diff --git a/src/api/kube-client.ts b/src/api/kube-client.ts
index 9dc0a63f4..5387c4b76 100644
--- a/src/api/kube-client.ts
+++ b/src/api/kube-client.ts
@@ -745,7 +745,11 @@ export class KubeClient {
     return conditions
   }
 
-  async getPodReadyConditionStatus(selector: string, namespace: string): Promise<string | undefined> {
+  async getPodReadyConditionStatus(selector: string, namespace: string): Promise<string[] | undefined> {
+    return this.getPodsReadyConditionStatus(selector, namespace, 1)
+  }
+
+  async getPodsReadyConditionStatus(selector: string, namespace: string, pods: number): Promise<string[] | undefined> {
     const k8sCoreApi = this.kubeConfig.makeApiClient(CoreV1Api)
     let res
     try {
@@ -758,33 +762,38 @@ export class KubeClient {
       throw new Error(`Get pods by selector "${selector}" returned an invalid response.`)
     }
 
-    if (res.body.items.length < 1) {
-      // No pods found by the specified selector. So, it's not ready.
-      return 'False'
-    }
-
-    if (res.body.items.length > 1) {
-      // Several pods found, rolling update?
+    if (res.body.items.length < pods) {
+      // Fewer than expected pods found by the specified selector. So, it's not ready.
       return
     }
 
-    if (!res.body.items[0].status || !res.body.items[0].status.conditions || !(res.body.items[0].status.conditions.length > 0)) {
+    if (res.body.items.length > pods) {
+      // More pods than expected found, rolling update?
       return
     }
 
-    const conditions = res.body.items[0].status.conditions
-    for (const condition of conditions) {
-      if (condition.type === 'Ready') {
-        return condition.status
+    return res.body.items.map(item => {
+      if (item.status && item.status.conditions) {
+        for (const condition of item.status.conditions) {
+          if (condition.type === 'Ready') {
+            return condition.status
+          }
+        }
       }
-    }
+
+      return 'False'
+    })
   }
 
   async waitForPodReady(selector: string, namespace: string, intervalMs = 500, timeoutMs = this.podReadyTimeout) {
+    await this.waitForPodsReady(selector, namespace, 1, intervalMs, timeoutMs)
+  }
+
+  async waitForPodsReady(selector: string, namespace: string, pods: number, intervalMs = 500, timeoutMs = this.podReadyTimeout) {
     const iterations = timeoutMs / intervalMs
     for (let index = 0; index < iterations; index++) {
-      const readyStatus = await this.getPodReadyConditionStatus(selector, namespace)
-      if (readyStatus === 'True') {
+      const readyStatus = await this.getPodsReadyConditionStatus(selector, namespace, pods)
+      if (readyStatus && readyStatus.every(status => status === 'True')) {
         return
       }
 
diff --git a/src/tasks/installers/dev-workspace/dev-workspace-tasks.ts b/src/tasks/installers/dev-workspace/dev-workspace-tasks.ts
index 1c2e0ae83..9b1fc93b7 100644
--- a/src/tasks/installers/dev-workspace/dev-workspace-tasks.ts
+++ b/src/tasks/installers/dev-workspace/dev-workspace-tasks.ts
@@ -133,7 +133,7 @@ export namespace DevWorkspacesTasks {
       task: async (ctx: any, task: any) => {
         const kubeHelper = KubeClient.getInstance()
         await kubeHelper.waitForPodReady('app.kubernetes.io/name=devworkspace-controller', ctx[DevWorkspaceContext.NAMESPACE])
-        await kubeHelper.waitForPodReady('app.kubernetes.io/name=devworkspace-webhook-server', ctx[DevWorkspaceContext.NAMESPACE])
+        await kubeHelper.waitForPodsReady('app.kubernetes.io/name=devworkspace-webhook-server', ctx[DevWorkspaceContext.NAMESPACE], 2)
         task.title = `${task.title}...[OK]`
       },
     }