Before upgrading, make sure you are allowing insecure registry access, or your newer docker won't be able to talk to the Deis registry:
sudo bash -c 'mkdir -p /etc/systemd/system/docker.service.d/; cat <<EOF > /etc/systemd/system/docker.service.d/50-insecure-registry.conf
[Service]
Environment="DOCKER_OPTS=--insecure-registry 10.0.0.0/8 --insecure-registry 172.16.0.0/12 --insecure-registry 192.168.0.0/16"
EOF
'