diff --git a/stacks/rbac/modules/rbac/apiserver-oidc.tf b/stacks/rbac/modules/rbac/apiserver-oidc.tf
index 6e54d203..f88bf924 100644
--- a/stacks/rbac/modules/rbac/apiserver-oidc.tf
+++ b/stacks/rbac/modules/rbac/apiserver-oidc.tf
@@ -1,6 +1,25 @@
-# Configure kube-apiserver for OIDC authentication
-# This SSHs to k8s-master and adds OIDC flags to the static pod manifest.
-# Kubelet auto-restarts the API server when the manifest changes.
+# Configure kube-apiserver authentication via a structured
+# AuthenticationConfiguration file (apiserver.config.k8s.io/v1, GA on k8s 1.30+).
+#
+# WHY structured config instead of the legacy --oidc-* flags: the apiserver can
+# only carry ONE legacy issuer, but we need TWO — the `kubernetes` app (kubectl
+# / kubelogin CLI) AND the `k8s-dashboard` app (oauth2-proxy in front of the
+# Kubernetes Dashboard). Structured config supports multiple JWT issuers.
+#
+# Both issuers map username<-email and groups<-groups with EMPTY prefixes, to
+# match the existing RBAC subjects (kind: User, name: <raw email>; group names
+# verbatim). Do NOT add a prefix or existing bindings break.
+#
+# DRIFT WARNING: this edits the kube-apiserver static-pod manifest on the single
+# master. A `kubeadm upgrade` regenerates that manifest and DROPS this flag (this
+# is exactly how OIDC silently broke before — the flag was wiped and the
+# content-hash trigger never re-fired). After any k8s control-plane upgrade,
+# re-apply the rbac stack to restore apiserver OIDC. See
+# docs/plans/2026-06-04-k8s-dashboard-sso-design.md.
+#
+# SAFETY: the remote script health-gates on /livez and AUTO-ROLLS-BACK the
+# manifest from a timestamped backup if the apiserver does not recover, so a
+# malformed config cannot leave the single master down.
 
 variable "k8s_master_host" {
   type    = string
@@ -22,6 +41,105 @@ variable "oidc_client_id" {
   default = "kubernetes"
 }
 
+variable "k8s_dashboard_issuer_url" {
+  type    = string
+  default = "https://authentik.viktorbarzin.me/application/o/k8s-dashboard/"
+}
+
+variable "k8s_dashboard_audience" {
+  type    = string
+  default = "k8s-dashboard"
+}
+
+locals {
+  apiserver_auth_config_yaml = <<-YAML
+    apiVersion: apiserver.config.k8s.io/v1
+    kind: AuthenticationConfiguration
+    jwt:
+      - issuer:
+          url: "${var.oidc_issuer_url}"
+          audiences:
+            - "${var.oidc_client_id}"
+        claimMappings:
+          username:
+            claim: email
+            prefix: ""
+          groups:
+            claim: groups
+            prefix: ""
+      - issuer:
+          url: "${var.k8s_dashboard_issuer_url}"
+          audiences:
+            - "${var.k8s_dashboard_audience}"
+        claimMappings:
+          username:
+            claim: email
+            prefix: ""
+          groups:
+            claim: groups
+            prefix: ""
+  YAML
+
+  # Indentation-safe manifest editor: appends the --authentication-config flag
+  # using the exact leading whitespace of the --authorization-mode line.
+  apiserver_flag_insert_py = <<-PY
+    import sys
+    p = sys.argv[1]
+    lines = open(p).read().splitlines(True)
+    out, done = [], False
+    for ln in lines:
+        out.append(ln)
+        if not done and '- --authorization-mode=' in ln:
+            indent = ln[:len(ln) - len(ln.lstrip())]
+            out.append(indent + '- --authentication-config=/etc/kubernetes/pki/auth-config.yaml\n')
+            done = True
+    open(p, 'w').writelines(out)
+    print('flag-inserted' if done else 'ANCHOR-NOT-FOUND')
+  PY
+
+  # Whole remote operation, base64-embedded for byte-exact transfer (no
+  # heredoc/escaping hazards across SSH).
+  apiserver_auth_remote_script = <<-SH
+    MANIFEST=/etc/kubernetes/manifests/kube-apiserver.yaml
+    AUTHCFG=/etc/kubernetes/pki/auth-config.yaml
+    TS=$(date +%s)
+
+    # 1. Write the structured AuthenticationConfiguration (hot-reloaded by the
+    #    apiserver on change; mounted into the pod via the existing pki hostPath).
+    echo '${base64encode(local.apiserver_auth_config_yaml)}' | base64 -d | sudo tee "$AUTHCFG" >/dev/null
+    sudo chmod 600 "$AUTHCFG"
+
+    # 2. Ensure the apiserver references it. Only touch the manifest (→ restart)
+    #    when the flag is missing; otherwise the file write above hot-reloads.
+    if ! sudo grep -q -- '--authentication-config=' "$MANIFEST"; then
+      sudo cp "$MANIFEST" "$MANIFEST.bak.$TS"
+      sudo sed -i '/--oidc-issuer-url/d;/--oidc-client-id/d;/--oidc-username-claim/d;/--oidc-groups-claim/d' "$MANIFEST"
+      echo '${base64encode(local.apiserver_flag_insert_py)}' | base64 -d | sudo python3 - "$MANIFEST"
+    fi
+
+    # 3. Fail loudly if the flag still isn't present (e.g. anchor not found).
+    if ! sudo grep -q -- '--authentication-config=' "$MANIFEST"; then
+      echo "ERROR: --authentication-config absent after edit"; exit 1
+    fi
+
+    # 4. Health-gate on /livez; auto-rollback the manifest if it never recovers.
+    echo "Waiting for kube-apiserver /livez ..."
+    ok=0
+    for i in $(seq 1 60); do
+      sleep 2
+      if curl -sk https://localhost:6443/livez 2>/dev/null | grep -q '^ok'; then ok=1; break; fi
+    done
+    if [ "$ok" != "1" ]; then
+      echo "kube-apiserver UNHEALTHY after change — rolling back"
+      BAK=$(ls -t "$MANIFEST".bak.* 2>/dev/null | head -1)
+      if [ -n "$BAK" ]; then sudo cp "$BAK" "$MANIFEST"; fi
+      for i in $(seq 1 60); do sleep 2; if curl -sk https://localhost:6443/livez 2>/dev/null | grep -q '^ok'; then break; fi; done
+      echo "rolled back to previous manifest"; exit 1
+    fi
+    echo "kube-apiserver healthy with multi-issuer --authentication-config"
+  SH
+}
+
 resource "null_resource" "apiserver_oidc_config" {
   connection {
     type        = "ssh"
@@ -32,27 +150,11 @@ resource "null_resource" "apiserver_oidc_config" {
 
   provisioner "remote-exec" {
     inline = [
-      # Check if OIDC flags already configured with the correct values
-      "if grep -q 'oidc-issuer-url=${var.oidc_issuer_url}' /etc/kubernetes/manifests/kube-apiserver.yaml && grep -q 'oidc-client-id=${var.oidc_client_id}' /etc/kubernetes/manifests/kube-apiserver.yaml; then echo 'OIDC flags already configured with correct values'; exit 0; fi",
-
-      # Remove any existing OIDC flags (in case values changed)
-      "sudo sed -i '/--oidc-issuer-url/d; /--oidc-client-id/d; /--oidc-username-claim/d; /--oidc-groups-claim/d' /etc/kubernetes/manifests/kube-apiserver.yaml",
-
-      # Backup the manifest
-      "sudo cp /etc/kubernetes/manifests/kube-apiserver.yaml /etc/kubernetes/manifests/kube-apiserver.yaml.bak",
-
-      # Add OIDC flags after the last --tls-private-key-file flag (safe insertion point)
-      "sudo sed -i '/- --tls-private-key-file/a\\    - --oidc-issuer-url=${var.oidc_issuer_url}\\n    - --oidc-client-id=${var.oidc_client_id}\\n    - --oidc-username-claim=email\\n    - --oidc-groups-claim=groups' /etc/kubernetes/manifests/kube-apiserver.yaml",
-
-      # Wait for API server to restart (kubelet watches the manifest)
-      "echo 'Waiting for API server to restart...'",
-      "sleep 30",
-      "sudo kubectl --kubeconfig=/etc/kubernetes/admin.conf get nodes || echo 'API server still restarting, check manually'",
+      "echo '${base64encode(local.apiserver_auth_remote_script)}' | base64 -d | bash",
     ]
   }
 
   triggers = {
-    oidc_issuer_url = var.oidc_issuer_url
-    oidc_client_id  = var.oidc_client_id
+    auth_config = sha256(local.apiserver_auth_config_yaml)
   }
 }