diff --git a/app/javascript/dashboard/components-next/captain/pageComponents/response/ResponseForm.vue b/app/javascript/dashboard/components-next/captain/pageComponents/response/ResponseForm.vue
index ce6370e98..985dc0620 100644
--- a/app/javascript/dashboard/components-next/captain/pageComponents/response/ResponseForm.vue
+++ b/app/javascript/dashboard/components-next/captain/pageComponents/response/ResponseForm.vue
@@ -2,7 +2,7 @@
 import { reactive, computed, watch } from 'vue';
 import { useI18n } from 'vue-i18n';
 import { useVuelidate } from '@vuelidate/core';
-import { required, minLength } from '@vuelidate/validators';
+import { required, minLength, maxLength } from '@vuelidate/validators';
 import { useMapGetter } from 'dashboard/composables/store';
 
 import Input from 'dashboard/components-next/input/Input.vue';
@@ -39,11 +39,17 @@ const initialState = {
   assistant_id: '',
 };
 
+const QUESTION_MAX_LENGTH = 255;
+
 const state = reactive({ ...initialState });
 
 const validationRules = computed(() => {
   const rules = {
-    question: { required, minLength: minLength(1) },
+    question: {
+      required,
+      minLength: minLength(1),
+      maxLength: maxLength(QUESTION_MAX_LENGTH),
+    },
     answer: { required, minLength: minLength(1) },
   };
 
@@ -123,6 +129,7 @@ watch(
       :placeholder="t('CAPTAIN.RESPONSES.FORM.QUESTION.PLACEHOLDER')"
       :message="formErrors.question"
       :message-type="formErrors.question ? 'error' : 'info'"
+      :maxlength="QUESTION_MAX_LENGTH"
     />
     <Editor
       v-model="state.answer"
diff --git a/app/javascript/dashboard/modules/conversations/components/MessageContextMenu.vue b/app/javascript/dashboard/modules/conversations/components/MessageContextMenu.vue
index b743144d2..fa2d867ce 100644
--- a/app/javascript/dashboard/modules/conversations/components/MessageContextMenu.vue
+++ b/app/javascript/dashboard/modules/conversations/components/MessageContextMenu.vue
@@ -18,6 +18,8 @@ import NextButton from 'dashboard/components-next/button/Button.vue';
 import Editor from 'dashboard/components-next/Editor/Editor.vue';
 import { useUISettings } from 'dashboard/composables/useUISettings';
 
+const FAQ_QUESTION_MAX_LENGTH = 255;
+
 export default {
   components: {
     AddCannedModal,
@@ -93,6 +95,11 @@ export default {
         this.message.content_attributes ?? this.message.contentAttributes
       );
     },
+    faqQuestion() {
+      return (this.plainTextContent || '')
+        .trim()
+        .slice(0, FAQ_QUESTION_MAX_LENGTH);
+    },
   },
   methods: {
     handleEnterKey(e) {
@@ -251,7 +258,7 @@ export default {
       ref="faqDialog"
       type="create"
       :selected-response="{
-        question: plainTextContent,
+        question: faqQuestion,
         assistant_id: copilotAssistant?.id,
       }"
       @close="hideFaqModal"
diff --git a/enterprise/app/models/captain/assistant_response.rb b/enterprise/app/models/captain/assistant_response.rb
index 12dcab1cc..646e5eb37 100644
--- a/enterprise/app/models/captain/assistant_response.rb
+++ b/enterprise/app/models/captain/assistant_response.rb
@@ -30,7 +30,7 @@ class Captain::AssistantResponse < ApplicationRecord
   belongs_to :documentable, polymorphic: true, optional: true
   has_neighbors :embedding, normalize: true
 
-  validates :question, presence: true
+  validates :question, presence: true, length: { maximum: 255 }
   validates :answer, presence: true
 
   before_validation :ensure_account
diff --git a/spec/enterprise/controllers/api/v1/accounts/captain/assistant_responses_controller_spec.rb b/spec/enterprise/controllers/api/v1/accounts/captain/assistant_responses_controller_spec.rb
index 038ee5e8d..4a26d4aac 100644
--- a/spec/enterprise/controllers/api/v1/accounts/captain/assistant_responses_controller_spec.rb
+++ b/spec/enterprise/controllers/api/v1/accounts/captain/assistant_responses_controller_spec.rb
@@ -197,6 +197,22 @@ RSpec.describe 'Api::V1::Accounts::Captain::AssistantResponses', type: :request
 
         expect(response).to have_http_status(:unprocessable_entity)
       end
+
+      it 'returns unprocessable entity when question exceeds 255 characters' do
+        long_question = 'a' * 256
+        post "/api/v1/accounts/#{account.id}/captain/assistant_responses",
+             params: {
+               assistant_response: {
+                 question: long_question,
+                 answer: 'Test answer',
+                 assistant_id: assistant.id
+               }
+             },
+             headers: admin.create_new_auth_token,
+             as: :json
+
+        expect(response).to have_http_status(:unprocessable_entity)
+      end
     end
   end