diff --git a/wgengine/router/router_linux.go b/wgengine/router/router_linux.go
index d6e10dac1..3ee1235d2 100644
--- a/wgengine/router/router_linux.go
+++ b/wgengine/router/router_linux.go
@@ -471,7 +471,42 @@ func (r *linuxRouter) delRoute(cidr netaddr.IPPrefix) error {
 	if r.ipRuleAvailable {
 		args = append(args, "table", tailscaleRouteTable)
 	}
-	return r.cmd.run(args...)
+	err := r.cmd.run(args...)
+	if err != nil {
+		ok, err := r.hasRoute(cidr)
+		if err != nil {
+			r.logf("warning: error checking whether %v even exists after error deleting it: %v", err)
+		} else {
+			if !ok {
+				r.logf("warning: tried to delete route %v but it was already gone; ignoring error", cidr)
+				return nil
+			}
+		}
+	}
+	return err
+}
+
+func dashFam(ip netaddr.IP) string {
+	if ip.Is6() {
+		return "-6"
+	}
+	return "-4"
+}
+
+func (r *linuxRouter) hasRoute(cidr netaddr.IPPrefix) (bool, error) {
+	args := []string{
+		"ip", dashFam(cidr.IP), "route", "show",
+		normalizeCIDR(cidr),
+		"dev", r.tunname,
+	}
+	if r.ipRuleAvailable {
+		args = append(args, "table", tailscaleRouteTable)
+	}
+	out, err := r.cmd.output(args...)
+	if err != nil {
+		return false, err
+	}
+	return len(out) > 0, nil
 }
 
 // upInterface brings up the tunnel interface.
@@ -980,25 +1015,43 @@ func cidrDiff(kind string, old map[netaddr.IPPrefix]bool, new []netaddr.IPPrefix
 		ret[cidr] = true
 	}
 
+	var delFail []error
 	for cidr := range old {
 		if newMap[cidr] {
 			continue
 		}
 		if err := del(cidr); err != nil {
 			logf("%s del failed: %v", kind, err)
-			return ret, err
+			delFail = append(delFail, err)
+		} else {
+			delete(ret, cidr)
 		}
-		delete(ret, cidr)
 	}
+	if len(delFail) == 1 {
+		return ret, delFail[0]
+	}
+	if len(delFail) > 0 {
+		return ret, fmt.Errorf("%d delete %s failures; first was: %w", len(delFail), kind, delFail[0])
+	}
+
+	var addFail []error
 	for cidr := range newMap {
 		if old[cidr] {
 			continue
 		}
 		if err := add(cidr); err != nil {
 			logf("%s add failed: %v", kind, err)
-			return ret, err
+			addFail = append(addFail, err)
+		} else {
+			ret[cidr] = true
 		}
-		ret[cidr] = true
+	}
+
+	if len(addFail) == 1 {
+		return ret, addFail[0]
+	}
+	if len(addFail) > 0 {
+		return ret, fmt.Errorf("%d add %s failures; first was: %w", len(addFail), kind, addFail[0])
 	}
 
 	return ret, nil
diff --git a/wgengine/router/router_linux_test.go b/wgengine/router/router_linux_test.go
index bcc93af8f..e500f408a 100644
--- a/wgengine/router/router_linux_test.go
+++ b/wgengine/router/router_linux_test.go
@@ -5,14 +5,18 @@
 package router
 
 import (
+	"bytes"
 	"errors"
 	"fmt"
 	"math/rand"
+	"os"
 	"sort"
 	"strings"
+	"sync/atomic"
 	"testing"
 
 	"github.com/google/go-cmp/cmp"
+	"github.com/tailscale/wireguard-go/tun"
 	"inet.af/netaddr"
 )
 
@@ -595,3 +599,69 @@ func (o *fakeOS) output(args ...string) ([]byte, error) {
 	}
 	return []byte(strings.Join(ret, "\n")), nil
 }
+
+var tunTestNum int64
+
+func createTestTUN(t *testing.T) tun.Device {
+	const minimalMTU = 1280
+	tunName := fmt.Sprintf("tuntest%d", atomic.AddInt64(&tunTestNum, 1))
+	tun, err := tun.CreateTUN(tunName, minimalMTU)
+	if err != nil {
+		t.Fatalf("CreateTUN(%q): %v", tunName, err)
+	}
+	return tun
+}
+
+func TestDelRouteIdempotent(t *testing.T) {
+	if os.Getuid() != 0 {
+		t.Skip("test requires root")
+	}
+	tun := createTestTUN(t)
+	defer tun.Close()
+
+	var logOutput bytes.Buffer
+	logf := func(format string, args ...interface{}) {
+		fmt.Fprintf(&logOutput, format, args...)
+		if !bytes.HasSuffix(logOutput.Bytes(), []byte("\n")) {
+			logOutput.WriteByte('\n')
+		}
+	}
+
+	r, err := newUserspaceRouter(logf, nil, tun)
+	if err != nil {
+		t.Fatal(err)
+	}
+	lr := r.(*linuxRouter)
+	if err := lr.upInterface(); err != nil {
+		t.Fatal(err)
+	}
+	for _, s := range []string{
+		"192.0.2.0/24",  // RFC 5737
+		"2001:DB8::/32", // RFC 3849
+	} {
+		cidr := netaddr.MustParseIPPrefix(s)
+		if err := lr.addRoute(cidr); err != nil {
+			t.Fatal(err)
+		}
+		for i := 0; i < 2; i++ {
+			if err := lr.delRoute(cidr); err != nil {
+				t.Fatalf("delRoute(i=%d): %v", i, err)
+			}
+		}
+	}
+
+	wantSubs := map[string]int{
+		"warning: tried to delete route 192.0.2.0/24 but it was already gone; ignoring error":  1,
+		"warning: tried to delete route 2001:db8::/32 but it was already gone; ignoring error": 1,
+	}
+	out := logOutput.String()
+	for sub, want := range wantSubs {
+		got := strings.Count(out, sub)
+		if got != want {
+			t.Errorf("log output substring %q occurred %d time; want %d", sub, got, want)
+		}
+	}
+	if t.Failed() {
+		t.Logf("Log output:\n%s", out)
+	}
+}