diff --git a/Gemfile b/Gemfile
index 144240b62..a21af8c01 100644
--- a/Gemfile
+++ b/Gemfile
@@ -39,6 +39,8 @@ gem 'rack-attack', '>= 6.7.0'
 gem 'down'
 # authentication type to fetch and send mail over oauth2.0
 gem 'gmail_xoauth'
+# Lock net-smtp to 0.3.4 to avoid issues with gmail_xoauth2
+gem 'net-smtp',  '~> 0.3.4'
 # Prevent CSV injection
 gem 'csv-safe'
 
diff --git a/Gemfile.lock b/Gemfile.lock
index 62c6829ed..96881eb30 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -479,7 +479,7 @@ GEM
       net-protocol
     net-protocol (0.2.2)
       timeout
-    net-smtp (0.4.0)
+    net-smtp (0.3.4)
       net-protocol
     netrc (0.11.0)
     newrelic-sidekiq-metrics (1.6.2)
@@ -903,6 +903,7 @@ DEPENDENCIES
   meta_request
   mock_redis
   neighbor
+  net-smtp (~> 0.3.4)
   newrelic-sidekiq-metrics (>= 1.6.2)
   newrelic_rpm
   omniauth (>= 2.1.2)
diff --git a/app/javascript/dashboard/components/widgets/conversation/Message.vue b/app/javascript/dashboard/components/widgets/conversation/Message.vue
index 8eb03137b..e6890535b 100644
--- a/app/javascript/dashboard/components/widgets/conversation/Message.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/Message.vue
@@ -1,7 +1,10 @@
 <template>
   <li v-if="shouldRenderMessage" :id="`message${data.id}`" :class="alignBubble">
     <div :class="wrapClass">
-      <div v-if="isFailed && !hasOneDayPassed" class="message-failed--alert">
+      <div
+        v-if="isFailed && !hasOneDayPassed && !isAnEmailInbox"
+        class="message-failed--alert"
+      >
         <woot-button
           v-tooltip.top-end="$t('CONVERSATION.TRY_AGAIN')"
           size="tiny"
@@ -203,6 +206,10 @@ export default {
       type: Boolean,
       default: false,
     },
+    isAnEmailInbox: {
+      type: Boolean,
+      default: false,
+    },
     inboxSupportsReplyTo: {
       type: Object,
       default: () => ({}),
diff --git a/app/javascript/dashboard/components/widgets/conversation/MessagesView.vue b/app/javascript/dashboard/components/widgets/conversation/MessagesView.vue
index 62eb6d739..7ff536942 100644
--- a/app/javascript/dashboard/components/widgets/conversation/MessagesView.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/MessagesView.vue
@@ -33,6 +33,7 @@
         :is-a-whatsapp-channel="isAWhatsAppChannel"
         :is-web-widget-inbox="isAWebWidgetInbox"
         :is-a-facebook-inbox="isAFacebookInbox"
+        :is-an-email-inbox="isAnEmailChannel"
         :is-instagram="isInstagramDM"
         :inbox-supports-reply-to="inboxSupportsReplyTo"
         :in-reply-to="getInReplyToMessage(message)"
diff --git a/app/workers/email_reply_worker.rb b/app/workers/email_reply_worker.rb
index dddbae3dd..20cc70d5e 100644
--- a/app/workers/email_reply_worker.rb
+++ b/app/workers/email_reply_worker.rb
@@ -8,6 +8,9 @@ class EmailReplyWorker
     return unless message.email_notifiable_message?
 
     # send the email
-    ConversationReplyMailer.with(account: message.account).email_reply(message).deliver_later
+    ConversationReplyMailer.with(account: message.account).email_reply(message).deliver_now
+  rescue StandardError => e
+    ChatwootExceptionTracker.new(e, account: message.account).capture_exception
+    message.update!(status: :failed, external_error: e.message)
   end
 end
diff --git a/spec/workers/email_reply_worker_spec.rb b/spec/workers/email_reply_worker_spec.rb
index dc2d83e2b..579378918 100644
--- a/spec/workers/email_reply_worker_spec.rb
+++ b/spec/workers/email_reply_worker_spec.rb
@@ -11,34 +11,48 @@ RSpec.describe EmailReplyWorker, type: :worker do
   let(:mailer_action) { double }
 
   describe '#perform' do
-    before do
-      allow(ConversationReplyMailer).to receive(:with).and_return(mailer)
-      allow(mailer).to receive(:email_reply).and_return(mailer_action)
-      allow(mailer_action).to receive(:deliver_later).and_return(true)
+    context 'when emails are successfully sent' do
+      before do
+        allow(ConversationReplyMailer).to receive(:with).and_return(mailer)
+        allow(mailer).to receive(:email_reply).and_return(mailer_action)
+        allow(mailer_action).to receive(:deliver_now).and_return(true)
+      end
+
+      it 'calls mailer action with message' do
+        described_class.new.perform(message.id)
+        expect(mailer).to have_received(:email_reply).with(message)
+        expect(mailer_action).to have_received(:deliver_now)
+      end
+
+      it 'does not call mailer action with a private message' do
+        described_class.new.perform(private_message.id)
+        expect(mailer).not_to have_received(:email_reply)
+        expect(mailer_action).not_to have_received(:deliver_now)
+      end
+
+      it 'calls mailer action with a CSAT message' do
+        described_class.new.perform(template_message.id)
+        expect(mailer).to have_received(:email_reply).with(template_message)
+        expect(mailer_action).to have_received(:deliver_now)
+      end
+
+      it 'does not call mailer action with an incoming message' do
+        described_class.new.perform(incoming_message.id)
+        expect(mailer).not_to have_received(:email_reply)
+        expect(mailer_action).not_to have_received(:deliver_now)
+      end
     end
 
-    it 'calls mailer action with message' do
-      described_class.new.perform(message.id)
-      expect(mailer).to have_received(:email_reply).with(message)
-      expect(mailer_action).to have_received(:deliver_later)
-    end
+    context 'when emails are not sent' do
+      before do
+        allow(ConversationReplyMailer).to receive(:with).and_return(mailer)
+        allow(mailer).to receive(:email_reply).and_return(mailer_action)
+        allow(mailer_action).to receive(:deliver_now).and_raise(ArgumentError)
+      end
 
-    it 'does not call mailer action with a private message' do
-      described_class.new.perform(private_message.id)
-      expect(mailer).not_to have_received(:email_reply)
-      expect(mailer_action).not_to have_received(:deliver_later)
-    end
-
-    it 'calls mailer action with a CSAT message' do
-      described_class.new.perform(template_message.id)
-      expect(mailer).to have_received(:email_reply).with(template_message)
-      expect(mailer_action).to have_received(:deliver_later)
-    end
-
-    it 'does not call mailer action with an incoming message' do
-      described_class.new.perform(incoming_message.id)
-      expect(mailer).not_to have_received(:email_reply)
-      expect(mailer_action).not_to have_received(:deliver_later)
+      it 'mark message as failed' do
+        expect { described_class.new.perform(message.id) }.to change { message.reload.status }.from('sent').to('failed')
+      end
     end
   end
 end