diff --git a/control/controlclient/direct.go b/control/controlclient/direct.go
index 97d45d2d2..ef32789b9 100644
--- a/control/controlclient/direct.go
+++ b/control/controlclient/direct.go
@@ -91,9 +91,14 @@ func (p *Persist) Pretty() string {
 	if !p.PrivateNodeKey.IsZero() {
 		nk = p.PrivateNodeKey.Public()
 	}
+	ss := func(k wgcfg.Key) string {
+		if k.IsZero() {
+			return ""
+		}
+		return k.ShortString()
+	}
 	return fmt.Sprintf("Persist{lm=%v, o=%v, n=%v u=%#v}",
-		mk.ShortString(), ok.ShortString(), nk.ShortString(),
-		p.LoginName)
+		ss(mk), ss(ok), ss(nk), p.LoginName)
 }
 
 // Direct is the client that connects to a tailcontrol server for a node.
diff --git a/ipn/local.go b/ipn/local.go
index dcbff9857..ad11fe202 100644
--- a/ipn/local.go
+++ b/ipn/local.go
@@ -419,7 +419,9 @@ func (b *LocalBackend) Start(opts Options) error {
 	b.serverURL = b.prefs.ControlURL
 	hostinfo.RoutableIPs = append(hostinfo.RoutableIPs, b.prefs.AdvertiseRoutes...)
 	hostinfo.RequestTags = append(hostinfo.RequestTags, b.prefs.AdvertiseTags...)
-	b.logf("Start: serverMode=%v; stateKey=%q; tags=%q; routes=%v; url=%v", b.inServerMode, b.stateKey, b.prefs.AdvertiseTags, b.prefs.AdvertiseRoutes, b.prefs.ControlURL)
+	if b.inServerMode || runtime.GOOS == "windows" {
+		b.logf("Start: serverMode=%v", b.inServerMode)
+	}
 	applyPrefsToHostinfo(hostinfo, b.prefs)
 
 	b.notify = opts.Notify
@@ -827,7 +829,7 @@ func (b *LocalBackend) loadStateLocked(key StateKey, prefs *Prefs, legacyPath st
 		// If the frontend (e.g. on Windows) supplied the
 		// optional/legacy machine key then it's used as the
 		// value instead of making up a new one.
-		b.logf("Using frontend prefs")
+		b.logf("using frontend prefs: %s", prefs.Pretty())
 		b.prefs = prefs.Clone()
 		if err := b.initMachineKeyLocked(); err != nil {
 			return fmt.Errorf("initMachineKeyLocked: %w", err)
@@ -839,13 +841,13 @@ func (b *LocalBackend) loadStateLocked(key StateKey, prefs *Prefs, legacyPath st
 	if prefs != nil {
 		// Backend owns the state, but frontend is trying to migrate
 		// state into the backend.
-		b.logf("Importing frontend prefs into backend store")
+		b.logf("importing frontend prefs into backend store; frontend prefs: %s", prefs.Pretty())
 		if err := b.store.WriteState(key, prefs.ToBytes()); err != nil {
 			return fmt.Errorf("store.WriteState: %v", err)
 		}
 	}
 
-	b.logf("Using backend prefs")
+	b.logf("using backend prefs")
 	bs, err := b.store.ReadState(key)
 	if err != nil {
 		if errors.Is(err, ErrStateNotExist) {
@@ -857,11 +859,11 @@ func (b *LocalBackend) loadStateLocked(key StateKey, prefs *Prefs, legacyPath st
 					}
 					b.prefs = NewPrefs()
 				} else {
-					b.logf("Imported state from relaynode for %q", key)
+					b.logf("imported prefs from relaynode for %q: %v", key, b.prefs.Pretty())
 				}
 			} else {
 				b.prefs = NewPrefs()
-				b.logf("Created empty state for %q", key)
+				b.logf("created empty state for %q: %s", key, b.prefs.Pretty())
 			}
 			if err := b.initMachineKeyLocked(); err != nil {
 				return fmt.Errorf("initMachineKeyLocked: %w", err)
@@ -874,6 +876,7 @@ func (b *LocalBackend) loadStateLocked(key StateKey, prefs *Prefs, legacyPath st
 	if err != nil {
 		return fmt.Errorf("PrefsFromBytes: %v", err)
 	}
+	b.logf("backend prefs for %q: %s", key, b.prefs.Pretty())
 	if err := b.initMachineKeyLocked(); err != nil {
 		return fmt.Errorf("initMachineKeyLocked: %w", err)
 	}
diff --git a/ipn/prefs.go b/ipn/prefs.go
index 8c1457e37..f3b63eeed 100644
--- a/ipn/prefs.go
+++ b/ipn/prefs.go
@@ -152,9 +152,15 @@ func (p *Prefs) pretty(goos string) string {
 	if len(p.AdvertiseRoutes) > 0 || p.NoSNAT {
 		fmt.Fprintf(&sb, "snat=%v ", !p.NoSNAT)
 	}
+	if len(p.AdvertiseTags) > 0 {
+		fmt.Fprintf(&sb, "tags=%s ", strings.Join(p.AdvertiseTags, ","))
+	}
 	if goos == "linux" {
 		fmt.Fprintf(&sb, "nf=%v ", p.NetfilterMode)
 	}
+	if p.ControlURL != "" && p.ControlURL != "https://login.tailscale.com" {
+		fmt.Fprintf(&sb, "url=%q ", p.ControlURL)
+	}
 	if p.Persist != nil {
 		sb.WriteString(p.Persist.Pretty())
 	} else {
diff --git a/ipn/prefs_test.go b/ipn/prefs_test.go
index 21e8e7b44..8b95d87a4 100644
--- a/ipn/prefs_test.go
+++ b/ipn/prefs_test.go
@@ -326,6 +326,32 @@ func TestPrefsPretty(t *testing.T) {
 			"windows",
 			"Prefs{ra=false dns=false want=true server=true Persist=nil}",
 		},
+		{
+			Prefs{
+				AllowSingleHosts: true,
+				WantRunning:      true,
+				ControlURL:       "http://localhost:1234",
+				AdvertiseTags:    []string{"tag:foo", "tag:bar"},
+			},
+			"darwin",
+			`Prefs{ra=false dns=false want=true tags=tag:foo,tag:bar url="http://localhost:1234" Persist=nil}`,
+		},
+		{
+			Prefs{
+				Persist: &controlclient.Persist{},
+			},
+			"linux",
+			`Prefs{ra=false mesh=false dns=false want=false routes=[] nf=off Persist{lm=, o=, n= u=""}}`,
+		},
+		{
+			Prefs{
+				Persist: &controlclient.Persist{
+					PrivateNodeKey: wgcfg.PrivateKey{1: 1},
+				},
+			},
+			"linux",
+			`Prefs{ra=false mesh=false dns=false want=false routes=[] nf=off Persist{lm=, o=, n=[B1VKl] u=""}}`,
+		},
 	}
 	for i, tt := range tests {
 		got := tt.p.pretty(tt.os)