diff --git a/cmd/tailscale/cli/cli_test.go b/cmd/tailscale/cli/cli_test.go
index fecdb76b2..6765a3cc9 100644
--- a/cmd/tailscale/cli/cli_test.go
+++ b/cmd/tailscale/cli/cli_test.go
@@ -402,6 +402,28 @@ func TestCheckForAccidentalSettingReverts(t *testing.T) {
 			},
 			want: accidentalUpPrefix + " --hostname=foo --exit-node=100.64.5.7",
 		},
+		{
+			name:  "ignore_login_server_synonym",
+			flags: []string{"--login-server=https://controlplane.tailscale.com"},
+			curPrefs: &ipn.Prefs{
+				ControlURL:       "https://login.tailscale.com",
+				AllowSingleHosts: true,
+				CorpDNS:          true,
+				NetfilterMode:    preftype.NetfilterOn,
+			},
+			want: "", // not an error
+		},
+		{
+			name:  "ignore_login_server_synonym_on_other_change",
+			flags: []string{"--netfilter-mode=off"},
+			curPrefs: &ipn.Prefs{
+				ControlURL:       "https://login.tailscale.com",
+				AllowSingleHosts: true,
+				CorpDNS:          false,
+				NetfilterMode:    preftype.NetfilterOn,
+			},
+			want: accidentalUpPrefix + " --netfilter-mode=off --accept-dns=false",
+		},
 	}
 	for _, tt := range tests {
 		t.Run(tt.name, func(t *testing.T) {
diff --git a/cmd/tailscale/cli/up.go b/cmd/tailscale/cli/up.go
index 5c0c3f905..4dbb63510 100644
--- a/cmd/tailscale/cli/up.go
+++ b/cmd/tailscale/cli/up.go
@@ -586,6 +586,9 @@ func checkForAccidentalSettingReverts(flagSet *flag.FlagSet, curPrefs, newPrefs
 		if reflect.DeepEqual(valCur, valNew) {
 			continue
 		}
+		if flagName == "login-server" && isLoginServerSynonym(valCur) && isLoginServerSynonym(valNew) {
+			continue
+		}
 		missing = append(missing, fmtFlagValueArg(flagName, valCur))
 	}
 	if len(missing) == 0 {
@@ -632,6 +635,10 @@ func applyImplicitPrefs(prefs, oldPrefs *ipn.Prefs, curUser string) {
 	}
 }
 
+func isLoginServerSynonym(val interface{}) bool {
+	return val == "https://login.tailscale.com" || val == "https://controlplane.tailscale.com"
+}
+
 func flagAppliesToOS(flag, goos string) bool {
 	switch flag {
 	case "netfilter-mode", "snat-subnet-routes":