diff --git a/Gemfile.lock b/Gemfile.lock
index 80e99067..2f301c3a 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -46,6 +46,7 @@ GEM
     erubis (2.7.0)
     excon (0.62.0)
     ffi (1.9.23)
+    ffi (1.9.23-x64-mingw32)
     fission (0.5.0)
       CFPropertyList (~> 2.2)
     fog (2.0.0)
@@ -230,6 +231,8 @@ GEM
     net-ssh (4.2.0)
     nokogiri (1.8.2)
       mini_portile2 (~> 2.3.0)
+    nokogiri (1.8.2-x64-mingw32)
+      mini_portile2 (~> 2.3.0)
     nori (2.6.0)
     rake (10.5.0)
     rb-fsevent (0.10.3)
@@ -291,6 +294,7 @@ GEM
 
 PLATFORMS
   ruby
+  x64-mingw32
 
 DEPENDENCIES
   coveralls
diff --git a/lib/vagrant-cloudstack/action/read_winrm_info.rb b/lib/vagrant-cloudstack/action/read_winrm_info.rb
index a643c09d..993238c1 100644
--- a/lib/vagrant-cloudstack/action/read_winrm_info.rb
+++ b/lib/vagrant-cloudstack/action/read_winrm_info.rb
@@ -43,15 +43,13 @@ def read_winrm_info(cloudstack, machine)
           # the username via winrm_info ... yet ;-)
 
           # Read password from file into domain_config
-          if domain_config.vm_password.nil?
-            vmcredentials_file = machine.data_dir.join("vmcredentials")
-            if vmcredentials_file.file?
-              vmcredentials_password = nil
-              File.read(vmcredentials_file).each_line do |line|
-                vmcredentials_password = line.strip
-              end
-              domain_config.vm_password = vmcredentials_password
+          vmcredentials_file = machine.data_dir.join("vmcredentials")
+          if vmcredentials_file.file?
+            vmcredentials_password = nil
+            File.read(vmcredentials_file).each_line do |line|
+              vmcredentials_password = line.strip
             end
+            domain_config.vm_password = vmcredentials_password
           end
 
           transport_info = transport_info.merge({
diff --git a/lib/vagrant-cloudstack/action/run_instance.rb b/lib/vagrant-cloudstack/action/run_instance.rb
index 12917d52..fb83d498 100644
--- a/lib/vagrant-cloudstack/action/run_instance.rb
+++ b/lib/vagrant-cloudstack/action/run_instance.rb
@@ -37,7 +37,9 @@ def call(env)
 
           store_volumes
 
-          store_password
+          password = wait_for_password
+
+          store_password(password)
 
           configure_networking
 
@@ -381,6 +383,14 @@ def get_communicator_short_name(communicator)
           communicator_short_names[communicator.class.name]
         end
 
+        def get_communicator_connect_attempts(communicator)
+          communicator_connect_attempts = {
+            'VagrantPlugins::CommunicatorSSH::Communicator' => 40,
+            'VagrantPlugins::CommunicatorWinRM::Communicator' => 1
+          }
+          return communicator_connect_attempts[communicator.class.name].nil? ? 1 : communicator_connect_attempts[communicator.class.name]
+        end
+
         def evaluate_pf_private_port
           return unless @domain_config.pf_private_port.nil?
 
@@ -488,9 +498,8 @@ def apply_port_forwarding_rule(rule)
               if response['queryasyncjobresultresponse']['jobstatus'] != 0
                 port_forwarding_rule = response['queryasyncjobresultresponse']['jobresult']['portforwardingrule']
                 break
-              else
-                sleep 2
               end
+              sleep 2
             end
           rescue Fog::Compute::Cloudstack::Error => e
             raise Errors::FogError, :message => e.message
@@ -717,9 +726,8 @@ def apply_firewall_rule(acl_name, options, response_string, type_string)
               if response['queryasyncjobresultresponse']['jobstatus'] != 0
                 firewall_rule = response['queryasyncjobresultresponse']['jobresult'][type_string]
                 break
-              else
-                sleep 2
               end
+              sleep 2
             end
           rescue Fog::Compute::Cloudstack::Error => e
             if e.message =~ /The range specified,.*conflicts with rule/
@@ -756,13 +764,13 @@ def generate_ssh_keypair(keyname, account = nil, domainid = nil, projectid = nil
           @domain_config.keypair =  sshkeypair['name']
         end
 
-        def store_password
+        def wait_for_password
           password = nil
-          if @server.password_enabled and @server.respond_to?('job_id')
+
+          if @server.respond_to?('job_id')
             server_job_result = @env[:cloudstack_compute].query_async_job_result({:jobid => @server.job_id})
             if server_job_result.nil?
-              @env[:ui].warn(' -- Failed to retrieve job_result for retrieving the password')
-              return
+              raise 'ERROR -- Failed to retrieve job_result'
             end
 
             while true
@@ -770,21 +778,33 @@ def store_password
               if server_job_result['queryasyncjobresultresponse']['jobstatus'] != 0
                 password = server_job_result['queryasyncjobresultresponse']['jobresult']['virtualmachine']['password']
                 break
-              else
-                sleep 2
               end
+              sleep 2
             end
 
             @env[:ui].info("Password of virtualmachine: #{password}")
-            # Set the password on the current communicator
-            @domain_config.vm_password = password
+          end
 
-            # Save password to file
-            vmcredentials_file = @env[:machine].data_dir.join('vmcredentials')
-            vmcredentials_file.open('w') do |f|
-              f.write("#{password}")
-            end
+          password
+        end
+
+        def store_password(password)
+          unless @server.password_enabled
+              @env[:ui].info("VM is not password-enabled. Using virtualmachine password from config")
+              if @domain_config.vm_password.nil?
+                fail "No vm_password configured but VM is not password enabled either!"
+              end
+              password = @domain_config.vm_password
+          end
+
+          # Save password to file
+          vmcredentials_file = @env[:machine].data_dir.join('vmcredentials')
+          vmcredentials_file.open('w') do |f|
+            f.write("#{password}")
           end
+
+          # Set the password on the current communicator
+          @domain_config.vm_password = password
         end
 
         def store_volumes
@@ -829,15 +849,18 @@ def wait_for_communicator_ready
           @env[:metrics]['instance_ssh_time'] = Util::Timer.time do
             # Wait for communicator to be ready.
             communicator_short_name = get_communicator_short_name(@env[:machine].communicate)
+            communicator_connect_attempts = get_communicator_connect_attempts(@env[:machine].communicate)
             @env[:ui].info(
               I18n.t('vagrant_cloudstack.waiting_for_communicator',
                      communicator: communicator_short_name.to_s.upcase)
             )
-            while true
+            connection_attempt = 0
+            while connection_attempt<communicator_connect_attempts
               # If we're interrupted then just back out
               break if @env[:interrupted]
               break if @env[:machine].communicate.ready?
               sleep 2
+              connection_attempt = connection_attempt + 1
             end
           end
           @logger.info("Time for SSH ready: #{@env[:metrics]['instance_ssh_time']}")
diff --git a/spec/vagrant-cloudstack/action/run_instance_spec.rb b/spec/vagrant-cloudstack/action/run_instance_spec.rb
index 8b57ebe7..e7088e51 100644
--- a/spec/vagrant-cloudstack/action/run_instance_spec.rb
+++ b/spec/vagrant-cloudstack/action/run_instance_spec.rb
@@ -260,7 +260,11 @@
 
       allow(machine).to receive(:provider_config).and_return(provider_config)
       expect(server).to receive(:wait_for).and_return(ready = true)
-      allow(server).to receive(:password_enabled).and_return(false)
+      allow(server).to receive(:password_enabled).and_return(true)
+      allow(server).to receive(:job_id).and_return(JOB_ID)
+      
+      expect(file).to receive(:write).with(GENERATED_PASSWORD)
+      allow(cloudstack_compute).to receive(:query_async_job_result).with(jobid: JOB_ID).and_return(fake_job_result)
       expect(cloudstack_compute).to receive(:servers).and_return(servers)
       allow(cloudstack_compute).to receive(:send).with(:list_zones, available: true).and_return(list_zones_response)
       allow(cloudstack_compute).to receive(:send).with(:list_service_offerings, listall: true)
@@ -289,6 +293,7 @@
           cfg.ssh_key = ssh_key
           cfg.security_groups = security_groups
           cfg.network_name = network_name
+          cfg.vm_password = GENERATED_PASSWORD
         end
         config.finalize!
         config.get_domain_config(:cloudstack)
@@ -354,8 +359,8 @@
           should eq true
         end
       end
-    end
-
+    end  
+      
     context 'in advanced zone' do
       let(:pf_ip_address) { nil }
       let(:pf_trusted_networks) { nil }
@@ -377,6 +382,7 @@
           cfg.pf_open_firewall = pf_open_firewall
           cfg.ssh_key = ssh_key
           cfg.disk_offering_name = disk_offering_name
+          cfg.vm_password = GENERATED_PASSWORD
         end
         config.finalize!
         config.get_domain_config(:cloudstack)
@@ -385,8 +391,6 @@
       let(:winrm_config) { double('VagrantPlugins::VagrantWinRM::WinRMConfig') }
 
       before(:each) do
-        allow(cloudstack_compute).to receive(:query_async_job_result).with(jobid: JOB_ID).and_return(fake_job_result)
-
         allow(cloudstack_compute).to receive(:send).with(:list_networks, {}).and_return(list_networks_response)
       end
 
@@ -427,11 +431,9 @@
         end
       end
 
-      context 'with generated password' do
+      context 'with static password' do
         before(:each) do
-          expect(server).to receive(:password_enabled).and_return(true)
-          allow(server).to receive(:job_id).and_return(JOB_ID)
-          expect(file).to receive(:write).with(GENERATED_PASSWORD)
+          expect(server).to receive(:password_enabled).and_return(false)
         end
 
         it 'starts a vm' do
@@ -606,4 +608,4 @@
       end
     end
   end
-end
+end
\ No newline at end of file