diff --git a/README.md b/README.md
index 7dfa2fef808..cdc953b66cc 100644
--- a/README.md
+++ b/README.md
@@ -135,7 +135,7 @@ Note: Upstart/SysV init based OS types are not supported.
   - [cri-o](http://cri-o.io/) v1.17 (experimental: see [CRI-O Note](docs/cri-o.md). Only on fedora, ubuntu and centos based OS)
 - Network Plugin
   - [cni-plugins](https://github.com/containernetworking/plugins) v0.8.7
-  - [calico](https://github.com/projectcalico/calico) v3.16.1
+  - [calico](https://github.com/projectcalico/calico) v3.16.2
   - [canal](https://github.com/projectcalico/canal) (given calico/flannel versions)
   - [cilium](https://github.com/cilium/cilium) v1.8.4
   - [contiv](https://github.com/contiv/install) v1.2.1
@@ -151,7 +151,7 @@ Note: Upstart/SysV init based OS types are not supported.
   - [rbd-provisioner](https://github.com/kubernetes-incubator/external-storage) v2.1.1-k8s1.11
   - [cert-manager](https://github.com/jetstack/cert-manager) v0.16.1
   - [coredns](https://github.com/coredns/coredns) v1.7.0
-  - [ingress-nginx](https://github.com/kubernetes/ingress-nginx) v0.40.1
+  - [ingress-nginx](https://github.com/kubernetes/ingress-nginx) v0.40.2
 
 Note: The list of validated [docker versions](https://kubernetes.io/docs/setup/production-environment/container-runtimes/#docker) is 1.13.1, 17.03, 17.06, 17.09, 18.06, 18.09 and 19.03. The recommended docker version is 19.03. The kubelet might break on docker's non-standard version numbering (it no longer uses semantic versioning). To ensure auto-updates don't break your cluster look into e.g. yum versionlock plugin or apt pin).
 
diff --git a/roles/bootstrap-os/files/bootstrap.sh b/roles/bootstrap-os/files/bootstrap.sh
index 0f4935cf8bf..f2ee7ae5e14 100755
--- a/roles/bootstrap-os/files/bootstrap.sh
+++ b/roles/bootstrap-os/files/bootstrap.sh
@@ -2,7 +2,7 @@
 set -e
 
 BINDIR="/opt/bin"
-PYPY_VERSION=7.3.1
+PYPY_VERSION=7.3.2
 PYPI_URL="https://downloads.python.org/pypy/pypy3.6-v${PYPY_VERSION}-linux64.tar.bz2"
 PYPI_HASH=f67cf1664a336a3e939b58b3cabfe47d893356bdc01f2e17bc912aaa6605db12
 
diff --git a/roles/download/defaults/main.yml b/roles/download/defaults/main.yml
index ffd4e2f79b5..380c9afe494 100644
--- a/roles/download/defaults/main.yml
+++ b/roles/download/defaults/main.yml
@@ -65,7 +65,7 @@ quay_image_repo: "quay.io"
 
 # TODO(mattymo): Move calico versions to roles/network_plugins/calico/defaults
 # after migration to container download
-calico_version: "v3.16.1"
+calico_version: "v3.16.2"
 calico_ctl_version: "{{ calico_version }}"
 calico_cni_version: "{{ calico_version }}"
 calico_policy_version: "{{ calico_version }}"
@@ -360,13 +360,13 @@ cni_binary_checksums:
   amd64: 977824932d5667c7a37aa6a3cbba40100a6873e7bd97e83e8be837e3e7afd0a8
 calicoctl_binary_checksums:
   arm:
-    v3.16.1: 0
+    v3.16.2: 0
     v3.15.2: 0
   amd64:
-    v3.16.1: 7c33a841fdf85409c2eee5b287e1212d6c7e82885ec9ffaf690b6019b7b80c1b
+    v3.16.2: 801b059a4fd0dac8795693026c69a79a00dd2353eff597cc36b79fcb6ec53a0a
     v3.15.2: 219ae954501cbe15daeda0ad52e13ec65f99c77548c7d3cbfc4ced5c7149fdf1
   arm64:
-    v3.16.1: d3cc8b721a862f0c50273706bf6d38e47ee9b932b8d90a0f0e51280594a6f242
+    v3.16.2: aa5695940ec8a36393725a5ce7b156f776fed8da38b994c0828d7f3a60e59bc6
     v3.15.2: 49165f9e4ad55402248b578310fcf68a57363f54e66be04ac24be9714899b4d5
 
 etcd_binary_checksum: "{{ etcd_binary_checksums[image_arch] }}"
@@ -448,7 +448,7 @@ ovn4nfv_k8s_plugin_image_tag: "{{ ovn4nfv_k8s_plugin_image_version }}"
 nginx_image_repo: "{{ docker_image_repo }}/library/nginx"
 nginx_image_tag: 1.19
 haproxy_image_repo: "{{ docker_image_repo }}/library/haproxy"
-haproxy_image_tag: 2.1
+haproxy_image_tag: 2.2
 
 # Coredns version should be supported by corefile-migration (or at least work with)
 # bundle with kubeadm; if not 'basic' upgrade can sometimes fail
@@ -456,8 +456,8 @@ coredns_version: "1.7.0"
 coredns_image_repo: "{{ docker_image_repo }}/coredns/coredns"
 coredns_image_tag: "{{ coredns_version }}"
 
-nodelocaldns_version: "1.15.13"
-nodelocaldns_image_repo: "{{ kube_image_repo }}/k8s-dns-node-cache"
+nodelocaldns_version: "1.15.14"
+nodelocaldns_image_repo: "{{ kube_image_repo }}/dns/k8s-dns-node-cache"
 nodelocaldns_image_tag: "{{ nodelocaldns_version }}"
 
 dnsautoscaler_version: 1.8.3
@@ -489,7 +489,7 @@ rbd_provisioner_image_tag: "v2.1.1-k8s1.11"
 local_path_provisioner_image_repo: "{{ docker_image_repo }}/rancher/local-path-provisioner"
 local_path_provisioner_image_tag: "v0.0.17"
 ingress_nginx_controller_image_repo: "{{ kube_image_repo }}/ingress-nginx/controller"
-ingress_nginx_controller_image_tag: "v0.40.1"
+ingress_nginx_controller_image_tag: "v0.40.2"
 ingress_ambassador_image_repo: "{{ quay_image_repo }}/datawire/ambassador-operator"
 ingress_ambassador_image_tag: "v1.2.9"
 alb_ingress_image_repo: "{{ docker_image_repo }}/amazon/aws-alb-ingress-controller"
diff --git a/test-infra/vagrant-docker/Dockerfile b/test-infra/vagrant-docker/Dockerfile
index cebd994d0b9..da873ef5376 100644
--- a/test-infra/vagrant-docker/Dockerfile
+++ b/test-infra/vagrant-docker/Dockerfile
@@ -3,7 +3,7 @@
 ARG KUBESPRAY_VERSION
 FROM quay.io/kubespray/kubespray:${KUBESPRAY_VERSION}
 
-ENV VAGRANT_VERSION=2.2.7
+ENV VAGRANT_VERSION=2.2.10
 ENV VAGRANT_DEFAULT_PROVIDER=libvirt
 
 RUN apt-get update && apt-get install -y wget libvirt-dev openssh-client rsync git