diff --git a/pkg/manager/internal.go b/pkg/manager/internal.go
index f8c5619110..c16a5bb5f3 100644
--- a/pkg/manager/internal.go
+++ b/pkg/manager/internal.go
@@ -67,6 +67,7 @@ type controllerManager struct {
 	// leaderElectionRunnables is the set of Controllers that the controllerManager injects deps into and Starts.
 	// These Runnables are managed by lead election.
 	leaderElectionRunnables []Runnable
+
 	// nonLeaderElectionRunnables is the set of webhook servers that the controllerManager injects deps into and Starts.
 	// These Runnables will not be blocked by lead election.
 	nonLeaderElectionRunnables []Runnable
@@ -577,10 +578,27 @@ func (cm *controllerManager) startNonLeaderElectionRunnables() {
 	cm.mu.Lock()
 	defer cm.mu.Unlock()
 
+	// First start any webhook servers, which includes conversion, validation, and defaulting
+	// webhooks that are registered.
+	//
+	// WARNING: Webhooks MUST start before any cache is populated, otherwise there is a race condition
+	// between conversion webhooks and the cache sync (usually initial list) which causes the webhooks
+	// to never start because no cache can be populated.
+	for _, c := range cm.nonLeaderElectionRunnables {
+		if _, ok := c.(*webhook.Server); ok {
+			cm.startRunnable(c)
+		}
+	}
+
+	// Start and wait for caches.
 	cm.waitForCache(cm.internalCtx)
 
 	// Start the non-leaderelection Runnables after the cache has synced
 	for _, c := range cm.nonLeaderElectionRunnables {
+		if _, ok := c.(*webhook.Server); ok {
+			continue
+		}
+
 		// Controllers block, but we want to return an error if any have an error starting.
 		// Write any Start errors to a channel so we can return them
 		cm.startRunnable(c)