diff --git a/.docker/ruby/Dockerfile b/.docker/ruby/Dockerfile
index 75c43f1f..af3a8643 100644
--- a/.docker/ruby/Dockerfile
+++ b/.docker/ruby/Dockerfile
@@ -12,9 +12,10 @@ RUN curl -sL https://deb.nodesource.com/setup_12.x | bash -
 
 RUN apt-get update -qq \
     && apt-get install -y --no-install-recommends build-essential \
-    libpq-dev postgresql-client \ 
+    libpq-dev postgresql-client \
     libxml2-dev libxslt1-dev \
     libmagickwand-dev imagemagick \
+    libidn11-dev \
     nodejs \
     yarn \
     && rm -rf /var/lib/apt/lists/*
diff --git a/.github/workflows/retrospring.yml b/.github/workflows/retrospring.yml
index b3c05641..7fe00b56 100644
--- a/.github/workflows/retrospring.yml
+++ b/.github/workflows/retrospring.yml
@@ -52,7 +52,7 @@ jobs:
         with:
           node-version: '12'
       - name: Install dependencies
-        run: sudo apt update && sudo apt-get install -y libpq-dev libxml2-dev libxslt1-dev libmagickwand-dev imagemagick
+        run: sudo apt update && sudo apt-get install -y libpq-dev libxml2-dev libxslt1-dev libmagickwand-dev imagemagick libidn11-dev
       - name: Copy default configuration
         run: |
           cp config/database.yml.postgres config/database.yml
diff --git a/Gemfile b/Gemfile
index 38b52e87..f4ac386d 100644
--- a/Gemfile
+++ b/Gemfile
@@ -57,6 +57,7 @@ gem 'omniauth-tumblr'
 
 # OAuth clients
 gem 'twitter'
+gem 'twitter-text'
 # To use a more recent Faraday version, a fork of this gem is required.
 gem 'tumblr_client', git: 'https://github.com/amplifr/tumblr_client'
 
diff --git a/Gemfile.lock b/Gemfile.lock
index b75205ba..5e9bf9a5 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -251,6 +251,7 @@ GEM
       concurrent-ruby (~> 1.0)
     i18n-js (3.6.0)
       i18n (>= 0.6.6)
+    idn-ruby (0.1.4)
     image_processing (1.12.1)
       mini_magick (>= 4.9.5, < 5)
       ruby-vips (>= 2.0.17, < 3)
@@ -534,6 +535,9 @@ GEM
       multipart-post (~> 2.0)
       naught (~> 1.0)
       simple_oauth (~> 0.3.0)
+    twitter-text (3.1.0)
+      idn-ruby
+      unf (~> 0.1.0)
     tzinfo (1.2.9)
       thread_safe (~> 0.1)
     uglifier (4.2.0)
@@ -632,6 +636,7 @@ DEPENDENCIES
   tumblr_client!
   turbolinks (~> 2.5.3)
   twitter
+  twitter-text
   uglifier (>= 1.3.0)
   web-console (< 4.0.0)
   webpacker (~> 5.2)
diff --git a/app/controllers/ajax/answer_controller.rb b/app/controllers/ajax/answer_controller.rb
index 37bc1ec0..7c5b48ea 100644
--- a/app/controllers/ajax/answer_controller.rb
+++ b/app/controllers/ajax/answer_controller.rb
@@ -48,7 +48,9 @@ class Ajax::AnswerController < AjaxController
     end
 
     services = JSON.parse params[:share]
-    ShareWorker.perform_async(current_user.id, answer.id, services)
+    services.each do |service|
+      ShareWorker.perform_async(current_user.id, answer.id, service)
+    end
 
 
     @response[:status] = :okay
diff --git a/app/models/services/twitter.rb b/app/models/services/twitter.rb
index 0726fe97..0e090bcd 100644
--- a/app/models/services/twitter.rb
+++ b/app/models/services/twitter.rb
@@ -27,16 +27,30 @@ class Services::Twitter < Service
     end
 
     def prepare_tweet(answer)
-      # TODO: improve this.
       question_content = twitter_markdown answer.question.content.gsub(/\@(\w+)/, '\1')
+      original_question_length = question_content.length
       answer_content = twitter_markdown answer.content
+      original_answer_length = answer_content.length
       answer_url = show_user_answer_url(
         id: answer.id,
         username: answer.user.screen_name,
         host: APP_CONFIG['hostname'],
         protocol: (APP_CONFIG['https'] ? :https : :http)
       )
-      "#{question_content[0..122]}#{'…' if question_content.length > 123}" \
-        " — #{answer_content[0..123]}#{'…' if answer_content.length > 124} #{answer_url}"
+
+      parsed_tweet = { :valid => false }
+      tweet_text = ""
+
+      until parsed_tweet[:valid]
+        tweet_text = "#{question_content[0..122]}#{'…' if original_question_length > [123, question_content.length].min}" \
+          " — #{answer_content[0..123]}#{'…' if original_answer_length > [124, answer_content.length].min} #{answer_url}"
+
+        parsed_tweet = Twitter::TwitterText::Validation::parse_tweet(tweet_text)
+
+        question_content = question_content[0..-2]
+        answer_content = answer_content[0..-2]
+      end
+
+      tweet_text
     end
 end
diff --git a/app/workers/share_worker.rb b/app/workers/share_worker.rb
index fc4eb5b9..d0964b3c 100644
--- a/app/workers/share_worker.rb
+++ b/app/workers/share_worker.rb
@@ -1,19 +1,19 @@
 class ShareWorker
   include Sidekiq::Worker
 
-  sidekiq_options queue: :share, retry: false
+  sidekiq_options queue: :share, retry: 5
 
   # @param user_id [Integer] the user id
   # @param answer_id [Integer] the user id
-  # @param services [Array] array containing strings
-  def perform(user_id, answer_id, services)
-    User.find(user_id).services.each do |service|
-      begin
-        service.post(Answer.find(answer_id)) if services.include? service.provider
-      rescue => e
-        logger.info "failed to post answer #{answer_id} to #{service.provider} for user #{user_id}: #{e.message}"
-        NewRelic::Agent.notice_error(e)
-      end
-    end
+  # @param service [String] the service to post to
+  def perform(user_id, answer_id, service)
+    service_type = "Services::#{service.camelize}"
+    user_service = User.find(user_id).services.find_by(type: service_type)
+
+    user_service.post(Answer.find(answer_id))
+  rescue => e
+    logger.info "failed to post answer #{answer_id} to #{service.provider} for user #{user_id}: #{e.message}"
+    NewRelic::Agent.notice_error(e)
+    raise
   end
 end
diff --git a/spec/controllers/ajax/answer_controller_spec.rb b/spec/controllers/ajax/answer_controller_spec.rb
index b234a41b..c73e901f 100644
--- a/spec/controllers/ajax/answer_controller_spec.rb
+++ b/spec/controllers/ajax/answer_controller_spec.rb
@@ -27,7 +27,9 @@ describe Ajax::AnswerController, :ajax_controller, type: :controller do
 
         it "enqueues a job for sharing the answer to social networks" do
           subject
-          expect(ShareWorker).to have_enqueued_sidekiq_job(user.id, Answer.last.id, shared_services)
+          shared_services.each do |service|
+            expect(ShareWorker).to have_enqueued_sidekiq_job(user.id, Answer.last.id, service)
+          end
         end
 
         include_examples "returns the expected response"
diff --git a/spec/models/services/twitter_spec.rb b/spec/models/services/twitter_spec.rb
new file mode 100644
index 00000000..a177993d
--- /dev/null
+++ b/spec/models/services/twitter_spec.rb
@@ -0,0 +1,46 @@
+# frozen_string_literal: true
+
+require 'rails_helper'
+
+describe Services::Twitter do
+  describe "#post" do
+    let(:user) { FactoryBot.create(:user) }
+    let(:service) { Services::Twitter.create(user: user) }
+    let(:answer) { FactoryBot.create(:answer, user: user,
+                                     content: 'a' * 255,
+                                     question_content: 'q' * 255) }
+    let(:twitter_client) { instance_double(Twitter::REST::Client) }
+
+    before do
+      allow(Twitter::REST::Client).to receive(:new).and_return(twitter_client)
+      allow(twitter_client).to receive(:update!)
+      stub_const("APP_CONFIG", {
+        'hostname' => 'example.com',
+        'https' => true,
+        'items_per_page' => 5,
+        'sharing' => {
+          'twitter' => {
+            'consumer_key' => 'AAA',
+          }
+        }
+      })
+    end
+
+    it "posts a shortened tweet" do
+      service.post(answer)
+
+      expect(twitter_client).to have_received(:update!).with("#{'q' * 123}… — #{'a' * 124}… https://example.com/#{user.screen_name}/a/#{answer.id}")
+    end
+    
+    it "posts an un-shortened tweet" do
+      answer.question.content = 'Why are raccoons so good?'
+      answer.question.save!
+      answer.content = 'Because they are good cunes.'
+      answer.save!
+
+      service.post(answer)
+
+      expect(twitter_client).to have_received(:update!).with("#{answer.question.content} — #{answer.content} https://example.com/#{user.screen_name}/a/#{answer.id}")
+    end
+  end
+end
\ No newline at end of file