diff --git a/internal/app/machined/pkg/system/services/etcd.go b/internal/app/machined/pkg/system/services/etcd.go
index c773cdbb97..7e31d028b5 100644
--- a/internal/app/machined/pkg/system/services/etcd.go
+++ b/internal/app/machined/pkg/system/services/etcd.go
@@ -221,7 +221,7 @@ func addMember(ctx context.Context, r runtime.Runtime, addrs []string, name stri
 
 	list, err := client.MemberList(ctx)
 	if err != nil {
-		return nil, 0, err
+		return nil, 0, fmt.Errorf("error getting etcd member list: %w", err)
 	}
 
 	for _, member := range list.Members {
@@ -232,31 +232,29 @@ func addMember(ctx context.Context, r runtime.Runtime, addrs []string, name stri
 
 	add, err := client.MemberAdd(ctx, addrs)
 	if err != nil {
-		return nil, 0, err
+		return nil, 0, fmt.Errorf("error adding member: %w", err)
 	}
 
 	list, err = client.MemberList(ctx)
 	if err != nil {
-		return nil, 0, err
+		return nil, 0, fmt.Errorf("error getting second etcd member list: %w", err)
 	}
 
 	return list, add.Member.ID, nil
 }
 
 func buildInitialCluster(ctx context.Context, r runtime.Runtime, name, ip string) (initial string, err error) {
-	err = retry.Constant(10*time.Minute, retry.WithUnits(3*time.Second), retry.WithJitter(time.Second)).Retry(func() error {
+	err = retry.Constant(10*time.Minute,
+		retry.WithUnits(3*time.Second),
+		retry.WithJitter(time.Second),
+		retry.WithErrorLogging(true),
+	).RetryWithContext(ctx, func(ctx context.Context) error {
 		var (
 			peerAddrs = []string{"https://" + net.FormatAddress(ip) + ":2380"}
 			resp      *clientv3.MemberListResponse
 			id        uint64
 		)
 
-		select {
-		case <-ctx.Done():
-			return retry.UnexpectedError(ctx.Err())
-		default:
-		}
-
 		attemptCtx, attemptCtxCancel := context.WithTimeout(ctx, 30*time.Second)
 		defer attemptCtxCancel()
 
diff --git a/internal/pkg/etcd/etcd.go b/internal/pkg/etcd/etcd.go
index df3b02ec34..26b8e1560d 100644
--- a/internal/pkg/etcd/etcd.go
+++ b/internal/pkg/etcd/etcd.go
@@ -46,7 +46,7 @@ func NewClient(endpoints []string) (client *Client, err error) {
 
 	tlsConfig, err := tlsInfo.ClientConfig()
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("error building etcd client TLS config: %w", err)
 	}
 
 	c, err := clientv3.New(clientv3.Config{
@@ -56,7 +56,7 @@ func NewClient(endpoints []string) (client *Client, err error) {
 		TLS:         tlsConfig,
 	})
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("error building etcd client: %w", err)
 	}
 
 	return &Client{Client: c}, nil
@@ -72,13 +72,13 @@ func NewLocalClient() (client *Client, err error) {
 func NewClientFromControlPlaneIPs(ctx context.Context, creds *x509.PEMEncodedCertificateAndKey, endpoint *url.URL) (client *Client, err error) {
 	h, err := kubernetes.NewTemporaryClientFromPKI(creds, endpoint)
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("error building kubernetes client from PKI: %w", err)
 	}
 
 	var endpoints []string
 
 	if endpoints, err = h.MasterIPs(ctx); err != nil {
-		return nil, err
+		return nil, fmt.Errorf("error getting kubernetes endpoints: %w", err)
 	}
 
 	// Etcd expects host:port format.