diff --git a/Gemfile b/Gemfile
index 711e744c3..7e7e6ea97 100644
--- a/Gemfile
+++ b/Gemfile
@@ -29,6 +29,8 @@ gem 'flag_shih_tzu'
 gem 'haikunator'
 # Template parsing safetly
 gem 'liquid'
+# Parse Markdown to HTML
+gem 'redcarpet'
 
 ##-- for active storage --##
 gem 'aws-sdk-s3', require: false
diff --git a/Gemfile.lock b/Gemfile.lock
index e0b382569..d9da65980 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -384,6 +384,7 @@ GEM
     rb-fsevent (0.10.4)
     rb-inotify (0.10.1)
       ffi (~> 1.0)
+    redcarpet (3.5.1)
     redis (4.2.1)
     redis-namespace (1.8.0)
       redis (>= 3.0.4)
@@ -628,6 +629,7 @@ DEPENDENCIES
   pundit
   rack-cors
   rails
+  redcarpet
   redis
   redis-namespace
   redis-rack-cache
diff --git a/app/builders/contact_builder.rb b/app/builders/contact_builder.rb
index 3e362c9b5..dc15a299a 100644
--- a/app/builders/contact_builder.rb
+++ b/app/builders/contact_builder.rb
@@ -5,7 +5,7 @@ class ContactBuilder
     contact_inbox = inbox.contact_inboxes.find_by(source_id: source_id)
     return contact_inbox if contact_inbox
 
-    build_contact
+    build_contact_inbox
   end
 
   private
@@ -26,16 +26,29 @@ class ContactBuilder
     ::ContactAvatarJob.perform_later(contact, contact_attributes[:avatar_url]) if contact_attributes[:avatar_url]
   end
 
-  def build_contact
-    ActiveRecord::Base.transaction do
-      contact = account.contacts.create!(
-        name: contact_attributes[:name],
-        phone_number: contact_attributes[:phone_number],
-        email: contact_attributes[:email],
-        identifier: contact_attributes[:identifier],
-        additional_attributes: contact_attributes[:additional_attributes]
-      )
+  def create_contact
+    account.contacts.create!(
+      name: contact_attributes[:name],
+      phone_number: contact_attributes[:phone_number],
+      email: contact_attributes[:email],
+      identifier: contact_attributes[:identifier],
+      additional_attributes: contact_attributes[:additional_attributes]
+    )
+  end
 
+  def find_contact
+    contact = nil
+
+    contact = account.contacts.find_by(identifier: contact_attributes[:identifier]) if contact_attributes[:identifier].present?
+
+    contact ||= account.contacts.find_by(email: contact_attributes[:email]) if contact_attributes[:email].present?
+
+    contact
+  end
+
+  def build_contact_inbox
+    ActiveRecord::Base.transaction do
+      contact = find_contact || create_contact
       contact_inbox = create_contact_inbox(contact)
       update_contact_avatar(contact)
       contact_inbox
diff --git a/app/mailers/conversation_reply_mailer.rb b/app/mailers/conversation_reply_mailer.rb
index ee3ef8239..165e9cff7 100644
--- a/app/mailers/conversation_reply_mailer.rb
+++ b/app/mailers/conversation_reply_mailer.rb
@@ -130,8 +130,8 @@ class ConversationReplyMailer < ApplicationMailer
   def conversation_reply_email_id
     content_attributes = @conversation.messages.incoming.last&.content_attributes
 
-    if content_attributes && content_attributes['email'] && content_attributes['message_id']
-      "<#{@conversation.messages.incoming.last.content_attributes['email']['message_id']}>"
+    if content_attributes && content_attributes['email'] && content_attributes['email']['message_id']
+      return "<#{content_attributes['email']['message_id']}>"
     end
 
     nil
diff --git a/app/views/mailers/conversation_reply_mailer/conversation_transcript.html.erb b/app/views/mailers/conversation_reply_mailer/conversation_transcript.html.erb
index 825d5ce3f..d8a3e0e9b 100644
--- a/app/views/mailers/conversation_reply_mailer/conversation_transcript.html.erb
+++ b/app/views/mailers/conversation_reply_mailer/conversation_transcript.html.erb
@@ -1,3 +1,4 @@
+<% markdown = Redcarpet::Markdown.new(Redcarpet::Render::HTML, autolink: true, tables: true) %>
 <% @messages.each do |message| %>
   <tr>
     <td>
@@ -7,7 +8,7 @@
   <tr>
     <td style="padding-bottom: 16px;">
       <% if message.content %>
-        <%= message.content %>
+        <%= markdown.render(message.content).html_safe %>
       <% end %>
       <% if message.attachments %>
         <% message.attachments.each do |attachment| %>
diff --git a/app/views/mailers/conversation_reply_mailer/reply_with_summary.html.erb b/app/views/mailers/conversation_reply_mailer/reply_with_summary.html.erb
index 5e182a273..d0b38a021 100644
--- a/app/views/mailers/conversation_reply_mailer/reply_with_summary.html.erb
+++ b/app/views/mailers/conversation_reply_mailer/reply_with_summary.html.erb
@@ -1,3 +1,4 @@
+<% markdown = Redcarpet::Markdown.new(Redcarpet::Render::HTML, autolink: true, tables: true) %>
 <p>Hi <%= @contact.name %>,</p>
 
 <p>You have new messages on your conversation.</p>
@@ -11,7 +12,7 @@
   <tr>
     <td style="padding: 10px 20px; margin: 5px 0 20px 0; background: #F2F3F7; border-radius: 10px; display: inline-block; font-family: "Helvetica Neue",Tahoma,Arial,sans-serif; text-align: start; unicode-bidi: plaintext;">
       <% if message.content %>
-        <%= message.content %>
+        <%= markdown.render(message.content).html_safe %>
       <% end %>
       <% if message.attachments %>
         <% message.attachments.each do |attachment| %>
diff --git a/app/views/mailers/conversation_reply_mailer/reply_without_summary.html.erb b/app/views/mailers/conversation_reply_mailer/reply_without_summary.html.erb
index 54f607c33..ed084b2ca 100644
--- a/app/views/mailers/conversation_reply_mailer/reply_without_summary.html.erb
+++ b/app/views/mailers/conversation_reply_mailer/reply_without_summary.html.erb
@@ -1,7 +1,9 @@
+<% markdown = Redcarpet::Markdown.new(Redcarpet::Render::HTML, autolink: true, tables: true) %>
+
 <% @messages.each do |message| %>
   <p style="font-family: Roboto,"Helvetica Neue",Tahoma,Arial,sans-serif; text-align: start; unicode-bidi: plaintext;">
     <% if message.content %>
-      <%= message.content.gsub("\n", "<br/>").html_safe %>
+      <%= markdown.render(message.content).html_safe %>
     <% end %>
     <% if message.attachments %>
       <% message.attachments.each do |attachment| %>