=3000"
 Environment="RAILS_ENV=production"
 Environment="NODE_ENV=production"
 Environment="RAILS_LOG_TO_STDOUT=true"
-Environment="GEM_HOME=/home/chatwoot/.rvm/gems/ruby-3.3.3"
-Environment="GEM_PATH=/home/chatwoot/.rvm/gems/ruby-3.3.3:/home/chatwoot/.rvm/gems/ruby-3.3.3@global"
+Environment="GEM_HOME=/home/chatwoot/.rvm/gems/ruby-3.4.4"
+Environment="GEM_PATH=/home/chatwoot/.rvm/gems/ruby-3.4.4:/home/chatwoot/.rvm/gems/ruby-3.4.4@global"
diff --git a/deployment/chatwoot-worker.1.service b/deployment/chatwoot-worker.1.service
index 04ee83a69..ea893d20c 100644
--- a/deployment/chatwoot-worker.1.service
+++ b/deployment/chatwoot-worker.1.service
@@ -21,10 +21,10 @@ MemoryHigh=1.4G
 MemorySwapMax=0
 OOMPolicy=stop
 
-Environment="PATH=/home/chatwoot/.rvm/gems/ruby-3.3.3/bin:/home/chatwoot/.rvm/gems/ruby-3.3.3@global/bin:/home/chatwoot/.rvm/rubies/ruby-3.3.3/bin:/home/chatwoot/.rvm/bin:/usr/local/sbin:/usr/local/bin:/usr/sbin:/usr/bin:/sbin:/bin:/snap/bin:/home/chatwoot/.rvm/bin:/home/chatwoot/.rvm/bin"
+Environment="PATH=/home/chatwoot/.rvm/gems/ruby-3.4.4/bin:/home/chatwoot/.rvm/gems/ruby-3.4.4@global/bin:/home/chatwoot/.rvm/rubies/ruby-3.4.4/bin:/home/chatwoot/.rvm/bin:/usr/local/sbin:/usr/local/bin:/usr/sbin:/usr/bin:/sbin:/bin:/snap/bin:/home/chatwoot/.rvm/bin:/home/chatwoot/.rvm/bin"
 Environment="PORT=3000"
 Environment="RAILS_ENV=production"
 Environment="NODE_ENV=production"
 Environment="RAILS_LOG_TO_STDOUT=true"
-Environment="GEM_HOME=/home/chatwoot/.rvm/gems/ruby-3.3.3"
-Environment="GEM_PATH=/home/chatwoot/.rvm/gems/ruby-3.3.3:/home/chatwoot/.rvm/gems/ruby-3.3.3@global"
+Environment="GEM_HOME=/home/chatwoot/.rvm/gems/ruby-3.4.4"
+Environment="GEM_PATH=/home/chatwoot/.rvm/gems/ruby-3.4.4:/home/chatwoot/.rvm/gems/ruby-3.4.4@global"
diff --git a/deployment/setup_20.04.sh b/deployment/setup_20.04.sh
index 7809b6d0e..75320bbd3 100644
--- a/deployment/setup_20.04.sh
+++ b/deployment/setup_20.04.sh
@@ -338,8 +338,8 @@ function setup_chatwoot() {
   sudo -i -u chatwoot << EOF
   rvm --version
   rvm autolibs disable
-  rvm install "ruby-3.3.3"
-  rvm use 3.3.3 --default
+  rvm install "ruby-3.4.4"
+  rvm use 3.4.4 --default
 
   git clone https://github.com/chatwoot/chatwoot.git
   cd chatwoot
diff --git a/docker/Dockerfile b/docker/Dockerfile
index 008884ce1..2d753337d 100644
--- a/docker/Dockerfile
+++ b/docker/Dockerfile
@@ -1,6 +1,6 @@
 # pre-build stage
 FROM node:23-alpine as node
-FROM ruby:3.3.3-alpine3.19 AS pre-builder
+FROM ruby:3.4.4-alpine3.21 AS pre-builder
 
 ARG NODE_VERSION="23.7.0"
 ARG PNPM_VERSION="10.2.0"
@@ -90,13 +90,13 @@ RUN if [ "$RAILS_ENV" = "production" ]; then \
 RUN git rev-parse HEAD > /app/.git_sha
 
 # Remove unnecessary files
-RUN rm -rf /gems/ruby/3.3.0/cache/*.gem \
-  && find /gems/ruby/3.3.0/gems/ \( -name "*.c" -o -name "*.o" \) -delete \
+RUN rm -rf /gems/ruby/3.4.0/cache/*.gem \
+  && find /gems/ruby/3.4.0/gems/ \( -name "*.c" -o -name "*.o" \) -delete \
   && rm -rf .git \
   && rm .gitignore
 
 # final build stage
-FROM ruby:3.3.3-alpine3.19
+FROM ruby:3.4.4-alpine3.21
 
 ARG NODE_VERSION="23.7.0"
 ARG PNPM_VERSION="10.2.0"
diff --git a/enterprise/app/controllers/api/v1/accounts/custom_roles_controller.rb b/enterprise/app/controllers/api/v1/accounts/custom_roles_controller.rb
index 01650a7de..2d6823b90 100644
--- a/enterprise/app/controllers/api/v1/accounts/custom_roles_controller.rb
+++ b/enterprise/app/controllers/api/v1/accounts/custom_roles_controller.rb
@@ -6,12 +6,12 @@ class Api::V1::Accounts::CustomRolesController < Api::V1::Accounts::EnterpriseAc
     @custom_roles = Current.account.custom_roles
   end
 
+  def show; end
+
   def create
     @custom_role = Current.account.custom_roles.create!(permitted_params)
   end
 
-  def show; end
-
   def update
     @custom_role.update!(permitted_params)
   end
diff --git a/enterprise/app/controllers/api/v1/accounts/sla_policies_controller.rb b/enterprise/app/controllers/api/v1/accounts/sla_policies_controller.rb
index e64256bc7..ec879b042 100644
--- a/enterprise/app/controllers/api/v1/accounts/sla_policies_controller.rb
+++ b/enterprise/app/controllers/api/v1/accounts/sla_policies_controller.rb
@@ -6,12 +6,12 @@ class Api::V1::Accounts::SlaPoliciesController < Api::V1::Accounts::EnterpriseAc
     @sla_policies = Current.account.sla_policies
   end
 
+  def show; end
+
   def create
     @sla_policy = Current.account.sla_policies.create!(permitted_params)
   end
 
-  def show; end
-
   def update
     @sla_policy.update!(permitted_params)
   end
diff --git a/enterprise/app/jobs/captain/conversation/response_builder_job.rb b/enterprise/app/jobs/captain/conversation/response_builder_job.rb
index 39a12b662..c661caebe 100644
--- a/enterprise/app/jobs/captain/conversation/response_builder_job.rb
+++ b/enterprise/app/jobs/captain/conversation/response_builder_job.rb
@@ -50,7 +50,7 @@ class Captain::Conversation::ResponseBuilderJob < ApplicationJob
   def message_content(message)
     return message.content if message.content.present?
 
-    'User has shared an attachment' if message.attachments.any?
+    return 'User has shared an attachment' if message.attachments.any?
 
     'User has shared a message without content'
   end
diff --git a/enterprise/app/services/captain/tool_registry_service.rb b/enterprise/app/services/captain/tool_registry_service.rb
index f2c234060..8d6632e57 100644
--- a/enterprise/app/services/captain/tool_registry_service.rb
+++ b/enterprise/app/services/captain/tool_registry_service.rb
@@ -1,23 +1,24 @@
 class Captain::ToolRegistryService
   attr_reader :registered_tools, :tools
 
-  def initialize(assistant)
+  def initialize(assistant, user: nil)
     @assistant = assistant
+    @user = user
     @registered_tools = []
     @tools = {}
   end
 
   def register_tool(tool_class)
-    tool = tool_class.new(@assistant)
+    tool = tool_class.new(@assistant, user: @user)
     return unless tool.active?
 
     @tools[tool.name] = tool
     @registered_tools << tool.to_registry_format
   end
 
-  def method_missing(method_name, *arguments)
+  def method_missing(method_name, *)
     if @tools.key?(method_name.to_s)
-      @tools[method_name.to_s].execute(*arguments)
+      @tools[method_name.to_s].execute(*)
     else
       super
     end
diff --git a/enterprise/app/services/captain/tools/base_service.rb b/enterprise/app/services/captain/tools/base_service.rb
index 9143726b7..72fde2df8 100644
--- a/enterprise/app/services/captain/tools/base_service.rb
+++ b/enterprise/app/services/captain/tools/base_service.rb
@@ -36,4 +36,18 @@ class Captain::Tools::BaseService
   def active?
     true
   end
+
+  private
+
+  def user_has_permission(permission)
+    return false if @user.blank?
+
+    account_user = AccountUser.find_by(account_id: @assistant.account_id, user_id: @user.id)
+    return false if account_user.blank?
+
+    return account_user.custom_role.permissions.include?(permission) if account_user.custom_role.present?
+
+    # Default permission for agents without custom roles
+    account_user.administrator? || account_user.agent?
+  end
 end
diff --git a/enterprise/app/services/captain/tools/copilot/get_article_service.rb b/enterprise/app/services/captain/tools/copilot/get_article_service.rb
new file mode 100644
index 000000000..9c2ee02da
--- /dev/null
+++ b/enterprise/app/services/captain/tools/copilot/get_article_service.rb
@@ -0,0 +1,39 @@
+class Captain::Tools::Copilot::GetArticleService < Captain::Tools::BaseService
+  def name
+    'get_article'
+  end
+
+  def description
+    'Get details of an article including its content and metadata'
+  end
+
+  def parameters
+    {
+      type: 'object',
+      properties: {
+        article_id: {
+          type: 'number',
+          description: 'The ID of the article to retrieve'
+        }
+      },
+      required: %w[article_id]
+    }
+  end
+
+  def execute(arguments)
+    article_id = arguments['article_id']
+
+    Rails.logger.info { "#{self.class.name}: Article ID: #{article_id}" }
+
+    return 'Missing required parameters' if article_id.blank?
+
+    article = Article.find_by(id: article_id, account_id: @assistant.account_id)
+    return 'Article not found' if article.nil?
+
+    article.to_llm_text
+  end
+
+  def active?
+    user_has_permission('knowledge_base_manage')
+  end
+end
diff --git a/enterprise/app/services/captain/tools/copilot/get_contact_service.rb b/enterprise/app/services/captain/tools/copilot/get_contact_service.rb
new file mode 100644
index 000000000..290433301
--- /dev/null
+++ b/enterprise/app/services/captain/tools/copilot/get_contact_service.rb
@@ -0,0 +1,39 @@
+class Captain::Tools::Copilot::GetContactService < Captain::Tools::BaseService
+  def name
+    'get_contact'
+  end
+
+  def description
+    'Get details of a contact including their profile information'
+  end
+
+  def parameters
+    {
+      type: 'object',
+      properties: {
+        contact_id: {
+          type: 'number',
+          description: 'The ID of the contact to retrieve'
+        }
+      },
+      required: %w[contact_id]
+    }
+  end
+
+  def execute(arguments)
+    contact_id = arguments['contact_id']
+
+    Rails.logger.info "#{self.class.name}: Contact ID: #{contact_id}"
+
+    return 'Missing required parameters' if contact_id.blank?
+
+    contact = Contact.find_by(id: contact_id, account_id: @assistant.account_id)
+    return 'Contact not found' if contact.nil?
+
+    contact.to_llm_text
+  end
+
+  def active?
+    user_has_permission('contact_manage')
+  end
+end
diff --git a/enterprise/app/services/captain/tools/copilot/get_conversation_service.rb b/enterprise/app/services/captain/tools/copilot/get_conversation_service.rb
new file mode 100644
index 000000000..64b52d012
--- /dev/null
+++ b/enterprise/app/services/captain/tools/copilot/get_conversation_service.rb
@@ -0,0 +1,41 @@
+class Captain::Tools::Copilot::GetConversationService < Captain::Tools::BaseService
+  def name
+    'get_conversation'
+  end
+
+  def description
+    'Get details of a conversation including messages and contact information'
+  end
+
+  def parameters
+    {
+      type: 'object',
+      properties: {
+        conversation_id: {
+          type: 'number',
+          description: 'The ID of the conversation to retrieve'
+        }
+      },
+      required: %w[conversation_id]
+    }
+  end
+
+  def execute(arguments)
+    conversation_id = arguments['conversation_id']
+
+    Rails.logger.info "#{self.class.name}: Conversation ID: #{conversation_id}"
+
+    return 'Missing required parameters' if conversation_id.blank?
+
+    conversation = Conversation.find_by(display_id: conversation_id, account_id: @assistant.account_id)
+    return 'Conversation not found' if conversation.blank?
+
+    conversation.to_llm_text
+  end
+
+  def active?
+    user_has_permission('conversation_manage') ||
+      user_has_permission('conversation_unassigned_manage') ||
+      user_has_permission('conversation_participating_manage')
+  end
+end
diff --git a/enterprise/app/services/captain/tools/copilot/search_articles_service.rb b/enterprise/app/services/captain/tools/copilot/search_articles_service.rb
new file mode 100644
index 000000000..5061968ad
--- /dev/null
+++ b/enterprise/app/services/captain/tools/copilot/search_articles_service.rb
@@ -0,0 +1,71 @@
+class Captain::Tools::Copilot::SearchArticlesService < Captain::Tools::BaseService
+  def name
+    'search_articles'
+  end
+
+  def description
+    'Search articles based on parameters'
+  end
+
+  def parameters
+    {
+      type: 'object',
+      properties: properties,
+      required: ['query']
+    }
+  end
+
+  def execute(arguments)
+    query = arguments['query']
+    category_id = arguments['category_id']
+    status = arguments['status']
+
+    Rails.logger.info "#{self.class.name}: Query: #{query}, Category ID: #{category_id}, Status: #{status}"
+
+    return 'Missing required parameters' if query.blank?
+
+    articles = fetch_articles(query, category_id, status)
+
+    return 'No articles found' unless articles.exists?
+
+    total_count = articles.count
+    articles = articles.limit(100)
+
+    <<~RESPONSE
+      #{total_count > 100 ? "Found #{total_count} articles (showing first 100)" : "Total number of articles: #{total_count}"}
+      #{articles.map(&:to_llm_text).join("\n---\n")}
+    RESPONSE
+  end
+
+  def active?
+    user_has_permission('knowledge_base_manage')
+  end
+
+  private
+
+  def fetch_articles(query, category_id, status)
+    articles = Article.where(account_id: @assistant.account_id)
+    articles = articles.where('title ILIKE :query OR content ILIKE :query', query: "%#{query}%") if query.present?
+    articles = articles.where(category_id: category_id) if category_id.present?
+    articles = articles.where(status: status) if status.present?
+    articles
+  end
+
+  def properties
+    {
+      query: {
+        type: 'string',
+        description: 'Search articles by title or content (partial match)'
+      },
+      category_id: {
+        type: 'number',
+        description: 'Filter articles by category ID'
+      },
+      status: {
+        type: 'string',
+        enum: %w[draft published archived],
+        description: 'Filter articles by status'
+      }
+    }
+  end
+end
diff --git a/enterprise/app/services/captain/tools/copilot/search_contacts_service.rb b/enterprise/app/services/captain/tools/copilot/search_contacts_service.rb
new file mode 100644
index 000000000..557fc731a
--- /dev/null
+++ b/enterprise/app/services/captain/tools/copilot/search_contacts_service.rb
@@ -0,0 +1,61 @@
+class Captain::Tools::Copilot::SearchContactsService < Captain::Tools::BaseService
+  def name
+    'search_contacts'
+  end
+
+  def description
+    'Search contacts based on query parameters'
+  end
+
+  def parameters
+    {
+      type: 'object',
+      properties: properties,
+      required: []
+    }
+  end
+
+  def execute(arguments)
+    email = arguments['email']
+    phone_number = arguments['phone_number']
+    name = arguments['name']
+
+    Rails.logger.info "#{self.class.name} Email: #{email}, Phone Number: #{phone_number}, Name: #{name}"
+
+    contacts = Contact.where(account_id: @assistant.account_id)
+    contacts = contacts.where(email: email) if email.present?
+    contacts = contacts.where(phone_number: phone_number) if phone_number.present?
+    contacts = contacts.where('LOWER(name) ILIKE ?', "%#{name.downcase}%") if name.present?
+
+    return 'No contacts found' unless contacts.exists?
+
+    contacts = contacts.limit(100)
+
+    <<~RESPONSE
+      #{contacts.map(&:to_llm_text).join("\n---\n")}
+    RESPONSE
+  end
+
+  def active?
+    user_has_permission('contact_manage')
+  end
+
+  private
+
+  def properties
+    {
+      email: {
+        type: 'string',
+        description: 'Filter contacts by email'
+      },
+      phone_number: {
+        type: 'string',
+        description: 'Filter contacts by phone number'
+      },
+      name: {
+        type: 'string',
+        description: 'Filter contacts by name (partial match)'
+      }
+    }
+  end
+end
diff --git a/enterprise/app/services/captain/tools/copilot/search_conversations_service.rb b/enterprise/app/services/captain/tools/copilot/search_conversations_service.rb
index 6b6b063ea..f97604793 100644
--- a/enterprise/app/services/captain/tools/copilot/search_conversations_service.rb
+++ b/enterprise/app/services/captain/tools/copilot/search_conversations_service.rb
@@ -33,6 +33,12 @@ class Captain::Tools::Copilot::SearchConversationsService < Captain::Tools::Base
     RESPONSE
   end
 
+  def active?
+    user_has_permission('conversation_manage') ||
+      user_has_permission('conversation_unassigned_manage') ||
+      user_has_permission('conversation_participating_manage')
+  end
+
   private
 
   def get_conversations(status, contact_id, priority)
diff --git a/spec/builders/v2/reports/conversations/report_builder_spec.rb b/spec/builders/v2/reports/conversations/report_builder_spec.rb
index d3cde98e6..db7a0ac45 100644
--- a/spec/builders/v2/reports/conversations/report_builder_spec.rb
+++ b/spec/builders/v2/reports/conversations/report_builder_spec.rb
@@ -33,12 +33,12 @@ describe V2::Reports::Conversations::ReportBuilder do
   end
 
   describe '#timeseries' do
-    include_examples 'valid metric handler', 'avg_first_response_time', :timeseries, V2::Reports::Timeseries::AverageReportBuilder
-    include_examples 'valid metric handler', 'conversations_count', :timeseries, V2::Reports::Timeseries::CountReportBuilder
+    it_behaves_like 'valid metric handler', 'avg_first_response_time', :timeseries, V2::Reports::Timeseries::AverageReportBuilder
+    it_behaves_like 'valid metric handler', 'conversations_count', :timeseries, V2::Reports::Timeseries::CountReportBuilder
   end
 
   describe '#aggregate_value' do
-    include_examples 'valid metric handler', 'avg_first_response_time', :aggregate_value, V2::Reports::Timeseries::AverageReportBuilder
-    include_examples 'valid metric handler', 'conversations_count', :aggregate_value, V2::Reports::Timeseries::CountReportBuilder
+    it_behaves_like 'valid metric handler', 'avg_first_response_time', :aggregate_value, V2::Reports::Timeseries::AverageReportBuilder
+    it_behaves_like 'valid metric handler', 'conversations_count', :aggregate_value, V2::Reports::Timeseries::CountReportBuilder
   end
 end
diff --git a/spec/enterprise/services/captain/tool_registry_service_spec.rb b/spec/enterprise/services/captain/tool_registry_service_spec.rb
index beb4a6a63..c8d97fe3a 100644
--- a/spec/enterprise/services/captain/tool_registry_service_spec.rb
+++ b/spec/enterprise/services/captain/tool_registry_service_spec.rb
@@ -4,7 +4,7 @@ require 'rails_helper'
 class TestTool < Captain::Tools::BaseService
   attr_accessor :tool_active
 
-  def initialize(*args)
+  def initialize(assistant, user: nil)
     super
     @tool_active = true
   end
diff --git a/spec/enterprise/services/captain/tools/copilot/get_article_service_spec.rb b/spec/enterprise/services/captain/tools/copilot/get_article_service_spec.rb
new file mode 100644
index 000000000..72f4e1cb4
--- /dev/null
+++ b/spec/enterprise/services/captain/tools/copilot/get_article_service_spec.rb
@@ -0,0 +1,112 @@
+require 'rails_helper'
+
+RSpec.describe Captain::Tools::Copilot::GetArticleService do
+  let(:account) { create(:account) }
+  let(:user) { create(:user, account: account) }
+  let(:assistant) { create(:captain_assistant, account: account) }
+  let(:service) { described_class.new(assistant, user: user) }
+
+  describe '#name' do
+    it 'returns the correct service name' do
+      expect(service.name).to eq('get_article')
+    end
+  end
+
+  describe '#description' do
+    it 'returns the service description' do
+      expect(service.description).to eq('Get details of an article including its content and metadata')
+    end
+  end
+
+  describe '#parameters' do
+    it 'returns the expected parameter schema' do
+      expect(service.parameters).to eq(
+        {
+          type: 'object',
+          properties: {
+            article_id: {
+              type: 'number',
+              description: 'The ID of the article to retrieve'
+            }
+          },
+          required: %w[article_id]
+        }
+      )
+    end
+  end
+
+  describe '#active?' do
+    context 'when user is an admin' do
+      let(:user) { create(:user, :administrator, account: account) }
+      let(:assistant) { create(:captain_assistant, account: account) }
+
+      it 'returns true' do
+        expect(service.active?).to be true
+      end
+    end
+
+    context 'when user has custom role with knowledge_base_manage permission' do
+      let(:user) { create(:user, account: account) }
+      let(:assistant) { create(:captain_assistant, account: account) }
+      let(:custom_role) { create(:custom_role, account: account, permissions: ['knowledge_base_manage']) }
+
+      before do
+        account_user = AccountUser.find_by(user: user, account: account)
+        account_user.update(role: :agent, custom_role: custom_role)
+      end
+
+      it 'returns true' do
+        expect(service.active?).to be true
+      end
+    end
+
+    context 'when user has custom role without knowledge_base_manage permission' do
+      let(:user) { create(:user, account: account) }
+      let(:assistant) { create(:captain_assistant, account: account) }
+      let(:custom_role) { create(:custom_role, account: account, permissions: []) }
+
+      before do
+        account_user = AccountUser.find_by(user: user, account: account)
+        account_user.update(role: :agent, custom_role: custom_role)
+      end
+
+      it 'returns false' do
+        expect(service.active?).to be false
+      end
+    end
+  end
+
+  describe '#execute' do
+    context 'when article_id is blank' do
+      it 'returns error message' do
+        expect(service.execute({})).to eq('Missing required parameters')
+      end
+    end
+
+    context 'when article is not found' do
+      it 'returns not found message' do
+        expect(service.execute({ 'article_id' => 999 })).to eq('Article not found')
+      end
+    end
+
+    context 'when article exists' do
+      let(:portal) { create(:portal, account: account) }
+      let(:article) { create(:article, account: account, portal: portal, author: user, title: 'Test Article', content: 'Content') }
+
+      it 'returns the article in llm text format' do
+        result = service.execute({ 'article_id' => article.id })
+        expect(result).to eq(article.to_llm_text)
+      end
+
+      context 'when article belongs to different account' do
+        let(:other_account) { create(:account) }
+        let(:other_portal) { create(:portal, account: other_account) }
+        let(:other_article) { create(:article, account: other_account, portal: other_portal, author: user, title: 'Other Article') }
+
+        it 'returns not found message' do
+          expect(service.execute({ 'article_id' => other_article.id })).to eq('Article not found')
+        end
+      end
+    end
+  end
+end
diff --git a/spec/enterprise/services/captain/tools/copilot/get_contact_service_spec.rb b/spec/enterprise/services/captain/tools/copilot/get_contact_service_spec.rb
new file mode 100644
index 000000000..de319bfa1
--- /dev/null
+++ b/spec/enterprise/services/captain/tools/copilot/get_contact_service_spec.rb
@@ -0,0 +1,110 @@
+require 'rails_helper'
+
+RSpec.describe Captain::Tools::Copilot::GetContactService do
+  let(:account) { create(:account) }
+  let(:user) { create(:user, account: account) }
+  let(:assistant) { create(:captain_assistant, account: account) }
+  let(:service) { described_class.new(assistant, user: user) }
+
+  describe '#name' do
+    it 'returns the correct service name' do
+      expect(service.name).to eq('get_contact')
+    end
+  end
+
+  describe '#description' do
+    it 'returns the service description' do
+      expect(service.description).to eq('Get details of a contact including their profile information')
+    end
+  end
+
+  describe '#parameters' do
+    it 'returns the expected parameter schema' do
+      expect(service.parameters).to eq(
+        {
+          type: 'object',
+          properties: {
+            contact_id: {
+              type: 'number',
+              description: 'The ID of the contact to retrieve'
+            }
+          },
+          required: %w[contact_id]
+        }
+      )
+    end
+  end
+
+  describe '#active?' do
+    context 'when user is an admin' do
+      let(:user) { create(:user, :administrator, account: account) }
+      let(:assistant) { create(:captain_assistant, account: account) }
+
+      it 'returns true' do
+        expect(service.active?).to be true
+      end
+    end
+
+    context 'when user has custom role with contact_manage permission' do
+      let(:user) { create(:user, account: account) }
+      let(:assistant) { create(:captain_assistant, account: account) }
+      let(:custom_role) { create(:custom_role, account: account, permissions: ['contact_manage']) }
+
+      before do
+        account_user = AccountUser.find_by(user: user, account: account)
+        account_user.update(role: :agent, custom_role: custom_role)
+      end
+
+      it 'returns true' do
+        expect(service.active?).to be true
+      end
+    end
+
+    context 'when user has custom role without contact_manage permission' do
+      let(:user) { create(:user, account: account) }
+      let(:assistant) { create(:captain_assistant, account: account) }
+      let(:custom_role) { create(:custom_role, account: account, permissions: []) }
+
+      before do
+        account_user = AccountUser.find_by(user: user, account: account)
+        account_user.update(role: :agent, custom_role: custom_role)
+      end
+
+      it 'returns false' do
+        expect(service.active?).to be false
+      end
+    end
+  end
+
+  describe '#execute' do
+    context 'when contact_id is blank' do
+      it 'returns error message' do
+        expect(service.execute({})).to eq('Missing required parameters')
+      end
+    end
+
+    context 'when contact is not found' do
+      it 'returns not found message' do
+        expect(service.execute({ 'contact_id' => 999 })).to eq('Contact not found')
+      end
+    end
+
+    context 'when contact exists' do
+      let(:contact) { create(:contact, account: account) }
+
+      it 'returns the contact in llm text format' do
+        result = service.execute({ 'contact_id' => contact.id })
+        expect(result).to eq(contact.to_llm_text)
+      end
+
+      context 'when contact belongs to different account' do
+        let(:other_account) { create(:account) }
+        let(:other_contact) { create(:contact, account: other_account) }
+
+        it 'returns not found message' do
+          expect(service.execute({ 'contact_id' => other_contact.id })).to eq('Contact not found')
+        end
+      end
+    end
+  end
+end
diff --git a/spec/enterprise/services/captain/tools/copilot/get_conversation_service_spec.rb b/spec/enterprise/services/captain/tools/copilot/get_conversation_service_spec.rb
new file mode 100644
index 000000000..4d7f1adc7
--- /dev/null
+++ b/spec/enterprise/services/captain/tools/copilot/get_conversation_service_spec.rb
@@ -0,0 +1,142 @@
+require 'rails_helper'
+
+RSpec.describe Captain::Tools::Copilot::GetConversationService do
+  let(:account) { create(:account) }
+  let(:user) { create(:user, account: account) }
+  let(:assistant) { create(:captain_assistant, account: account) }
+  let(:service) { described_class.new(assistant, user: user) }
+
+  describe '#name' do
+    it 'returns the correct service name' do
+      expect(service.name).to eq('get_conversation')
+    end
+  end
+
+  describe '#description' do
+    it 'returns the service description' do
+      expect(service.description).to eq('Get details of a conversation including messages and contact information')
+    end
+  end
+
+  describe '#parameters' do
+    it 'returns the expected parameter schema' do
+      expect(service.parameters).to eq(
+        {
+          type: 'object',
+          properties: {
+            conversation_id: {
+              type: 'number',
+              description: 'The ID of the conversation to retrieve'
+            }
+          },
+          required: %w[conversation_id]
+        }
+      )
+    end
+  end
+
+  describe '#active?' do
+    context 'when user is an admin' do
+      let(:user) { create(:user, :administrator, account: account) }
+      let(:assistant) { create(:captain_assistant, account: account) }
+
+      it 'returns true' do
+        expect(service.active?).to be true
+      end
+    end
+
+    context 'when user has custom role with conversation_manage permission' do
+      let(:user) { create(:user, account: account) }
+      let(:assistant) { create(:captain_assistant, account: account) }
+      let(:custom_role) { create(:custom_role, account: account, permissions: ['conversation_manage']) }
+
+      before do
+        account_user = AccountUser.find_by(user: user, account: account)
+        account_user.update(role: :agent, custom_role: custom_role)
+      end
+
+      it 'returns true' do
+        expect(service.active?).to be true
+      end
+    end
+
+    context 'when user has custom role with conversation_unassigned_manage permission' do
+      let(:user) { create(:user, account: account) }
+      let(:assistant) { create(:captain_assistant, account: account) }
+      let(:custom_role) { create(:custom_role, account: account, permissions: ['conversation_unassigned_manage']) }
+
+      before do
+        account_user = AccountUser.find_by(user: user, account: account)
+        account_user.update(role: :agent, custom_role: custom_role)
+      end
+
+      it 'returns true' do
+        expect(service.active?).to be true
+      end
+    end
+
+    context 'when user has custom role with conversation_participating_manage permission' do
+      let(:user) { create(:user, account: account) }
+      let(:assistant) { create(:captain_assistant, account: account) }
+      let(:custom_role) { create(:custom_role, account: account, permissions: ['conversation_participating_manage']) }
+
+      before do
+        account_user = AccountUser.find_by(user: user, account: account)
+        account_user.update(role: :agent, custom_role: custom_role)
+      end
+
+      it 'returns true' do
+        expect(service.active?).to be true
+      end
+    end
+
+    context 'when user has custom role without any conversation permissions' do
+      let(:user) { create(:user, account: account) }
+      let(:assistant) { create(:captain_assistant, account: account) }
+      let(:custom_role) { create(:custom_role, account: account, permissions: []) }
+
+      before do
+        account_user = AccountUser.find_by(user: user, account: account)
+        account_user.update(role: :agent, custom_role: custom_role)
+      end
+
+      it 'returns false' do
+        expect(service.active?).to be false
+      end
+    end
+  end
+
+  describe '#execute' do
+    context 'when conversation_id is blank' do
+      it 'returns error message' do
+        expect(service.execute({})).to eq('Missing required parameters')
+      end
+    end
+
+    context 'when conversation is not found' do
+      it 'returns not found message' do
+        expect(service.execute({ 'conversation_id' => 999 })).to eq('Conversation not found')
+      end
+    end
+
+    context 'when conversation exists' do
+      let(:inbox) { create(:inbox, account: account) }
+      let(:conversation) { create(:conversation, account: account, inbox: inbox) }
+
+      it 'returns the conversation in llm text format' do
+        result = service.execute({ 'conversation_id' => conversation.display_id })
+        expect(result).to eq(conversation.to_llm_text)
+      end
+
+      context 'when conversation belongs to different account' do
+        let(:other_account) { create(:account) }
+        let(:other_inbox) { create(:inbox, account: other_account) }
+        let(:other_conversation) { create(:conversation, account: other_account, inbox: other_inbox) }
+
+        it 'returns not found message' do
+          expect(service.execute({ 'conversation_id' => other_conversation.display_id })).to eq('Conversation not found')
+        end
+      end
+    end
+  end
+end
diff --git a/spec/enterprise/services/captain/tools/copilot/search_articles_service_spec.rb b/spec/enterprise/services/captain/tools/copilot/search_articles_service_spec.rb
new file mode 100644
index 000000000..e4504d7bd
--- /dev/null
+++ b/spec/enterprise/services/captain/tools/copilot/search_articles_service_spec.rb
@@ -0,0 +1,167 @@
+require 'rails_helper'
+
+RSpec.describe Captain::Tools::Copilot::SearchArticlesService do
+  let(:account) { create(:account) }
+  let(:user) { create(:user, account: account) }
+  let(:assistant) { create(:captain_assistant, account: account) }
+  let(:service) { described_class.new(assistant, user: user) }
+
+  describe '#name' do
+    it 'returns the correct service name' do
+      expect(service.name).to eq('search_articles')
+    end
+  end
+
+  describe '#description' do
+    it 'returns the service description' do
+      expect(service.description).to eq('Search articles based on parameters')
+    end
+  end
+
+  describe '#parameters' do
+    it 'returns the expected parameter schema' do
+      expect(service.parameters).to eq(
+        {
+          type: 'object',
+          properties: {
+            query: {
+              type: 'string',
+              description: 'Search articles by title or content (partial match)'
+            },
+            category_id: {
+              type: 'number',
+              description: 'Filter articles by category ID'
+            },
+            status: {
+              type: 'string',
+              enum: %w[draft published archived],
+              description: 'Filter articles by status'
+            }
+          },
+          required: ['query']
+        }
+      )
+    end
+  end
+
+  describe '#active?' do
+    context 'when user is an admin' do
+      let(:user) { create(:user, :administrator, account: account) }
+      let(:assistant) { create(:captain_assistant, account: account) }
+
+      it 'returns true' do
+        expect(service.active?).to be true
+      end
+    end
+
+    context 'when user is an agent' do
+      let(:user) { create(:user, account: account) }
+      let(:assistant) { create(:captain_assistant, account: account) }
+
+      it 'returns true' do
+        expect(service.active?).to be true
+      end
+    end
+
+    context 'when user has custom role with knowledge_base_manage permission' do
+      let(:user) { create(:user, account: account) }
+      let(:assistant) { create(:captain_assistant, account: account) }
+      let(:custom_role) { create(:custom_role, account: account, permissions: ['knowledge_base_manage']) }
+
+      before do
+        account_user = AccountUser.find_by(user: user, account: account)
+        account_user.update(role: :agent, custom_role: custom_role)
+      end
+
+      it 'returns true' do
+        expect(service.active?).to be true
+      end
+    end
+
+    context 'when user has custom role without knowledge_base_manage permission' do
+      let(:user) { create(:user, account: account) }
+      let(:assistant) { create(:captain_assistant, account: account) }
+      let(:custom_role) { create(:custom_role, account: account, permissions: []) }
+
+      before do
+        account_user = AccountUser.find_by(user: user, account: account)
+        account_user.update(role: :agent, custom_role: custom_role)
+      end
+
+      it 'returns false' do
+        expect(service.active?).to be false
+      end
+    end
+  end
+
+  describe '#execute' do
+    context 'when query is blank' do
+      it 'returns error message' do
+        expect(service.execute({})).to eq('Missing required parameters')
+      end
+    end
+
+    context 'when no articles are found' do
+      before do
+        allow(Article).to receive(:where).and_return(Article.none)
+      end
+
+      it 'returns no articles found message' do
+        expect(service.execute({ 'query' => 'test' })).to eq('No articles found')
+      end
+    end
+
+    context 'when articles are found' do
+      let(:portal) { create(:portal, account: account) }
+      let(:article1) { create(:article, account: account, portal: portal, author: user, title: 'Test Article 1', content: 'Content 1') }
+      let(:article2) { create(:article, account: account, portal: portal, author: user, title: 'Test Article 2', content: 'Content 2') }
+
+      before do
+        article1
+        article2
+      end
+
+      it 'returns formatted articles with count' do
+        result = service.execute({ 'query' => 'Test' })
+        expect(result).to include('Total number of articles: 2')
+        expect(result).to include(article1.to_llm_text)
+        expect(result).to include(article2.to_llm_text)
+      end
+
+      context 'when filtered by category' do
+        let(:category) { create(:category, slug: 'test-category', portal: portal, account: account) }
+        let(:article3) { create(:article, account: account, portal: portal, author: user, category: category, title: 'Test Article 3') }
+
+        before do
+          article3
+        end
+
+        it 'returns only articles from the specified category' do
+          result = service.execute({ 'query' => 'Test', 'category_id' => category.id })
+          expect(result).to include('Total number of articles: 1')
+          expect(result).to include(article3.to_llm_text)
+          expect(result).not_to include(article1.to_llm_text)
+          expect(result).not_to include(article2.to_llm_text)
+        end
+      end
+
+      context 'when filtered by status' do
+        let(:article3) do
+          create(:article, account: account, portal: portal, author: user, title: 'Test Article 3', status: 'published')
+        end
+        let(:article4) { create(:article, account: account, portal: portal, author: user, title: 'Test Article 4', status: 'draft') }
+
+        before do
+          article3
+          article4
+        end
+
+        it 'returns only articles with the specified status' do
+          result = service.execute({ 'query' => 'Test', 'status' => 'published' })
+          expect(result).to include(article3.to_llm_text)
+          expect(result).not_to include(article4.to_llm_text)
+        end
+      end
+    end
+  end
+end
diff --git a/spec/enterprise/services/captain/tools/copilot/search_contacts_service_spec.rb b/spec/enterprise/services/captain/tools/copilot/search_contacts_service_spec.rb
new file mode 100644
index 000000000..f54b2eddf
--- /dev/null
+++ b/spec/enterprise/services/captain/tools/copilot/search_contacts_service_spec.rb
@@ -0,0 +1,113 @@
+require 'rails_helper'
+
+RSpec.describe Captain::Tools::Copilot::SearchContactsService do
+  let(:account) { create(:account) }
+  let(:user) { create(:user, account: account) }
+  let(:assistant) { create(:captain_assistant, account: account) }
+  let(:service) { described_class.new(assistant, user: user) }
+
+  describe '#name' do
+    it 'returns the correct service name' do
+      expect(service.name).to eq('search_contacts')
+    end
+  end
+
+  describe '#description' do
+    it 'returns the service description' do
+      expect(service.description).to eq('Search contacts based on query parameters')
+    end
+  end
+
+  describe '#parameters' do
+    it 'returns the expected parameter schema' do
+      expect(service.parameters).to eq(
+        {
+          type: 'object',
+          properties: {
+            email: {
+              type: 'string',
+              description: 'Filter contacts by email'
+            },
+            phone_number: {
+              type: 'string',
+              description: 'Filter contacts by phone number'
+            },
+            name: {
+              type: 'string',
+              description: 'Filter contacts by name (partial match)'
+            }
+          },
+          required: []
+        }
+      )
+    end
+  end
+
+  describe '#active?' do
+    context 'when user has contact_manage permission' do
+      let(:user) { create(:user, account: account) }
+      let(:assistant) { create(:captain_assistant, account: account) }
+      let(:custom_role) { create(:custom_role, account: account, permissions: ['contact_manage']) }
+
+      before do
+        account_user = AccountUser.find_by(user: user, account: account)
+        account_user.update(role: :agent, custom_role: custom_role)
+      end
+
+      it 'returns true' do
+        expect(service.active?).to be true
+      end
+    end
+
+    context 'when user does not have contact_manage permission' do
+      let(:user) { create(:user, account: account) }
+      let(:assistant) { create(:captain_assistant, account: account) }
+      let(:custom_role) { create(:custom_role, account: account, permissions: []) }
+
+      before do
+        account_user = AccountUser.find_by(user: user, account: account)
+        account_user.update(role: :agent, custom_role: custom_role)
+      end
+
+      it 'returns false' do
+        expect(service.active?).to be false
+      end
+    end
+  end
+
+  describe '#execute' do
+    context 'when contacts are found' do
+      let(:contact1) { create(:contact, account: account, email: 'test1@example.com', name: 'Test Contact 1', phone_number: '+1234567890') }
+      let(:contact2) { create(:contact, account: account, email: 'test2@example.com', name: 'Test Contact 2', phone_number: '+1234567891') }
+
+      before do
+        contact1
+        contact2
+      end
+
+      it 'returns contacts when filtered by email' do
+        result = service.execute({ 'email' => 'test1@example.com' })
+        expect(result).to include(contact1.to_llm_text)
+        expect(result).not_to include(contact2.to_llm_text)
+      end
+
+      it 'returns contacts when filtered by phone number' do
+        result = service.execute({ 'phone_number' => '+1234567890' })
+        expect(result).to include(contact1.to_llm_text)
+        expect(result).not_to include(contact2.to_llm_text)
+      end
+
+      it 'returns contacts when filtered by name' do
+        result = service.execute({ 'name' => 'Contact 1' })
+        expect(result).to include(contact1.to_llm_text)
+        expect(result).not_to include(contact2.to_llm_text)
+      end
+
+      it 'returns all matching contacts when no filters are provided' do
+        result = service.execute({})
+        expect(result).to include(contact1.to_llm_text)
+        expect(result).to include(contact2.to_llm_text)
+      end
+    end
+  end
+end
diff --git a/spec/enterprise/services/captain/tools/copilot/search_conversations_service_spec.rb b/spec/enterprise/services/captain/tools/copilot/search_conversations_service_spec.rb
index e60ad6f28..ab0865bc2 100644
--- a/spec/enterprise/services/captain/tools/copilot/search_conversations_service_spec.rb
+++ b/spec/enterprise/services/captain/tools/copilot/search_conversations_service_spec.rb
@@ -26,6 +26,64 @@ RSpec.describe Captain::Tools::Copilot::SearchConversationsService do
     end
   end
 
+  describe '#active?' do
+    context 'when user has conversation_manage permission' do
+      let(:custom_role) { create(:custom_role, account: account, permissions: ['conversation_manage']) }
+      let(:user) { create(:user, account: account) }
+
+      before do
+        account_user = AccountUser.find_by(user: user, account: account)
+        account_user.update(role: :agent, custom_role: custom_role)
+      end
+
+      it 'returns true' do
+        expect(service.active?).to be true
+      end
+    end
+
+    context 'when user has conversation_unassigned_manage permission' do
+      let(:custom_role) { create(:custom_role, account: account, permissions: ['conversation_unassigned_manage']) }
+      let(:user) { create(:user, account: account) }
+
+      before do
+        account_user = AccountUser.find_by(user: user, account: account)
+        account_user.update(role: :agent, custom_role: custom_role)
+      end
+
+      it 'returns true' do
+        expect(service.active?).to be true
+      end
+    end
+
+    context 'when user has conversation_participating_manage permission' do
+      let(:custom_role) { create(:custom_role, account: account, permissions: ['conversation_participating_manage']) }
+      let(:user) { create(:user, account: account) }
+
+      before do
+        account_user = AccountUser.find_by(user: user, account: account)
+        account_user.update(role: :agent, custom_role: custom_role)
+      end
+
+      it 'returns true' do
+        expect(service.active?).to be true
+      end
+    end
+
+    context 'when user has no relevant conversation permissions' do
+      let(:custom_role) { create(:custom_role, account: account, permissions: []) }
+      let(:user) { create(:user, account: account) }
+
+      before do
+        account_user = AccountUser.find_by(user: user, account: account)
+        account_user.update(role: :agent, custom_role: custom_role)
+      end
+
+      it 'returns false' do
+        expect(service.active?).to be false
+      end
+    end
+  end
+
   describe '#execute' do
     let(:contact) { create(:contact, account: account) }
     let!(:open_conversation) { create(:conversation, account: account, contact: contact, status: 'open', priority: 'high') }
diff --git a/spec/models/conversation_spec.rb b/spec/models/conversation_spec.rb
index 9395f3e55..aef91603d 100644
--- a/spec/models/conversation_spec.rb
+++ b/spec/models/conversation_spec.rb
@@ -793,8 +793,8 @@ RSpec.describe Conversation do
     end
 
     context 'when a new conversation is created' do
-      it 'sets last_activity_at to the created_at time' do
-        expect(conversation.last_activity_at).to eq(conversation.created_at)
+      it 'sets last_activity_at to the created_at time (within DB precision)' do
+        expect(conversation.last_activity_at).to be_within(1.second).of(conversation.created_at)
       end
     end
 
diff --git a/spec/services/crm/leadsquared/mappers/conversation_mapper_spec.rb b/spec/services/crm/leadsquared/mappers/conversation_mapper_spec.rb
index 29f7136f1..85bb08d74 100644
--- a/spec/services/crm/leadsquared/mappers/conversation_mapper_spec.rb
+++ b/spec/services/crm/leadsquared/mappers/conversation_mapper_spec.rb
@@ -183,7 +183,7 @@ RSpec.describe Crm::Leadsquared::Mappers::ConversationMapper do
         expect(result.length).to be <= described_class::ACTIVITY_NOTE_MAX_SIZE + 100
 
         # Verify that not all messages are included (some were truncated)
-        expect(messages.count).to be > result.scan(/John Doe:/).count
+        expect(messages.count).to be > result.scan('John Doe:').count
       end
 
       it 'respects the ACTIVITY_NOTE_MAX_SIZE constant' do