diff --git a/Gemfile b/Gemfile
index b81fdf10..146097c2 100644
--- a/Gemfile
+++ b/Gemfile
@@ -47,6 +47,7 @@ gem 'acme-client', {
   git: 'https://github.com/jhass/acme-client.git',
   branch: 'no_activesupport'
 }
+gem 'http'
 
 platform :mri, :rbx do
   gem 'magic' # sudo apt-get install file, For OSX: brew install libmagic
diff --git a/Gemfile.lock b/Gemfile.lock
index 6d6e5e7c..7c29ab70 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -97,8 +97,15 @@ GEM
     hiredis (0.6.1)
     hoe (3.14.2)
       rake (>= 0.8, < 11.0)
+    http (2.0.1)
+      addressable (~> 2.3)
+      http-cookie (~> 1.0)
+      http-form_data (~> 1.0.1)
+      http_parser.rb (~> 0.6.0)
     http-cookie (1.0.2)
       domain_name (~> 0.5)
+    http-form_data (1.0.1)
+    http_parser.rb (0.6.0)
     i18n (0.7.0)
     io-extra (1.2.8)
     jimson-temp (0.9.5)
@@ -280,6 +287,7 @@ DEPENDENCIES
   geoip
   hiredis
   hoe (= 3.14.2)
+  http
   io-extra
   jdbc-postgres
   jruby-openssl
diff --git a/workers/lets_encrypt_worker.rb b/workers/lets_encrypt_worker.rb
index d1a6eb99..d042164e 100644
--- a/workers/lets_encrypt_worker.rb
+++ b/workers/lets_encrypt_worker.rb
@@ -1,6 +1,7 @@
 class LetsEncryptWorker
   class NotAuthorizedYetError < StandardError; end
   class VerificationTimeoutError < StandardError; end
+  class VerifyNotFoundWithDomain < StandardError; end
   include Sidekiq::Worker
   sidekiq_options queue: :lets_encrypt_worker, retry: 100, backtrace: true
 
@@ -36,9 +37,18 @@ class LetsEncryptWorker
       FileUtils.mkdir_p File.join(site.base_files_path, File.dirname(challenge.filename)) if index == 0
       File.write File.join(site.base_files_path, challenge.filename), challenge.file_content
 
+      # Ensure that both domains work before sending request. Let's Encrypt has a low
+      # pending request limit, and it takes one week (!) to flush out.
+      sleep 2
+      challenge_url = "#{domain}/#{challenge.filename}"
+      ["http://#{challenge_url}", "http://www.#{challenge_url}"].each do |url|
+        res = HTTP.follow.get(url)
+        raise VerifyNotFoundWithDomain unless res.status == 200
+      end
+
       challenge.request_verification
 
-      sleep 1
+      sleep 60
       attempts = 0
 
       begin