diff --git a/.github/workflows/auto-assign-pr.yml b/.github/workflows/auto-assign-pr.yml
new file mode 100644
index 000000000..98df89707
--- /dev/null
+++ b/.github/workflows/auto-assign-pr.yml
@@ -0,0 +1,28 @@
+name: Auto-assign PR to Author
+
+on:
+  pull_request:
+    types: [opened]
+
+jobs:
+  auto-assign:
+    runs-on: ubuntu-latest
+    permissions:
+      pull-requests: write
+    steps:
+      - name: Auto-assign PR to author
+        uses: actions/github-script@v7
+        with:
+          script: |
+            const { owner, repo } = context.repo;
+            const pull_number = context.payload.pull_request.number;
+            const author = context.payload.pull_request.user.login;
+            
+            await github.rest.issues.addAssignees({
+              owner,
+              repo,
+              issue_number: pull_number,
+              assignees: [author]
+            });
+            
+            console.log(`Assigned PR #${pull_number} to ${author}`);
\ No newline at end of file
diff --git a/app/javascript/dashboard/components-next/breadcrumb/Breadcrumb.vue b/app/javascript/dashboard/components-next/breadcrumb/Breadcrumb.vue
index 8ca325607..8a1b26e90 100644
--- a/app/javascript/dashboard/components-next/breadcrumb/Breadcrumb.vue
+++ b/app/javascript/dashboard/components-next/breadcrumb/Breadcrumb.vue
@@ -15,8 +15,8 @@ const emit = defineEmits(['click']);
 
 const { t } = useI18n();
 
-const onClick = event => {
-  emit('click', event);
+const onClick = (item, index) => {
+  emit('click', item, index);
 };
 </script>
 
@@ -24,22 +24,25 @@ const onClick = event => {
   <nav :aria-label="t('BREADCRUMB.ARIA_LABEL')" class="flex items-center h-8">
     <ol class="flex items-center mb-0">
       <li v-for="(item, index) in items" :key="index" class="flex items-center">
+        <Icon
+          v-if="index > 0"
+          icon="i-lucide-chevron-right"
+          class="flex-shrink-0 mx-2 size-4 text-n-slate-11 dark:text-n-slate-11"
+        />
+
+        <!-- Render as button for all except the last item -->
         <button
-          v-if="index === 0"
+          v-if="index !== items.length - 1"
           class="inline-flex items-center justify-center min-w-0 gap-2 p-0 text-sm font-medium transition-all duration-200 ease-in-out border-0 rounded-lg text-n-slate-11 hover:text-n-slate-12 outline-transparent max-w-56"
-          @click="onClick"
+          @click="onClick(item, index)"
         >
           <span class="min-w-0 truncate">{{ item.label }}</span>
         </button>
-        <template v-else>
-          <Icon
-            icon="i-lucide-chevron-right"
-            class="flex-shrink-0 mx-2 size-4 text-n-slate-11 dark:text-n-slate-11"
-          />
-          <span class="text-sm truncate text-n-slate-12 max-w-56">
-            {{ item.emoji ? item.emoji : '' }} {{ item.label }}
-          </span>
-        </template>
+
+        <!-- The last breadcrumb item is plain text -->
+        <span v-else class="text-sm truncate text-n-slate-12 max-w-56">
+          {{ item.emoji ? item.emoji : '' }} {{ item.label }}
+        </span>
       </li>
     </ol>
   </nav>
diff --git a/app/javascript/dashboard/components-next/captain/SettingsPageLayout.vue b/app/javascript/dashboard/components-next/captain/SettingsPageLayout.vue
new file mode 100644
index 000000000..4a48794b3
--- /dev/null
+++ b/app/javascript/dashboard/components-next/captain/SettingsPageLayout.vue
@@ -0,0 +1,91 @@
+<script setup>
+import { useRouter } from 'vue-router';
+import PaginationFooter from 'dashboard/components-next/pagination/PaginationFooter.vue';
+import Spinner from 'dashboard/components-next/spinner/Spinner.vue';
+import Breadcrumb from 'dashboard/components-next/breadcrumb/Breadcrumb.vue';
+
+defineProps({
+  isFetching: {
+    type: Boolean,
+    default: false,
+  },
+  isEmpty: {
+    type: Boolean,
+    default: false,
+  },
+  currentPage: {
+    type: Number,
+    default: 1,
+  },
+  totalCount: {
+    type: Number,
+    default: 100,
+  },
+  itemsPerPage: {
+    type: Number,
+    default: 25,
+  },
+  showPaginationFooter: {
+    type: Boolean,
+    default: false,
+  },
+  breadcrumbItems: {
+    type: Array,
+    default: () => [],
+  },
+});
+
+const emit = defineEmits(['update:currentPage']);
+
+const router = useRouter();
+
+const handlePageChange = event => {
+  emit('update:currentPage', event);
+};
+
+const handleBreadcrumbClick = item => {
+  router.push({
+    name: item.routeName,
+  });
+};
+</script>
+
+<template>
+  <section
+    class="my-4 px-10 flex flex-col w-full h-screen overflow-y-auto bg-n-background"
+  >
+    <div class="max-w-[60rem] mx-auto flex flex-col w-full h-full">
+      <header class="mb-7 sticky top-0 z-10 bg-n-background">
+        <Breadcrumb :items="breadcrumbItems" @click="handleBreadcrumbClick" />
+      </header>
+      <main class="flex gap-16 w-full flex-1 pb-16">
+        <section
+          v-if="$slots.body || $slots.emptyState || isFetching"
+          class="flex flex-col w-full"
+        >
+          <div
+            v-if="isFetching"
+            class="flex items-center justify-center py-10 text-n-slate-11"
+          >
+            <Spinner />
+          </div>
+          <div v-else-if="isEmpty">
+            <slot name="emptyState" />
+          </div>
+          <slot v-else name="body" />
+        </section>
+        <section v-if="$slots.controls" class="flex w-full">
+          <slot name="controls" />
+        </section>
+      </main>
+      <footer v-if="showPaginationFooter" class="sticky bottom-0 z-10 pb-4">
+        <PaginationFooter
+          :current-page="currentPage"
+          :total-items="totalCount"
+          :items-per-page="itemsPerPage"
+          @update:current-page="handlePageChange"
+        />
+      </footer>
+    </div>
+  </section>
+</template>
diff --git a/app/javascript/dashboard/components-next/captain/assistant/ResponseCard.vue b/app/javascript/dashboard/components-next/captain/assistant/ResponseCard.vue
index 7879411c8..a924ca228 100644
--- a/app/javascript/dashboard/components-next/captain/assistant/ResponseCard.vue
+++ b/app/javascript/dashboard/components-next/captain/assistant/ResponseCard.vue
@@ -55,6 +55,10 @@ const props = defineProps({
     type: Boolean,
     default: false,
   },
+  showMenu: {
+    type: Boolean,
+    default: true,
+  },
 });
 
 const emit = defineEmits(['action', 'navigate', 'select', 'hover']);
@@ -130,7 +134,7 @@ const handleDocumentableClick = () => {
       <span class="text-base text-n-slate-12 line-clamp-1">
         {{ question }}
       </span>
-      <div v-if="!compact" class="flex items-center gap-2">
+      <div v-if="!compact && showMenu" class="flex items-center gap-2">
         <Policy
           v-on-clickaway="() => toggleDropdown(false)"
           :permissions="['administrator']"
diff --git a/app/javascript/dashboard/components-next/captain/pageComponents/assistant/settings/AssistantBasicSettingsForm.vue b/app/javascript/dashboard/components-next/captain/pageComponents/assistant/settings/AssistantBasicSettingsForm.vue
new file mode 100644
index 000000000..236791793
--- /dev/null
+++ b/app/javascript/dashboard/components-next/captain/pageComponents/assistant/settings/AssistantBasicSettingsForm.vue
@@ -0,0 +1,151 @@
+<script setup>
+import { reactive, computed, watch } from 'vue';
+import { useI18n } from 'vue-i18n';
+import { useVuelidate } from '@vuelidate/core';
+import { required, minLength } from '@vuelidate/validators';
+
+import Input from 'dashboard/components-next/input/Input.vue';
+import Button from 'dashboard/components-next/button/Button.vue';
+import Editor from 'dashboard/components-next/Editor/Editor.vue';
+
+const props = defineProps({
+  assistant: {
+    type: Object,
+    default: () => ({}),
+  },
+});
+
+const emit = defineEmits(['submit']);
+
+const { t } = useI18n();
+
+const initialState = {
+  name: '',
+  description: '',
+  productName: '',
+  features: {
+    conversationFaqs: false,
+    memories: false,
+  },
+};
+
+const state = reactive({ ...initialState });
+
+const validationRules = {
+  name: { required, minLength: minLength(1) },
+  description: { required, minLength: minLength(1) },
+  productName: { required, minLength: minLength(1) },
+};
+
+const v$ = useVuelidate(validationRules, state);
+
+const getErrorMessage = field => {
+  return v$.value[field].$error ? v$.value[field].$errors[0].$message : '';
+};
+
+const formErrors = computed(() => ({
+  name: getErrorMessage('name'),
+  description: getErrorMessage('description'),
+  productName: getErrorMessage('productName'),
+}));
+
+const updateStateFromAssistant = assistant => {
+  const { config = {} } = assistant;
+  state.name = assistant.name;
+  state.description = assistant.description;
+  state.productName = config.product_name;
+  state.features = {
+    conversationFaqs: config.feature_faq || false,
+    memories: config.feature_memory || false,
+  };
+};
+
+const handleBasicInfoUpdate = async () => {
+  const result = await Promise.all([
+    v$.value.name.$validate(),
+    v$.value.description.$validate(),
+    v$.value.productName.$validate(),
+  ]).then(results => results.every(Boolean));
+  if (!result) return;
+
+  const payload = {
+    name: state.name,
+    description: state.description,
+    config: {
+      ...props.assistant.config,
+      product_name: state.productName,
+      feature_faq: state.features.conversationFaqs,
+      feature_memory: state.features.memories,
+    },
+  };
+
+  emit('submit', payload);
+};
+
+watch(
+  () => props.assistant,
+  newAssistant => {
+    if (newAssistant) updateStateFromAssistant(newAssistant);
+  },
+  { immediate: true }
+);
+</script>
+
+<template>
+  <div class="flex flex-col gap-6">
+    <Input
+      v-model="state.name"
+      :label="t('CAPTAIN.ASSISTANTS.FORM.NAME.LABEL')"
+      :placeholder="t('CAPTAIN.ASSISTANTS.FORM.NAME.PLACEHOLDER')"
+      :message="formErrors.name"
+      :message-type="formErrors.name ? 'error' : 'info'"
+    />
+
+    <Input
+      v-model="state.productName"
+      :label="t('CAPTAIN.ASSISTANTS.FORM.PRODUCT_NAME.LABEL')"
+      :placeholder="t('CAPTAIN.ASSISTANTS.FORM.PRODUCT_NAME.PLACEHOLDER')"
+      :message="formErrors.productName"
+      :message-type="formErrors.productName ? 'error' : 'info'"
+    />
+
+    <Editor
+      v-model="state.description"
+      :label="t('CAPTAIN.ASSISTANTS.FORM.DESCRIPTION.LABEL')"
+      :placeholder="t('CAPTAIN.ASSISTANTS.FORM.DESCRIPTION.PLACEHOLDER')"
+      :message="formErrors.description"
+      :message-type="formErrors.description ? 'error' : 'info'"
+    />
+
+    <div class="flex flex-col gap-2">
+      <label class="text-sm font-medium text-n-slate-12">
+        {{ t('CAPTAIN.ASSISTANTS.FORM.FEATURES.TITLE') }}
+      </label>
+      <div class="flex flex-col gap-2">
+        <label class="flex items-center gap-2">
+          <input
+            v-model="state.features.conversationFaqs"
+            type="checkbox"
+            class="form-checkbox"
+          />
+          {{ t('CAPTAIN.ASSISTANTS.FORM.FEATURES.ALLOW_CONVERSATION_FAQS') }}
+        </label>
+        <label class="flex items-center gap-2">
+          <input
+            v-model="state.features.memories"
+            type="checkbox"
+            class="form-checkbox"
+          />
+          {{ t('CAPTAIN.ASSISTANTS.FORM.FEATURES.ALLOW_MEMORIES') }}
+        </label>
+      </div>
+    </div>
+
+    <div>
+      <Button
+        :label="t('CAPTAIN.ASSISTANTS.FORM.UPDATE')"
+        @click="handleBasicInfoUpdate"
+      />
+    </div>
+  </div>
+</template>
diff --git a/app/javascript/dashboard/components-next/captain/pageComponents/assistant/settings/AssistantControlItems.vue b/app/javascript/dashboard/components-next/captain/pageComponents/assistant/settings/AssistantControlItems.vue
new file mode 100644
index 000000000..2bbede899
--- /dev/null
+++ b/app/javascript/dashboard/components-next/captain/pageComponents/assistant/settings/AssistantControlItems.vue
@@ -0,0 +1,43 @@
+<script setup>
+import { useRouter } from 'vue-router';
+import Button from 'dashboard/components-next/button/Button.vue';
+
+defineProps({
+  controlItem: {
+    type: Object,
+    default: () => ({}),
+  },
+});
+
+const router = useRouter();
+
+const onClick = name => {
+  router.push({ name });
+};
+</script>
+
+<template>
+  <div
+    :key="controlItem.name"
+    class="pt-3 ltr:pl-4 rtl:pr-4 ltr:pr-2 rtl:pl-2 pb-5 gap-2 flex flex-col w-full shadow outline-1 outline outline-n-container rounded-2xl bg-n-solid-2 cursor-pointer"
+    @click="onClick(controlItem.routeName)"
+  >
+    <div class="flex items-center justify-between w-full gap-1 h-8">
+      <span class="text-sm font-medium text-n-slate-12 line-clamp-1">
+        {{ controlItem.name }}
+      </span>
+      <div class="flex items-center gap-2">
+        <Button
+          icon="i-lucide-chevron-right"
+          slate
+          ghost
+          xs
+          @click="onClick(controlItem.routeName)"
+        />
+      </div>
+    </div>
+    <span class="text-n-slate-11 text-sm leading-[21px] line-clamp-5">
+      {{ controlItem.description }}
+    </span>
+  </div>
+</template>
diff --git a/app/javascript/dashboard/components-next/captain/pageComponents/assistant/settings/AssistantSystemSettingsForm.vue b/app/javascript/dashboard/components-next/captain/pageComponents/assistant/settings/AssistantSystemSettingsForm.vue
new file mode 100644
index 000000000..b86bdacb4
--- /dev/null
+++ b/app/javascript/dashboard/components-next/captain/pageComponents/assistant/settings/AssistantSystemSettingsForm.vue
@@ -0,0 +1,125 @@
+<script setup>
+import { reactive, computed, watch } from 'vue';
+import { useI18n } from 'vue-i18n';
+import { useVuelidate } from '@vuelidate/core';
+import { minLength } from '@vuelidate/validators';
+
+import Button from 'dashboard/components-next/button/Button.vue';
+import Editor from 'dashboard/components-next/Editor/Editor.vue';
+
+const props = defineProps({
+  assistant: {
+    type: Object,
+    default: () => ({}),
+  },
+});
+
+const emit = defineEmits(['submit']);
+
+const { t } = useI18n();
+
+const initialState = {
+  handoffMessage: '',
+  resolutionMessage: '',
+  temperature: 1,
+};
+
+const state = reactive({ ...initialState });
+
+const validationRules = {
+  handoffMessage: { minLength: minLength(1) },
+  resolutionMessage: { minLength: minLength(1) },
+};
+
+const v$ = useVuelidate(validationRules, state);
+
+const getErrorMessage = field => {
+  return v$.value[field].$error ? v$.value[field].$errors[0].$message : '';
+};
+
+const formErrors = computed(() => ({
+  handoffMessage: getErrorMessage('handoffMessage'),
+  resolutionMessage: getErrorMessage('resolutionMessage'),
+}));
+
+const updateStateFromAssistant = assistant => {
+  const { config = {} } = assistant;
+  state.handoffMessage = config.handoff_message;
+  state.resolutionMessage = config.resolution_message;
+  state.temperature = config.temperature || 1;
+};
+
+const handleSystemMessagesUpdate = async () => {
+  const result = await Promise.all([
+    v$.value.handoffMessage.$validate(),
+    v$.value.resolutionMessage.$validate(),
+  ]).then(results => results.every(Boolean));
+  if (!result) return;
+
+  const payload = {
+    config: {
+      ...props.assistant.config,
+      handoff_message: state.handoffMessage,
+      resolution_message: state.resolutionMessage,
+      temperature: state.temperature || 1,
+    },
+  };
+
+  emit('submit', payload);
+};
+
+watch(
+  () => props.assistant,
+  newAssistant => {
+    if (newAssistant) updateStateFromAssistant(newAssistant);
+  },
+  { immediate: true }
+);
+</script>
+
+<template>
+  <div class="flex flex-col gap-6">
+    <Editor
+      v-model="state.handoffMessage"
+      :label="t('CAPTAIN.ASSISTANTS.FORM.HANDOFF_MESSAGE.LABEL')"
+      :placeholder="t('CAPTAIN.ASSISTANTS.FORM.HANDOFF_MESSAGE.PLACEHOLDER')"
+      :message="formErrors.handoffMessage"
+      :message-type="formErrors.handoffMessage ? 'error' : 'info'"
+    />
+
+    <Editor
+      v-model="state.resolutionMessage"
+      :label="t('CAPTAIN.ASSISTANTS.FORM.RESOLUTION_MESSAGE.LABEL')"
+      :placeholder="t('CAPTAIN.ASSISTANTS.FORM.RESOLUTION_MESSAGE.PLACEHOLDER')"
+      :message="formErrors.resolutionMessage"
+      :message-type="formErrors.resolutionMessage ? 'error' : 'info'"
+    />
+
+    <div class="flex flex-col gap-2">
+      <label class="text-sm font-medium text-n-slate-12">
+        {{ t('CAPTAIN.ASSISTANTS.FORM.TEMPERATURE.LABEL') }}
+      </label>
+      <div class="flex items-center gap-4">
+        <input
+          v-model="state.temperature"
+          type="range"
+          min="0"
+          max="1"
+          step="0.1"
+          class="w-full"
+        />
+        <span class="text-sm text-n-slate-12">{{ state.temperature }}</span>
+      </div>
+      <p class="text-sm text-n-slate-11 italic">
+        {{ t('CAPTAIN.ASSISTANTS.FORM.TEMPERATURE.DESCRIPTION') }}
+      </p>
+    </div>
+
+    <div>
+      <Button
+        :label="t('CAPTAIN.ASSISTANTS.FORM.UPDATE')"
+        @click="handleSystemMessagesUpdate"
+      />
+    </div>
+  </div>
+</template>
diff --git a/app/javascript/dashboard/featureFlags.js b/app/javascript/dashboard/featureFlags.js
index 1a6ada9fa..98234539b 100644
--- a/app/javascript/dashboard/featureFlags.js
+++ b/app/javascript/dashboard/featureFlags.js
@@ -36,6 +36,7 @@ export const FEATURE_FLAGS = {
   REPORT_V4: 'report_v4',
   CHANNEL_INSTAGRAM: 'channel_instagram',
   CONTACT_CHATWOOT_SUPPORT_TEAM: 'contact_chatwoot_support_team',
+  CAPTAIN_V2: 'captain_integration_v2',
 };
 
 export const PREMIUM_FEATURES = [
@@ -44,4 +45,5 @@ export const PREMIUM_FEATURES = [
   FEATURE_FLAGS.CUSTOM_ROLES,
   FEATURE_FLAGS.AUDIT_LOGS,
   FEATURE_FLAGS.HELP_CENTER,
+  FEATURE_FLAGS.CAPTAIN_V2,
 ];
diff --git a/app/javascript/dashboard/i18n/locale/en/integrations.json b/app/javascript/dashboard/i18n/locale/en/integrations.json
index b3e091722..fc8cff644 100644
--- a/app/javascript/dashboard/i18n/locale/en/integrations.json
+++ b/app/javascript/dashboard/i18n/locale/en/integrations.json
@@ -478,6 +478,37 @@
         "ERROR_MESSAGE": "There was an error updating the assistant, please try again.",
         "NOT_FOUND": "Could not find the assistant. Please try again."
       },
+      "SETTINGS": {
+        "BREADCRUMB": {
+          "ASSISTANT": "Assistant"
+        },
+        "BASIC_SETTINGS": {
+          "TITLE": "Basic settings",
+          "DESCRIPTION": "Customize what the assistant says when ending a conversation or transferring to a human."
+        },
+        "SYSTEM_SETTINGS": {
+          "TITLE": "System settings",
+          "DESCRIPTION": "Customize what the assistant says when ending a conversation or transferring to a human."
+        },
+        "CONTROL_ITEMS": {
+          "TITLE": "The Fun Stuff",
+          "DESCRIPTION": "Add more control to the assistant. (a bit more visual like a story : Query guardrail → scenarios → output) Nudges user to actually utilise these.",
+          "OPTIONS": {
+            "GUARDRAILS": {
+              "TITLE": "Guardrails",
+              "DESCRIPTION": "Keeps things on track—only the kinds of questions you want your assistant to answer, nothing off-limits or off-topic."
+            },
+            "SCENARIOS": {
+              "TITLE": "Scenarios",
+              "DESCRIPTION": "Give your assistant some context—like “what to do when a user is stuck,” or “how to act during a refund request.”"
+            },
+            "RESPONSE_GUIDELINES": {
+              "TITLE": "Response guidelines",
+              "DESCRIPTION": "The vibe and structure of your assistant’s replies—clear and friendly? Short and snappy? Detailed and formal?"
+            }
+          }
+        }
+      },
       "OPTIONS": {
         "EDIT_ASSISTANT": "Edit Assistant",
         "DELETE_ASSISTANT": "Delete Assistant",
diff --git a/app/javascript/dashboard/routes/dashboard/captain/assistants/Edit.vue b/app/javascript/dashboard/routes/dashboard/captain/assistants/Edit.vue
index 8b64e2663..2b2506934 100644
--- a/app/javascript/dashboard/routes/dashboard/captain/assistants/Edit.vue
+++ b/app/javascript/dashboard/routes/dashboard/captain/assistants/Edit.vue
@@ -5,10 +5,13 @@ import { useStore } from 'dashboard/composables/store';
 import { useMapGetter } from 'dashboard/composables/store';
 import { useAlert } from 'dashboard/composables';
 import { useI18n } from 'vue-i18n';
+import { FEATURE_FLAGS } from 'dashboard/featureFlags';
 import PageLayout from 'dashboard/components-next/captain/PageLayout.vue';
 import EditAssistantForm from '../../../../components-next/captain/pageComponents/assistant/EditAssistantForm.vue';
 import AssistantPlayground from 'dashboard/components-next/captain/assistant/AssistantPlayground.vue';
 
+import AssistantSettings from 'dashboard/routes/dashboard/captain/assistants/settings/Settings.vue';
+
 const route = useRoute();
 const store = useStore();
 const { t } = useI18n();
@@ -19,6 +22,16 @@ const assistant = computed(() =>
   store.getters['captainAssistants/getRecord'](Number(assistantId))
 );
 
+const isFeatureEnabledonAccount = useMapGetter(
+  'accounts/isFeatureEnabledonAccount'
+);
+const currentAccountId = useMapGetter('getCurrentAccountId');
+
+const isCaptainV2Enabled = isFeatureEnabledonAccount.value(
+  currentAccountId.value,
+  FEATURE_FLAGS.CAPTAIN_V2
+);
+
 const isAssistantAvailable = computed(() => !!assistant.value?.id);
 
 const handleSubmit = async updatedAssistant => {
@@ -36,14 +49,16 @@ const handleSubmit = async updatedAssistant => {
 };
 
 onMounted(() => {
-  if (!isAssistantAvailable.value) {
+  if (!isAssistantAvailable.value || !isCaptainV2Enabled) {
     store.dispatch('captainAssistants/show', assistantId);
   }
 });
 </script>
 
 <template>
+  <AssistantSettings v-if="isCaptainV2Enabled" />
   <PageLayout
+    v-else
     :header-title="assistant?.name"
     :show-pagination-footer="false"
     :is-fetching="isFetching"
diff --git a/app/javascript/dashboard/routes/dashboard/captain/assistants/settings/Settings.vue b/app/javascript/dashboard/routes/dashboard/captain/assistants/settings/Settings.vue
new file mode 100644
index 000000000..c39d685cc
--- /dev/null
+++ b/app/javascript/dashboard/routes/dashboard/captain/assistants/settings/Settings.vue
@@ -0,0 +1,154 @@
+<script setup>
+import { computed, onMounted } from 'vue';
+import { useRoute } from 'vue-router';
+import { useI18n } from 'vue-i18n';
+import { useAlert } from 'dashboard/composables';
+import { useStore } from 'dashboard/composables/store';
+import { useMapGetter } from 'dashboard/composables/store';
+import SettingsPageLayout from 'dashboard/components-next/captain/SettingsPageLayout.vue';
+import SettingsHeader from 'dashboard/components-next/captain/pageComponents/settings/SettingsHeader.vue';
+import AssistantBasicSettingsForm from 'dashboard/components-next/captain/pageComponents/assistant/settings/AssistantBasicSettingsForm.vue';
+import AssistantSystemSettingsForm from 'dashboard/components-next/captain/pageComponents/assistant/settings/AssistantSystemSettingsForm.vue';
+import AssistantControlItems from 'dashboard/components-next/captain/pageComponents/assistant/settings/AssistantControlItems.vue';
+
+const { t } = useI18n();
+const route = useRoute();
+const store = useStore();
+const assistantId = route.params.assistantId;
+const uiFlags = useMapGetter('captainAssistants/getUIFlags');
+const isFetching = computed(() => uiFlags.value.fetchingItem);
+const assistant = computed(() =>
+  store.getters['captainAssistants/getRecord'](Number(assistantId))
+);
+
+const isAssistantAvailable = computed(() => !!assistant.value?.id);
+
+const controlItems = computed(() => {
+  return [
+    {
+      name: t(
+        'CAPTAIN.ASSISTANTS.SETTINGS.CONTROL_ITEMS.OPTIONS.GUARDRAILS.TITLE'
+      ),
+      description: t(
+        'CAPTAIN.ASSISTANTS.SETTINGS.CONTROL_ITEMS.OPTIONS.GUARDRAILS.DESCRIPTION'
+      ),
+      // routeName: 'captain_assistants_guardrails_index',
+    },
+    {
+      name: t(
+        'CAPTAIN.ASSISTANTS.SETTINGS.CONTROL_ITEMS.OPTIONS.SCENARIOS.TITLE'
+      ),
+      description: t(
+        'CAPTAIN.ASSISTANTS.SETTINGS.CONTROL_ITEMS.OPTIONS.SCENARIOS.DESCRIPTION'
+      ),
+      // routeName: 'captain_assistants_scenarios_index',
+    },
+    {
+      name: t(
+        'CAPTAIN.ASSISTANTS.SETTINGS.CONTROL_ITEMS.OPTIONS.RESPONSE_GUIDELINES.TITLE'
+      ),
+      description: t(
+        'CAPTAIN.ASSISTANTS.SETTINGS.CONTROL_ITEMS.OPTIONS.RESPONSE_GUIDELINES.DESCRIPTION'
+      ),
+      // routeName: 'captain_assistants_guidelines_index',
+    },
+  ];
+});
+
+const breadcrumbItems = computed(() => {
+  const activeControlItem = controlItems.value?.find(
+    item => item.routeName === route.name
+  );
+
+  return [
+    {
+      label: t('CAPTAIN.ASSISTANTS.SETTINGS.BREADCRUMB.ASSISTANT'),
+      routeName: 'captain_assistants_index',
+    },
+    { label: assistant.value?.name, routeName: 'captain_assistants_edit' },
+    ...(activeControlItem
+      ? [
+          {
+            label: activeControlItem.name,
+            routeName: activeControlItem.routeName,
+          },
+        ]
+      : []),
+  ];
+});
+
+const handleSubmit = async updatedAssistant => {
+  try {
+    await store.dispatch('captainAssistants/update', {
+      id: assistantId,
+      ...updatedAssistant,
+    });
+    useAlert(t('CAPTAIN.ASSISTANTS.EDIT.SUCCESS_MESSAGE'));
+  } catch (error) {
+    const errorMessage =
+      error?.message || t('CAPTAIN.ASSISTANTS.EDIT.ERROR_MESSAGE');
+    useAlert(errorMessage);
+  }
+};
+
+onMounted(() => {
+  if (!isAssistantAvailable.value) {
+    store.dispatch('captainAssistants/show', assistantId);
+  }
+});
+</script>
+
+<template>
+  <SettingsPageLayout
+    :breadcrumb-items="breadcrumbItems"
+    :is-fetching="isFetching"
+    class="[&>div]:max-w-[80rem]"
+  >
+    <template #body>
+      <div class="flex flex-col gap-6">
+        <div class="flex flex-col gap-6">
+          <SettingsHeader
+            :heading="t('CAPTAIN.ASSISTANTS.SETTINGS.BASIC_SETTINGS.TITLE')"
+            :description="
+              t('CAPTAIN.ASSISTANTS.SETTINGS.BASIC_SETTINGS.DESCRIPTION')
+            "
+          />
+          <AssistantBasicSettingsForm
+            :assistant="assistant"
+            @submit="handleSubmit"
+          />
+        </div>
+        <span class="h-px w-full bg-n-weak mt-2" />
+        <div class="flex flex-col gap-6">
+          <SettingsHeader
+            :heading="t('CAPTAIN.ASSISTANTS.SETTINGS.SYSTEM_SETTINGS.TITLE')"
+            :description="
+              t('CAPTAIN.ASSISTANTS.SETTINGS.SYSTEM_SETTINGS.DESCRIPTION')
+            "
+          />
+          <AssistantSystemSettingsForm
+            :assistant="assistant"
+            @submit="handleSubmit"
+          />
+        </div>
+      </div>
+    </template>
+    <template #controls>
+      <div class="flex flex-col gap-6">
+        <SettingsHeader
+          :heading="t('CAPTAIN.ASSISTANTS.SETTINGS.CONTROL_ITEMS.TITLE')"
+          :description="
+            t('CAPTAIN.ASSISTANTS.SETTINGS.CONTROL_ITEMS.DESCRIPTION')
+          "
+        />
+        <div class="flex flex-col gap-6">
+          <AssistantControlItems
+            v-for="item in controlItems"
+            :key="item.name"
+            :control-item="item"
+          />
+        </div>
+      </div>
+    </template>
+  </SettingsPageLayout>
+</template>
diff --git a/app/javascript/dashboard/routes/dashboard/captain/captain.routes.js b/app/javascript/dashboard/routes/dashboard/captain/captain.routes.js
index 17afeca14..7294a7433 100644
--- a/app/javascript/dashboard/routes/dashboard/captain/captain.routes.js
+++ b/app/javascript/dashboard/routes/dashboard/captain/captain.routes.js
@@ -3,6 +3,7 @@ import { INSTALLATION_TYPES } from 'dashboard/constants/installationTypes';
 import { frontendURL } from '../../../helper/URLHelper';
 import AssistantIndex from './assistants/Index.vue';
 import AssistantEdit from './assistants/Edit.vue';
+// import AssistantSettings from './assistants/settings/Settings.vue';
 import AssistantInboxesIndex from './assistants/inboxes/Index.vue';
 import DocumentsIndex from './documents/Index.vue';
 import ResponsesIndex from './responses/Index.vue';
diff --git a/app/javascript/dashboard/routes/dashboard/captain/responses/Index.vue b/app/javascript/dashboard/routes/dashboard/captain/responses/Index.vue
index e771e72ed..85e7f1ed0 100644
--- a/app/javascript/dashboard/routes/dashboard/captain/responses/Index.vue
+++ b/app/javascript/dashboard/routes/dashboard/captain/responses/Index.vue
@@ -55,6 +55,12 @@ const statusOptions = computed(() =>
   }))
 );
 
+const filteredResponses = computed(() => {
+  return selectedStatus.value === 'pending'
+    ? responses.value.filter(r => r.status === 'pending')
+    : responses.value;
+});
+
 const selectedStatusLabel = computed(() => {
   const status = statusOptions.value.find(
     option => option.value === selectedStatus.value
@@ -94,7 +100,9 @@ const handleEdit = () => {
 };
 
 const handleAction = ({ action, id }) => {
-  selectedResponse.value = responses.value.find(response => id === response.id);
+  selectedResponse.value = filteredResponses.value.find(
+    response => id === response.id
+  );
   nextTick(() => {
     if (action === 'delete') {
       handleDelete();
@@ -139,7 +147,7 @@ const hoveredCard = ref(null);
 
 const bulkSelectionState = computed(() => {
   const selectedCount = bulkSelectedIds.value.size;
-  const totalCount = responses.value?.length || 0;
+  const totalCount = filteredResponses.value?.length || 0;
 
   return {
     hasSelected: selectedCount > 0,
@@ -152,13 +160,13 @@ const bulkCheckbox = computed({
   get: () => bulkSelectionState.value.allSelected,
   set: value => {
     bulkSelectedIds.value = value
-      ? new Set(responses.value.map(r => r.id))
+      ? new Set(filteredResponses.value.map(r => r.id))
       : new Set();
   },
 });
 
 const buildSelectedCountLabel = computed(() => {
-  const count = responses.value?.length || 0;
+  const count = filteredResponses.value?.length || 0;
   return bulkSelectionState.value.allSelected
     ? t('CAPTAIN.RESPONSES.UNSELECT_ALL', { count })
     : t('CAPTAIN.RESPONSES.SELECT_ALL', { count });
@@ -174,6 +182,24 @@ const handleCardSelect = id => {
   bulkSelectedIds.value = selected;
 };
 
+const fetchResponseAfterBulkAction = () => {
+  const hasNoResponsesLeft = filteredResponses.value?.length === 0;
+  const currentPage = responseMeta.value?.page;
+
+  if (hasNoResponsesLeft) {
+    // Page is now empty after bulk action.
+    // Fetch the previous page if not already on the first page.
+    const pageToFetch = currentPage > 1 ? currentPage - 1 : currentPage;
+    fetchResponses(pageToFetch);
+  } else {
+    // Page still has responses left, re-fetch the same page.
+    fetchResponses(currentPage);
+  }
+
+  // Clear selection
+  bulkSelectedIds.value = new Set();
+};
+
 const handleBulkApprove = async () => {
   try {
     await store.dispatch(
@@ -181,8 +207,7 @@ const handleBulkApprove = async () => {
       Array.from(bulkSelectedIds.value)
     );
 
-    // Clear selection
-    bulkSelectedIds.value = new Set();
+    fetchResponseAfterBulkAction();
     useAlert(t('CAPTAIN.RESPONSES.BULK_APPROVE.SUCCESS_MESSAGE'));
   } catch (error) {
     useAlert(
@@ -205,23 +230,13 @@ const onPageChange = page => {
 };
 
 const onDeleteSuccess = () => {
-  if (responses.value?.length === 0 && responseMeta.value?.page > 1) {
+  if (filteredResponses.value?.length === 0 && responseMeta.value?.page > 1) {
     onPageChange(responseMeta.value.page - 1);
   }
 };
 
 const onBulkDeleteSuccess = () => {
-  // Only fetch if no records left
-  if (responses.value?.length === 0) {
-    const page =
-      responseMeta.value?.page > 1
-        ? responseMeta.value.page - 1
-        : responseMeta.value.page;
-    fetchResponses(page);
-  }
-
-  // Clear selection
-  bulkSelectedIds.value = new Set();
+  fetchResponseAfterBulkAction();
 };
 
 const handleStatusFilterChange = ({ value }) => {
@@ -249,8 +264,8 @@ onMounted(() => {
     :header-title="$t('CAPTAIN.RESPONSES.HEADER')"
     :button-label="$t('CAPTAIN.RESPONSES.ADD_NEW')"
     :is-fetching="isFetching"
-    :is-empty="!responses.length"
-    :show-pagination-footer="!isFetching && !!responses.length"
+    :is-empty="!filteredResponses.length"
+    :show-pagination-footer="!isFetching && !!filteredResponses.length"
     :feature-flag="FEATURE_FLAGS.CAPTAIN"
     @update:current-page="onPageChange"
     @click="handleCreate"
@@ -368,7 +383,7 @@ onMounted(() => {
 
       <div class="flex flex-col gap-4">
         <ResponseCard
-          v-for="response in responses"
+          v-for="response in filteredResponses"
           :id="response.id"
           :key="response.id"
           :question="response.question"
@@ -380,6 +395,7 @@ onMounted(() => {
           :updated-at="response.updated_at"
           :is-selected="bulkSelectedIds.has(response.id)"
           :selectable="hoveredCard === response.id || bulkSelectedIds.size > 0"
+          :show-menu="!bulkSelectedIds.has(response.id)"
           @action="handleAction"
           @navigate="handleNavigationAction"
           @select="handleCardSelect"
diff --git a/app/javascript/dashboard/routes/dashboard/settings/inbox/Index.vue b/app/javascript/dashboard/routes/dashboard/settings/inbox/Index.vue
index aae2263a7..c4cf5f5ad 100644
--- a/app/javascript/dashboard/routes/dashboard/settings/inbox/Index.vue
+++ b/app/javascript/dashboard/routes/dashboard/settings/inbox/Index.vue
@@ -1,12 +1,16 @@
 <script setup>
+import { computed, ref } from 'vue';
+import { useI18n } from 'vue-i18n';
 import { useAlert } from 'dashboard/composables';
 import Thumbnail from 'dashboard/components/widgets/Thumbnail.vue';
 import { useAdmin } from 'dashboard/composables/useAdmin';
 import SettingsLayout from '../SettingsLayout.vue';
 import BaseSettingsHeader from '../components/BaseSettingsHeader.vue';
-import { computed, ref } from 'vue';
-import { useI18n } from 'vue-i18n';
-import { useStoreGetters, useStore } from 'dashboard/composables/store';
+import {
+  useMapGetter,
+  useStoreGetters,
+  useStore,
+} from 'dashboard/composables/store';
 import ChannelName from './components/ChannelName.vue';
 import ChannelIcon from 'next/icon/ChannelIcon.vue';
 import Button from 'dashboard/components-next/button/Button.vue';
@@ -19,7 +23,12 @@ const { isAdmin } = useAdmin();
 const showDeletePopup = ref(false);
 const selectedInbox = ref({});
 
-const inboxesList = computed(() => getters['inboxes/getInboxes'].value);
+const inboxes = useMapGetter('inboxes/getInboxes');
+
+const inboxesList = computed(() => {
+  return inboxes.value?.slice().sort((a, b) => a.name.localeCompare(b.name));
+});
+
 const uiFlags = computed(() => getters['inboxes/getUIFlags'].value);
 
 const deleteConfirmText = computed(
diff --git a/config/features.yml b/config/features.yml
index 5171b1c01..d41f705ad 100644
--- a/config/features.yml
+++ b/config/features.yml
@@ -176,3 +176,7 @@
 - name: notion_integration
   display_name: Notion Integration
   enabled: false
+- name: captain_integration_v2
+  display_name: Captain V2
+  enabled: false
+  premium: true
diff --git a/enterprise/app/controllers/api/v1/accounts/captain/assistants_controller.rb b/enterprise/app/controllers/api/v1/accounts/captain/assistants_controller.rb
index 913998f6c..47dc4bd59 100644
--- a/enterprise/app/controllers/api/v1/accounts/captain/assistants_controller.rb
+++ b/enterprise/app/controllers/api/v1/accounts/captain/assistants_controller.rb
@@ -25,8 +25,8 @@ class Api::V1::Accounts::Captain::AssistantsController < Api::V1::Accounts::Base
 
   def playground
     response = Captain::Llm::AssistantChatService.new(assistant: @assistant).generate_response(
-      params[:message_content],
-      message_history
+      additional_message: params[:message_content],
+      message_history: message_history
     )
 
     render json: response
diff --git a/enterprise/app/jobs/captain/conversation/response_builder_job.rb b/enterprise/app/jobs/captain/conversation/response_builder_job.rb
index f341a6e98..b207bd2a4 100644
--- a/enterprise/app/jobs/captain/conversation/response_builder_job.rb
+++ b/enterprise/app/jobs/captain/conversation/response_builder_job.rb
@@ -1,6 +1,7 @@
 class Captain::Conversation::ResponseBuilderJob < ApplicationJob
   MAX_MESSAGE_LENGTH = 10_000
-  retry_on ActiveStorage::FileNotFoundError, attempts: 3
+  retry_on ActiveStorage::FileNotFoundError, attempts: 3, wait: 2.seconds
+  retry_on Faraday::BadRequestError, attempts: 3, wait: 2.seconds
 
   def perform(conversation, assistant)
     @conversation = conversation
@@ -13,7 +14,7 @@ class Captain::Conversation::ResponseBuilderJob < ApplicationJob
       generate_and_process_response
     end
   rescue StandardError => e
-    raise e if e.is_a?(ActiveStorage::FileNotFoundError)
+    raise e if e.is_a?(ActiveStorage::FileNotFoundError) || e.is_a?(Faraday::BadRequestError)
 
     handle_error(e)
   ensure
@@ -26,8 +27,7 @@ class Captain::Conversation::ResponseBuilderJob < ApplicationJob
 
   def generate_and_process_response
     @response = Captain::Llm::AssistantChatService.new(assistant: @assistant).generate_response(
-      @conversation.messages.incoming.last.content,
-      collect_previous_messages
+      message_history: collect_previous_messages
     )
 
     return process_action('handoff') if handoff_requested?
@@ -43,39 +43,19 @@ class Captain::Conversation::ResponseBuilderJob < ApplicationJob
       .where(message_type: [:incoming, :outgoing])
       .where(private: false)
       .map do |message|
-        {
-          content: message_content(message),
-          role: determine_role(message)
-        }
-      end
-  end
-
-  def message_content(message)
-    return message.content if message.content.present?
-    return 'User has shared a message without content' unless message.attachments.any?
-
-    audio_transcriptions = extract_audio_transcriptions(message.attachments)
-    return audio_transcriptions if audio_transcriptions.present?
-
-    'User has shared an attachment'
-  end
-
-  def extract_audio_transcriptions(attachments)
-    audio_attachments = attachments.where(file_type: :audio)
-    return '' if audio_attachments.blank?
-
-    transcriptions = ''
-    audio_attachments.each do |attachment|
-      result = Messages::AudioTranscriptionService.new(attachment).perform
-      transcriptions += result[:transcriptions] if result[:success]
+      {
+        content: prepare_multimodal_message_content(message),
+        role: determine_role(message)
+      }
     end
-    transcriptions
   end
 
   def determine_role(message)
-    return 'system' if message.content.blank?
+    message.message_type == 'incoming' ? 'user' : 'assistant'
+  end
 
-    message.message_type == 'incoming' ? 'user' : 'system'
+  def prepare_multimodal_message_content(message)
+    Captain::OpenAiMessageBuilderService.new(message: message).generate_content
   end
 
   def handoff_requested?
diff --git a/enterprise/app/services/captain/llm/assistant_chat_service.rb b/enterprise/app/services/captain/llm/assistant_chat_service.rb
index 569931d44..ca8fafaa0 100644
--- a/enterprise/app/services/captain/llm/assistant_chat_service.rb
+++ b/enterprise/app/services/captain/llm/assistant_chat_service.rb
@@ -12,9 +12,16 @@ class Captain::Llm::AssistantChatService < Llm::BaseOpenAiService
     register_tools
   end
 
-  def generate_response(input, previous_messages = [], role = 'user')
-    @messages += previous_messages
-    @messages << { role: role, content: input } if input.present?
+  # additional_message: A single message (String) from the user that should be appended to the chat.
+  #                    It can be an empty String or nil when you only want to supply historical messages.
+  # message_history:   An Array of already formatted messages that provide the previous context.
+  # role:              The role for the additional_message (defaults to `user`).
+  #
+  # NOTE: Parameters are provided as keyword arguments to improve clarity and avoid relying on
+  # positional ordering.
+  def generate_response(additional_message: nil, message_history: [], role: 'user')
+    @messages += message_history
+    @messages << { role: role, content: additional_message } if additional_message.present?
     request_chat_completion
   end
 
diff --git a/enterprise/app/services/captain/open_ai_message_builder_service.rb b/enterprise/app/services/captain/open_ai_message_builder_service.rb
new file mode 100644
index 000000000..43d2851c9
--- /dev/null
+++ b/enterprise/app/services/captain/open_ai_message_builder_service.rb
@@ -0,0 +1,60 @@
+class Captain::OpenAiMessageBuilderService
+  pattr_initialize [:message!]
+
+  def generate_content
+    parts = []
+    parts << text_part(@message.content) if @message.content.present?
+    parts.concat(attachment_parts(@message.attachments)) if @message.attachments.any?
+
+    return 'Message without content' if parts.blank?
+    return parts.first[:text] if parts.one? && parts.first[:type] == 'text'
+
+    parts
+  end
+
+  private
+
+  def text_part(text)
+    { type: 'text', text: text }
+  end
+
+  def image_part(image_url)
+    { type: 'image_url', image_url: { url: image_url } }
+  end
+
+  def attachment_parts(attachments)
+    image_attachments = attachments.where(file_type: :image)
+    image_content = image_parts(image_attachments)
+
+    transcription = extract_audio_transcriptions(attachments)
+    transcription_part = text_part(transcription) if transcription.present?
+
+    attachment_part = text_part('User has shared an attachment') if attachments.where.not(file_type: %i[image audio]).exists?
+
+    [image_content, transcription_part, attachment_part].flatten.compact
+  end
+
+  def image_parts(image_attachments)
+    image_attachments.each_with_object([]) do |attachment, parts|
+      url = get_attachment_url(attachment)
+      parts << image_part(url) if url.present?
+    end
+  end
+
+  def get_attachment_url(attachment)
+    return attachment.download_url if attachment.download_url.present?
+    return attachment.external_url if attachment.external_url.present?
+
+    attachment.file.attached? ? attachment.file_url : nil
+  end
+
+  def extract_audio_transcriptions(attachments)
+    audio_attachments = attachments.where(file_type: :audio)
+    return '' if audio_attachments.blank?
+
+    audio_attachments.map do |attachment|
+      result = Messages::AudioTranscriptionService.new(attachment).perform
+      result[:success] ? result[:transcriptions] : ''
+    end.join
+  end
+end
\ No newline at end of file
diff --git a/enterprise/app/services/enterprise/message_templates/hook_execution_service.rb b/enterprise/app/services/enterprise/message_templates/hook_execution_service.rb
index 92ccba553..ac1c3a95d 100644
--- a/enterprise/app/services/enterprise/message_templates/hook_execution_service.rb
+++ b/enterprise/app/services/enterprise/message_templates/hook_execution_service.rb
@@ -1,13 +1,34 @@
 module Enterprise::MessageTemplates::HookExecutionService
+  MAX_ATTACHMENT_WAIT_SECONDS = 4
+
   def trigger_templates
     super
     return unless should_process_captain_response?
     return perform_handoff unless inbox.captain_active?
 
-    Captain::Conversation::ResponseBuilderJob.perform_later(
-      conversation,
-      conversation.inbox.captain_assistant
-    )
+    schedule_captain_response
+  end
+
+  private
+
+  def schedule_captain_response
+    job_args = [conversation, conversation.inbox.captain_assistant]
+
+    if message.attachments.blank?
+      Captain::Conversation::ResponseBuilderJob.perform_later(*job_args)
+    else
+      wait_time = calculate_attachment_wait_time
+      Captain::Conversation::ResponseBuilderJob.set(wait: wait_time).perform_later(*job_args)
+    end
+  end
+
+  def calculate_attachment_wait_time
+    attachment_count = message.attachments.size
+    base_wait = 1.second
+
+    # Wait longer for more attachments or larger files
+    additional_wait = [attachment_count * 1, MAX_ATTACHMENT_WAIT_SECONDS].min.seconds
+    base_wait + additional_wait
   end
 
   def should_process_captain_response?
diff --git a/spec/enterprise/controllers/api/v1/accounts/captain/assistants_controller_spec.rb b/spec/enterprise/controllers/api/v1/accounts/captain/assistants_controller_spec.rb
index 1f6d83d80..80be6f30f 100644
--- a/spec/enterprise/controllers/api/v1/accounts/captain/assistants_controller_spec.rb
+++ b/spec/enterprise/controllers/api/v1/accounts/captain/assistants_controller_spec.rb
@@ -211,8 +211,8 @@ RSpec.describe 'Api::V1::Accounts::Captain::Assistants', type: :request do
 
         expect(response).to have_http_status(:success)
         expect(chat_service).to have_received(:generate_response).with(
-          valid_params[:message_content],
-          valid_params[:message_history]
+          additional_message: valid_params[:message_content],
+          message_history: valid_params[:message_history]
         )
         expect(json_response[:content]).to eq('Assistant response')
       end
@@ -232,8 +232,8 @@ RSpec.describe 'Api::V1::Accounts::Captain::Assistants', type: :request do
 
         expect(response).to have_http_status(:success)
         expect(chat_service).to have_received(:generate_response).with(
-          params_without_history[:message_content],
-          []
+          additional_message: params_without_history[:message_content],
+          message_history: []
         )
       end
     end
diff --git a/spec/enterprise/jobs/captain/conversation/response_builder_job_spec.rb b/spec/enterprise/jobs/captain/conversation/response_builder_job_spec.rb
index 1e4a6e824..c21205d52 100644
--- a/spec/enterprise/jobs/captain/conversation/response_builder_job_spec.rb
+++ b/spec/enterprise/jobs/captain/conversation/response_builder_job_spec.rb
@@ -30,5 +30,142 @@ RSpec.describe Captain::Conversation::ResponseBuilderJob, type: :job do
       account.reload
       expect(account.usage_limits[:captain][:responses][:consumed]).to eq(1)
     end
+
+    context 'when message contains an image' do
+      let(:message_with_image) { create(:message, conversation: conversation, message_type: :incoming, content: 'Can you help with this error?') }
+      let(:image_attachment) { message_with_image.attachments.create!(account: account, file_type: :image, external_url: 'https://example.com/error.jpg') }
+
+      before do
+        image_attachment
+      end
+
+      it 'includes image URL directly in the message content for OpenAI vision analysis' do
+        # Expect the generate_response to receive multimodal content with image URL
+        expect(mock_llm_chat_service).to receive(:generate_response) do |**kwargs|
+          history = kwargs[:message_history]
+          last_entry = history.last
+          expect(last_entry[:content]).to be_an(Array)
+          expect(last_entry[:content].any? { |part| part[:type] == 'text' && part[:text] == 'Can you help with this error?' }).to be true
+          expect(last_entry[:content].any? do |part|
+            part[:type] == 'image_url' && part[:image_url][:url] == 'https://example.com/error.jpg'
+          end).to be true
+          { 'response' => 'I can see the error in your image. It appears to be a database connection issue.' }
+        end
+
+        described_class.perform_now(conversation, assistant)
+      end
+    end
+  end
+
+  describe 'retry mechanisms for image processing' do
+    let(:conversation) { create(:conversation, inbox: inbox, account: account) }
+    let(:mock_llm_chat_service) { instance_double(Captain::Llm::AssistantChatService) }
+    let(:mock_message_builder) { instance_double(Captain::OpenAiMessageBuilderService) }
+
+    before do
+      create(:message, conversation: conversation, content: 'Hello with image', message_type: :incoming)
+      allow(Captain::Llm::AssistantChatService).to receive(:new).and_return(mock_llm_chat_service)
+      allow(Captain::OpenAiMessageBuilderService).to receive(:new).with(message: anything).and_return(mock_message_builder)
+      allow(mock_message_builder).to receive(:generate_content).and_return('Hello with image')
+      allow(mock_llm_chat_service).to receive(:generate_response).and_return({ 'response' => 'Test response' })
+    end
+
+    context 'when ActiveStorage::FileNotFoundError occurs' do
+      it 'handles file errors and triggers handoff' do
+        allow(mock_message_builder).to receive(:generate_content)
+          .and_raise(ActiveStorage::FileNotFoundError, 'Image file not found')
+
+        # For retryable errors, the job should handle them and proceed with handoff
+        described_class.perform_now(conversation, assistant)
+
+        # Verify handoff occurred due to repeated failures
+        expect(conversation.reload.status).to eq('open')
+      end
+
+      it 'succeeds when no error occurs' do
+        # Don't raise any error, should succeed normally
+        allow(mock_message_builder).to receive(:generate_content)
+          .and_return('Image content processed successfully')
+
+        described_class.perform_now(conversation, assistant)
+
+        expect(conversation.messages.outgoing.count).to eq(1)
+        expect(conversation.messages.outgoing.last.content).to eq('Test response')
+      end
+    end
+
+    context 'when Faraday::BadRequestError occurs' do
+      it 'handles API errors and triggers handoff' do
+        allow(mock_llm_chat_service).to receive(:generate_response)
+          .and_raise(Faraday::BadRequestError, 'Bad request to image service')
+
+        described_class.perform_now(conversation, assistant)
+        expect(conversation.reload.status).to eq('open')
+      end
+
+      it 'succeeds when no error occurs' do
+        # Don't raise any error, should succeed normally
+        allow(mock_llm_chat_service).to receive(:generate_response)
+          .and_return({ 'response' => 'Response after retry' })
+
+        described_class.perform_now(conversation, assistant)
+
+        expect(conversation.messages.outgoing.last.content).to eq('Response after retry')
+      end
+    end
+
+    context 'when image processing fails permanently' do
+      before do
+        allow(mock_message_builder).to receive(:generate_content)
+          .and_raise(ActiveStorage::FileNotFoundError, 'Image permanently unavailable')
+      end
+
+      it 'triggers handoff after max retries' do
+        # Since perform_now re-raises retryable errors, simulate the final failure after retries
+        allow(mock_message_builder).to receive(:generate_content)
+          .and_raise(StandardError, 'Max retries exceeded')
+
+        expect(ChatwootExceptionTracker).to receive(:new).and_call_original
+
+        described_class.perform_now(conversation, assistant)
+
+        expect(conversation.reload.status).to eq('open')
+      end
+    end
+
+    context 'when non-retryable error occurs' do
+      let(:standard_error) { StandardError.new('Generic error') }
+
+      before do
+        allow(mock_llm_chat_service).to receive(:generate_response).and_raise(standard_error)
+      end
+
+      it 'handles error and triggers handoff' do
+        expect(ChatwootExceptionTracker).to receive(:new)
+          .with(standard_error, account: account)
+          .and_call_original
+
+        described_class.perform_now(conversation, assistant)
+
+        expect(conversation.reload.status).to eq('open')
+      end
+
+      it 'ensures Current.executed_by is reset' do
+        expect(Current).to receive(:executed_by=).with(assistant)
+        expect(Current).to receive(:executed_by=).with(nil)
+
+        described_class.perform_now(conversation, assistant)
+      end
+    end
+  end
+
+  describe 'job configuration' do
+    it 'has retry_on configuration for retryable errors' do
+      expect(described_class).to respond_to(:retry_on)
+    end
+
+    it 'defines MAX_MESSAGE_LENGTH constant' do
+      expect(described_class::MAX_MESSAGE_LENGTH).to eq(10_000)
+    end
   end
 end
diff --git a/spec/enterprise/services/captain/open_ai_message_builder_service_spec.rb b/spec/enterprise/services/captain/open_ai_message_builder_service_spec.rb
new file mode 100644
index 000000000..76e91ae7a
--- /dev/null
+++ b/spec/enterprise/services/captain/open_ai_message_builder_service_spec.rb
@@ -0,0 +1,310 @@
+require 'rails_helper'
+
+RSpec.describe Captain::OpenAiMessageBuilderService do
+  subject(:service) { described_class.new(message: message) }
+
+  let(:message) { create(:message, content: 'Hello world') }
+
+  describe '#generate_content' do
+    context 'when message has only text content' do
+      it 'returns the text content directly' do
+        expect(service.generate_content).to eq('Hello world')
+      end
+    end
+
+    context 'when message has no content and no attachments' do
+      let(:message) { create(:message, content: nil) }
+
+      it 'returns default message' do
+        expect(service.generate_content).to eq('Message without content')
+      end
+    end
+
+    context 'when message has text content and attachments' do
+      before do
+        attachment = message.attachments.build(account_id: message.account_id, file_type: :image, external_url: 'https://example.com/image.jpg')
+        attachment.save!
+      end
+
+      it 'returns an array of content parts' do
+        result = service.generate_content
+        expect(result).to be_an(Array)
+        expect(result).to include({ type: 'text', text: 'Hello world' })
+        expect(result).to include({ type: 'image_url', image_url: { url: 'https://example.com/image.jpg' } })
+      end
+    end
+
+    context 'when message has only non-text attachments' do
+      let(:message) { create(:message, content: nil) }
+
+      before do
+        attachment = message.attachments.build(account_id: message.account_id, file_type: :image, external_url: 'https://example.com/image.jpg')
+        attachment.save!
+      end
+
+      it 'returns an array of content parts without text' do
+        result = service.generate_content
+        expect(result).to be_an(Array)
+        expect(result).to include({ type: 'image_url', image_url: { url: 'https://example.com/image.jpg' } })
+        expect(result).not_to include(hash_including(type: 'text', text: 'Hello world'))
+      end
+    end
+  end
+
+  describe '#attachment_parts' do
+    let(:message) { create(:message, content: nil) }
+    let(:attachments) { message.attachments }
+
+    context 'with image attachments' do
+      before do
+        attachment = message.attachments.build(account_id: message.account_id, file_type: :image, external_url: 'https://example.com/image.jpg')
+        attachment.save!
+      end
+
+      it 'includes image parts' do
+        result = service.send(:attachment_parts, attachments)
+        expect(result).to include({ type: 'image_url', image_url: { url: 'https://example.com/image.jpg' } })
+      end
+    end
+
+    context 'with audio attachments' do
+      let(:audio_attachment) do
+        attachment = message.attachments.build(account_id: message.account_id, file_type: :audio)
+        attachment.save!
+        attachment
+      end
+
+      before do
+        allow(Messages::AudioTranscriptionService).to receive(:new).with(audio_attachment).and_return(
+          instance_double(Messages::AudioTranscriptionService, perform: { success: true, transcriptions: 'Audio transcription text' })
+        )
+      end
+
+      it 'includes transcription text part' do
+        audio_attachment # trigger creation
+        result = service.send(:attachment_parts, attachments)
+        expect(result).to include({ type: 'text', text: 'Audio transcription text' })
+      end
+    end
+
+    context 'with other file types' do
+      before do
+        attachment = message.attachments.build(account_id: message.account_id, file_type: :file)
+        attachment.save!
+      end
+
+      it 'includes generic attachment message' do
+        result = service.send(:attachment_parts, attachments)
+        expect(result).to include({ type: 'text', text: 'User has shared an attachment' })
+      end
+    end
+
+    context 'with mixed attachment types' do
+      let(:image_attachment) do
+        attachment = message.attachments.build(account_id: message.account_id, file_type: :image, external_url: 'https://example.com/image.jpg')
+        attachment.save!
+        attachment
+      end
+
+      let(:audio_attachment) do
+        attachment = message.attachments.build(account_id: message.account_id, file_type: :audio)
+        attachment.save!
+        attachment
+      end
+
+      let(:document_attachment) do
+        attachment = message.attachments.build(account_id: message.account_id, file_type: :file)
+        attachment.save!
+        attachment
+      end
+
+      before do
+        allow(Messages::AudioTranscriptionService).to receive(:new).with(audio_attachment).and_return(
+          instance_double(Messages::AudioTranscriptionService, perform: { success: true, transcriptions: 'Audio text' })
+        )
+      end
+
+      it 'includes all relevant parts' do
+        image_attachment    # trigger creation
+        audio_attachment    # trigger creation
+        document_attachment # trigger creation
+
+        result = service.send(:attachment_parts, attachments)
+        expect(result).to include({ type: 'image_url', image_url: { url: 'https://example.com/image.jpg' } })
+        expect(result).to include({ type: 'text', text: 'Audio text' })
+        expect(result).to include({ type: 'text', text: 'User has shared an attachment' })
+      end
+    end
+  end
+
+  describe '#image_parts' do
+    let(:message) { create(:message, content: nil) }
+
+    context 'with valid image attachments' do
+      let(:image1) do
+        attachment = message.attachments.build(account_id: message.account_id, file_type: :image, external_url: 'https://example.com/image1.jpg')
+        attachment.save!
+        attachment
+      end
+
+      let(:image2) do
+        attachment = message.attachments.build(account_id: message.account_id, file_type: :image, external_url: 'https://example.com/image2.jpg')
+        attachment.save!
+        attachment
+      end
+
+      it 'returns image parts for all valid images' do
+        image1 # trigger creation
+        image2 # trigger creation
+
+        image_attachments = message.attachments.where(file_type: :image)
+        result = service.send(:image_parts, image_attachments)
+
+        expect(result).to include({ type: 'image_url', image_url: { url: 'https://example.com/image1.jpg' } })
+        expect(result).to include({ type: 'image_url', image_url: { url: 'https://example.com/image2.jpg' } })
+      end
+    end
+
+    context 'with image attachments without URLs' do
+      let(:image_attachment) do
+        attachment = message.attachments.build(account_id: message.account_id, file_type: :image, external_url: nil)
+        attachment.save!
+        attachment
+      end
+
+      before do
+        allow(image_attachment).to receive(:file).and_return(instance_double(ActiveStorage::Attached::One, attached?: false))
+      end
+
+      it 'skips images without valid URLs' do
+        image_attachment # trigger creation
+
+        image_attachments = message.attachments.where(file_type: :image)
+        result = service.send(:image_parts, image_attachments)
+
+        expect(result).to be_empty
+      end
+    end
+  end
+
+  describe '#get_attachment_url' do
+    let(:attachment) do
+      attachment = message.attachments.build(account_id: message.account_id, file_type: :image)
+      attachment.save!
+      attachment
+    end
+
+    context 'when attachment has external_url' do
+      before { attachment.update(external_url: 'https://example.com/image.jpg') }
+
+      it 'returns external_url' do
+        expect(service.send(:get_attachment_url, attachment)).to eq('https://example.com/image.jpg')
+      end
+    end
+
+    context 'when attachment has attached file' do
+      before do
+        attachment.update(external_url: nil)
+        allow(attachment).to receive(:file).and_return(instance_double(ActiveStorage::Attached::One, attached?: true))
+        allow(attachment).to receive(:file_url).and_return('https://local.com/file.jpg')
+        allow(attachment).to receive(:download_url).and_return('')
+      end
+
+      it 'returns file_url' do
+        expect(service.send(:get_attachment_url, attachment)).to eq('https://local.com/file.jpg')
+      end
+    end
+
+    context 'when attachment has no URL or file' do
+      before do
+        attachment.update(external_url: nil)
+        allow(attachment).to receive(:file).and_return(instance_double(ActiveStorage::Attached::One, attached?: false))
+      end
+
+      it 'returns nil' do
+        expect(service.send(:get_attachment_url, attachment)).to be_nil
+      end
+    end
+  end
+
+  describe '#extract_audio_transcriptions' do
+    let(:message) { create(:message, content: nil) }
+
+    context 'with no audio attachments' do
+      it 'returns empty string' do
+        result = service.send(:extract_audio_transcriptions, message.attachments)
+        expect(result).to eq('')
+      end
+    end
+
+    context 'with successful audio transcriptions' do
+      let(:audio1) do
+        attachment = message.attachments.build(account_id: message.account_id, file_type: :audio)
+        attachment.save!
+        attachment
+      end
+
+      let(:audio2) do
+        attachment = message.attachments.build(account_id: message.account_id, file_type: :audio)
+        attachment.save!
+        attachment
+      end
+
+      before do
+        allow(Messages::AudioTranscriptionService).to receive(:new).with(audio1).and_return(
+          instance_double(Messages::AudioTranscriptionService, perform: { success: true, transcriptions: 'First audio text. ' })
+        )
+        allow(Messages::AudioTranscriptionService).to receive(:new).with(audio2).and_return(
+          instance_double(Messages::AudioTranscriptionService, perform: { success: true, transcriptions: 'Second audio text.' })
+        )
+      end
+
+      it 'concatenates all successful transcriptions' do
+        audio1 # trigger creation
+        audio2 # trigger creation
+
+        attachments = message.attachments
+        result = service.send(:extract_audio_transcriptions, attachments)
+        expect(result).to eq('First audio text. Second audio text.')
+      end
+    end
+
+    context 'with failed audio transcriptions' do
+      let(:audio_attachment) do
+        attachment = message.attachments.build(account_id: message.account_id, file_type: :audio)
+        attachment.save!
+        attachment
+      end
+
+      before do
+        allow(Messages::AudioTranscriptionService).to receive(:new).with(audio_attachment).and_return(
+          instance_double(Messages::AudioTranscriptionService, perform: { success: false, transcriptions: nil })
+        )
+      end
+
+      it 'returns empty string for failed transcriptions' do
+        audio_attachment # trigger creation
+
+        attachments = message.attachments
+        result = service.send(:extract_audio_transcriptions, attachments)
+        expect(result).to eq('')
+      end
+    end
+  end
+
+  describe 'private helper methods' do
+    describe '#text_part' do
+      it 'returns correct text part format' do
+        result = service.send(:text_part, 'Hello world')
+        expect(result).to eq({ type: 'text', text: 'Hello world' })
+      end
+    end
+
+    describe '#image_part' do
+      it 'returns correct image part format' do
+        result = service.send(:image_part, 'https://example.com/image.jpg')
+        expect(result).to eq({ type: 'image_url', image_url: { url: 'https://example.com/image.jpg' } })
+      end
+    end
+  end
+end