found the issue again in a 4.10.0-0.nightly-2022-06-08-150219 Disconnected UPI on AZURE & OVN IPSEC cluster upgrade to 4.11.0-0.nightly-2022-06-23-044003
monitoring is degraded
status:
  conditions:
  - lastTransitionTime: "2022-06-23T23:20:58Z"
    message: Rolling out the stack.
    reason: RollOutInProgress
    status: "True"
    type: Progressing
  - lastTransitionTime: "2022-06-23T22:35:57Z"
    message: 'Failed to rollout the stack. Error: updating prometheus operator: reconciling
      Prometheus Operator Admission Webhook Deployment failed: updating Deployment
      object failed: waiting for DeploymentRollout of openshift-monitoring/prometheus-operator-admission-webhook:
      the number of pods targeted by the deployment (3 pods) is different from the
      number of pods targeted by the deployment that have the desired template spec
      (1 pods)'
    reason: UpdatingPrometheusOperatorFailed
    status: "True"
    type: Degraded

deployment.yaml file
  status:
    availableReplicas: 2
    conditions:
    - lastTransitionTime: "2022-06-23T21:22:50Z"
      lastUpdateTime: "2022-06-23T21:22:50Z"
      message: Deployment has minimum availability.
      reason: MinimumReplicasAvailable
      status: "True"
      type: Available
    - lastTransitionTime: "2022-06-23T22:30:57Z"
      lastUpdateTime: "2022-06-23T22:30:57Z"
      message: ReplicaSet "prometheus-operator-admission-webhook-78fd9c895d" has timed
        out progressing.
      reason: ProgressDeadlineExceeded
      status: "False"
      type: Progressing
    observedGeneration: 2
    readyReplicas: 2
    replicas: 3
    unavailableReplicas: 1
    updatedReplicas: 1

check the prometheus-operator-admission-webhook pods, there are 2 normal running pods
prometheus-operator-admission-webhook-74f7bb977f-b9vxd
prometheus-operator-admission-webhook-74f7bb977f-lq5xl

1 Pending pod, ReplicaSet is prometheus-operator-admission-webhook-78fd9c895d, same with the error in deployment.yaml
prometheus-operator-admission-webhook-78fd9c895d-bjqwj
status:
  conditions:
  - lastProbeTime: null
    lastTransitionTime: "2022-06-23T22:20:56Z"
    message: '0/5 nodes are available: 2 node(s) didn''t match pod anti-affinity rules,
      3 node(s) had untolerated taint {node-role.kubernetes.io/master: }. preemption:
      0/5 nodes are available: 2 node(s) didn''t match pod anti-affinity rules, 3
      Preemption is not helpful for scheduling.'
    reason: Unschedulable
    status: "False"
    type: PodScheduled
  phase: Pending
  qosClass: Burstable

*** Bug 2105174 has been marked as a duplicate of this bug. ***

Encounter the issue again
Version-Release number of selected component (if applicable):
4.11.0-0.nightly-2022-06-30-005428

1. % oc get node
NAME                       STATUS   ROLES    AGE     VERSION
ge1n1-b5fdg-master-0       Ready    master   4d22h   v1.24.0+9ddc8b1
ge1n1-b5fdg-master-1       Ready    master   4d22h   v1.24.0+9ddc8b1
ge1n1-b5fdg-master-2       Ready    master   4d22h   v1.24.0+9ddc8b1
ge1n1-b5fdg-worker-qjshm   Ready    worker   4d22h   v1.24.0+9ddc8b1
ge1n1-b5fdg-worker-vjcsp   Ready    worker   4d22h   v1.24.0+9ddc8b
2. % oc -n openshift-monitoring describe pod prometheus-operator-admission-webhook-555d9654f8-ft2jv 
---
Events:
  Type     Reason            Age                  From               Message
  ----     ------            ----                 ----               -------
  Warning  FailedScheduling  10h (x292 over 18h)  default-scheduler  0/5 nodes are available: 2 node(s) didn't match pod anti-affinity rules, 3 node(s) had untolerated taint {node-role.kubernetes.io/master: }. preemption: 0/5 nodes are available: 2 node(s) didn't match pod anti-affinity rules, 3 Preemption is not helpful for scheduling.
3. % oc describe co monitoring
    Last Transition Time:  2022-07-07T13:02:15Z
    Message:               Failed to rollout the stack. Error: updating prometheus operator: reconciling Prometheus Operator Admission Webhook Deployment failed: updating Deployment object failed: waiting for DeploymentRollout of openshift-monitoring/prometheus-operator-admission-webhook: the number of pods targeted by the deployment (3 pods) is different from the number of pods targeted by the deployment that have the desired template spec (1 pods)
    Reason:                UpdatingPrometheusOperatorFailed
    Status:                True
    Type:                  Degraded
  Extension:               <nil>

The availableReplicas of prometheus-operator-admission-webhook are from 'replicas - maxUnavailable' to 'replicas + maxSurge', that is, from 2 to 2 for round down 2*25% is zero. Suppose maxUnavailable and  maxSurge are not reasonable.

Both maxSurge and maxUnavailable can be specified as either an integer (e.g. 2) or a percentage (e.g. 50%), and they cannot both be zero. When specified as an integer, it represents the actual number of pods; when specifying a percentage, that percentage of the desired number of pods is used, rounded down.

found the issue again in a 4.11 to 4.12 upgrade cluster which has 2 workers
NAME                                STATUS   ROLES                  AGE   VERSION
wduan-0714a-az-q2ps8-master-0       Ready    control-plane,master   20h   v1.24.0+9546431
wduan-0714a-az-q2ps8-master-1       Ready    control-plane,master   20h   v1.24.0+9546431
wduan-0714a-az-q2ps8-master-2       Ready    control-plane,master   20h   v1.24.0+9546431
wduan-0714a-az-q2ps8-worker-4288p   Ready    worker                 20h   v1.24.0+9546431
wduan-0714a-az-q2ps8-worker-4cmx5   Ready    worker                 20h   v1.24.0+9546431

# oc -n openshift-monitoring get rs
NAME                                               DESIRED   CURRENT   READY   AGE
cluster-monitoring-operator-5bbfd998c6             0         0         0       15h
cluster-monitoring-operator-7df87f6db              0         0         0       14h
cluster-monitoring-operator-848799d46f             1         1         1       42m
cluster-monitoring-operator-f794d99fb              0         0         0       20h
kube-state-metrics-6d685b8687                      0         0         0       15h
kube-state-metrics-764c7cbcb                       0         0         0       20h
kube-state-metrics-f64d8dfd5                       1         1         1       14h
openshift-state-metrics-65f58d4c67                 0         0         0       15h
openshift-state-metrics-686fcb4d58                 1         1         1       14h
prometheus-adapter-58c87f9b89                      0         0         0       14h
prometheus-adapter-757f89985b                      0         0         0       93m
prometheus-adapter-77749dbccb                      0         0         0       92m
prometheus-adapter-78745d5d6f                      2         2         2       91m
prometheus-adapter-7bd4745484                      0         0         0       20h
prometheus-adapter-c49dd8496                       0         0         0       15h
prometheus-operator-5c58cf67d5                     0         0         0       20h
prometheus-operator-76f79c8d85                     0         0         0       15h
prometheus-operator-7cdc95fdb4                     1         1         1       14h
prometheus-operator-admission-webhook-5b9ff5ddbf   1         1         0       41m
prometheus-operator-admission-webhook-67f97cf577   2         2         2       14h
telemeter-client-66989bbb48                        1         1         1       14h
telemeter-client-fb5b896cf                         0         0         0       15h
thanos-querier-6cfb6bd748                          0         0         0       15h
thanos-querier-8678f9995c                          2         2         2       14h

# oc -n openshift-monitoring get pod -o wide | grep prometheus-operator-admission-webhook
prometheus-operator-admission-webhook-5b9ff5ddbf-p8kmz   0/1     Pending   0          44m   <none>           <none>                              <none>           <none>
prometheus-operator-admission-webhook-67f97cf577-46jvl   1/1     Running   0          13h   10.128.2.7       wduan-0714a-az-q2ps8-worker-4288p   <none>           <none>
prometheus-operator-admission-webhook-67f97cf577-r5mvt   1/1     Running   0          14h   10.131.0.9       wduan-0714a-az-q2ps8-worker-4cmx5   <none>           <none>


# oc -n openshift-monitoring describe pod prometheus-operator-admission-webhook-5b9ff5ddbf-p8kmz
...
Events:
  Type     Reason            Age   From               Message
  ----     ------            ----  ----               -------
  Warning  FailedScheduling  44m   default-scheduler  0/5 nodes are available: 2 node(s) didn't match pod anti-affinity rules, 3 node(s) had untolerated taint {node-role.kubernetes.io/master: }. preemption: 0/5 nodes are available: 2 node(s) didn't match pod anti-affinity rules, 3 Preemption is not helpful for scheduling.
  Warning  FailedScheduling  44m   default-scheduler  0/5 nodes are available: 2 node(s) didn't match pod anti-affinity rules, 3 node(s) had untolerated taint {node-role.kubernetes.io/master: }. preemption: 0/5 nodes are available: 2 node(s) didn't match pod anti-affinity rules, 3 Preemption is not helpful for scheduling.

checked, maxSurge and maxUnavailable are 25%
# oc -n openshift-monitoring get deploy prometheus-operator-admission-webhook -oyaml | grep -E "maxUnavailable|maxSurge"
      maxSurge: 25%
      maxUnavailable: 25%
from https://kubernetes.io/docs/concepts/workloads/controllers/deployment/
Max Unavailable
.spec.strategy.rollingUpdate.maxUnavailable is an optional field that specifies the maximum number of Pods that can be unavailable during the update process. The value can be an absolute number (for example, 5) or a percentage of desired Pods (for example, 10%). The absolute number is calculated from percentage by rounding down

and
Max Surge 
.spec.strategy.rollingUpdate.maxSurge is an optional field that specifies the maximum number of Pods that can be created over the desired number of Pods. The value can be an absolute number (for example, 5) or a percentage of desired Pods (for example, 10%). The value cannot be 0 if MaxUnavailable is 0. The absolute number is calculated from the percentage by rounding up.

for maxSurge, since the absolute number is calculated from the percentage by rounding up, and for maxUnavailable, the absolute number is calculated from percentage by rounding down, then the existing prometheus-operator-admission-webhook replicas are between [replicas - maxUnavailable] and [replicas + maxSurge]. for the 2 workers cluster, 
maxUnavailable replicas = 2 * 25%， rounding down， result is 0, maxSurge replicas = 2 * 25%， rounding up， result is 1
then the existing replicas is 2 - 0 <= replicas number <= 3, since the podAntiAffinity rule, no more prometheus-operator-admission-webhook could be scaled up, and no pod is removed. change the maxUnavailable to 1 may fix the issue in 2 workers cluster

    spec:
      affinity:
        podAntiAffinity:
          requiredDuringSchedulingIgnoredDuringExecution:
          - labelSelector:
              matchLabels:
                app.kubernetes.io/name: prometheus-operator-admission-webhook
                app.kubernetes.io/part-of: openshift-monitoring
            namespaces:
            - openshift-monitoring
            topologyKey: kubernetes.io/hostname

Setting blocker+ with JP's ack since this can impact customer upgrades getting stuck.

ipi-on-vsphere, 2 workers cluster, upgrade from 4.10.0-0.nightly-2022-07-16-173050 to 4.11.0-0.nightly-2022-07-16-020951, then continue to upgrade 4.12.0-0.nightly-2022-07-15-235709, 4.12.0-0.nightly-2022-07-17-174647,  prometheus-operator-admission-webhook pods and monitoring operator are normal, no issue now
# oc get node
NAME                     STATUS   ROLES    AGE     VERSION
***-4g69p-master-0       Ready    master   4h50m   v1.24.0+9546431
***-4g69p-master-1       Ready    master   4h49m   v1.24.0+9546431
***-4g69p-master-2       Ready    master   4h50m   v1.24.0+9546431
***-4g69p-worker-v4l9p   Ready    worker   4h40m   v1.24.0+9546431
***-4g69p-worker-vr5md   Ready    worker   4h40m   v1.24.0+9546431

# oc get clusterversion version -oyaml
...
    desired:
      image: registry.ci.openshift.org/ocp/release:4.12.0-0.nightly-2022-07-17-174647
      version: 4.12.0-0.nightly-2022-07-17-174647
    history:
    - completionTime: "2022-07-18T08:38:45Z"
      image: registry.ci.openshift.org/ocp/release:4.12.0-0.nightly-2022-07-17-174647
      startedTime: "2022-07-18T08:11:24Z"
      state: Completed
      verified: false
      version: 4.12.0-0.nightly-2022-07-17-174647
    - completionTime: "2022-07-18T07:38:45Z"
      image: registry.ci.openshift.org/ocp/release:4.12.0-0.nightly-2022-07-15-235709
      startedTime: "2022-07-18T06:40:15Z"
      state: Completed
      verified: false
      version: 4.12.0-0.nightly-2022-07-15-235709
    - completionTime: "2022-07-18T04:12:49Z"
      image: registry.ci.openshift.org/ocp/release:4.11.0-0.nightly-2022-07-16-020951
      startedTime: "2022-07-18T03:08:48Z"
      state: Completed
      verified: false
      version: 4.11.0-0.nightly-2022-07-16-020951
    - completionTime: "2022-07-18T02:39:46Z"
      image: registry.ci.openshift.org/ocp/release@sha256:e56645bcabe38850b37f2c7a70fbf890819eedda63898c703b78c1d5005a91ae
      startedTime: "2022-07-18T02:22:23Z"
      state: Completed
      verified: false
      version: 4.10.0-0.nightly-2022-07-16-173050

# oc get co monitoring
NAME         VERSION                              AVAILABLE   PROGRESSING   DEGRADED   SINCE   MESSAGE
monitoring   4.12.0-0.nightly-2022-07-17-174647   True        False         False      6h21m   


# oc -n openshift-monitoring get pod -o wide | grep prometheus-operator-admission-webhook
prometheus-operator-admission-webhook-6cff644fdf-6j92x   1/1     Running   0          90m    10.131.0.6       ***-4g69p-worker-v4l9p   <none>           <none>
prometheus-operator-admission-webhook-6cff644fdf-mdj26   1/1     Running   0          95m    10.128.2.10      ***-4g69p-worker-vr5md   <none>           <none>

# oc -n openshift-monitoring get deploy prometheus-operator-admission-webhook -oyaml | grep -E "maxUnavailable|maxSurge"
      maxSurge: 25%
      maxUnavailable: 1

# oc -n openshift-monitoring get rs | grep prometheus-operator-admission-webhook
prometheus-operator-admission-webhook-67f97cf577   0         0         0       5h25m
prometheus-operator-admission-webhook-6cff644fdf   2         2         2       115m

Since the problem described in this bug report should be
resolved in a recent advisory, it has been closed with a
resolution of ERRATA.

For information on the advisory (Moderate: OpenShift Container Platform 4.12.0 bug fix and security update), and where to find the updated
files, follow the link below.

If the solution does not work for you, open a new bug report.

https://access.redhat.com/errata/RHSA-2022:7399