diff --git a/cluster.yml b/cluster.yml
index 4fc852d97..6a9de14da 100644
--- a/cluster.yml
+++ b/cluster.yml
@@ -94,6 +94,7 @@
   roles:
     - { role: kubespray-defaults}
     - { role: kubernetes-apps/rotate_tokens, tags: rotate_tokens, when: "secret_changed|default(false)" }
+    - { role: win_nodes/kubernetes_patch, tags: win_nodes, when: "kubeadm_enabled" }
 
 - hosts: kube-master
   any_errors_fatal: "{{ any_errors_fatal | default(true) }}"
diff --git a/roles/dnsmasq/templates/dnsmasq-autoscaler.yml.j2 b/roles/dnsmasq/templates/dnsmasq-autoscaler.yml.j2
index a6d1df934..4489e2418 100644
--- a/roles/dnsmasq/templates/dnsmasq-autoscaler.yml.j2
+++ b/roles/dnsmasq/templates/dnsmasq-autoscaler.yml.j2
@@ -52,3 +52,6 @@ spec:
             - --default-params={"linear":{"nodesPerReplica":{{ dnsmasq_nodes_per_replica }},"preventSinglePointFailure":true}}
             - --logtostderr=true
             - --v={{ kube_log_level }}
+      # When having win nodes in cluster without this patch, this pod cloud try to be created in windows
+      nodeSelector:
+        beta.kubernetes.io/os: linux
diff --git a/roles/dnsmasq/templates/dnsmasq-deploy.yml.j2 b/roles/dnsmasq/templates/dnsmasq-deploy.yml.j2
index 0fb6045e8..c3a32f02e 100644
--- a/roles/dnsmasq/templates/dnsmasq-deploy.yml.j2
+++ b/roles/dnsmasq/templates/dnsmasq-deploy.yml.j2
@@ -24,6 +24,9 @@ spec:
       tolerations:
         - effect: NoSchedule
           operator: Exists
+      # When having win nodes in cluster without this patch, this pod cloud try to be created in windows
+      nodeSelector:
+        beta.kubernetes.io/os: linux
       containers:
         - name: dnsmasq
           image: "{{ dnsmasq_image_repo }}:{{ dnsmasq_image_tag }}"
diff --git a/roles/docker/tasks/main.yml b/roles/docker/tasks/main.yml
index d2426769f..5835dff10 100644
--- a/roles/docker/tasks/main.yml
+++ b/roles/docker/tasks/main.yml
@@ -138,6 +138,15 @@
     msg: "{{available_packages}}"
   when: docker_task_result|failed
 
+# This is required to ensure any apt upgrade will not break kubernetes
+- name: Set docker pin priority to apt_preferences on Debian family
+  template:
+    src: "apt_preferences.d/debian_docker.j2"
+    dest: "/etc/apt/preferences.d/docker"
+    owner: "root"
+    mode: 0644
+  when: not (ansible_os_family in ["CoreOS", "Container Linux by CoreOS", "RedHat", "Suse"] or is_atomic)
+
 - name: ensure service is started if docker packages are already present
   service:
     name: docker
diff --git a/roles/docker/templates/apt_preferences.d/debian_docker.j2 b/roles/docker/templates/apt_preferences.d/debian_docker.j2
new file mode 100644
index 000000000..f21008b6c
--- /dev/null
+++ b/roles/docker/templates/apt_preferences.d/debian_docker.j2
@@ -0,0 +1,3 @@
+Package: docker-ce
+Pin: version {{ docker_version }}.*
+Pin-Priority: 1001
\ No newline at end of file
diff --git a/roles/etcd/tasks/main.yml b/roles/etcd/tasks/main.yml
index 38df04d73..db59a983f 100644
--- a/roles/etcd/tasks/main.yml
+++ b/roles/etcd/tasks/main.yml
@@ -6,7 +6,6 @@
     - facts
 
 - include_tasks: "gen_certs_{{ cert_management }}.yml"
-  when:
   tags:
     - etcd-secrets
 
diff --git a/roles/kubernetes-apps/ansible/templates/kubedns-autoscaler.yml.j2 b/roles/kubernetes-apps/ansible/templates/kubedns-autoscaler.yml.j2
index 11c8d37f0..e726e8d2a 100644
--- a/roles/kubernetes-apps/ansible/templates/kubedns-autoscaler.yml.j2
+++ b/roles/kubernetes-apps/ansible/templates/kubedns-autoscaler.yml.j2
@@ -28,6 +28,9 @@ spec:
       labels:
         k8s-app: kubedns-autoscaler
     spec:
+      # When having win nodes in cluster without this patch, this pod cloud try to be created in windows
+      nodeSelector:
+        beta.kubernetes.io/os: linux
       tolerations:
         - effect: NoSchedule
           operator: Equal
diff --git a/roles/kubernetes-apps/ansible/templates/kubedns-deploy.yml.j2 b/roles/kubernetes-apps/ansible/templates/kubedns-deploy.yml.j2
index 549d93c14..96ef72283 100644
--- a/roles/kubernetes-apps/ansible/templates/kubedns-deploy.yml.j2
+++ b/roles/kubernetes-apps/ansible/templates/kubedns-deploy.yml.j2
@@ -27,6 +27,9 @@ spec:
       annotations:
         scheduler.alpha.kubernetes.io/critical-pod: ''
     spec:
+      # When having win nodes in cluster without this patch, this pod cloud try to be created in windows
+      nodeSelector:
+        beta.kubernetes.io/os: linux
       tolerations:
       - key: "CriticalAddonsOnly"
         operator: "Exists"
diff --git a/roles/kubernetes-apps/ansible/templates/netchecker-agent-ds.yml.j2 b/roles/kubernetes-apps/ansible/templates/netchecker-agent-ds.yml.j2
index 431448231..a2c4850c4 100644
--- a/roles/kubernetes-apps/ansible/templates/netchecker-agent-ds.yml.j2
+++ b/roles/kubernetes-apps/ansible/templates/netchecker-agent-ds.yml.j2
@@ -15,6 +15,9 @@ spec:
       tolerations:
         - effect: NoSchedule
           operator: Exists
+      # When having win nodes in cluster without this patch, this pod cloud try to be created in windows
+      nodeSelector:
+        beta.kubernetes.io/os: linux
       containers:
         - name: netchecker-agent
           image: "{{ agent_img }}"
diff --git a/roles/kubernetes-apps/ansible/templates/netchecker-agent-hostnet-ds.yml.j2 b/roles/kubernetes-apps/ansible/templates/netchecker-agent-hostnet-ds.yml.j2
index ad32d509a..f046e8f4b 100644
--- a/roles/kubernetes-apps/ansible/templates/netchecker-agent-hostnet-ds.yml.j2
+++ b/roles/kubernetes-apps/ansible/templates/netchecker-agent-hostnet-ds.yml.j2
@@ -13,6 +13,9 @@ spec:
         app: netchecker-agent-hostnet
     spec:
       hostNetwork: True
+      # When having win nodes in cluster without this patch, this pod cloud try to be created in windows
+      nodeSelector:
+        beta.kubernetes.io/os: linux
 {% if kube_version | version_compare('v1.6', '>=') %}
       dnsPolicy: ClusterFirstWithHostNet
 {% endif %}
diff --git a/roles/kubernetes-apps/efk/fluentd/templates/fluentd-ds.yml.j2 b/roles/kubernetes-apps/efk/fluentd/templates/fluentd-ds.yml.j2
index 6e9ad30c0..03b118f8d 100644
--- a/roles/kubernetes-apps/efk/fluentd/templates/fluentd-ds.yml.j2
+++ b/roles/kubernetes-apps/efk/fluentd/templates/fluentd-ds.yml.j2
@@ -29,6 +29,9 @@ spec:
     spec:
       priorityClassName: system-node-critical
       serviceAccountName: efk
+      # When having win nodes in cluster without this patch, this pod cloud try to be created in windows
+      nodeSelector:
+        beta.kubernetes.io/os: linux
       containers:
       - name: fluentd-es
         image: "{{ fluentd_image_repo }}:{{ fluentd_image_tag }}"
diff --git a/roles/kubernetes-apps/ingress_controller/ingress_nginx/templates/deploy-default-backend.yml.j2 b/roles/kubernetes-apps/ingress_controller/ingress_nginx/templates/deploy-default-backend.yml.j2
index 884b6d79b..0578844f9 100644
--- a/roles/kubernetes-apps/ingress_controller/ingress_nginx/templates/deploy-default-backend.yml.j2
+++ b/roles/kubernetes-apps/ingress_controller/ingress_nginx/templates/deploy-default-backend.yml.j2
@@ -42,3 +42,6 @@ spec:
             requests:
               cpu: 10m
               memory: 20Mi
+      # When having win nodes in cluster without this patch, this pod cloud try to be created in windows
+      nodeSelector:
+        beta.kubernetes.io/os: linux
diff --git a/roles/kubernetes/master/tasks/kubeadm-setup.yml b/roles/kubernetes/master/tasks/kubeadm-setup.yml
index d6ef52a61..827154612 100644
--- a/roles/kubernetes/master/tasks/kubeadm-setup.yml
+++ b/roles/kubernetes/master/tasks/kubeadm-setup.yml
@@ -121,6 +121,7 @@
     --ignore-preflight-errors=all
     --allow-experimental-upgrades
     --allow-release-candidate-upgrades
+    --force
   register: kubeadm_upgrade
   # Retry is because upload config sometimes fails
   retries: 3
diff --git a/roles/kubernetes/node/templates/manifests/kube-proxy.manifest.j2 b/roles/kubernetes/node/templates/manifests/kube-proxy.manifest.j2
index d1292887a..ece9be10c 100644
--- a/roles/kubernetes/node/templates/manifests/kube-proxy.manifest.j2
+++ b/roles/kubernetes/node/templates/manifests/kube-proxy.manifest.j2
@@ -12,6 +12,9 @@ spec:
 {% if kube_version | version_compare('v1.6', '>=') %}
   dnsPolicy: ClusterFirst
 {% endif %}
+  # When having win nodes in cluster without this patch, this pod cloud try to be created in windows
+  nodeSelector:
+    beta.kubernetes.io/os: linux
   containers:
   - name: kube-proxy
     image: {{ hyperkube_image_repo }}:{{ hyperkube_image_tag }}
diff --git a/roles/kubernetes/node/templates/manifests/nginx-proxy.manifest.j2 b/roles/kubernetes/node/templates/manifests/nginx-proxy.manifest.j2
index a1e9a7815..756eba7ee 100644
--- a/roles/kubernetes/node/templates/manifests/nginx-proxy.manifest.j2
+++ b/roles/kubernetes/node/templates/manifests/nginx-proxy.manifest.j2
@@ -7,6 +7,9 @@ metadata:
     k8s-app: kube-nginx
 spec:
   hostNetwork: true
+  # When having win nodes in cluster without this patch, this pod cloud try to be created in windows
+  nodeSelector:
+    beta.kubernetes.io/os: linux
   containers:
   - name: nginx-proxy
     image: {{ nginx_image_repo }}:{{ nginx_image_tag }}
diff --git a/roles/network_plugin/flannel/templates/cni-flannel.yml.j2 b/roles/network_plugin/flannel/templates/cni-flannel.yml.j2
index b201e8e7f..de9be8d9e 100644
--- a/roles/network_plugin/flannel/templates/cni-flannel.yml.j2
+++ b/roles/network_plugin/flannel/templates/cni-flannel.yml.j2
@@ -53,6 +53,9 @@ spec:
         k8s-app: flannel
     spec:
       serviceAccountName: flannel
+      # When having win nodes in cluster without this patch, this pod cloud try to be created in windows
+      nodeSelector:
+        beta.kubernetes.io/os: linux
       containers:
       - name: kube-flannel
         image: {{ flannel_image_repo }}:{{ flannel_image_tag }}
diff --git a/roles/win_nodes/kubernetes_patch/defaults/main.yml b/roles/win_nodes/kubernetes_patch/defaults/main.yml
new file mode 100644
index 000000000..587f73ab4
--- /dev/null
+++ b/roles/win_nodes/kubernetes_patch/defaults/main.yml
@@ -0,0 +1,3 @@
+---
+
+kubernetes_user_manifests_path: "{{ ansible_env.HOME }}/kube-manifests"
diff --git a/roles/win_nodes/kubernetes_patch/files/nodeselector-os-linux-patch.json b/roles/win_nodes/kubernetes_patch/files/nodeselector-os-linux-patch.json
new file mode 100644
index 000000000..d718ff446
--- /dev/null
+++ b/roles/win_nodes/kubernetes_patch/files/nodeselector-os-linux-patch.json
@@ -0,0 +1 @@
+{"spec":{"template":{"spec":{"nodeSelector":{"beta.kubernetes.io/os":"linux"}}}}}
\ No newline at end of file
diff --git a/roles/win_nodes/kubernetes_patch/tasks/main.yml b/roles/win_nodes/kubernetes_patch/tasks/main.yml
new file mode 100644
index 000000000..8d88818a5
--- /dev/null
+++ b/roles/win_nodes/kubernetes_patch/tasks/main.yml
@@ -0,0 +1,34 @@
+---
+
+- name: Ensure that user manifests directory exists
+  file:
+    path: "{{ kubernetes_user_manifests_path }}/kubernetes"
+    state: directory
+    recurse: yes
+  tags: [init, cni]
+
+- name: Apply kube-proxy nodeselector
+  block:
+    - name: Copy kube-proxy daemonset nodeselector patch
+      copy:
+        src: nodeselector-os-linux-patch.json
+        dest: "{{ kubernetes_user_manifests_path }}/nodeselector-os-linux-patch.json"
+
+    # Due to https://github.com/kubernetes/kubernetes/issues/58212 we cannot rely on exit code for "kubectl patch"
+    - name: Check current nodeselector for kube-proxy daemonset
+      shell: kubectl get ds kube-proxy --namespace=kube-system -o jsonpath='{.spec.template.spec.nodeSelector.beta\.kubernetes\.io/os}'
+      register: current_kube_proxy_state
+
+    - name: Apply nodeselector patch for kube-proxy daemonset
+      shell: kubectl patch ds kube-proxy --namespace=kube-system --type=strategic -p "$(cat nodeselector-os-linux-patch.json)"
+      args:
+        chdir: "{{ kubernetes_user_manifests_path }}"
+      register: patch_kube_proxy_state
+      when: current_kube_proxy_state.stdout | trim | lower != "linux"
+
+    - debug: msg={{ patch_kube_proxy_state.stdout_lines }}
+      when: patch_kube_proxy_state is not skipped
+
+    - debug: msg={{ patch_kube_proxy_state.stderr_lines }}
+      when: patch_kube_proxy_state is not skipped
+  tags: init