diff --git a/app/controllers/super_admin/push_diagnostics_controller.rb b/app/controllers/super_admin/push_diagnostics_controller.rb
new file mode 100644
index 000000000..c33cfdc1e
--- /dev/null
+++ b/app/controllers/super_admin/push_diagnostics_controller.rb
@@ -0,0 +1,68 @@
+class SuperAdmin::PushDiagnosticsController < SuperAdmin::ApplicationController
+  def show
+    @query = params[:user_query].to_s.strip
+    @user = resolve_user(@query)
+    @subscriptions = @user ? @user.notification_subscriptions.order(:id) : []
+    @results = []
+  end
+
+  def create
+    @user = User.find_by(id: params[:user_id])
+    return redirect_to super_admin_push_diagnostics_path, alert: I18n.t('super_admin.push_diagnostics.user_not_found') if @user.nil?
+
+    ids = parsed_subscription_ids
+    if ids.empty?
+      return redirect_to super_admin_push_diagnostics_path(user_query: @user.id),
+                         alert: I18n.t('super_admin.push_diagnostics.no_subscriptions_to_test')
+    end
+
+    run_test_and_render(ids)
+  end
+
+  def destroy_subscriptions
+    user = User.find_by(id: params[:user_id])
+    return redirect_to super_admin_push_diagnostics_path, alert: I18n.t('super_admin.push_diagnostics.user_not_found') if user.nil?
+
+    ids = parsed_subscription_ids
+    if ids.empty?
+      return redirect_to super_admin_push_diagnostics_path(user_query: user.id),
+                         alert: I18n.t('super_admin.push_diagnostics.no_subscriptions_to_delete')
+    end
+
+    deleted_count = user.notification_subscriptions.where(id: ids).destroy_all.size
+    log_super_admin_action("deleted #{deleted_count} subscriptions for user #{user.id}: #{ids}")
+    redirect_to super_admin_push_diagnostics_path(user_query: user.id),
+                notice: I18n.t('super_admin.push_diagnostics.subscriptions_deleted', count: deleted_count)
+  end
+
+  private
+
+  def run_test_and_render(ids)
+    @query = @user.id.to_s
+    @subscriptions = @user.notification_subscriptions.order(:id)
+    @results = Notification::PushTestService.new(
+      user: @user, subscription_ids: ids,
+      title: params[:push_title], body: params[:push_body]
+    ).perform
+
+    log_super_admin_action("test sent for user #{@user.id} subscriptions #{ids}")
+    render :show
+  end
+
+  def log_super_admin_action(message)
+    Rails.logger.info(
+      "[SuperAdmin] push diagnostics #{message} " \
+      "(actor_id=#{current_super_admin&.id}, actor_email=#{current_super_admin&.email})"
+    )
+  end
+
+  def resolve_user(query)
+    return if query.blank?
+
+    query.match?(/\A\d+\z/) ? User.find_by(id: query) : User.from_email(query)
+  end
+
+  def parsed_subscription_ids
+    Array(params[:subscription_ids]).reject(&:blank?).map(&:to_i)
+  end
+end
diff --git a/app/javascript/dashboard/components-next/NewConversation/ComposeConversation.vue b/app/javascript/dashboard/components-next/NewConversation/ComposeConversation.vue
index 1ab370901..02a00c703 100644
--- a/app/javascript/dashboard/components-next/NewConversation/ComposeConversation.vue
+++ b/app/javascript/dashboard/components-next/NewConversation/ComposeConversation.vue
@@ -233,6 +233,7 @@ onMounted(() => resetContacts());
   <Popover
     ref="popoverRef"
     :align="align"
+    :show-content-border="false"
     @show="onPopoverShow"
     @hide="onPopoverHide"
   >
diff --git a/app/javascript/dashboard/components-next/NewConversation/components/ActionButtons.vue b/app/javascript/dashboard/components-next/NewConversation/components/ActionButtons.vue
index 3ce9aec86..3b31874a7 100644
--- a/app/javascript/dashboard/components-next/NewConversation/components/ActionButtons.vue
+++ b/app/javascript/dashboard/components-next/NewConversation/components/ActionButtons.vue
@@ -18,6 +18,7 @@ const props = defineProps({
   isEmailOrWebWidgetInbox: { type: Boolean, default: false },
   isTwilioSmsInbox: { type: Boolean, default: false },
   isTwilioWhatsAppInbox: { type: Boolean, default: false },
+  // eslint-disable-next-line vue/no-unused-properties
   messageTemplates: { type: Array, default: () => [] },
   channelType: { type: String, default: '' },
   isLoading: { type: Boolean, default: false },
@@ -199,7 +200,6 @@ useEventListener(document, 'paste', onPaste);
       <WhatsAppOptions
         v-if="isWhatsappInbox"
         :inbox-id="inboxId"
-        :message-templates="messageTemplates"
         @send-message="emit('sendWhatsappMessage', $event)"
       />
       <ContentTemplateSelector
diff --git a/app/javascript/dashboard/components-next/NewConversation/components/ContentTemplateForm.vue b/app/javascript/dashboard/components-next/NewConversation/components/ContentTemplateForm.vue
index 18a219605..20f32e854 100644
--- a/app/javascript/dashboard/components-next/NewConversation/components/ContentTemplateForm.vue
+++ b/app/javascript/dashboard/components-next/NewConversation/components/ContentTemplateForm.vue
@@ -24,9 +24,7 @@ const handleBack = () => {
 </script>
 
 <template>
-  <div
-    class="absolute top-full mt-1.5 max-h-[30rem] overflow-y-auto ltr:left-0 rtl:right-0 flex flex-col gap-4 px-4 pt-6 pb-5 items-start w-[28.75rem] h-auto bg-n-solid-2 border border-n-strong shadow-sm rounded-lg"
-  >
+  <div class="flex flex-col gap-4 px-4 pt-6 pb-5 items-start w-[28.75rem]">
     <div class="w-full">
       <ContentTemplateParser
         :template="template"
diff --git a/app/javascript/dashboard/components-next/NewConversation/components/ContentTemplateSelector.vue b/app/javascript/dashboard/components-next/NewConversation/components/ContentTemplateSelector.vue
index 684429182..f2061c775 100644
--- a/app/javascript/dashboard/components-next/NewConversation/components/ContentTemplateSelector.vue
+++ b/app/javascript/dashboard/components-next/NewConversation/components/ContentTemplateSelector.vue
@@ -6,6 +6,7 @@ import { useMapGetter } from 'dashboard/composables/store';
 import Icon from 'dashboard/components-next/icon/Icon.vue';
 import Button from 'dashboard/components-next/button/Button.vue';
 import Input from 'dashboard/components-next/input/Input.vue';
+import Popover from 'dashboard/components-next/popover/Popover.vue';
 import ContentTemplateForm from './ContentTemplateForm.vue';
 
 const props = defineProps({
@@ -22,7 +23,6 @@ const inbox = useMapGetter('inboxes/getInbox');
 
 const searchQuery = ref('');
 const selectedTemplate = ref(null);
-const showTemplatesMenu = ref(false);
 
 const contentTemplates = computed(() => {
   const inboxData = inbox.value(props.inboxId);
@@ -39,29 +39,36 @@ const filteredTemplates = computed(() => {
   );
 });
 
-const handleTriggerClick = () => {
+const handlePopoverShow = () => {
   searchQuery.value = '';
-  showTemplatesMenu.value = !showTemplatesMenu.value;
+  selectedTemplate.value = null;
+};
+
+const handlePopoverHide = () => {
+  selectedTemplate.value = null;
 };
 
 const handleTemplateClick = template => {
   selectedTemplate.value = template;
-  showTemplatesMenu.value = false;
 };
 
 const handleBack = () => {
   selectedTemplate.value = null;
-  showTemplatesMenu.value = true;
 };
 
-const handleSendMessage = template => {
+const handleSendMessage = (template, hide) => {
   emit('sendMessage', template);
-  selectedTemplate.value = null;
+  hide();
 };
 </script>
 
 <template>
-  <div class="relative">
+  <Popover
+    align="start"
+    disable-mobile-view
+    @show="handlePopoverShow"
+    @hide="handlePopoverHide"
+  >
     <Button
       icon="i-ph-whatsapp-logo"
       :label="t('COMPOSE_NEW_CONVERSATION.FORM.TWILIO_OPTIONS.LABEL')"
@@ -69,56 +76,59 @@ const handleSendMessage = template => {
       size="sm"
       :disabled="selectedTemplate"
       class="!text-xs font-medium"
-      @click="handleTriggerClick"
     />
-    <div
-      v-if="showTemplatesMenu"
-      class="absolute top-full mt-1.5 max-h-96 overflow-y-auto ltr:left-0 rtl:right-0 flex flex-col gap-2 p-4 items-center w-[21.875rem] h-auto bg-n-solid-2 border border-n-strong shadow-sm rounded-lg"
-    >
-      <div class="w-full">
-        <Input
-          v-model="searchQuery"
-          type="search"
-          :placeholder="
-            t('COMPOSE_NEW_CONVERSATION.FORM.TWILIO_OPTIONS.SEARCH_PLACEHOLDER')
-          "
-          custom-input-class="ltr:pl-10 rtl:pr-10"
-        >
-          <template #prefix>
-            <Icon
-              icon="i-lucide-search"
-              class="absolute top-2 size-3.5 ltr:left-3 rtl:right-3"
-            />
-          </template>
-        </Input>
-      </div>
+    <template #content="{ hide }">
       <div
-        v-for="template in filteredTemplates"
-        :key="template.content_sid"
-        tabindex="0"
-        class="flex flex-col gap-2 p-2 w-full rounded-lg cursor-pointer dark:hover:bg-n-alpha-3 hover:bg-n-alpha-1"
-        @click="handleTemplateClick(template)"
+        v-if="!selectedTemplate"
+        class="flex flex-col gap-2 p-4 items-center w-[21.875rem]"
       >
-        <div class="flex justify-between items-center">
-          <span class="text-sm text-n-slate-12">{{
-            template.friendly_name
-          }}</span>
+        <div class="w-full">
+          <Input
+            v-model="searchQuery"
+            type="search"
+            :placeholder="
+              t(
+                'COMPOSE_NEW_CONVERSATION.FORM.TWILIO_OPTIONS.SEARCH_PLACEHOLDER'
+              )
+            "
+            custom-input-class="ltr:pl-10 rtl:pr-10"
+          >
+            <template #prefix>
+              <Icon
+                icon="i-lucide-search"
+                class="absolute top-2 size-3.5 ltr:left-3 rtl:right-3"
+              />
+            </template>
+          </Input>
         </div>
-        <p class="mb-0 text-xs leading-5 text-n-slate-11 line-clamp-2">
-          {{ template.body || t('CONTENT_TEMPLATES.PICKER.NO_CONTENT') }}
-        </p>
+        <div
+          v-for="template in filteredTemplates"
+          :key="template.content_sid"
+          tabindex="0"
+          class="flex flex-col gap-2 p-2 w-full rounded-lg cursor-pointer dark:hover:bg-n-alpha-3 hover:bg-n-alpha-1"
+          @click="handleTemplateClick(template)"
+        >
+          <div class="flex justify-between items-center">
+            <span class="text-sm text-n-slate-12">{{
+              template.friendly_name
+            }}</span>
+          </div>
+          <p class="mb-0 text-xs leading-5 text-n-slate-11 line-clamp-2">
+            {{ template.body || t('CONTENT_TEMPLATES.PICKER.NO_CONTENT') }}
+          </p>
+        </div>
+        <template v-if="filteredTemplates.length === 0">
+          <p class="pt-2 w-full text-sm text-n-slate-11">
+            {{ t('COMPOSE_NEW_CONVERSATION.FORM.TWILIO_OPTIONS.EMPTY_STATE') }}
+          </p>
+        </template>
       </div>
-      <template v-if="filteredTemplates.length === 0">
-        <p class="pt-2 w-full text-sm text-n-slate-11">
-          {{ t('COMPOSE_NEW_CONVERSATION.FORM.TWILIO_OPTIONS.EMPTY_STATE') }}
-        </p>
-      </template>
-    </div>
-    <ContentTemplateForm
-      v-if="selectedTemplate"
-      :template="selectedTemplate"
-      @send-message="handleSendMessage"
-      @back="handleBack"
-    />
-  </div>
+      <ContentTemplateForm
+        v-else
+        :template="selectedTemplate"
+        @send-message="payload => handleSendMessage(payload, hide)"
+        @back="handleBack"
+      />
+    </template>
+  </Popover>
 </template>
diff --git a/app/javascript/dashboard/components-next/NewConversation/components/WhatsAppOptions.vue b/app/javascript/dashboard/components-next/NewConversation/components/WhatsAppOptions.vue
index e5350c1fb..10068ec3d 100644
--- a/app/javascript/dashboard/components-next/NewConversation/components/WhatsAppOptions.vue
+++ b/app/javascript/dashboard/components-next/NewConversation/components/WhatsAppOptions.vue
@@ -5,6 +5,7 @@ import { useMapGetter } from 'dashboard/composables/store';
 
 import Icon from 'dashboard/components-next/icon/Icon.vue';
 import Button from 'dashboard/components-next/button/Button.vue';
+import Popover from 'dashboard/components-next/popover/Popover.vue';
 import WhatsappTemplate from './WhatsappTemplate.vue';
 
 const props = defineProps({
@@ -24,8 +25,6 @@ const getFilteredWhatsAppTemplates = useMapGetter(
 const searchQuery = ref('');
 const selectedTemplate = ref(null);
 
-const showTemplatesMenu = ref(false);
-
 const whatsAppTemplateMessages = computed(() => {
   return getFilteredWhatsAppTemplates.value(props.inboxId);
 });
@@ -40,29 +39,36 @@ const getTemplateBody = template => {
   return template.components.find(component => component.type === 'BODY').text;
 };
 
-const handleTriggerClick = () => {
+const handlePopoverShow = () => {
   searchQuery.value = '';
-  showTemplatesMenu.value = !showTemplatesMenu.value;
+  selectedTemplate.value = null;
+};
+
+const handlePopoverHide = () => {
+  selectedTemplate.value = null;
 };
 
 const handleTemplateClick = template => {
   selectedTemplate.value = template;
-  showTemplatesMenu.value = false;
 };
 
 const handleBack = () => {
   selectedTemplate.value = null;
-  showTemplatesMenu.value = true;
 };
 
-const handleSendMessage = template => {
+const handleSendMessage = (template, hide) => {
   emit('sendMessage', template);
-  selectedTemplate.value = null;
+  hide();
 };
 </script>
 
 <template>
-  <div class="relative">
+  <Popover
+    align="start"
+    disable-mobile-view
+    @show="handlePopoverShow"
+    @hide="handlePopoverHide"
+  >
     <Button
       icon="i-ri-whatsapp-line"
       :label="t('COMPOSE_NEW_CONVERSATION.FORM.WHATSAPP_OPTIONS.LABEL')"
@@ -70,50 +76,53 @@ const handleSendMessage = template => {
       size="sm"
       :disabled="selectedTemplate"
       class="!text-xs font-medium"
-      @click="handleTriggerClick"
     />
-    <div
-      v-if="showTemplatesMenu"
-      class="absolute top-full mt-1.5 max-h-96 overflow-y-auto ltr:left-0 rtl:right-0 flex flex-col gap-2 p-4 items-center w-[21.875rem] h-auto bg-n-solid-2 border border-n-strong shadow-sm rounded-lg"
-    >
-      <div class="relative w-full">
-        <Icon
-          icon="i-lucide-search"
-          class="absolute size-3.5 top-2 ltr:left-3 rtl:right-3"
-        />
-        <input
-          v-model="searchQuery"
-          type="search"
-          :placeholder="
-            t(
-              'COMPOSE_NEW_CONVERSATION.FORM.WHATSAPP_OPTIONS.SEARCH_PLACEHOLDER'
-            )
-          "
-          class="w-full h-8 py-2 ltr:pl-10 rtl:pr-10 ltr:pr-2 rtl:pl-2 text-sm reset-base outline-none border-none rounded-lg bg-n-alpha-black2 dark:bg-n-solid-1 text-n-slate-12"
-        />
-      </div>
+    <template #content="{ hide }">
       <div
-        v-for="template in filteredTemplates"
-        :key="template.id"
-        class="flex flex-col gap-2 p-2 w-full rounded-lg cursor-pointer dark:hover:bg-n-alpha-3 hover:bg-n-alpha-1"
-        @click="handleTemplateClick(template)"
+        v-if="!selectedTemplate"
+        class="flex flex-col gap-2 p-4 items-center w-[21.875rem]"
       >
-        <span class="text-sm text-n-slate-12">{{ template.name }}</span>
-        <p class="mb-0 text-xs leading-5 text-n-slate-11 line-clamp-2">
-          {{ getTemplateBody(template) }}
-        </p>
+        <div class="relative w-full">
+          <Icon
+            icon="i-lucide-search"
+            class="absolute size-3.5 top-2 ltr:left-3 rtl:right-3"
+          />
+          <input
+            v-model="searchQuery"
+            type="search"
+            :placeholder="
+              t(
+                'COMPOSE_NEW_CONVERSATION.FORM.WHATSAPP_OPTIONS.SEARCH_PLACEHOLDER'
+              )
+            "
+            class="w-full h-8 py-2 ltr:pl-10 rtl:pr-10 ltr:pr-2 rtl:pl-2 text-sm reset-base outline-none border-none rounded-lg bg-n-alpha-black2 dark:bg-n-solid-1 text-n-slate-12"
+          />
+        </div>
+        <div
+          v-for="template in filteredTemplates"
+          :key="template.id"
+          class="flex flex-col gap-2 p-2 w-full rounded-lg cursor-pointer dark:hover:bg-n-alpha-3 hover:bg-n-alpha-1"
+          @click="handleTemplateClick(template)"
+        >
+          <span class="text-sm text-n-slate-12">{{ template.name }}</span>
+          <p class="mb-0 text-xs leading-5 text-n-slate-11 line-clamp-2">
+            {{ getTemplateBody(template) }}
+          </p>
+        </div>
+        <template v-if="filteredTemplates.length === 0">
+          <p class="pt-2 w-full text-sm text-n-slate-11">
+            {{
+              t('COMPOSE_NEW_CONVERSATION.FORM.WHATSAPP_OPTIONS.EMPTY_STATE')
+            }}
+          </p>
+        </template>
       </div>
-      <template v-if="filteredTemplates.length === 0">
-        <p class="pt-2 w-full text-sm text-n-slate-11">
-          {{ t('COMPOSE_NEW_CONVERSATION.FORM.WHATSAPP_OPTIONS.EMPTY_STATE') }}
-        </p>
-      </template>
-    </div>
-    <WhatsappTemplate
-      v-if="selectedTemplate"
-      :template="selectedTemplate"
-      @send-message="handleSendMessage"
-      @back="handleBack"
-    />
-  </div>
+      <WhatsappTemplate
+        v-else
+        :template="selectedTemplate"
+        @send-message="payload => handleSendMessage(payload, hide)"
+        @back="handleBack"
+      />
+    </template>
+  </Popover>
 </template>
diff --git a/app/javascript/dashboard/components-next/NewConversation/components/WhatsappTemplate.vue b/app/javascript/dashboard/components-next/NewConversation/components/WhatsappTemplate.vue
index 8e655fcfb..03789839a 100644
--- a/app/javascript/dashboard/components-next/NewConversation/components/WhatsappTemplate.vue
+++ b/app/javascript/dashboard/components-next/NewConversation/components/WhatsappTemplate.vue
@@ -24,9 +24,7 @@ const handleBack = () => {
 </script>
 
 <template>
-  <div
-    class="absolute top-full mt-1.5 max-h-[30rem] overflow-y-auto ltr:left-0 rtl:right-0 flex flex-col gap-4 px-4 pt-6 pb-5 items-start w-[28.75rem] h-auto bg-n-solid-2 border border-n-strong shadow-sm rounded-lg"
-  >
+  <div class="flex flex-col gap-4 px-4 pt-6 pb-5 items-start w-[28.75rem]">
     <div class="w-full">
       <WhatsAppTemplateParser
         :template="template"
diff --git a/app/javascript/dashboard/components-next/popover/Popover.vue b/app/javascript/dashboard/components-next/popover/Popover.vue
index 18e711c12..5b67e572f 100644
--- a/app/javascript/dashboard/components-next/popover/Popover.vue
+++ b/app/javascript/dashboard/components-next/popover/Popover.vue
@@ -12,6 +12,14 @@ const props = defineProps({
     default: 'end',
     validator: v => ['start', 'end'].includes(v),
   },
+  disableMobileView: {
+    type: Boolean,
+    default: false,
+  },
+  showContentBorder: {
+    type: Boolean,
+    default: true,
+  },
 });
 
 const emit = defineEmits(['show', 'hide']);
@@ -22,7 +30,8 @@ const popoverRef = ref(null);
 const mobileContentRef = ref(null);
 
 const breakpoints = useBreakpoints(breakpointsTailwind);
-const isMobile = breakpoints.smaller('md');
+const belowMd = breakpoints.smaller('md');
+const isMobile = computed(() => !props.disableMobileView && belowMd.value);
 const showPopover = computed(() => isActive.value && !isMobile.value);
 
 const { fixedPosition, updatePosition } = useDropdownPosition(
@@ -99,9 +108,13 @@ defineExpose({ show, hide, toggle });
           { ignore: clickOutsideIgnore },
         ]"
         data-popover-content
-        class="relative w-full max-w-lg max-h-[calc(100vh-4rem)] mx-4 overflow-y-auto bg-n-alpha-3 backdrop-blur-[100px] shadow-xl rounded-xl"
+        class="relative flex flex-col w-full max-w-lg max-h-[calc(100vh-4rem)] mx-4 bg-n-alpha-3 backdrop-blur-[100px] shadow-xl rounded-xl"
       >
-        <slot name="content" :hide="hide" />
+        <div
+          class="flex-1 min-h-0 overflow-y-auto overscroll-contain rounded-xl"
+        >
+          <slot name="content" :hide="hide" />
+        </div>
       </div>
     </div>
 
@@ -113,9 +126,14 @@ defineExpose({ show, hide, toggle });
       data-popover-content
       :class="fixedPosition.class"
       :style="fixedPosition.style"
-      class="bg-n-alpha-3 backdrop-blur-[100px] shadow-xl rounded-xl overflow-y-auto max-h-[calc(100vh-2rem)]"
+      class="flex flex-col bg-n-alpha-3 backdrop-blur-[100px] shadow-xl rounded-xl"
     >
-      <slot name="content" :hide="hide" />
+      <div
+        class="flex-1 min-h-0 overflow-y-auto overscroll-contain rounded-xl"
+        :class="{ 'border border-n-strong': showContentBorder }"
+      >
+        <slot name="content" :hide="hide" />
+      </div>
     </div>
   </TeleportWithDirection>
 </template>
diff --git a/app/javascript/dashboard/modules/contact/ContactDeleteModal.vue b/app/javascript/dashboard/modules/contact/ContactDeleteModal.vue
index 3bf48e184..617b0456f 100644
--- a/app/javascript/dashboard/modules/contact/ContactDeleteModal.vue
+++ b/app/javascript/dashboard/modules/contact/ContactDeleteModal.vue
@@ -60,9 +60,7 @@ const onDelete = async hide => {
   <Popover @hide="$emit('close')">
     <slot name="trigger" />
     <template #content="{ hide }">
-      <div
-        class="w-full md:w-80 p-6 flex flex-col gap-4 border-0 md:border rounded-xl md:border-n-strong"
-      >
+      <div class="w-full md:w-80 p-6 flex flex-col gap-4">
         <div class="flex flex-col gap-2">
           <h3 class="text-base font-medium leading-6 text-n-slate-12">
             {{ $t('DELETE_CONTACT.CONFIRM.TITLE') }}
diff --git a/app/javascript/dashboard/modules/contact/ContactMergeModal.vue b/app/javascript/dashboard/modules/contact/ContactMergeModal.vue
index 1a343f777..be06581a6 100644
--- a/app/javascript/dashboard/modules/contact/ContactMergeModal.vue
+++ b/app/javascript/dashboard/modules/contact/ContactMergeModal.vue
@@ -72,9 +72,7 @@ const onMergeContacts = async (parentContactId, hide) => {
   <Popover @hide="$emit('close')">
     <slot name="trigger" />
     <template #content="{ hide }">
-      <div
-        class="w-full md:w-96 p-6 flex flex-col gap-4 border-0 md:border rounded-xl md:border-n-strong"
-      >
+      <div class="w-full md:w-96 p-6 flex flex-col gap-4">
         <div class="flex flex-col gap-2">
           <h3 class="text-base font-medium leading-6 text-n-slate-12">
             {{ $t('MERGE_CONTACTS.TITLE') }}
diff --git a/app/presenters/messages/search_data_presenter.rb b/app/presenters/messages/search_data_presenter.rb
index 7a6260686..e90c9b600 100644
--- a/app/presenters/messages/search_data_presenter.rb
+++ b/app/presenters/messages/search_data_presenter.rb
@@ -39,7 +39,8 @@ class Messages::SearchDataPresenter < SimpleDelegator
   end
 
   def content_attributes_data
-    email_subject = content_attributes.dig(:email, :subject)
+    email_subject = content_attributes.dig(:email, :subject).presence ||
+                    conversation.additional_attributes&.dig('mail_subject').presence
     return {} if email_subject.blank?
 
     { email: { subject: email_subject } }
diff --git a/app/services/notification/push_test_service.rb b/app/services/notification/push_test_service.rb
new file mode 100644
index 000000000..4b2bec177
--- /dev/null
+++ b/app/services/notification/push_test_service.rb
@@ -0,0 +1,160 @@
+class Notification::PushTestService
+  pattr_initialize [:user!, :subscription_ids!, :title, :body]
+
+  DEFAULT_TITLE = '%<installation_name>s notification test'.freeze
+  DEFAULT_BODY = 'This is a test from our team to check notification delivery on your device. No action needed.'.freeze
+
+  def self.default_title
+    format(DEFAULT_TITLE, installation_name: GlobalConfigService.load('INSTALLATION_NAME', 'Chatwoot'))
+  end
+
+  def self.default_body
+    DEFAULT_BODY
+  end
+
+  def perform
+    selected_subscriptions.map { |subscription| test_send(subscription) }
+  end
+
+  private
+
+  def resolved_title
+    title.presence || self.class.default_title
+  end
+
+  def resolved_body
+    body.presence || self.class.default_body
+  end
+
+  def selected_subscriptions
+    user.notification_subscriptions.where(id: subscription_ids).order(:id)
+  end
+
+  def test_send(subscription)
+    if subscription.browser_push?
+      test_browser_push(subscription)
+    elsif subscription.fcm?
+      test_fcm(subscription)
+    else
+      result(subscription, subscription.subscription_type.to_s, :skipped, 'Unknown subscription type')
+    end
+  end
+
+  def test_browser_push(subscription)
+    return result(subscription, 'browser_push', :skipped, 'VAPID keys not configured') unless VapidService.public_key
+
+    WebPush.payload_send(**browser_push_payload(subscription))
+    result(subscription, 'browser_push', :success, 'Web push accepted by endpoint')
+  rescue StandardError => e
+    result(subscription, 'browser_push', :failure, "#{e.class.name}: #{e.message}")
+  end
+
+  def test_fcm(subscription)
+    if firebase_credentials_present?
+      test_fcm_direct(subscription)
+    elsif chatwoot_hub_enabled?
+      test_fcm_via_hub(subscription)
+    else
+      result(subscription, 'fcm', :skipped, 'No Firebase credentials and push relay disabled')
+    end
+  end
+
+  def test_fcm_direct(subscription)
+    fcm_service = Notification::FcmService.new(
+      GlobalConfigService.load('FIREBASE_PROJECT_ID', nil),
+      GlobalConfigService.load('FIREBASE_CREDENTIALS', nil)
+    )
+    response = fcm_service.fcm_client.send_v1(fcm_options(subscription))
+    status_code = response[:status_code].to_i
+    status = status_code.between?(200, 299) ? :success : :failure
+    result(subscription, 'fcm', status, "HTTP #{status_code} — #{response[:body]}")
+  rescue StandardError => e
+    result(subscription, 'fcm', :failure, "#{e.class.name}: #{e.message}")
+  end
+
+  def test_fcm_via_hub(subscription)
+    response = ChatwootHub.send_push_with_response(fcm_options(subscription))
+    result(subscription, 'fcm_via_hub', :success, "HTTP #{response.code} — #{response.body}")
+  rescue RestClient::ExceptionWithResponse => e
+    result(subscription, 'fcm_via_hub', :failure, "HTTP #{e.response&.code} — #{e.response&.body}")
+  rescue StandardError => e
+    result(subscription, 'fcm_via_hub', :failure, "#{e.class.name}: #{e.message}")
+  end
+
+  def firebase_credentials_present?
+    GlobalConfigService.load('FIREBASE_PROJECT_ID', nil) && GlobalConfigService.load('FIREBASE_CREDENTIALS', nil)
+  end
+
+  def chatwoot_hub_enabled?
+    ActiveModel::Type::Boolean.new.cast(ENV.fetch('ENABLE_PUSH_RELAY_SERVER', true))
+  end
+
+  def browser_push_payload(subscription)
+    {
+      message: JSON.generate(
+        title: resolved_title,
+        tag: "super_admin_test_#{Time.zone.now.to_i}",
+        url: ENV.fetch('FRONTEND_URL', 'https://app.chatwoot.com')
+      ),
+      endpoint: subscription.subscription_attributes['endpoint'],
+      p256dh: subscription.subscription_attributes['p256dh'],
+      auth: subscription.subscription_attributes['auth'],
+      vapid: {
+        subject: ENV.fetch('FRONTEND_URL', 'https://app.chatwoot.com'),
+        public_key: VapidService.public_key,
+        private_key: VapidService.private_key
+      },
+      ssl_timeout: 5,
+      open_timeout: 5,
+      read_timeout: 5
+    }
+  end
+
+  def fcm_options(subscription)
+    {
+      'token': subscription.subscription_attributes['push_token'],
+      'data': { payload: { data: { notification: { type: 'test' } } }.to_json },
+      'notification': { title: resolved_title, body: resolved_body },
+      'android': { priority: 'high' },
+      'apns': { payload: { aps: { sound: 'default', category: Time.zone.now.to_i.to_s } } },
+      'fcm_options': { analytics_label: 'SuperAdminTest' }
+    }
+  end
+
+  def result(subscription, type, status, message)
+    attrs = subscription.subscription_attributes || {}
+    {
+      id: subscription.id,
+      type: type.to_s,
+      device: device_label(subscription, attrs),
+      token_tail: token_tail(subscription, attrs),
+      status: status,
+      message: message
+    }
+  end
+
+  def device_label(subscription, attrs)
+    if subscription.browser_push?
+      endpoint_host(attrs['endpoint'].to_s)
+    else
+      attrs['device_id'].present? ? "…#{attrs['device_id'].to_s.last(6)}" : '—'
+    end
+  end
+
+  def endpoint_host(endpoint)
+    return '—' if endpoint.blank?
+
+    URI.parse(endpoint).host.presence || endpoint
+  rescue URI::InvalidURIError
+    endpoint
+  end
+
+  def token_tail(subscription, attrs)
+    if subscription.browser_push?
+      endpoint = attrs['endpoint'].to_s
+      endpoint.present? ? "…#{endpoint.last(6)}" : '—'
+    else
+      attrs['push_token'].present? ? "…#{attrs['push_token'].to_s.last(6)}" : '—'
+    end
+  end
+end
diff --git a/app/views/super_admin/application/_navigation.html.erb b/app/views/super_admin/application/_navigation.html.erb
index 787576d33..da3a024f8 100644
--- a/app/views/super_admin/application/_navigation.html.erb
+++ b/app/views/super_admin/application/_navigation.html.erb
@@ -32,7 +32,7 @@ as defined by the routes in the `admin/` namespace
     <ul class="my-4">
       <%= render partial: "nav_item", locals: { icon: 'icon-grid-line', url: super_admin_root_url, label: 'Dashboard' } %>
       <% Administrate::Namespace.new(namespace).resources.each do |resource| %>
-        <% next if ["account_users", "access_tokens", "installation_configs", "dashboard", "devise/sessions", "app_configs", "instance_statuses", "settings"].include?  resource.resource %>
+        <% next if ["account_users", "access_tokens", "installation_configs", "dashboard", "devise/sessions", "app_configs", "instance_statuses", "settings", "push_diagnostics"].include?  resource.resource %>
         <%= render partial: "nav_item", locals: {
             icon: sidebar_icons[resource.resource.to_sym],
             url: resource_index_route(resource),
@@ -48,6 +48,7 @@ as defined by the routes in the `admin/` namespace
     <ul class="my-4">
       <%= render partial: "nav_item", locals: { icon: 'icon-mist-fill', url: sidekiq_web_url, label: 'Sidekiq Dashboard' } %>
       <%= render partial: "nav_item", locals: { icon: 'icon-health-book-line', url: super_admin_instance_status_url, label: 'Instance Health' } %>
+      <%= render partial: "nav_item", locals: { icon: 'icon-mail-send-fill', url: super_admin_push_diagnostics_url, label: 'Push Diagnostics' } %>
       <%= render partial: "nav_item", locals: { icon: 'icon-dashboard-line', url: '/', label: 'Agent Dashboard' } %>
       <%= render partial: "nav_item", locals: { icon: 'icon-logout-circle-r-line', url: super_admin_logout_url, label: 'Logout' } %>
     </ul>
diff --git a/app/views/super_admin/push_diagnostics/show.html.erb b/app/views/super_admin/push_diagnostics/show.html.erb
new file mode 100644
index 000000000..736a77cd8
--- /dev/null
+++ b/app/views/super_admin/push_diagnostics/show.html.erb
@@ -0,0 +1,190 @@
+<% content_for(:title) do %>Push Diagnostics<% end %>
+
+<header class="main-content__header" role="banner">
+  <h1 class="main-content__page-title" id="page-title">Push Diagnostics</h1>
+</header>
+
+<section class="main-content__body">
+  <p class="text-sm text-slate-600 mb-6">
+    Send a test push notification to a specific user's registered devices to diagnose delivery issues.
+    Results show the raw FCM / Web Push / relay response so you can see exactly what failed.
+  </p>
+
+  <div class="mb-8">
+    <h2 class="text-base font-semibold mb-2">1. Look up user</h2>
+    <%= form_with url: super_admin_push_diagnostics_path, method: :get, local: true, class: 'flex gap-2 items-center' do |f| %>
+      <%= f.text_field :user_query,
+                       value: @query,
+                       placeholder: 'user@example.com or numeric user ID',
+                       class: 'border border-slate-100 p-1.5 rounded-md w-80' %>
+      <%= f.submit 'Look up', class: 'border border-slate-200 bg-slate-50 px-3 py-1.5 rounded-md cursor-pointer' %>
+    <% end %>
+    <% if @query.present? && @user.nil? %>
+      <p class="text-sm text-red-600 mt-2">No user found for "<%= @query %>".</p>
+    <% end %>
+  </div>
+
+  <% if @user %>
+    <div class="mb-6 border border-slate-100 rounded-md p-4 bg-slate-25">
+      <p class="text-sm">
+        <strong><%= @user.name %></strong>
+        &middot; <%= @user.email %>
+        &middot; ID <%= @user.id %>
+      </p>
+      <% if @user.accounts.any? %>
+        <p class="text-xs text-slate-500 mt-1">
+          Accounts:
+          <% @user.accounts.each_with_index do |account, index| %>
+            <%= ', ' if index.positive? %>
+            <%= account.name %> (ID <%= account.id %>)
+          <% end %>
+        </p>
+      <% end %>
+    </div>
+
+    <div class="mb-8">
+      <h2 class="text-base font-semibold mb-2">2. Select subscriptions (<%= @subscriptions.count %>)</h2>
+      <p class="text-xs text-amber-700 mb-3">
+        ⚠️ This sends a real push to every selected device. Use only when diagnosing a reported issue.
+      </p>
+
+      <% if @subscriptions.empty? %>
+        <p class="text-sm text-slate-600">This user has no push subscriptions registered.</p>
+      <% else %>
+        <%= form_with url: super_admin_push_diagnostics_path, method: :post, local: true do |f| %>
+          <%= f.hidden_field :user_id, value: @user.id %>
+          <div class="mb-4 max-w-2xl">
+            <div class="mb-3">
+              <%= label_tag :push_title, 'Title', class: 'block text-xs font-medium text-slate-600 mb-1' %>
+              <%= text_field_tag :push_title,
+                                  params[:push_title].presence || Notification::PushTestService.default_title,
+                                  class: 'border border-slate-100 p-1.5 rounded-md w-full text-sm' %>
+            </div>
+            <div>
+              <%= label_tag :push_body, 'Body', class: 'block text-xs font-medium text-slate-600 mb-1' %>
+              <%= text_area_tag :push_body,
+                                 params[:push_body].presence || Notification::PushTestService.default_body,
+                                 rows: 2,
+                                 class: 'border border-slate-100 p-1.5 rounded-md w-full text-sm' %>
+            </div>
+            <p class="text-xs text-slate-400 mt-1">Customers will see this text as a real push notification on their device.</p>
+          </div>
+          <table class="w-full text-sm border border-slate-100 rounded-md">
+            <thead class="text-left text-xs text-slate-500 bg-slate-25">
+              <tr>
+                <th class="px-3 py-2 align-middle first:!pl-4 last:!pr-4"><input type="checkbox" id="toggle-all"></th>
+                <th class="px-3 py-2 first:!pl-4 last:!pr-4">ID</th>
+                <th class="px-3 py-2 first:!pl-4 last:!pr-4">Type</th>
+                <th class="px-3 py-2 first:!pl-4 last:!pr-4">Device / endpoint</th>
+                <th class="px-3 py-2 first:!pl-4 last:!pr-4">Push token</th>
+                <th class="px-3 py-2 first:!pl-4 last:!pr-4">Device details</th>
+                <th class="px-3 py-2 first:!pl-4 last:!pr-4">Created</th>
+                <th class="px-3 py-2 first:!pl-4 last:!pr-4">Last updated</th>
+              </tr>
+            </thead>
+            <tbody>
+              <% @subscriptions.each do |sub| %>
+                <% attrs = (sub.subscription_attributes || {}).stringify_keys %>
+                <% if sub.browser_push? %>
+                  <% endpoint = attrs['endpoint'].to_s %>
+                  <% host = (begin; URI.parse(endpoint).host; rescue URI::InvalidURIError; nil; end) %>
+                  <% device_display = host.presence || endpoint.presence || '—' %>
+                  <% token_display = endpoint.present? ? "…#{endpoint.last(6)}" : '—' %>
+                <% else %>
+                  <% device_display = attrs['device_id'].present? ? "…#{attrs['device_id'].to_s.last(6)}" : '—' %>
+                  <% token_display = attrs['push_token'].present? ? "…#{attrs['push_token'].to_s.last(6)}" : '—' %>
+                <% end %>
+                <% extra_attrs = attrs.except('endpoint', 'p256dh', 'auth', 'push_token', 'device_id') %>
+                <tr class="border-t border-slate-100 align-middle">
+                  <td class="px-3 py-2 first:!pl-4 last:!pr-4">
+                    <%= check_box_tag 'subscription_ids[]', sub.id, false, class: 'subscription-checkbox' %>
+                  </td>
+                  <td class="px-3 py-2 first:!pl-4 last:!pr-4"><%= sub.id %></td>
+                  <td class="px-3 py-2 first:!pl-4 last:!pr-4"><%= sub.subscription_type %></td>
+                  <td class="px-3 py-2 first:!pl-4 last:!pr-4 font-mono text-xs break-all"><%= device_display %></td>
+                  <td class="px-3 py-2 first:!pl-4 last:!pr-4 font-mono text-xs break-all"><%= token_display %></td>
+                  <td class="px-3 py-2 first:!pl-4 last:!pr-4 text-xs align-top">
+                    <% if extra_attrs.present? %>
+                      <% extra_attrs.each do |k, v| %>
+                        <div><span class="text-slate-500"><%= k %>:</span> <span class="font-mono"><%= v.to_s.truncate(40) %></span></div>
+                      <% end %>
+                    <% else %>
+                      <span class="text-slate-400">—</span>
+                    <% end %>
+                  </td>
+                  <td class="px-3 py-2 first:!pl-4 last:!pr-4 whitespace-nowrap"><%= sub.created_at.strftime('%Y-%m-%d %H:%M') %></td>
+                  <td class="px-3 py-2 first:!pl-4 last:!pr-4 whitespace-nowrap">
+                    <%= sub.updated_at.strftime('%Y-%m-%d %H:%M') %>
+                    <span class="text-xs text-slate-400">(<%= time_ago_in_words(sub.updated_at) %> ago)</span>
+                  </td>
+                </tr>
+              <% end %>
+            </tbody>
+          </table>
+          <div class="mt-4 flex gap-2">
+            <%= f.submit 'Send Test Push to Selected',
+                         class: 'border border-slate-200 bg-slate-50 px-3 py-1.5 rounded-md cursor-pointer font-medium' %>
+            <%= submit_tag 'Delete Selected Subscriptions',
+                           formaction: destroy_subscriptions_super_admin_push_diagnostics_path,
+                           formmethod: 'post',
+                           data: { confirm: "Delete the selected subscription(s)? The user won't receive pushes on those devices until their app re-registers." },
+                           class: 'border border-red-200 bg-red-50 text-red-700 px-3 py-1.5 rounded-md cursor-pointer font-medium' %>
+          </div>
+        <% end %>
+      <% end %>
+    </div>
+
+    <% if @results.present? %>
+      <div class="mb-8">
+        <h2 class="text-base font-semibold mb-2">3. Results</h2>
+        <table class="w-full text-sm border border-slate-100 rounded-md">
+          <thead class="text-left text-xs text-slate-500 bg-slate-25">
+            <tr>
+              <th class="px-3 py-2 first:!pl-4 last:!pr-4">Sub ID</th>
+              <th class="px-3 py-2 first:!pl-4 last:!pr-4">Type</th>
+              <th class="px-3 py-2 first:!pl-4 last:!pr-4">Device</th>
+              <th class="px-3 py-2 first:!pl-4 last:!pr-4">Push token</th>
+              <th class="px-3 py-2 first:!pl-4 last:!pr-4">Status</th>
+              <th class="px-3 py-2 first:!pl-4 last:!pr-4">Details</th>
+            </tr>
+          </thead>
+          <tbody>
+            <% @results.each do |r| %>
+              <tr class="border-t border-slate-100 align-top">
+                <td class="px-3 py-2 first:!pl-4 last:!pr-4"><%= r[:id] %></td>
+                <td class="px-3 py-2 first:!pl-4 last:!pr-4"><%= r[:type] %></td>
+                <td class="px-3 py-2 first:!pl-4 last:!pr-4 font-mono text-xs break-all"><%= r[:device] %></td>
+                <td class="px-3 py-2 first:!pl-4 last:!pr-4 font-mono text-xs break-all"><%= r[:token_tail] %></td>
+                <td class="px-3 py-2 first:!pl-4 last:!pr-4">
+                  <%
+                    color = {
+                      success: 'bg-green-100 text-green-800',
+                      failure: 'bg-red-100 text-red-800',
+                      skipped: 'bg-slate-100 text-slate-600'
+                    }[r[:status]]
+                  %>
+                  <span class="px-2 py-0.5 rounded-full text-xs <%= color %>"><%= r[:status] %></span>
+                </td>
+                <td class="px-3 py-2 first:!pl-4 last:!pr-4 font-mono text-xs break-all whitespace-pre-wrap"><%= r[:message] %></td>
+              </tr>
+            <% end %>
+          </tbody>
+        </table>
+      </div>
+    <% end %>
+  <% end %>
+</section>
+
+<% content_for :javascript do %>
+  <script>
+    document.addEventListener('DOMContentLoaded', () => {
+      const toggle = document.getElementById('toggle-all');
+      if (!toggle) return;
+      toggle.addEventListener('change', (event) => {
+        document.querySelectorAll('.subscription-checkbox').forEach((cb) => {
+          cb.checked = event.target.checked;
+        });
+      });
+    });
+  </script>
+<% end %>
diff --git a/config/locales/en.yml b/config/locales/en.yml
index 057f41b81..1841db332 100644
--- a/config/locales/en.yml
+++ b/config/locales/en.yml
@@ -496,3 +496,9 @@ en:
       subject: 'Finish setting up %{custom_domain}'
     ssl_status:
       custom_domain_not_configured: 'Custom domain is not configured'
+  super_admin:
+    push_diagnostics:
+      user_not_found: 'User not found.'
+      no_subscriptions_to_test: 'Select at least one subscription to test.'
+      no_subscriptions_to_delete: 'Select at least one subscription to delete.'
+      subscriptions_deleted: "Deleted %{count} subscription(s). The user's device(s) will re-register on next app launch."
diff --git a/config/routes.rb b/config/routes.rb
index 31453b157..2461539ad 100644
--- a/config/routes.rb
+++ b/config/routes.rb
@@ -625,6 +625,9 @@ Rails.application.routes.draw do
       root to: 'dashboard#index'
 
       resource :app_config, only: [:show, :create]
+      resource :push_diagnostics, only: [:show, :create] do
+        post :destroy_subscriptions, on: :collection
+      end
 
       # order of resources affect the order of sidebar navigation in super admin
       resources :accounts, only: [:index, :new, :create, :show, :edit, :update, :destroy] do
diff --git a/enterprise/app/jobs/captain/documents/perform_sync_job.rb b/enterprise/app/jobs/captain/documents/perform_sync_job.rb
new file mode 100644
index 000000000..baa9c03d2
--- /dev/null
+++ b/enterprise/app/jobs/captain/documents/perform_sync_job.rb
@@ -0,0 +1,97 @@
+class Captain::Documents::PerformSyncJob < MutexApplicationJob
+  queue_as :low
+
+  LOCK_TIMEOUT = 10.minutes
+
+  # Safety net for anything we didn't rescue by name — parser bugs, ActiveRecord blips,
+  # random infra issues. Three attempts lets a real hiccup recover. The exhaustion block
+  # absorbs the final exception so Sidekiq doesn't layer its own retry policy on top, and
+  # is the single place we report to Sentry — handle_unexpected_failure logs but does not
+  # capture, so a deterministic bug emits one Sentry event instead of one per attempt.
+  # Goes first because retry_on handlers dispatch bottom-to-top.
+  retry_on StandardError, wait: 5.seconds, attempts: 3 do |job, error|
+    document = job.arguments.first
+    ChatwootExceptionTracker.new(error, account: document.account).capture_exception
+    job.send(:log_sync_outcome, document, result: :unexpected_retry_exhausted,
+                                          error_code: 'sync_error',
+                                          exception_class: error.class.name)
+  end
+
+  # Permanent errors (404, 403, empty content) — no point retrying, discard immediately.
+  # Document is already marked failed by SyncService before the exception reaches here.
+  discard_on(Captain::Documents::SyncService::PermanentSyncError)
+
+  # TransientSyncError is raised by SyncService when the customer's site is unreachable —
+  # timeouts, TLS errors, 5xx, connection drops. Four attempts with backoff gives the site
+  # a chance to recover before we give up.
+  #
+  # The exhaustion block absorbs the exception so it doesn't propagate to Sentry —
+  # site flakiness isn't an application bug.
+  retry_on(
+    Captain::Documents::SyncService::TransientSyncError,
+    wait: ->(executions) { [30.seconds, 2.minutes, 5.minutes][executions - 1] || 5.minutes },
+    attempts: 4
+  ) do |job, error|
+    document = job.arguments.first
+    job.send(:log_sync_outcome, document, result: :transient_retry_exhausted, error_code: error.message)
+  end
+
+  discard_on ActiveJob::DeserializationError
+  discard_on ActiveRecord::RecordNotFound
+
+  def perform(document)
+    start_time = Time.current
+    return if document.pdf_document?
+
+    with_lock(lock_key(document), LOCK_TIMEOUT) do
+      document.update!(sync_status: :syncing, last_sync_attempted_at: Time.current)
+      result = Captain::Documents::SyncService.new(document.reload).perform
+      log_sync_outcome(document, result: result, duration_ms: duration_ms_since(start_time))
+    end
+  rescue LockAcquisitionError
+    log_sync_outcome(document, result: :already_syncing)
+  rescue Captain::Documents::SyncService::PermanentSyncError => e
+    log_failure_and_raise(document, :permanent_failure, e, start_time)
+  rescue Captain::Documents::SyncService::TransientSyncError => e
+    log_failure_and_raise(document, :transient_failure, e, start_time)
+  rescue StandardError => e
+    handle_unexpected_failure(document, e, start_time)
+  end
+
+  private
+
+  def log_sync_outcome(document, **fields)
+    payload = {
+      document_id: document.id,
+      account_id: document.account_id,
+      assistant_id: document.assistant_id
+    }.merge(fields)
+    Rails.logger.info("[Captain::Documents::PerformSyncJob] #{payload.to_json}")
+  end
+
+  def log_failure_and_raise(document, result, error, start_time)
+    log_sync_outcome(document, result: result, error_code: error.message,
+                               duration_ms: duration_ms_since(start_time))
+    raise error
+  end
+
+  def handle_unexpected_failure(document, error, start_time)
+    document.update!(
+      sync_status: :failed,
+      last_sync_error_code: 'sync_error',
+      last_sync_attempted_at: Time.current
+    )
+    log_sync_outcome(document, result: :unexpected_failure, error_code: 'sync_error',
+                               exception_class: error.class.name,
+                               duration_ms: duration_ms_since(start_time))
+    raise error
+  end
+
+  def lock_key(document)
+    format(::Redis::Alfred::CAPTAIN_DOCUMENT_SYNC_MUTEX, document_id: document.id)
+  end
+
+  def duration_ms_since(start_time)
+    ((Time.current - start_time) * 1000).round
+  end
+end
diff --git a/enterprise/app/jobs/captain/documents/response_builder_job.rb b/enterprise/app/jobs/captain/documents/response_builder_job.rb
index 553cec110..60f1fa2cf 100644
--- a/enterprise/app/jobs/captain/documents/response_builder_job.rb
+++ b/enterprise/app/jobs/captain/documents/response_builder_job.rb
@@ -62,7 +62,7 @@ class Captain::Documents::ResponseBuilderJob < ApplicationJob
   end
 
   def reset_previous_responses(response_document)
-    response_document.responses.destroy_all
+    response_document.responses.where(edited: false).destroy_all
   end
 
   def create_response(faq, document)
diff --git a/enterprise/app/models/captain/document.rb b/enterprise/app/models/captain/document.rb
index d8e07a2d9..2abf18437 100644
--- a/enterprise/app/models/captain/document.rb
+++ b/enterprise/app/models/captain/document.rb
@@ -62,6 +62,7 @@ class Captain::Document < ApplicationRecord
 
   def pdf_document?
     return true if pdf_file.attached? && pdf_file.blob.content_type == 'application/pdf'
+    return true if external_link&.start_with?('PDF:')
 
     external_link&.ends_with?('.pdf')
   end
@@ -90,6 +91,14 @@ class Captain::Document < ApplicationRecord
     self.metadata = (metadata || {}).merge('last_sync_error_code' => value)
   end
 
+  def sync_step
+    metadata&.dig('sync_step')
+  end
+
+  def store_sync_step(step)
+    update!(metadata: (metadata || {}).merge('sync_step' => step))
+  end
+
   def openai_file_id
     metadata&.dig('openai_file_id')
   end
diff --git a/enterprise/app/services/captain/documents/single_page_fetcher.rb b/enterprise/app/services/captain/documents/single_page_fetcher.rb
new file mode 100644
index 000000000..115cd55b0
--- /dev/null
+++ b/enterprise/app/services/captain/documents/single_page_fetcher.rb
@@ -0,0 +1,80 @@
+class Captain::Documents::SinglePageFetcher
+  Result = Struct.new(:success, :title, :content, :error_code, keyword_init: true)
+
+  CONTENT_MAX_LENGTH = 200_000
+  TITLE_MAX_LENGTH = 255 # captain_documents.name is a varchar(255)
+
+  def initialize(url)
+    @url = url
+  end
+
+  def fetch
+    result = firecrawl_configured? ? fetch_with_firecrawl : fetch_with_fallback
+    validate_content(result)
+  rescue Net::ReadTimeout, Net::OpenTimeout, Errno::ETIMEDOUT
+    Result.new(success: false, error_code: 'timeout')
+  rescue SocketError, Errno::ECONNREFUSED, Errno::ECONNRESET, OpenSSL::SSL::SSLError
+    Result.new(success: false, error_code: 'fetch_failed')
+  end
+
+  private
+
+  def firecrawl_configured?
+    InstallationConfig.find_by(name: 'CAPTAIN_FIRECRAWL_API_KEY')&.value.present?
+  end
+
+  def fetch_with_firecrawl
+    response = Captain::Tools::FirecrawlService.new.scrape(@url)
+    handle_firecrawl_response(response)
+  end
+
+  def handle_firecrawl_response(response)
+    return Result.new(success: false, error_code: http_error_code(response.code)) unless response.success?
+
+    data = response.parsed_response&.dig('data')
+    target_error = firecrawl_target_error_code(data)
+    return Result.new(success: false, error_code: target_error) if target_error
+
+    Result.new(
+      success: true,
+      title: data&.dig('metadata', 'title')&.truncate(TITLE_MAX_LENGTH, omission: ''),
+      content: data&.dig('markdown')&.truncate(CONTENT_MAX_LENGTH, omission: '')
+    )
+  end
+
+  # Firecrawl returns API 200 even when the scraped page itself failed —
+  # the target page's real status lives in data.metadata.statusCode.
+  def firecrawl_target_error_code(data)
+    status = data&.dig('metadata', 'statusCode')
+    return nil if status.blank? || (200..299).cover?(status)
+
+    http_error_code(status)
+  end
+
+  def fetch_with_fallback
+    response = HTTParty.get(@url)
+    return Result.new(success: false, error_code: http_error_code(response.code)) unless response.success?
+
+    parser = Captain::Tools::HtmlPageParser.new(response.body)
+    Result.new(
+      success: true,
+      title: parser.title&.truncate(TITLE_MAX_LENGTH, omission: ''),
+      content: parser.body_markdown&.truncate(CONTENT_MAX_LENGTH, omission: '')
+    )
+  end
+
+  def validate_content(result)
+    return result unless result.success && result.content.blank?
+
+    Result.new(success: false, error_code: 'content_empty')
+  end
+
+  def http_error_code(status_code)
+    case status_code
+    when 404 then 'not_found'
+    when 401, 403 then 'access_denied'
+    when 408, 504 then 'timeout'
+    else 'fetch_failed'
+    end
+  end
+end
diff --git a/enterprise/app/services/captain/documents/sync_service.rb b/enterprise/app/services/captain/documents/sync_service.rb
new file mode 100644
index 000000000..5dcb52447
--- /dev/null
+++ b/enterprise/app/services/captain/documents/sync_service.rb
@@ -0,0 +1,76 @@
+class Captain::Documents::SyncService
+  class PermanentSyncError < StandardError
+  end
+
+  class TransientSyncError < StandardError
+  end
+
+  PERMANENT_ERROR_CODES = %w[not_found access_denied content_empty].freeze
+
+  def initialize(document)
+    @document = document
+  end
+
+  def perform
+    @document.store_sync_step('fetching')
+    result = Captain::Documents::SinglePageFetcher.new(@document.external_link).fetch
+
+    unless result.success
+      mark_failed(result.error_code)
+      raise_for_error_code(result.error_code)
+    end
+
+    @document.store_sync_step('comparing')
+    fingerprint = compute_fingerprint(result.content)
+
+    if fingerprint == @document.content_fingerprint
+      mark_synced
+      return :unchanged
+    end
+
+    @document.store_sync_step('updating')
+    update_content(result, fingerprint)
+    :updated
+  end
+
+  private
+
+  def compute_fingerprint(content)
+    Digest::SHA256.hexdigest(content.gsub(/\s+/, ' ').strip)
+  end
+
+  def mark_failed(error_code)
+    @document.update!(
+      sync_status: :failed,
+      last_sync_error_code: error_code,
+      last_sync_attempted_at: Time.current
+    )
+  end
+
+  def mark_synced
+    @document.update!(
+      sync_status: :synced,
+      last_synced_at: Time.current,
+      last_sync_attempted_at: Time.current,
+      last_sync_error_code: nil
+    )
+  end
+
+  def update_content(result, fingerprint)
+    @document.update!(
+      content: result.content,
+      name: result.title.presence || @document.name,
+      content_fingerprint: fingerprint,
+      sync_status: :synced,
+      last_synced_at: Time.current,
+      last_sync_attempted_at: Time.current,
+      last_sync_error_code: nil
+    )
+  end
+
+  def raise_for_error_code(error_code)
+    raise PermanentSyncError, error_code if PERMANENT_ERROR_CODES.include?(error_code)
+
+    raise TransientSyncError, error_code
+  end
+end
diff --git a/enterprise/app/services/captain/tools/firecrawl_service.rb b/enterprise/app/services/captain/tools/firecrawl_service.rb
index 397c3ad63..fc7448593 100644
--- a/enterprise/app/services/captain/tools/firecrawl_service.rb
+++ b/enterprise/app/services/captain/tools/firecrawl_service.rb
@@ -1,4 +1,6 @@
 class Captain::Tools::FirecrawlService
+  BASE_URL = 'https://api.firecrawl.dev/v1'.freeze
+
   def initialize
     @api_key = InstallationConfig.find_by!(name: 'CAPTAIN_FIRECRAWL_API_KEY').value
     raise 'Missing API key' if @api_key.empty?
@@ -6,7 +8,7 @@ class Captain::Tools::FirecrawlService
 
   def perform(url, webhook_url, crawl_limit = 10)
     HTTParty.post(
-      'https://api.firecrawl.dev/v1/crawl',
+      "#{BASE_URL}/crawl",
       body: crawl_payload(url, webhook_url, crawl_limit),
       headers: headers
     )
@@ -14,6 +16,14 @@ class Captain::Tools::FirecrawlService
     raise "Failed to crawl URL: #{e.message}"
   end
 
+  def scrape(url)
+    HTTParty.post(
+      "#{BASE_URL}/scrape",
+      body: scrape_payload(url),
+      headers: headers
+    )
+  end
+
   private
 
   def crawl_payload(url, webhook_url, crawl_limit)
@@ -31,6 +41,10 @@ class Captain::Tools::FirecrawlService
     }.to_json
   end
 
+  def scrape_payload(url)
+    { url: url, formats: ['markdown'], excludeTags: ['iframe'] }.to_json
+  end
+
   def headers
     {
       'Authorization' => "Bearer #{@api_key}",
diff --git a/enterprise/app/services/captain/tools/html_page_parser.rb b/enterprise/app/services/captain/tools/html_page_parser.rb
new file mode 100644
index 000000000..a7afb52cf
--- /dev/null
+++ b/enterprise/app/services/captain/tools/html_page_parser.rb
@@ -0,0 +1,15 @@
+class Captain::Tools::HtmlPageParser
+  attr_reader :doc
+
+  def initialize(html)
+    @doc = Nokogiri::HTML(html)
+  end
+
+  def title
+    @doc.at_xpath('//title')&.text&.strip
+  end
+
+  def body_markdown
+    ReverseMarkdown.convert(@doc.at_xpath('//body'), unknown_tags: :bypass, github_flavored: true)
+  end
+end
diff --git a/enterprise/app/services/captain/tools/simple_page_crawl_service.rb b/enterprise/app/services/captain/tools/simple_page_crawl_service.rb
index 65731ad90..5eaee6e5e 100644
--- a/enterprise/app/services/captain/tools/simple_page_crawl_service.rb
+++ b/enterprise/app/services/captain/tools/simple_page_crawl_service.rb
@@ -3,7 +3,8 @@ class Captain::Tools::SimplePageCrawlService
 
   def initialize(external_link)
     @external_link = external_link
-    @doc = Nokogiri::HTML(HTTParty.get(external_link).body)
+    @parser = Captain::Tools::HtmlPageParser.new(HTTParty.get(external_link).body)
+    @doc = @parser.doc
   end
 
   def page_links
@@ -11,12 +12,11 @@ class Captain::Tools::SimplePageCrawlService
   end
 
   def page_title
-    title_element = @doc.at_xpath('//title')
-    title_element&.text&.strip
+    @parser.title
   end
 
   def body_text_content
-    ReverseMarkdown.convert @doc.at_xpath('//body'), unknown_tags: :bypass, github_flavored: true
+    @parser.body_markdown
   end
 
   def meta_description
diff --git a/enterprise/app/services/enterprise/billing/topup_checkout_service.rb b/enterprise/app/services/enterprise/billing/topup_checkout_service.rb
index d0ec3e372..00e2b1646 100644
--- a/enterprise/app/services/enterprise/billing/topup_checkout_service.rb
+++ b/enterprise/app/services/enterprise/billing/topup_checkout_service.rb
@@ -79,7 +79,12 @@ class Enterprise::Billing::TopupCheckoutService
   def finalize_and_pay(invoice_id)
     Stripe::Invoice.finalize_invoice(invoice_id, { auto_advance: false })
     invoice = Stripe::Invoice.retrieve(invoice_id)
-    Stripe::Invoice.pay(invoice_id) unless invoice.status == 'paid'
+    return if invoice.status == 'paid'
+
+    Stripe::Invoice.pay(invoice_id)
+  rescue Stripe::CardError
+    Stripe::Invoice.void_invoice(invoice_id)
+    raise
   end
 
   def fulfill_credits(credits, topup_option)
diff --git a/lib/chatwoot_hub.rb b/lib/chatwoot_hub.rb
index be5a07e05..95679ed73 100644
--- a/lib/chatwoot_hub.rb
+++ b/lib/chatwoot_hub.rb
@@ -106,14 +106,18 @@ class ChatwootHub
   end
 
   def self.send_push(fcm_options)
-    info = { fcm_options: fcm_options }
-    RestClient.post(push_notification_url, info.merge(instance_config).to_json, { content_type: :json, accept: :json })
+    send_push_with_response(fcm_options)
   rescue *ExceptionList::REST_CLIENT_EXCEPTIONS => e
     Rails.logger.error "Exception: #{e.message}"
   rescue StandardError => e
     ChatwootExceptionTracker.new(e).capture_exception
   end
 
+  def self.send_push_with_response(fcm_options)
+    info = { fcm_options: fcm_options }
+    RestClient.post(push_notification_url, info.merge(instance_config).to_json, { content_type: :json, accept: :json })
+  end
+
   def self.emit_event(event_name, event_data)
     return if ENV['DISABLE_TELEMETRY']
 
diff --git a/lib/redis/redis_keys.rb b/lib/redis/redis_keys.rb
index 59e33036d..893fb50ef 100644
--- a/lib/redis/redis_keys.rb
+++ b/lib/redis/redis_keys.rb
@@ -44,6 +44,7 @@ module Redis::RedisKeys
   SLACK_MESSAGE_MUTEX = 'SLACK_MESSAGE_LOCK::%<conversation_id>s::%<reference_id>s'.freeze
   EMAIL_MESSAGE_MUTEX = 'EMAIL_CHANNEL_LOCK::%<inbox_id>s'.freeze
   CRM_PROCESS_MUTEX = 'CRM_PROCESS_MUTEX::%<hook_id>s'.freeze
+  CAPTAIN_DOCUMENT_SYNC_MUTEX = 'CAPTAIN_DOCUMENT_SYNC_LOCK::%<document_id>s'.freeze
 
   ## Auto Assignment Keys
   # Track conversation assignments to agents for rate limiting
diff --git a/spec/enterprise/models/captain/document_spec.rb b/spec/enterprise/models/captain/document_spec.rb
index e6543e0d7..af6c1cb58 100644
--- a/spec/enterprise/models/captain/document_spec.rb
+++ b/spec/enterprise/models/captain/document_spec.rb
@@ -55,6 +55,11 @@ RSpec.describe Captain::Document, type: :model do
         expect(doc.pdf_document?).to be true
       end
 
+      it 'returns true for PDF:-prefixed external links even when the blob is missing' do
+        doc = build(:captain_document, external_link: 'PDF: report_20250101120000')
+        expect(doc.pdf_document?).to be true
+      end
+
       it 'returns false for non-PDF documents' do
         doc = build(:captain_document, external_link: 'https://example.com')
         expect(doc.pdf_document?).to be false
diff --git a/spec/presenters/messages/search_data_presenter_spec.rb b/spec/presenters/messages/search_data_presenter_spec.rb
index 7b3d4acb9..48faec12a 100644
--- a/spec/presenters/messages/search_data_presenter_spec.rb
+++ b/spec/presenters/messages/search_data_presenter_spec.rb
@@ -58,6 +58,35 @@ RSpec.describe Messages::SearchDataPresenter do
       end
     end
 
+    context 'when the message has no email subject but the conversation has a mail_subject' do
+      before do
+        conversation.update!(additional_attributes: { 'mail_subject' => 'Conversation Subject' })
+      end
+
+      it 'falls back to the conversation mail_subject' do
+        content_attrs = presenter.search_data[:content_attributes]
+        expect(content_attrs[:email][:subject]).to eq('Conversation Subject')
+      end
+    end
+
+    context 'when both the message email subject and conversation mail_subject are set' do
+      before do
+        conversation.update!(additional_attributes: { 'mail_subject' => 'Conversation subject' })
+        message.update!(content_attributes: { email: { subject: 'Message subject' } })
+      end
+
+      it 'prefers the message-level email subject' do
+        content_attrs = presenter.search_data[:content_attributes]
+        expect(content_attrs[:email][:subject]).to eq('Message subject')
+      end
+    end
+
+    context 'when neither message nor conversation has an email subject' do
+      it 'omits the email subject from content_attributes' do
+        expect(presenter.search_data[:content_attributes]).to eq({})
+      end
+    end
+
     context 'with campaign and automation data' do
       before do
         message.update(