diff --git a/Dockerfile b/Dockerfile
index d75852e..91fa54d 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -81,8 +81,7 @@ RUN ARCH=${TARGETARCH:-amd64} && \
     echo "Downloading gcloud SDK from: ${url}" && \
     curl -o "/tmp/${filename}" -fsSL "${url}" && \
     echo "${GCLOUD_SHA256} /tmp/${filename}" | sha256sum -c - && \
-    tar -xz -C /tmp -f "/tmp/${filename}" && \
-    /tmp/google-cloud-sdk/bin/gcloud components install gke-gcloud-auth-plugin --quiet
+    tar -xz -C /tmp -f "/tmp/${filename}"
 
 # Stage 2: Runtime image based on Red Hat UBI Minimal
 FROM registry.access.redhat.com/ubi9/ubi-minimal:latest@sha256:83006d535923fcf1345067873524a3980316f51794f01d8655be55d6e9387183
@@ -164,6 +163,7 @@ RUN ARCH=${TARGETARCH:-amd64} && \
 # Copy gcloud SDK from builder stage (extracted there to avoid UBI filesystem restrictions)
 COPY --from=builder /tmp/google-cloud-sdk /opt/google-cloud-sdk
 RUN ln -s /opt/google-cloud-sdk/bin/gcloud /usr/local/bin/gcloud && \
+    /opt/google-cloud-sdk/bin/gcloud components install gke-gcloud-auth-plugin --quiet && \
     ln -s /opt/google-cloud-sdk/bin/gke-gcloud-auth-plugin /usr/local/bin/gke-gcloud-auth-plugin
 
 # 2. AWS (EKS) - aws-iam-authenticator
diff --git a/internal/env/env.go b/internal/env/env.go
index efdff66..dd81693 100644
--- a/internal/env/env.go
+++ b/internal/env/env.go
@@ -9,6 +9,8 @@ import (
 	"os/exec"
 	"path/filepath"
 	"strings"
+	"sync"
+	"time"
 
 	"github.com/stackrox/roxie/internal/containerutil"
 	"github.com/stackrox/roxie/internal/logger"
@@ -18,6 +20,7 @@ import (
 var (
 	RunningInContainer   bool
 	RunningInteractively bool
+	initializationMutex  sync.Mutex
 )
 
 // ClusterType represents different types of Kubernetes clusters
@@ -69,10 +72,10 @@ func isRunningInteractively() bool {
 // ensureInitialized performs lazy initialization of cluster information
 // This avoids contacting the cluster on package import
 func ensureInitialized(log *logger.Logger) error {
+	initializationMutex.Lock()
+	defer initializationMutex.Unlock()
+
 	if !initialized {
-		if RunningInContainer {
-			log.Dim("Running containerized.")
-		}
 		kubeConfig, err := fetchKubeConfig(log)
 		if err != nil {
 			return err
@@ -133,14 +136,36 @@ type KubeCluster struct {
 }
 
 // Initialize performs environment initialization and sets the global variables.
+// Retries on failure to handle race conditions during container startup, which I have
+// observed in relation with podman :U mounts: the container was starting before the gcloud config
+// was writable by the container user, hence GKE authentication failed immediately.
 func Initialize(log *logger.Logger) error {
 	if log == nil {
 		log = logger.New()
 	}
-	if err := ensureInitialized(log); err != nil {
-		return fmt.Errorf("failed to initialize environment: %w", err)
+	if RunningInContainer {
+		log.Dim("Running containerized.")
 	}
-	return nil
+
+	const maxRetries = 3
+	const delay = 500 * time.Millisecond
+	var lastErr error
+
+	for attempt := 1; attempt <= maxRetries; attempt++ {
+		err := ensureInitialized(log)
+		if err == nil {
+			return nil
+		}
+
+		lastErr = err
+
+		if attempt < maxRetries {
+			log.Dimf("Attempt %d/%d failed: %v, retrying...", attempt, maxRetries, err)
+			time.Sleep(delay)
+		}
+	}
+
+	return fmt.Errorf("failed to initialize environment after %d attempts: %w", maxRetries, lastErr)
 }
 
 // detectClusterType implements the cluster type detection logic