diff --git a/agent/consul/autopilot/autopilot.go b/agent/consul/autopilot/autopilot.go
index b50252ce510c..5b449e24ff1d 100644
--- a/agent/consul/autopilot/autopilot.go
+++ b/agent/consul/autopilot/autopilot.go
@@ -222,7 +222,9 @@ func (a *Autopilot) pruneDeadServers() error {
 
 	// Only do removals if a minority of servers will be affected.
 	peers := NumPeers(raftConfig)
-	if removalCount < peers/2 {
+	// For failure tolerance of F we need n = 2F+1 servers.
+	// This means we can safely remove up to (n-1)/2 servers
+	if removalCount <= (peers-1)/2 {
 		for _, node := range failed {
 			a.logger.Printf("[INFO] autopilot: Attempting removal of failed server node %q", node)
 			go serfLAN.RemoveFailedNode(node)
diff --git a/agent/consul/autopilot_test.go b/agent/consul/autopilot_test.go
index ea88dcca3205..b6ae4ffeb463 100644
--- a/agent/consul/autopilot_test.go
+++ b/agent/consul/autopilot_test.go
@@ -9,6 +9,7 @@ import (
 	"github.com/hashicorp/consul/testutil/retry"
 	"github.com/hashicorp/raft"
 	"github.com/hashicorp/serf/serf"
+	"github.com/stretchr/testify/require"
 )
 
 func TestAutopilot_IdempotentShutdown(t *testing.T) {
@@ -36,7 +37,7 @@ func testCleanupDeadServer(t *testing.T, raftVersion int) {
 	conf := func(c *Config) {
 		c.Datacenter = "dc1"
 		c.Bootstrap = false
-		c.BootstrapExpect = 3
+		c.BootstrapExpect = 5
 		c.RaftConfig.ProtocolVersion = raft.ProtocolVersion(raftVersion)
 	}
 	dir1, s1 := testServerWithConfig(t, conf)
@@ -51,23 +52,49 @@ func testCleanupDeadServer(t *testing.T, raftVersion int) {
 	defer os.RemoveAll(dir3)
 	defer s3.Shutdown()
 
-	servers := []*Server{s1, s2, s3}
+	dir4, s4 := testServerWithConfig(t, conf)
+	defer os.RemoveAll(dir4)
+	defer s4.Shutdown()
+
+	dir5, s5 := testServerWithConfig(t, conf)
+	defer os.RemoveAll(dir5)
+	defer s5.Shutdown()
+
+	servers := []*Server{s1, s2, s3, s4, s5}
 
 	// Try to join
 	joinLAN(t, s2, s1)
 	joinLAN(t, s3, s1)
+	joinLAN(t, s4, s1)
+	joinLAN(t, s5, s1)
 
 	for _, s := range servers {
-		retry.Run(t, func(r *retry.R) { r.Check(wantPeers(s, 3)) })
+		retry.Run(t, func(r *retry.R) { r.Check(wantPeers(s, 5)) })
 	}
 
-	// Bring up a new server
-	dir4, s4 := testServerWithConfig(t, conf)
-	defer os.RemoveAll(dir4)
-	defer s4.Shutdown()
+	require := require.New(t)
+	testrpc.WaitForLeader(t, s1.RPC, "dc1")
+	leaderIndex := -1
+	for i, s := range servers {
+		if s.IsLeader() {
+			leaderIndex = i
+			break
+		}
+	}
+	require.NotEqual(leaderIndex, -1)
+
+	// Shutdown two non-leader servers
+	killed := make(map[string]struct{})
+	for i, s := range servers {
+		if i != leaderIndex {
+			s.Shutdown()
+			killed[string(s.config.NodeID)] = struct{}{}
+		}
+		if len(killed) == 2 {
+			break
+		}
+	}
 
-	// Kill a non-leader server
-	s3.Shutdown()
 	retry.Run(t, func(r *retry.R) {
 		alive := 0
 		for _, m := range s1.LANMembers() {
@@ -75,18 +102,17 @@ func testCleanupDeadServer(t *testing.T, raftVersion int) {
 				alive++
 			}
 		}
-		if alive != 2 {
-			r.Fatal(nil)
+		if alive != 3 {
+			r.Fatal("Expected three alive servers")
 		}
 	})
 
-	// Join the new server
-	joinLAN(t, s4, s1)
-	servers[2] = s4
-
-	// Make sure the dead server is removed and we're back to 3 total peers
+	// Make sure the dead servers are removed and we're back to 3 total peers
 	for _, s := range servers {
-		retry.Run(t, func(r *retry.R) { r.Check(wantPeers(s, 3)) })
+		_, killed := killed[string(s.config.NodeID)]
+		if !killed {
+			retry.Run(t, func(r *retry.R) { r.Check(wantPeers(s, 3)) })
+		}
 	}
 }