diff --git a/server/etcdmain/etcd.go b/server/etcdmain/etcd.go
index f35ebde6b55..40f7059044c 100644
--- a/server/etcdmain/etcd.go
+++ b/server/etcdmain/etcd.go
@@ -19,6 +19,7 @@ import (
 	"os"
 	"runtime"
 	"strings"
+	"time"
 
 	"go.etcd.io/etcd/client/pkg/v3/fileutil"
 	"go.etcd.io/etcd/client/pkg/v3/logutil"
@@ -207,6 +208,8 @@ func startEtcd(cfg *embed.Config) (<-chan struct{}, <-chan error, error) {
 	select {
 	case <-e.Server.ReadyNotify(): // wait for e.Server to join the cluster
 	case <-e.Server.StopNotify(): // publish aborted from 'ErrStopped'
+	case <-time.After(cfg.ExperimentalWaitClusterReadyTimeout):
+		e.GetLogger().Warn("startEtcd: timed out waiting for the ready notification")
 	}
 	return e.Server.StopNotify(), e.Err(), nil
 }
diff --git a/tests/e2e/cluster_downgrade_test.go b/tests/e2e/cluster_downgrade_test.go
index 4e032e1b3e8..89cbc75e980 100644
--- a/tests/e2e/cluster_downgrade_test.go
+++ b/tests/e2e/cluster_downgrade_test.go
@@ -61,7 +61,7 @@ func testDowngradeUpgrade(t *testing.T, clusterSize int) {
 
 	t.Log("Downgrade enabled, validating if cluster is ready for downgrade")
 	for i := 0; i < len(epc.Procs); i++ {
-		expectLog(t, epc.Procs[i], "The server is ready to downgrade")
+		e2e.AssertProcessLogs(t, epc.Procs[i], "The server is ready to downgrade")
 		validateVersion(t, epc.Cfg, epc.Procs[i], version.Versions{Cluster: lastVersionStr, Server: currentVersionStr})
 	}
 	t.Log("Cluster is ready for downgrade")
@@ -73,7 +73,7 @@ func testDowngradeUpgrade(t *testing.T, clusterSize int) {
 		startEtcd(t, epc.Procs[i], lastReleaseBinary)
 	}
 	t.Log("All members downgraded, validating downgrade")
-	expectLog(t, leader(t, epc), "the cluster has been downgraded")
+	e2e.AssertProcessLogs(t, leader(t, epc), "the cluster has been downgraded")
 	for i := 0; i < len(epc.Procs); i++ {
 		validateVersion(t, epc.Cfg, epc.Procs[i], version.Versions{Cluster: lastVersionStr, Server: lastVersionStr})
 	}
@@ -164,17 +164,6 @@ func validateVersion(t *testing.T, cfg *e2e.EtcdProcessClusterConfig, member e2e
 	}
 }
 
-func expectLog(t *testing.T, ep e2e.EtcdProcess, expectLog string) {
-	t.Helper()
-	var err error
-	testutils.ExecuteWithTimeout(t, 30*time.Second, func() {
-		_, err = ep.Logs().Expect(expectLog)
-	})
-	if err != nil {
-		t.Fatal(err)
-	}
-}
-
 func leader(t *testing.T, epc *e2e.EtcdProcessCluster) e2e.EtcdProcess {
 	ctx, cancel := context.WithTimeout(context.Background(), time.Second*10)
 	defer cancel()
diff --git a/tests/e2e/ctl_v3_grpc_test.go b/tests/e2e/ctl_v3_grpc_test.go
index 1c0bf8474de..991cdbd260e 100644
--- a/tests/e2e/ctl_v3_grpc_test.go
+++ b/tests/e2e/ctl_v3_grpc_test.go
@@ -151,7 +151,7 @@ func firstMatch(t *testing.T, expectLine string, logs ...e2e.LogsExpect) string
 	match := make(chan string, len(logs))
 	for i := range logs {
 		go func(l e2e.LogsExpect) {
-			line, _ := l.Expect(expectLine)
+			line, _ := l.ExpectWithContext(context.TODO(), expectLine)
 			match <- line
 		}(logs[i])
 	}
diff --git a/tests/e2e/no_quorum_ready_test.go b/tests/e2e/no_quorum_ready_test.go
new file mode 100644
index 00000000000..126a040b0a3
--- /dev/null
+++ b/tests/e2e/no_quorum_ready_test.go
@@ -0,0 +1,44 @@
+// Copyright 2021 The etcd Authors
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+package e2e
+
+import (
+	"testing"
+
+	"go.etcd.io/etcd/tests/v3/framework/e2e"
+)
+
+func TestInitDaemonNotifyWithoutQuorum(t *testing.T) {
+	// Initialize a cluster with 3 members
+	epc, err := e2e.InitEtcdProcessCluster(t, e2e.NewConfigAutoTLS())
+	if err != nil {
+		t.Fatalf("Failed to initilize the etcd cluster: %v", err)
+	}
+
+	// Remove two members, so that only one etcd will get started
+	epc.Procs = epc.Procs[:1]
+
+	// Start the etcd cluster with only one member
+	if err := epc.Start(); err != nil {
+		t.Fatalf("Failed to start the etcd cluster: %v", err)
+	}
+
+	// Expect log message indicating time out waiting for quorum hit
+	e2e.AssertProcessLogs(t, epc.Procs[0], "startEtcd: timed out waiting for the ready notification")
+	// Expect log message indicating systemd notify message has been sent
+	e2e.AssertProcessLogs(t, epc.Procs[0], "notifying init daemon")
+
+	epc.Close()
+}
diff --git a/tests/framework/e2e/etcd_process.go b/tests/framework/e2e/etcd_process.go
index 69426066e3f..9a5c94a14a9 100644
--- a/tests/framework/e2e/etcd_process.go
+++ b/tests/framework/e2e/etcd_process.go
@@ -15,9 +15,12 @@
 package e2e
 
 import (
+	"context"
 	"fmt"
 	"net/url"
 	"os"
+	"testing"
+	"time"
 
 	"go.uber.org/zap"
 
@@ -48,7 +51,7 @@ type EtcdProcess interface {
 }
 
 type LogsExpect interface {
-	Expect(string) (string, error)
+	ExpectWithContext(context.Context, string) (string, error)
 	Lines() []string
 	LineCount() int
 }
@@ -179,3 +182,14 @@ func (ep *EtcdServerProcess) Logs() LogsExpect {
 	}
 	return ep.proc
 }
+
+func AssertProcessLogs(t *testing.T, ep EtcdProcess, expectLog string) {
+	t.Helper()
+	var err error
+	ctx, cancel := context.WithTimeout(context.Background(), 30*time.Second)
+	defer cancel()
+	_, err = ep.Logs().ExpectWithContext(ctx, expectLog)
+	if err != nil {
+		t.Fatal(err)
+	}
+}