diff --git a/app/lib/dolist/api.rb b/app/lib/dolist/api.rb
index 8ae14c2f6..08ba7d57f 100644
--- a/app/lib/dolist/api.rb
+++ b/app/lib/dolist/api.rb
@@ -1,8 +1,15 @@
+require "support/jsv"
+
 class Dolist::API
   CONTACT_URL = "https://apiv9.dolist.net/v1/contacts/read?AccountID=%{account_id}"
   EMAIL_LOGS_URL = "https://apiv9.dolist.net/v1/statistics/email/sendings/transactional/search?AccountID=%{account_id}"
   EMAIL_KEY = 7
   DOLIST_WEB_DASHBOARD = "https://campaign.dolist.net/#/%{account_id}/contacts/%{contact_id}/sendings"
+  EMAIL_MESSAGES_ADRESSES_REPLIES = "https://apiv9.dolist.net/v1/email/messages/addresses/replies?AccountID=%{account_id}"
+  EMAIL_MESSAGES_ADRESSES_PACKSENDERS = "https://apiv9.dolist.net/v1/email/messages/addresses/packsenders?AccountID=%{account_id}"
+  EMAIL_SENDING_TRANSACTIONAL = "https://apiv9.dolist.net/v1/email/sendings/transactional?AccountID=%{account_id}"
+  EMAIL_SENDING_TRANSACTIONAL_ATTACHMENT = "https://apiv9.dolist.net/v1/email/sendings/transactional/attachment?AccountID=%{account_id}"
+  EMAIL_SENDING_TRANSACTIONAL_SEARCH = "https://apiv9.dolist.net/v1/email/sendings/transactional/search?AccountID=%{account_id}"
 
   class_attribute :limit_remaining, :limit_reset_at
 
@@ -23,12 +30,74 @@ class Dolist::API
 
       sleep (limit_reset_at - Time.zone.now).ceil
     end
+
+    def sendable?(mail)
+      # Mail having attachments are not yet supported in our account
+      mail.attachments.none? { !_1.inline? }
+    end
   end
 
   def properly_configured?
     client_key.present?
   end
 
+  def send_email(mail)
+    if mail.attachments.any? { !_1.inline? }
+      return send_email_with_attachment(mail)
+    end
+
+    body = { "TransactionalSending": prepare_mail_body(mail) }
+
+    url = format_url(EMAIL_SENDING_TRANSACTIONAL)
+    post(url, body.to_json)
+  end
+
+  def send_email_with_attachment(mail)
+    uri = URI(format_url(EMAIL_SENDING_TRANSACTIONAL_ATTACHMENT))
+
+    request = Net::HTTP::Post.new(uri)
+
+    default_headers.each do |key, value|
+      next if key.to_s == "Content-Type"
+      request[key] = value
+    end
+
+    boundary = "---011000010111000001101001" # any random string not present in the body
+    request.content_type = "multipart/form-data; boundary=#{boundary}"
+
+    body = "--#{boundary}\r\n"
+
+    base64_files(mail.attachments).each do |file|
+      body << "Content-Disposition: form-data; name=\"#{file.field_name}\"; filename=\"#{file.filename}\"\r\n"
+      body << "Content-Type: #{file.mime_type}\r\n"
+      body << "\r\n"
+      body << file.content
+      body << "\r\n"
+    end
+
+    body << "\r\n--#{boundary}\r\n"
+    body << "Content-Disposition: form-data; name=\"TransactionalSending\"\r\n"
+    body << "Content-Type: text/plain; charset=utf-8\r\n"
+    body << "\r\n"
+    body << prepare_mail_body(mail).to_jsv
+
+    body << "\r\n--#{boundary}--\r\n"
+    body << "\r\n"
+
+    request.body = body
+
+    http = Net::HTTP.new(uri.host, uri.port)
+    http.use_ssl = true
+
+    response = http.request(request)
+
+    if response.body.empty?
+      fail "Dolist API returned an empty response"
+    else
+      JSON.parse(response.body)
+    end
+  end
+
   def sent_mails(email_address)
     contact_id = fetch_contact_id(email_address)
     if contact_id.nil?
@@ -44,9 +113,47 @@ class Dolist::API
     []
   end
 
+  def senders
+    get format_url(EMAIL_MESSAGES_ADRESSES_PACKSENDERS)
+  end
+
+  def replies
+    get format_url(EMAIL_MESSAGES_ADRESSES_REPLIES)
+  end
+
   private
 
-  def headers
+  def format_url(base)
+    format(base, account_id: account_id)
+  end
+
+  def sender_id
+    Rails.cache.fetch("dolist_api_sender_id", expires_in: 1.hour) do
+      senders.dig("ItemList", 0, "Sender", "ID")
+    end
+  end
+
+  def get(url)
+    response = Typhoeus.get(url, headers: default_headers).tap do
+      self.class.save_rate_limit_headers(_1.headers)
+    end
+
+    JSON.parse(response.response_body)
+  end
+
+  def post(url, body)
+    response = Typhoeus.post(url, body:, headers: default_headers).tap do
+      self.class.save_rate_limit_headers(_1.headers)
+    end
+
+    if response.response_body.empty?
+      fail "Empty response from Dolist API"
+    else
+      JSON.parse(response.response_body)
+    end
+  end
+
+  def default_headers
     {
       "Content-Type": 'application/json',
       "Accept": 'application/json',
@@ -82,12 +189,32 @@ class Dolist::API
     post(url, body)["ItemList"]
   end
 
-  def post(url, body)
-    response = Typhoeus.post(url, body:, headers:).tap do
-      self.class.save_rate_limit_headers(_1.headers)
-    end
-
-    JSON.parse(response.response_body)
+  def prepare_mail_body(mail)
+    {
+      "Type": "TransactionalService",
+      "Contact": {
+        "FieldList": [
+          {
+            "ID": EMAIL_KEY,
+            "Value": mail.to.first
+          }
+        ]
+      },
+      "Message": {
+        "Name": mail['X-Dolist-Message-Name'].value,
+        "Subject": mail.subject,
+        "SenderID": sender_id,
+        "ForceHttp": true,
+        "Format": "html",
+        "DisableOpenTracking": true,
+        "IsTrackingValidated": true
+      },
+      "MessageContent": {
+        "SourceCode":  mail_source_code(mail),
+        "EncodingType": "UTF8",
+        "EnableTrackingDetection": false
+      }
+    }
   end
 
   def to_sent_mail(email_address, contact_id, dolist_message)
@@ -112,4 +239,24 @@ class Dolist::API
       status
     end
   end
+
+  def mail_source_code(mail)
+    if mail.html_part.nil? && mail.text_part.nil?
+      mail.decoded
+    else
+      mail.html_part.body.decoded
+    end
+  end
+
+  def base64_files(attachments)
+    attachments.map do |attachment|
+      raise ArgumentError, "Dolist API does not support non PDF attachments. Given #{attachment.filename} which has mime_type=#{attachment.mime_type}" unless attachment.mime_type == "application/pdf"
+
+      field_name = File.basename(attachment.filename, File.extname(attachment.filename))
+      attachment_content = attachment.body.decoded
+      attachment_base64 = Base64.strict_encode64(attachment_content)
+
+      Dolist::Base64File.new(field_name:, filename: attachment.filename, mime_type: attachment.mime_type, content: attachment_base64)
+    end
+  end
 end
diff --git a/app/lib/dolist/base64_file.rb b/app/lib/dolist/base64_file.rb
new file mode 100644
index 000000000..8afcf2024
--- /dev/null
+++ b/app/lib/dolist/base64_file.rb
@@ -0,0 +1,3 @@
+module Dolist
+  Base64File = Struct.new(:field_name, :filename, :mime_type, :content, keyword_init: true)
+end
diff --git a/app/lib/mail_delivery_error.rb b/app/lib/mail_delivery_error.rb
index 4ce1cffed..630496528 100644
--- a/app/lib/mail_delivery_error.rb
+++ b/app/lib/mail_delivery_error.rb
@@ -3,4 +3,10 @@
 # so it would be shallowed otherwise.
 #
 # TODO: add a test which verify that the error will permit the job to retry
-class MailDeliveryError < Exception; end # rubocop:disable Lint/InheritException
+class MailDeliveryError < Exception # rubocop:disable Lint/InheritException
+  def initialize(original_exception)
+    super(original_exception.message)
+
+    set_backtrace(original_exception.backtrace)
+  end
+end
diff --git a/app/views/layouts/mailers/layout.html.erb b/app/views/layouts/mailers/layout.html.erb
index 6175243c6..70562a48b 100644
--- a/app/views/layouts/mailers/layout.html.erb
+++ b/app/views/layouts/mailers/layout.html.erb
@@ -108,6 +108,7 @@
                 <div class="mj-column-per-100 outlook-group-fix" style="vertical-align:top;display:inline-block;direction:ltr;font-size:13px;text-align:left;width:100%;">
                   <table role="presentation" cellpadding="0" cellspacing="0" width="100%" border="0">
                     <tbody>
+                      <%= yield(:procedure_logo) %>
                       <tr>
                         <td style="word-wrap:break-word;font-size:0px;padding:0px 25px 0px 25px;padding-top:0px;padding-bottom:0px;" align="left">
                           <div class="" style="cursor:auto;color:#55575d;font-family:Helvetica, Arial, sans-serif;font-size:13px;line-height:22px;text-align:left;">
diff --git a/lib/support/jsv.rb b/lib/support/jsv.rb
new file mode 100644
index 000000000..0d09cf69d
--- /dev/null
+++ b/lib/support/jsv.rb
@@ -0,0 +1,9 @@
+# spec by dolist https://api.dolist.com/ConvertJSON-to-JSV.html
+#
+require_relative "jsv/core_ext/array"
+require_relative "jsv/core_ext/false_class"
+require_relative "jsv/core_ext/hash"
+require_relative "jsv/core_ext/number"
+require_relative "jsv/core_ext/string"
+require_relative "jsv/core_ext/symbol"
+require_relative "jsv/core_ext/true_class"
diff --git a/lib/support/jsv/core_ext/array.rb b/lib/support/jsv/core_ext/array.rb
new file mode 100644
index 000000000..67c262513
--- /dev/null
+++ b/lib/support/jsv/core_ext/array.rb
@@ -0,0 +1,5 @@
+class Array
+  def to_jsv
+    "[" + reject(&:nil?).map(&:to_jsv).join(",") + "]"
+  end
+end
diff --git a/lib/support/jsv/core_ext/false_class.rb b/lib/support/jsv/core_ext/false_class.rb
new file mode 100644
index 000000000..171eb991b
--- /dev/null
+++ b/lib/support/jsv/core_ext/false_class.rb
@@ -0,0 +1,5 @@
+class TrueClass
+  def to_jsv
+    "True"
+  end
+end
diff --git a/lib/support/jsv/core_ext/hash.rb b/lib/support/jsv/core_ext/hash.rb
new file mode 100644
index 000000000..3fc326552
--- /dev/null
+++ b/lib/support/jsv/core_ext/hash.rb
@@ -0,0 +1,11 @@
+class Hash
+  def to_jsv
+    js_array = filter_map do |key, value|
+      next if value.nil? # skip nil values
+
+      "#{key.to_jsv}:#{value.to_jsv}"
+    end
+
+    "{" + js_array.join(",") + "}"
+  end
+end
diff --git a/lib/support/jsv/core_ext/number.rb b/lib/support/jsv/core_ext/number.rb
new file mode 100644
index 000000000..def9ee63d
--- /dev/null
+++ b/lib/support/jsv/core_ext/number.rb
@@ -0,0 +1,5 @@
+class Numeric
+  def to_jsv
+    self
+  end
+end
diff --git a/lib/support/jsv/core_ext/string.rb b/lib/support/jsv/core_ext/string.rb
new file mode 100644
index 000000000..fb1cc0a8a
--- /dev/null
+++ b/lib/support/jsv/core_ext/string.rb
@@ -0,0 +1,12 @@
+class String
+  JSV_REGEX_SPECIAL_CHARS = /[\[\]\{\}"\,]/.freeze
+
+  def to_jsv
+    double_quoted = self.gsub('"', '""')
+    if match?(JSV_REGEX_SPECIAL_CHARS)
+      "\"#{double_quoted}\""
+    else
+      double_quoted
+    end
+  end
+end
diff --git a/lib/support/jsv/core_ext/symbol.rb b/lib/support/jsv/core_ext/symbol.rb
new file mode 100644
index 000000000..44c26d6c3
--- /dev/null
+++ b/lib/support/jsv/core_ext/symbol.rb
@@ -0,0 +1,5 @@
+class Symbol
+  def to_jsv
+    to_s.to_jsv
+  end
+end
diff --git a/lib/support/jsv/core_ext/true_class.rb b/lib/support/jsv/core_ext/true_class.rb
new file mode 100644
index 000000000..090ebe9f7
--- /dev/null
+++ b/lib/support/jsv/core_ext/true_class.rb
@@ -0,0 +1,5 @@
+class FalseClass
+  def to_jsv
+    "False"
+  end
+end
diff --git a/spec/lib/support/jsv_spec.rb b/spec/lib/support/jsv_spec.rb
new file mode 100644
index 000000000..f3b9670d0
--- /dev/null
+++ b/spec/lib/support/jsv_spec.rb
@@ -0,0 +1,75 @@
+require_relative "../../../lib/support/jsv"
+
+describe ".to_jsv support" do
+  it "converts a Hash to JSV" do
+    expect({}.to_jsv).to eq("{}")
+    expect({ "a" => "b" }.to_jsv).to eq("{a:b}")
+  end
+
+  it "converts an Array to JSV" do
+    expect([].to_jsv).to eq("[]")
+    expect(["a", "b"].to_jsv).to eq("[a,b]")
+  end
+
+  it "converts a String to JSV" do
+    expect("".to_jsv).to eq("")
+    expect("a".to_jsv).to eq("a")
+
+    # escape special characters
+    expect("a[b".to_jsv).to eq('"a[b"')
+    expect("a]b".to_jsv).to eq('"a]b"')
+    expect("a,b".to_jsv).to eq('"a,b"')
+    expect("a{b".to_jsv).to eq('"a{b"')
+    expect("a}b".to_jsv).to eq('"a}b"')
+    expect('a"b'.to_jsv).to eq('"a""b"')
+  end
+
+  it "skip null values" do
+    expect({ "a" => nil }.to_jsv).to eq("{}")
+    expect([nil].to_jsv).to eq("[]")
+  end
+
+  it "converts symbols like strings" do
+    expect({ a: :b }.to_jsv).to eq("{a:b}")
+  end
+
+  it "converts booleans" do
+    expect(true.to_jsv).to eq("True")
+    expect(false.to_jsv).to eq("False")
+  end
+
+  it "converts numbers" do
+    expect(1.to_jsv).to eq(1)
+    expect(3.14.to_jsv).to eq(3.14)
+  end
+
+  it "converts nested structures" do
+    expect({ "a" => { "b" => "c" } }.to_jsv).to eq("{a:{b:c}}")
+    expect({ "a" => ["b", "c"] }.to_jsv).to eq("{a:[b,c]}")
+  end
+
+  it "converts relastic structures" do
+    hash = {
+      Type: :TransactionalService,
+      "Contact": {
+        "FieldList": [
+          {
+            "ID": 3,
+            "Value": "glou[0]"
+          }
+        ]
+      },
+      "Message": {
+        "Subject": "You, and me",
+        "ForceHttp": true,
+        "IsTrackingValidated": false,
+        "IgnoreMe": nil,
+        "SourceCode":  "<html><body><p>Un mail tout simple pour commencer</p></body></html>",
+        "SourceWithQuote": 'Ceci est une double quote: "'
+      }
+    }
+
+    expected = '{Type:TransactionalService,Contact:{FieldList:[{ID:3,Value:"glou[0]"}]},Message:{Subject:"You, and me",ForceHttp:True,IsTrackingValidated:False,SourceCode:<html><body><p>Un mail tout simple pour commencer</p></body></html>,SourceWithQuote:"Ceci est une double quote: """}}'
+    expect(hash.to_jsv).to eq(expected)
+  end
+end
diff --git a/spec/mailers/previews/dossier_mailer_preview.rb b/spec/mailers/previews/dossier_mailer_preview.rb
index 61fad6354..2ef877538 100644
--- a/spec/mailers/previews/dossier_mailer_preview.rb
+++ b/spec/mailers/previews/dossier_mailer_preview.rb
@@ -1,7 +1,7 @@
 # Preview all emails at http://localhost:3000/rails/mailers/dossier_mailer
 class DossierMailerPreview < ActionMailer::Preview
   def notify_new_draft
-    DossierMailer.notify_new_draft(draft)
+    DossierMailer.with(dossier: draft).notify_new_draft
   end
 
   def notify_new_answer