diff --git a/hscontrol/state/node_store.go b/hscontrol/state/node_store.go
index 13c165d96..979c2156b 100644
--- a/hscontrol/state/node_store.go
+++ b/hscontrol/state/node_store.go
@@ -763,7 +763,7 @@ func resolveGivenName(
 func bumpedLabel(base string, n int) string {
 	suffix := "-" + strconv.Itoa(n)
 
-	return base[:min(len(base), util.LabelHostnameLength-len(suffix))] + suffix
+	return strings.TrimRight(base[:min(len(base), util.LabelHostnameLength-len(suffix))], "-") + suffix
 }
 
 // snapshotFromNodes builds a Snapshot from nodes. With reusePeers the
diff --git a/hscontrol/state/node_store_hostname_test.go b/hscontrol/state/node_store_hostname_test.go
index f9a01d88d..d8e8b8b68 100644
--- a/hscontrol/state/node_store_hostname_test.go
+++ b/hscontrol/state/node_store_hostname_test.go
@@ -7,9 +7,11 @@ import (
 	"testing"
 
 	"github.com/juanfont/headscale/hscontrol/types"
+	"github.com/juanfont/headscale/hscontrol/util"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 	"tailscale.com/tailcfg"
+	"tailscale.com/util/dnsname"
 )
 
 func TestNewNodeStoreBumpsDuplicateNames(t *testing.T) {
@@ -308,3 +310,65 @@ func TestSetGivenNameIdempotent(t *testing.T) {
 	require.NoError(t, err)
 	require.Equal(t, "laptop", view.GivenName())
 }
+
+func TestPutNodeGivenNameBumpFitsDNSLabel(t *testing.T) {
+	maxLabel := strings.Repeat("a", util.LabelHostnameLength)
+
+	tests := []struct {
+		name     string
+		hostname string
+		holders  int
+		want     string
+	}{
+		{name: "short base keeps full base", hostname: "laptop", holders: 1, want: "laptop-1"},
+		{name: "max length base trimmed for one digit suffix", hostname: maxLabel, holders: 1, want: strings.Repeat("a", 61) + "-1"},
+		{name: "max length base trimmed for two digit suffix", hostname: maxLabel, holders: 10, want: strings.Repeat("a", 60) + "-10"},
+		{name: "hyphen left at cut point is stripped", hostname: strings.Repeat("a", 60) + "-bb", holders: 1, want: strings.Repeat("a", 60) + "-1"},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			store := NewNodeStore(nil, allowAllPeersFunc, TestBatchSize, TestBatchTimeout)
+
+			store.Start()
+			defer store.Stop()
+
+			for id := range tt.holders {
+				store.PutNode(createTestNode(types.NodeID(id+1), 1, "alice", tt.hostname)) //nolint:gosec // test ids
+			}
+
+			got := store.PutNode(createTestNode(types.NodeID(tt.holders+1), 1, "alice", tt.hostname)).GivenName() //nolint:gosec // test ids
+
+			require.Equal(t, tt.want, got)
+			require.NoError(t, dnsname.ValidLabel(got))
+		})
+	}
+}
+
+func TestIsAutoDerivedGivenName(t *testing.T) {
+	maxLabel := strings.Repeat("a", util.LabelHostnameLength)
+
+	tests := []struct {
+		name     string
+		given    string
+		hostname string
+		want     bool
+	}{
+		{name: "sanitised hostname", given: "laptop", hostname: "laptop", want: true},
+		{name: "short bump", given: "laptop-1", hostname: "laptop", want: true},
+		{name: "signed suffix is not a generated name", given: "laptop-+1", hostname: "laptop", want: false},
+		{name: "trimmed max length bump", given: strings.Repeat("a", 61) + "-1", hostname: maxLabel, want: true},
+		{name: "hyphen trimmed at cut point", given: strings.Repeat("a", 60) + "-1", hostname: strings.Repeat("a", 60) + "-bb", want: true},
+		{name: "legacy hyphen kept at cut point", given: strings.Repeat("a", 60) + "--1", hostname: strings.Repeat("a", 60) + "-bb", want: true},
+		{name: "zero padded suffix is not a generated name", given: "laptop-01", hostname: "laptop", want: false},
+		{name: "admin name with repeated hyphen", given: "laptop--1", hostname: "laptop", want: false},
+		{name: "trimmed prefix with mismatched suffix length", given: strings.Repeat("a", 61) + "-10", hostname: maxLabel, want: false},
+		{name: "admin rename", given: "workstation", hostname: "laptop", want: false},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			require.Equal(t, tt.want, isAutoDerivedGivenName(tt.given, tt.hostname))
+		})
+	}
+}
diff --git a/hscontrol/state/state.go b/hscontrol/state/state.go
index 57ef214e6..5c386d097 100644
--- a/hscontrol/state/state.go
+++ b/hscontrol/state/state.go
@@ -4125,8 +4125,18 @@ func isAutoDerivedGivenName(given, hostname string) bool {
 	}
 
 	n, err := strconv.Atoi(suffix)
+	if err != nil {
+		return false
+	}
 
-	return err == nil && given == bumpedLabel(base, n)
+	if given == bumpedLabel(base, n) {
+		return true
+	}
+
+	// Keep following labels generated before cut-point hyphens were trimmed.
+	suffix = "-" + strconv.Itoa(n)
+
+	return given == base[:min(len(base), util.LabelHostnameLength-len(suffix))]+suffix
 }
 
 func dnsMetadataChanged(previous, reported *tailcfg.Hostinfo) bool {