diff --git a/pkg/scripts/os_debian.go b/pkg/scripts/os_debian.go
index d146ff211..5e171ac00 100644
--- a/pkg/scripts/os_debian.go
+++ b/pkg/scripts/os_debian.go
@@ -43,6 +43,14 @@ Acquire::http::Proxy "{{ .HTTP_PROXY }}";
 {{- end }}
 EOF
 
+# Removing deprecated Kubernetes repositories from apt sources is needed when upgrading from older KubeOne versions,
+# otherwise, apt-get update will fail to upgrade the packages.
+{{- if .CONFIGURE_REPOSITORIES }}
+if sudo grep -q "deb http://apt.kubernetes.io/ kubernetes-xenial main" /etc/apt/sources.list.d/kubernetes.list; then
+  rm -f /etc/apt/sources.list.d/kubernetes.list
+fi
+{{- end }}
+
 sudo apt-get update
 sudo DEBIAN_FRONTEND=noninteractive apt-get install --option "Dpkg::Options::=--force-confold" -y --no-install-recommends \
 	apt-transport-https \
diff --git a/pkg/scripts/testdata/TestKubeadmDebian-cilium_cluster.golden b/pkg/scripts/testdata/TestKubeadmDebian-cilium_cluster.golden
index 98fc1ca12..ac78bc1fe 100644
--- a/pkg/scripts/testdata/TestKubeadmDebian-cilium_cluster.golden
+++ b/pkg/scripts/testdata/TestKubeadmDebian-cilium_cluster.golden
@@ -49,6 +49,12 @@ Acquire::https::Proxy "http://https.proxy";
 Acquire::http::Proxy "http://http.proxy";
 EOF
 
+# Removing deprecated Kubernetes repositories from apt sources is needed when upgrading from older KubeOne versions,
+# otherwise, apt-get update will fail to upgrade the packages.
+if sudo grep -q "deb http://apt.kubernetes.io/ kubernetes-xenial main" /etc/apt/sources.list.d/kubernetes.list; then
+  rm -f /etc/apt/sources.list.d/kubernetes.list
+fi
+
 sudo apt-get update
 sudo DEBIAN_FRONTEND=noninteractive apt-get install --option "Dpkg::Options::=--force-confold" -y --no-install-recommends \
 	apt-transport-https \
diff --git a/pkg/scripts/testdata/TestKubeadmDebian-nutanix_cluster.golden b/pkg/scripts/testdata/TestKubeadmDebian-nutanix_cluster.golden
index 82d926fa6..69810cc25 100644
--- a/pkg/scripts/testdata/TestKubeadmDebian-nutanix_cluster.golden
+++ b/pkg/scripts/testdata/TestKubeadmDebian-nutanix_cluster.golden
@@ -49,6 +49,12 @@ Acquire::https::Proxy "http://https.proxy";
 Acquire::http::Proxy "http://http.proxy";
 EOF
 
+# Removing deprecated Kubernetes repositories from apt sources is needed when upgrading from older KubeOne versions,
+# otherwise, apt-get update will fail to upgrade the packages.
+if sudo grep -q "deb http://apt.kubernetes.io/ kubernetes-xenial main" /etc/apt/sources.list.d/kubernetes.list; then
+  rm -f /etc/apt/sources.list.d/kubernetes.list
+fi
+
 sudo apt-get update
 sudo DEBIAN_FRONTEND=noninteractive apt-get install --option "Dpkg::Options::=--force-confold" -y --no-install-recommends \
 	apt-transport-https \
diff --git a/pkg/scripts/testdata/TestKubeadmDebian-with_containerd.golden b/pkg/scripts/testdata/TestKubeadmDebian-with_containerd.golden
index 98fc1ca12..ac78bc1fe 100644
--- a/pkg/scripts/testdata/TestKubeadmDebian-with_containerd.golden
+++ b/pkg/scripts/testdata/TestKubeadmDebian-with_containerd.golden
@@ -49,6 +49,12 @@ Acquire::https::Proxy "http://https.proxy";
 Acquire::http::Proxy "http://http.proxy";
 EOF
 
+# Removing deprecated Kubernetes repositories from apt sources is needed when upgrading from older KubeOne versions,
+# otherwise, apt-get update will fail to upgrade the packages.
+if sudo grep -q "deb http://apt.kubernetes.io/ kubernetes-xenial main" /etc/apt/sources.list.d/kubernetes.list; then
+  rm -f /etc/apt/sources.list.d/kubernetes.list
+fi
+
 sudo apt-get update
 sudo DEBIAN_FRONTEND=noninteractive apt-get install --option "Dpkg::Options::=--force-confold" -y --no-install-recommends \
 	apt-transport-https \
diff --git a/pkg/scripts/testdata/TestKubeadmDebian-with_containerd_with_insecure_registry.golden b/pkg/scripts/testdata/TestKubeadmDebian-with_containerd_with_insecure_registry.golden
index 94bb10a9a..56ec4a7ea 100644
--- a/pkg/scripts/testdata/TestKubeadmDebian-with_containerd_with_insecure_registry.golden
+++ b/pkg/scripts/testdata/TestKubeadmDebian-with_containerd_with_insecure_registry.golden
@@ -49,6 +49,12 @@ Acquire::https::Proxy "http://https.proxy";
 Acquire::http::Proxy "http://http.proxy";
 EOF
 
+# Removing deprecated Kubernetes repositories from apt sources is needed when upgrading from older KubeOne versions,
+# otherwise, apt-get update will fail to upgrade the packages.
+if sudo grep -q "deb http://apt.kubernetes.io/ kubernetes-xenial main" /etc/apt/sources.list.d/kubernetes.list; then
+  rm -f /etc/apt/sources.list.d/kubernetes.list
+fi
+
 sudo apt-get update
 sudo DEBIAN_FRONTEND=noninteractive apt-get install --option "Dpkg::Options::=--force-confold" -y --no-install-recommends \
 	apt-transport-https \
diff --git a/pkg/scripts/testdata/TestUpgradeKubeadmAndCNIDebian.golden b/pkg/scripts/testdata/TestUpgradeKubeadmAndCNIDebian.golden
index dc9529469..ba0d3de93 100644
--- a/pkg/scripts/testdata/TestUpgradeKubeadmAndCNIDebian.golden
+++ b/pkg/scripts/testdata/TestUpgradeKubeadmAndCNIDebian.golden
@@ -49,6 +49,12 @@ Acquire::https::Proxy "http://https.proxy";
 Acquire::http::Proxy "http://http.proxy";
 EOF
 
+# Removing deprecated Kubernetes repositories from apt sources is needed when upgrading from older KubeOne versions,
+# otherwise, apt-get update will fail to upgrade the packages.
+if sudo grep -q "deb http://apt.kubernetes.io/ kubernetes-xenial main" /etc/apt/sources.list.d/kubernetes.list; then
+  rm -f /etc/apt/sources.list.d/kubernetes.list
+fi
+
 sudo apt-get update
 sudo DEBIAN_FRONTEND=noninteractive apt-get install --option "Dpkg::Options::=--force-confold" -y --no-install-recommends \
 	apt-transport-https \
diff --git a/pkg/scripts/testdata/TestUpgradeKubeletAndKubectlDebian.golden b/pkg/scripts/testdata/TestUpgradeKubeletAndKubectlDebian.golden
index fd617433a..378a179ac 100644
--- a/pkg/scripts/testdata/TestUpgradeKubeletAndKubectlDebian.golden
+++ b/pkg/scripts/testdata/TestUpgradeKubeletAndKubectlDebian.golden
@@ -49,6 +49,12 @@ Acquire::https::Proxy "http://https.proxy";
 Acquire::http::Proxy "http://http.proxy";
 EOF
 
+# Removing deprecated Kubernetes repositories from apt sources is needed when upgrading from older KubeOne versions,
+# otherwise, apt-get update will fail to upgrade the packages.
+if sudo grep -q "deb http://apt.kubernetes.io/ kubernetes-xenial main" /etc/apt/sources.list.d/kubernetes.list; then
+  rm -f /etc/apt/sources.list.d/kubernetes.list
+fi
+
 sudo apt-get update
 sudo DEBIAN_FRONTEND=noninteractive apt-get install --option "Dpkg::Options::=--force-confold" -y --no-install-recommends \
 	apt-transport-https \