diff --git a/packages/envd/internal/api/init.go b/packages/envd/internal/api/init.go
index 4d0081b0a2..557dc4b94a 100644
--- a/packages/envd/internal/api/init.go
+++ b/packages/envd/internal/api/init.go
@@ -131,8 +131,12 @@ func (a *API) PostInit(w http.ResponseWriter, r *http.Request) {
 		a.initLock.Lock()
 		defer a.initLock.Unlock()
 
-		// Update data only if the request is newer or if there's no timestamp at all
-		if initRequest.Timestamp == nil || a.lastSetTime.SetToGreater(initRequest.Timestamp.UnixNano()) {
+		// Update data only if the request is newer or if there's no timestamp at all.
+		// We check without mutating so that a failed SetData doesn't permanently
+		// raise lastSetTime — retries with the same pinned Timestamp must be able
+		// to re-run SetData until it succeeds.
+		shouldRun := initRequest.Timestamp == nil || initRequest.Timestamp.UnixNano() > a.lastSetTime.Load()
+		if shouldRun {
 			err = a.SetData(ctx, logger, initRequest)
 			if err != nil {
 				switch {
@@ -146,6 +150,9 @@ func (a *API) PostInit(w http.ResponseWriter, r *http.Request) {
 
 				return
 			}
+			if initRequest.Timestamp != nil {
+				a.lastSetTime.SetToGreater(initRequest.Timestamp.UnixNano())
+			}
 		}
 	}
 
diff --git a/packages/envd/internal/utils/atomic.go b/packages/envd/internal/utils/atomic.go
index d34d6afc70..438cf9b41c 100644
--- a/packages/envd/internal/utils/atomic.go
+++ b/packages/envd/internal/utils/atomic.go
@@ -25,3 +25,11 @@ func (a *AtomicMax) SetToGreater(newValue int64) bool {
 
 	return true
 }
+
+// Load returns the current value.
+func (a *AtomicMax) Load() int64 {
+	a.mu.Lock()
+	defer a.mu.Unlock()
+
+	return a.val
+}
diff --git a/packages/envd/pkg/version.go b/packages/envd/pkg/version.go
index 88bc32c769..4cfbb08b29 100644
--- a/packages/envd/pkg/version.go
+++ b/packages/envd/pkg/version.go
@@ -1,3 +1,3 @@
 package pkg
 
-const Version = "0.5.23"
+const Version = "0.5.24"
diff --git a/packages/orchestrator/pkg/sandbox/envd.go b/packages/orchestrator/pkg/sandbox/envd.go
index 49ffe1ccd0..c5af3dbfa6 100644
--- a/packages/orchestrator/pkg/sandbox/envd.go
+++ b/packages/orchestrator/pkg/sandbox/envd.go
@@ -37,6 +37,9 @@ func (s *Sandbox) doRequestWithInfiniteRetries(
 ) (*http.Response, int64, error) {
 	requestCount := int64(0)
 
+	// Pin Timestamp once so envd's lastSetTime.SetToGreater guard can skip
+	// re-delivered retries instead of re-running SetData against dead sockets.
+	now := time.Now()
 	jsonBody := &envd.PostInitJSONBody{
 		LifecycleID:    s.LifecycleID,
 		EnvVars:        s.Config.Envd.Vars,
@@ -46,16 +49,15 @@ func (s *Sandbox) doRequestWithInfiniteRetries(
 		DefaultWorkdir: utils.DerefOrDefault(s.Config.Envd.DefaultWorkdir, ""),
 		VolumeMounts:   s.convertMounts(s.Config.VolumeMounts),
 		CaBundle:       s.CABundle,
+		Timestamp:      now,
 	}
 
-	for {
-		jsonBody.Timestamp = time.Now()
-
-		body, err := json.Marshal(jsonBody)
-		if err != nil {
-			return nil, requestCount, err
-		}
+	body, err := json.Marshal(jsonBody)
+	if err != nil {
+		return nil, requestCount, err
+	}
 
+	for {
 		requestCount++
 		reqCtx, cancel := context.WithTimeout(ctx, s.internalConfig.EnvdInitRequestTimeout)
 		request, err := http.NewRequestWithContext(reqCtx, method, address, bytes.NewReader(body))