diff --git a/app/javascript/dashboard/api/captain/messageReports.js b/app/javascript/dashboard/api/captain/messageReports.js
new file mode 100644
index 000000000..2df1e5747
--- /dev/null
+++ b/app/javascript/dashboard/api/captain/messageReports.js
@@ -0,0 +1,9 @@
+import ApiClient from '../ApiClient';
+
+class MessageReports extends ApiClient {
+  constructor() {
+    super('captain/message_reports', { accountScoped: true });
+  }
+}
+
+export default new MessageReports();
diff --git a/app/javascript/dashboard/components-next/message/Message.vue b/app/javascript/dashboard/components-next/message/Message.vue
index 0ef64eedf..cd3c7d5dc 100644
--- a/app/javascript/dashboard/components-next/message/Message.vue
+++ b/app/javascript/dashboard/components-next/message/Message.vue
@@ -147,8 +147,14 @@ const { t } = useI18n();
 const route = useRoute();
 const inboxGetter = useMapGetter('inboxes/getInbox');
 const inbox = computed(() => inboxGetter.value(props.inboxId) || {});
+const isOnChatwootCloud = useMapGetter('globalConfig/isOnChatwootCloud');
 const { replaceInstallationName } = useBranding();
 
+const isCaptainMessage = computed(() => {
+  const senderType = props.sender?.type ?? props.senderType;
+  return senderType === SENDER_TYPES.CAPTAIN_ASSISTANT;
+});
+
 /**
  * Computes the message variant based on props
  * @type {import('vue').ComputedRef<'user'|'agent'|'activity'|'private'|'bot'|'template'>}
@@ -390,6 +396,10 @@ const contextMenuEnabledOptions = computed(() => {
       !props.private &&
       props.inboxSupportsReplyTo.outgoing &&
       !isFailedOrProcessing,
+    report:
+      isOnChatwootCloud.value &&
+      isCaptainMessage.value &&
+      !isMessageDeleted.value,
   };
 });
 
diff --git a/app/javascript/dashboard/i18n/locale/en/conversation.json b/app/javascript/dashboard/i18n/locale/en/conversation.json
index 045b8d0d9..c34ed44de 100644
--- a/app/javascript/dashboard/i18n/locale/en/conversation.json
+++ b/app/javascript/dashboard/i18n/locale/en/conversation.json
@@ -304,6 +304,25 @@
         "MESSAGE": "You cannot undo this action",
         "DELETE": "Delete",
         "CANCEL": "Cancel"
+      },
+      "REPORT_MESSAGE": {
+        "LABEL": "Report message",
+        "TITLE": "Report Captain message",
+        "DESCRIPTION": "Found an issue with this AI response? Let us know what went wrong and our team will review it to help improve Captain's accuracy.",
+        "PROBLEM_TYPE": "Problem type",
+        "PROBLEM_TYPE_PLACEHOLDER": "Select a problem type",
+        "DESCRIPTION_LABEL": "Description",
+        "DESCRIPTION_PLACEHOLDER": "Describe the problem in detail",
+        "SUBMIT": "Report",
+        "SUCCESS": "Thanks for reporting. Our team will take a look.",
+        "ERROR": "Could not report this message. Please try again.",
+        "REASONS": {
+          "incorrect_information": "Incorrect information",
+          "inappropriate_response": "Inappropriate response",
+          "incomplete_response": "Incomplete response",
+          "outdated_information": "Outdated information",
+          "other": "Other"
+        }
       }
     },
     "SIDEBAR": {
diff --git a/app/javascript/dashboard/modules/conversations/components/MessageContextMenu.vue b/app/javascript/dashboard/modules/conversations/components/MessageContextMenu.vue
index a100b379f..4cfde97aa 100644
--- a/app/javascript/dashboard/modules/conversations/components/MessageContextMenu.vue
+++ b/app/javascript/dashboard/modules/conversations/components/MessageContextMenu.vue
@@ -14,6 +14,7 @@ import {
 import MenuItem from '../../../components/widgets/conversation/contextMenu/menuItem.vue';
 import { useTrack } from 'dashboard/composables';
 import NextButton from 'dashboard/components-next/button/Button.vue';
+import ReportCaptainMessageDialog from './ReportCaptainMessageDialog.vue';
 
 export default {
   components: {
@@ -21,6 +22,7 @@ export default {
     MenuItem,
     ContextMenu,
     NextButton,
+    ReportCaptainMessageDialog,
   },
   props: {
     message: {
@@ -152,6 +154,10 @@ export default {
     closeDeleteModal() {
       this.showDeleteModal = false;
     },
+    openReportDialog() {
+      this.handleClose();
+      this.$refs.reportDialog?.open();
+    },
   },
 };
 </script>
@@ -243,6 +249,16 @@ export default {
           variant="icon"
           @click.stop="showCannedResponseModal"
         />
+        <hr v-if="enabledOptions['report']" />
+        <MenuItem
+          v-if="enabledOptions['report']"
+          :option="{
+            icon: 'warning',
+            label: $t('CONVERSATION.CONTEXT_MENU.REPORT_MESSAGE.LABEL'),
+          }"
+          variant="icon"
+          @click.stop="openReportDialog"
+        />
         <hr v-if="enabledOptions['delete']" />
         <MenuItem
           v-if="enabledOptions['delete']"
@@ -255,6 +271,11 @@ export default {
         />
       </div>
     </ContextMenu>
+    <ReportCaptainMessageDialog
+      v-if="enabledOptions['report']"
+      ref="reportDialog"
+      :message-id="messageId"
+    />
   </div>
 </template>
 
diff --git a/app/javascript/dashboard/modules/conversations/components/ReportCaptainMessageDialog.vue b/app/javascript/dashboard/modules/conversations/components/ReportCaptainMessageDialog.vue
new file mode 100644
index 000000000..4d36efe78
--- /dev/null
+++ b/app/javascript/dashboard/modules/conversations/components/ReportCaptainMessageDialog.vue
@@ -0,0 +1,119 @@
+<script setup>
+import { computed, reactive, ref } from 'vue';
+import { useI18n } from 'vue-i18n';
+import { useAlert } from 'dashboard/composables';
+import MessageReportsAPI from 'dashboard/api/captain/messageReports';
+
+import Dialog from 'dashboard/components-next/dialog/Dialog.vue';
+import Select from 'dashboard/components-next/select/Select.vue';
+import TextArea from 'dashboard/components-next/textarea/TextArea.vue';
+
+const props = defineProps({
+  messageId: { type: [Number, String], required: true },
+});
+
+const { t } = useI18n();
+const dialogRef = ref(null);
+const isLoading = ref(false);
+
+const REPORT_REASONS = [
+  'incorrect_information',
+  'inappropriate_response',
+  'incomplete_response',
+  'outdated_information',
+  'other',
+];
+
+const reasonOptions = computed(() =>
+  REPORT_REASONS.map(value => ({
+    value,
+    label: t(`CONVERSATION.CONTEXT_MENU.REPORT_MESSAGE.REASONS.${value}`),
+  }))
+);
+
+const form = reactive({ reportReason: '', description: '' });
+
+const isFormInvalid = computed(() => !form.reportReason);
+
+const resetForm = () => {
+  form.reportReason = '';
+  form.description = '';
+};
+
+const open = () => {
+  resetForm();
+  dialogRef.value?.open();
+};
+
+const close = () => {
+  dialogRef.value?.close();
+};
+
+const handleConfirm = async () => {
+  if (isFormInvalid.value) return;
+
+  isLoading.value = true;
+  try {
+    await MessageReportsAPI.create({
+      message_id: props.messageId,
+      report_reason: form.reportReason,
+      description: form.description.trim() || null,
+    });
+    useAlert(t('CONVERSATION.CONTEXT_MENU.REPORT_MESSAGE.SUCCESS'));
+    close();
+  } catch (error) {
+    useAlert(t('CONVERSATION.CONTEXT_MENU.REPORT_MESSAGE.ERROR'));
+  } finally {
+    isLoading.value = false;
+  }
+};
+
+defineExpose({ open, close });
+</script>
+
+<template>
+  <Dialog
+    ref="dialogRef"
+    :title="t('CONVERSATION.CONTEXT_MENU.REPORT_MESSAGE.TITLE')"
+    :description="t('CONVERSATION.CONTEXT_MENU.REPORT_MESSAGE.DESCRIPTION')"
+    :confirm-button-label="t('CONVERSATION.CONTEXT_MENU.REPORT_MESSAGE.SUBMIT')"
+    :is-loading="isLoading"
+    :disable-confirm-button="isFormInvalid"
+    @confirm="handleConfirm"
+  >
+    <div class="flex flex-col gap-4">
+      <div class="flex flex-col gap-1">
+        <label class="text-sm font-medium text-n-slate-12">
+          {{ t('CONVERSATION.CONTEXT_MENU.REPORT_MESSAGE.PROBLEM_TYPE') }}
+        </label>
+        <Select
+          v-model="form.reportReason"
+          class="!w-full [&>select]:w-full"
+          :options="reasonOptions"
+          :placeholder="
+            t(
+              'CONVERSATION.CONTEXT_MENU.REPORT_MESSAGE.PROBLEM_TYPE_PLACEHOLDER'
+            )
+          "
+        />
+      </div>
+      <div class="flex flex-col gap-1">
+        <label class="text-sm font-medium text-n-slate-12">
+          {{ t('CONVERSATION.CONTEXT_MENU.REPORT_MESSAGE.DESCRIPTION_LABEL') }}
+        </label>
+        <TextArea
+          v-model="form.description"
+          class="w-full"
+          :placeholder="
+            t(
+              'CONVERSATION.CONTEXT_MENU.REPORT_MESSAGE.DESCRIPTION_PLACEHOLDER'
+            )
+          "
+          :max-length="500"
+          show-character-count
+          auto-height
+        />
+      </div>
+    </div>
+  </Dialog>
+</template>
diff --git a/config/routes.rb b/config/routes.rb
index f86e3f2cb..64e1df440 100644
--- a/config/routes.rb
+++ b/config/routes.rb
@@ -74,6 +74,7 @@ Rails.application.routes.draw do
               resources :scenarios
             end
             resources :assistant_responses
+            resources :message_reports, only: [:create]
             resources :bulk_actions, only: [:create]
             resources :copilot_threads, only: [:index, :create] do
               resources :copilot_messages, only: [:index, :create]
diff --git a/db/migrate/20260620000000_create_captain_message_reports.rb b/db/migrate/20260620000000_create_captain_message_reports.rb
new file mode 100644
index 000000000..41fc2f037
--- /dev/null
+++ b/db/migrate/20260620000000_create_captain_message_reports.rb
@@ -0,0 +1,14 @@
+class CreateCaptainMessageReports < ActiveRecord::Migration[7.1]
+  def change
+    create_table :captain_message_reports do |t|
+      t.references :account, null: false
+      t.references :conversation, null: false
+      t.references :message, null: false
+      t.references :user, null: false
+      t.string :report_reason, null: false
+      t.text :description
+
+      t.timestamps
+    end
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index cbddbcce2..a3513ca83 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -10,7 +10,7 @@
 #
 # It's strongly recommended that you check this file into your version control system.
 
-ActiveRecord::Schema[7.1].define(version: 2026_06_11_184600) do
+ActiveRecord::Schema[7.1].define(version: 2026_06_20_000000) do
   # These extensions should be enabled to support this database
   enable_extension "pg_stat_statements"
   enable_extension "pg_trgm"
@@ -399,6 +399,21 @@ ActiveRecord::Schema[7.1].define(version: 2026_06_11_184600) do
     t.index ["inbox_id"], name: "index_captain_inboxes_on_inbox_id"
   end
 
+  create_table "captain_message_reports", force: :cascade do |t|
+    t.bigint "account_id", null: false
+    t.bigint "conversation_id", null: false
+    t.bigint "message_id", null: false
+    t.bigint "user_id", null: false
+    t.string "report_reason", null: false
+    t.text "description"
+    t.datetime "created_at", null: false
+    t.datetime "updated_at", null: false
+    t.index ["account_id"], name: "index_captain_message_reports_on_account_id"
+    t.index ["conversation_id"], name: "index_captain_message_reports_on_conversation_id"
+    t.index ["message_id"], name: "index_captain_message_reports_on_message_id"
+    t.index ["user_id"], name: "index_captain_message_reports_on_user_id"
+  end
+
   create_table "captain_scenarios", force: :cascade do |t|
     t.string "title"
     t.text "description"
diff --git a/enterprise/app/controllers/api/v1/accounts/captain/message_reports_controller.rb b/enterprise/app/controllers/api/v1/accounts/captain/message_reports_controller.rb
new file mode 100644
index 000000000..abce5ffcc
--- /dev/null
+++ b/enterprise/app/controllers/api/v1/accounts/captain/message_reports_controller.rb
@@ -0,0 +1,38 @@
+class Api::V1::Accounts::Captain::MessageReportsController < Api::V1::Accounts::BaseController
+  before_action :ensure_cloud_installation
+  before_action :set_message
+  before_action :authorize_conversation
+  before_action :ensure_captain_message
+
+  def create
+    @message_report = @message.message_reports.create!(
+      user: Current.user,
+      report_reason: permitted_params[:report_reason],
+      description: permitted_params[:description]
+    )
+  end
+
+  private
+
+  def ensure_cloud_installation
+    render json: { error: 'Not available' }, status: :not_found unless ChatwootApp.chatwoot_cloud?
+  end
+
+  def set_message
+    @message = Current.account.messages.find(permitted_params[:message_id])
+  end
+
+  def authorize_conversation
+    authorize @message.conversation, :show?
+  end
+
+  def ensure_captain_message
+    return if @message.sender_type == 'Captain::Assistant'
+
+    render json: { error: 'Only Captain messages can be reported' }, status: :unprocessable_entity
+  end
+
+  def permitted_params
+    params.permit(:message_id, :report_reason, :description)
+  end
+end
diff --git a/enterprise/app/models/captain/message_report.rb b/enterprise/app/models/captain/message_report.rb
new file mode 100644
index 000000000..4fcb609fe
--- /dev/null
+++ b/enterprise/app/models/captain/message_report.rb
@@ -0,0 +1,46 @@
+# == Schema Information
+#
+# Table name: captain_message_reports
+#
+#  id              :bigint           not null, primary key
+#  description     :text
+#  report_reason   :string           not null
+#  created_at      :datetime         not null
+#  updated_at      :datetime         not null
+#  account_id      :bigint           not null
+#  conversation_id :bigint           not null
+#  message_id      :bigint           not null
+#  user_id         :bigint           not null
+#
+# Indexes
+#
+#  index_captain_message_reports_on_account_id       (account_id)
+#  index_captain_message_reports_on_conversation_id  (conversation_id)
+#  index_captain_message_reports_on_message_id       (message_id)
+#  index_captain_message_reports_on_user_id          (user_id)
+#
+class Captain::MessageReport < ApplicationRecord
+  self.table_name = 'captain_message_reports'
+
+  REPORT_REASONS = %w[incorrect_information inappropriate_response incomplete_response outdated_information other].freeze
+
+  belongs_to :account
+  # `Captain::Conversation` exists as a job namespace, so the association would
+  # resolve to that module instead of the top-level model without this override.
+  belongs_to :conversation, class_name: '::Conversation'
+  belongs_to :message
+  belongs_to :user
+
+  validates :report_reason, presence: true, inclusion: { in: REPORT_REASONS }
+
+  before_validation :ensure_account_and_conversation
+
+  private
+
+  def ensure_account_and_conversation
+    return if message.blank?
+
+    self.account ||= message.account
+    self.conversation ||= message.conversation
+  end
+end
diff --git a/enterprise/app/models/enterprise/concerns/message.rb b/enterprise/app/models/enterprise/concerns/message.rb
index cfdea430b..3c7cdc3f7 100644
--- a/enterprise/app/models/enterprise/concerns/message.rb
+++ b/enterprise/app/models/enterprise/concerns/message.rb
@@ -3,5 +3,6 @@ module Enterprise::Concerns::Message
 
   included do
     has_one :call, dependent: :nullify
+    has_many :message_reports, class_name: 'Captain::MessageReport', dependent: :destroy_async
   end
 end
diff --git a/enterprise/app/views/api/v1/accounts/captain/message_reports/create.json.jbuilder b/enterprise/app/views/api/v1/accounts/captain/message_reports/create.json.jbuilder
new file mode 100644
index 000000000..f45c0078b
--- /dev/null
+++ b/enterprise/app/views/api/v1/accounts/captain/message_reports/create.json.jbuilder
@@ -0,0 +1,7 @@
+json.id @message_report.id
+json.message_id @message_report.message_id
+json.conversation_id @message_report.conversation_id
+json.user_id @message_report.user_id
+json.report_reason @message_report.report_reason
+json.description @message_report.description
+json.created_at @message_report.created_at.to_i
diff --git a/spec/enterprise/controllers/api/v1/accounts/captain/message_reports_controller_spec.rb b/spec/enterprise/controllers/api/v1/accounts/captain/message_reports_controller_spec.rb
new file mode 100644
index 000000000..129888812
--- /dev/null
+++ b/spec/enterprise/controllers/api/v1/accounts/captain/message_reports_controller_spec.rb
@@ -0,0 +1,117 @@
+require 'rails_helper'
+
+RSpec.describe 'Api::V1::Accounts::Captain::MessageReports', type: :request do
+  let(:account) { create(:account) }
+  let(:agent) { create(:user, account: account, role: :agent) }
+  let(:inbox) { create(:inbox, account: account) }
+  let(:conversation) { create(:conversation, account: account, inbox: inbox) }
+  let(:assistant) { create(:captain_assistant, account: account) }
+  let(:message) do
+    create(:message, account: account, conversation: conversation, message_type: :outgoing, sender: assistant)
+  end
+
+  before { create(:inbox_member, user: agent, inbox: inbox) }
+
+  def json_response
+    JSON.parse(response.body, symbolize_names: true)
+  end
+
+  describe 'POST /api/v1/accounts/:account_id/captain/message_reports' do
+    let(:valid_params) do
+      {
+        message_id: message.id,
+        report_reason: 'incorrect_information',
+        description: 'The generated citation is wrong.'
+      }
+    end
+
+    context 'when it is an unauthenticated user' do
+      it 'returns unauthorized' do
+        post "/api/v1/accounts/#{account.id}/captain/message_reports", params: valid_params, as: :json
+
+        expect(response).to have_http_status(:unauthorized)
+      end
+    end
+
+    context 'when the installation is not on Chatwoot cloud' do
+      before { InstallationConfig.where(name: 'DEPLOYMENT_ENV').first_or_initialize.update!(value: 'self_hosted') }
+
+      it 'returns not found' do
+        post "/api/v1/accounts/#{account.id}/captain/message_reports",
+             params: valid_params, headers: agent.create_new_auth_token, as: :json
+
+        expect(response).to have_http_status(:not_found)
+      end
+
+      it 'does not create a report' do
+        expect do
+          post "/api/v1/accounts/#{account.id}/captain/message_reports",
+               params: valid_params, headers: agent.create_new_auth_token, as: :json
+        end.not_to change(Captain::MessageReport, :count)
+      end
+    end
+
+    context 'when on Chatwoot cloud' do
+      before { InstallationConfig.where(name: 'DEPLOYMENT_ENV').first_or_initialize.update!(value: 'cloud') }
+
+      it 'creates a message report for the reporting agent' do
+        expect do
+          post "/api/v1/accounts/#{account.id}/captain/message_reports",
+               params: valid_params, headers: agent.create_new_auth_token, as: :json
+        end.to change(Captain::MessageReport, :count).by(1)
+
+        report = Captain::MessageReport.last
+        aggregate_failures do
+          expect(response).to have_http_status(:success)
+          expect(report.message_id).to eq(message.id)
+          expect(report.conversation_id).to eq(conversation.id)
+          expect(report.user_id).to eq(agent.id)
+          expect(report.report_reason).to eq('incorrect_information')
+          expect(report.description).to eq('The generated citation is wrong.')
+          expect(json_response[:report_reason]).to eq('incorrect_information')
+        end
+      end
+
+      it 'returns not found when the message does not belong to the account' do
+        other_message = create(:message)
+
+        post "/api/v1/accounts/#{account.id}/captain/message_reports",
+             params: valid_params.merge(message_id: other_message.id),
+             headers: agent.create_new_auth_token, as: :json
+
+        expect(response).to have_http_status(:not_found)
+      end
+
+      it 'returns unprocessable entity for an invalid report reason' do
+        post "/api/v1/accounts/#{account.id}/captain/message_reports",
+             params: valid_params.merge(report_reason: 'invalid_reason'),
+             headers: agent.create_new_auth_token, as: :json
+
+        expect(response).to have_http_status(:unprocessable_entity)
+      end
+
+      it 'does not allow an agent without access to the conversation to report' do
+        other_agent = create(:user, account: account, role: :agent)
+
+        expect do
+          post "/api/v1/accounts/#{account.id}/captain/message_reports",
+               params: valid_params, headers: other_agent.create_new_auth_token, as: :json
+        end.not_to change(Captain::MessageReport, :count)
+
+        expect(response).to have_http_status(:unauthorized)
+      end
+
+      it 'rejects messages that were not sent by a Captain assistant' do
+        non_captain_message = create(:message, account: account, conversation: conversation)
+
+        expect do
+          post "/api/v1/accounts/#{account.id}/captain/message_reports",
+               params: valid_params.merge(message_id: non_captain_message.id),
+               headers: agent.create_new_auth_token, as: :json
+        end.not_to change(Captain::MessageReport, :count)
+
+        expect(response).to have_http_status(:unprocessable_entity)
+      end
+    end
+  end
+end
diff --git a/spec/enterprise/models/captain/message_report_spec.rb b/spec/enterprise/models/captain/message_report_spec.rb
new file mode 100644
index 000000000..ded42890c
--- /dev/null
+++ b/spec/enterprise/models/captain/message_report_spec.rb
@@ -0,0 +1,40 @@
+require 'rails_helper'
+
+RSpec.describe Captain::MessageReport, type: :model do
+  describe 'associations' do
+    it { is_expected.to belong_to(:account) }
+    it { is_expected.to belong_to(:conversation) }
+    it { is_expected.to belong_to(:message) }
+    it { is_expected.to belong_to(:user) }
+
+    it 'resolves the conversation association to the top-level Conversation model' do
+      # `Captain::Conversation` exists as a job namespace, so without an explicit
+      # class_name the association would resolve to that module instead.
+      expect(described_class.reflect_on_association(:conversation).klass).to eq(Conversation)
+    end
+  end
+
+  describe 'validations' do
+    it { is_expected.to validate_presence_of(:report_reason) }
+    it { is_expected.to validate_inclusion_of(:report_reason).in_array(described_class::REPORT_REASONS) }
+  end
+
+  describe 'callbacks' do
+    let(:account) { create(:account) }
+    let(:conversation) { create(:conversation, account: account) }
+    let(:message) { create(:message, account: account, conversation: conversation) }
+
+    it 'derives the account and conversation from the message' do
+      report = described_class.create!(message: message, user: create(:user, account: account), report_reason: 'other')
+
+      expect(report.account).to eq(account)
+      expect(report.conversation).to eq(conversation)
+    end
+  end
+
+  describe 'factory' do
+    it 'creates a valid message report' do
+      expect(build(:captain_message_report)).to be_valid
+    end
+  end
+end
diff --git a/spec/factories/captain/message_report.rb b/spec/factories/captain/message_report.rb
new file mode 100644
index 000000000..d7f1cfca0
--- /dev/null
+++ b/spec/factories/captain/message_report.rb
@@ -0,0 +1,8 @@
+FactoryBot.define do
+  factory :captain_message_report, class: 'Captain::MessageReport' do
+    report_reason { 'incorrect_information' }
+    description { 'The generated citation is wrong.' }
+    association :message
+    association :user
+  end
+end