diff --git a/config/application.rb b/config/application.rb
index b09f714e..2b831302 100644
--- a/config/application.rb
+++ b/config/application.rb
@@ -52,8 +52,8 @@ module Greenlight
     config.bigbluebutton_secret_default = "8cd8ef52e8e101574e400365b55e11a6"
 
     # Use standalone BigBlueButton server.
-    config.bigbluebutton_endpoint = ENV["BIGBLUEBUTTON_ENDPOINT"] || config.bigbluebutton_endpoint_default
-    config.bigbluebutton_secret = ENV["BIGBLUEBUTTON_SECRET"] || config.bigbluebutton_secret_default
+    config.bigbluebutton_endpoint = ENV["BIGBLUEBUTTON_ENDPOINT"].present? ? ENV["BIGBLUEBUTTON_ENDPOINT"] : config.bigbluebutton_endpoint_default
+    config.bigbluebutton_secret = ENV["BIGBLUEBUTTON_SECRET"].present? ? ENV["BIGBLUEBUTTON_SECRET"] : config.bigbluebutton_secret_default
 
     # Fix endpoint format if required.
     config.bigbluebutton_endpoint += "/" unless config.bigbluebutton_endpoint.ends_with?('/')
diff --git a/lib/tasks/configuration.rake b/lib/tasks/configuration.rake
index 602f245c..9e720988 100644
--- a/lib/tasks/configuration.rake
+++ b/lib/tasks/configuration.rake
@@ -16,15 +16,17 @@ namespace :conf do
     end
     passed
 
+    endpoint = fix_endpoint_format(ENV['BIGBLUEBUTTON_ENDPOINT'])
+
     # Tries to establish a connection to the BBB server from Greenlight
     print "Checking Connection"
-    test_request(ENV['BIGBLUEBUTTON_ENDPOINT'])
+    test_request(endpoint)
     passed
 
     # Tests the checksum on the getMeetings api call
     print "Checking Secret"
     checksum = Digest::SHA1.hexdigest("getMeetings#{ENV['BIGBLUEBUTTON_SECRET']}")
-    test_request("#{ENV['BIGBLUEBUTTON_ENDPOINT']}getMeetings?checksum=#{checksum}")
+    test_request("#{endpoint}getMeetings?checksum=#{checksum}")
     passed
 
     if ENV['ALLOW_MAIL_NOTIFICATIONS'] == 'true'
@@ -61,6 +63,15 @@ rescue => e
   failed("Error connecting to BigBlueButton server - #{e}")
 end
 
+def fix_endpoint_format(url)
+  # Fix endpoint format if required.
+  url += "/" unless url.ends_with?('/')
+  url += "api/" if url.ends_with?('bigbluebutton/')
+  url += "bigbluebutton/api/" unless url.ends_with?('bigbluebutton/api/')
+
+  url
+end
+
 def failed(msg)
   print(": Failed\n#{msg}\n")
   exit