diff --git a/internal/deepprint/deepprint.go b/internal/deepprint/deepprint.go
new file mode 100644
index 000000000..5ff94bafb
--- /dev/null
+++ b/internal/deepprint/deepprint.go
@@ -0,0 +1,89 @@
+// Package deepprint walks a Go value recursively, in a predictable
+// order, without looping, and prints each value out to a given
+// Writer, which is assumed to be a hash.Hash, as this package doesn't
+// format things nicely.
+//
+// This is intended as a lighter version of go-spew, etc. We don't need its
+// features when our writer is just a hash.
+package deepprint
+
+import (
+	"crypto/sha256"
+	"fmt"
+	"io"
+	"reflect"
+)
+
+func Hash(v interface{}) string {
+	h := sha256.New()
+	Print(h, v)
+	return fmt.Sprintf("%x", h.Sum(nil))
+}
+
+func Print(w io.Writer, v interface{}) {
+	print(w, reflect.ValueOf(v), make(map[uintptr]bool))
+}
+
+func print(w io.Writer, v reflect.Value, visited map[uintptr]bool) {
+	if !v.IsValid() {
+		return
+	}
+	switch v.Kind() {
+	default:
+		panic(fmt.Sprintf("unhandled kind %v for type %v", v.Kind(), v.Type()))
+	case reflect.Ptr:
+		ptr := v.Pointer()
+		if visited[ptr] {
+			return
+		}
+		visited[ptr] = true
+		print(w, v.Elem(), visited)
+		return
+	case reflect.Struct:
+		fmt.Fprintf(w, "struct{\n")
+		t := v.Type()
+		for i, n := 0, v.NumField(); i < n; i++ {
+			sf := t.Field(i)
+			fmt.Fprintf(w, "%s: ", sf.Name)
+			print(w, v.Field(i), visited)
+			fmt.Fprintf(w, "\n")
+		}
+	case reflect.Slice, reflect.Array:
+		if v.Type().Elem().Kind() == reflect.Uint8 && v.CanInterface() {
+			fmt.Fprintf(w, "%q", v.Interface())
+			return
+		}
+		fmt.Fprintf(w, "[%d]{\n", v.Len())
+		for i, ln := 0, v.Len(); i < ln; i++ {
+			fmt.Fprintf(w, " [%d]: ", i)
+			print(w, v.Index(i), visited)
+			fmt.Fprintf(w, "\n")
+		}
+		fmt.Fprintf(w, "}\n")
+	case reflect.Interface:
+		print(w, v.Elem(), visited)
+	case reflect.Map:
+		sm := newSortedMap(v)
+		fmt.Fprintf(w, "map[%d]{\n", len(sm.Key))
+		for i, k := range sm.Key {
+			print(w, k, visited)
+			fmt.Fprintf(w, ": ")
+			print(w, sm.Value[i], visited)
+			fmt.Fprintf(w, "\n")
+		}
+		fmt.Fprintf(w, "}\n")
+
+	case reflect.String:
+		fmt.Fprintf(w, "%s", v.String())
+	case reflect.Bool:
+		fmt.Fprintf(w, "%v", v.Bool())
+	case reflect.Int, reflect.Int8, reflect.Int16, reflect.Int32, reflect.Int64:
+		fmt.Fprintf(w, "%v", v.Int())
+	case reflect.Uint, reflect.Uint8, reflect.Uint16, reflect.Uint32, reflect.Uint64, reflect.Uintptr:
+		fmt.Fprintf(w, "%v", v.Uint())
+	case reflect.Float32, reflect.Float64:
+		fmt.Fprintf(w, "%v", v.Float())
+	case reflect.Complex64, reflect.Complex128:
+		fmt.Fprintf(w, "%v", v.Complex())
+	}
+}
diff --git a/internal/deepprint/deepprint_test.go b/internal/deepprint/deepprint_test.go
new file mode 100644
index 000000000..b9c9bcf8b
--- /dev/null
+++ b/internal/deepprint/deepprint_test.go
@@ -0,0 +1,63 @@
+package deepprint
+
+import (
+	"bytes"
+	"testing"
+
+	"github.com/tailscale/wireguard-go/wgcfg"
+	"inet.af/netaddr"
+	"tailscale.com/wgengine/router"
+)
+
+func TestDeepPrint(t *testing.T) {
+	// v contains the types of values we care about for our current callers.
+	// Mostly we're just testing that we don't panic on handled types.
+	v := getVal()
+
+	var buf bytes.Buffer
+	Print(&buf, v)
+	t.Logf("Got: %s", buf.Bytes())
+
+	hash1 := Hash(v)
+	t.Logf("hash: %v", hash1)
+	for i := 0; i < 20; i++ {
+		hash2 := Hash(getVal())
+		if hash1 != hash2 {
+			t.Error("second hash didn't match")
+		}
+	}
+}
+
+func getVal() []interface{} {
+	return []interface{}{
+		&wgcfg.Config{
+			Name:       "foo",
+			Addresses:  []wgcfg.CIDR{{Mask: 5, IP: wgcfg.IP{Addr: [16]byte{3: 3}}}},
+			ListenPort: 5,
+			Peers: []wgcfg.Peer{
+				{
+					Endpoints: []wgcfg.Endpoint{
+						{
+							Host: "foo",
+							Port: 5,
+						},
+					},
+				},
+			},
+		},
+		&router.Config{
+			DNS: []netaddr.IP{netaddr.IPv4(8, 8, 8, 8)},
+		},
+		map[string]string{
+			"key1": "val1",
+			"key2": "val2",
+			"key3": "val3",
+			"key4": "val4",
+			"key5": "val5",
+			"key6": "val6",
+			"key7": "val7",
+			"key8": "val8",
+			"key9": "val9",
+		},
+	}
+}
diff --git a/internal/deepprint/fmtsort.go b/internal/deepprint/fmtsort.go
new file mode 100644
index 000000000..b2a820039
--- /dev/null
+++ b/internal/deepprint/fmtsort.go
@@ -0,0 +1,218 @@
+// Copyright 2018 The Go Authors. All rights reserved.
+// Use of this source code is governed by a BSD-style
+// license that can be found in the LICENSE file.
+
+// This is a copy of Go's src/internal/fmtsort/sort.go
+
+package deepprint
+
+import (
+	"reflect"
+	"sort"
+)
+
+// Note: Throughout this package we avoid calling reflect.Value.Interface as
+// it is not always legal to do so and it's easier to avoid the issue than to face it.
+
+// sortedMap represents a map's keys and values. The keys and values are
+// aligned in index order: Value[i] is the value in the map corresponding to Key[i].
+type sortedMap struct {
+	Key   []reflect.Value
+	Value []reflect.Value
+}
+
+func (o *sortedMap) Len() int           { return len(o.Key) }
+func (o *sortedMap) Less(i, j int) bool { return compare(o.Key[i], o.Key[j]) < 0 }
+func (o *sortedMap) Swap(i, j int) {
+	o.Key[i], o.Key[j] = o.Key[j], o.Key[i]
+	o.Value[i], o.Value[j] = o.Value[j], o.Value[i]
+}
+
+// Sort accepts a map and returns a sortedMap that has the same keys and
+// values but in a stable sorted order according to the keys, modulo issues
+// raised by unorderable key values such as NaNs.
+//
+// The ordering rules are more general than with Go's < operator:
+//
+//  - when applicable, nil compares low
+//  - ints, floats, and strings order by <
+//  - NaN compares less than non-NaN floats
+//  - bool compares false before true
+//  - complex compares real, then imag
+//  - pointers compare by machine address
+//  - channel values compare by machine address
+//  - structs compare each field in turn
+//  - arrays compare each element in turn.
+//    Otherwise identical arrays compare by length.
+//  - interface values compare first by reflect.Type describing the concrete type
+//    and then by concrete value as described in the previous rules.
+//
+func newSortedMap(mapValue reflect.Value) *sortedMap {
+	if mapValue.Type().Kind() != reflect.Map {
+		return nil
+	}
+	// Note: this code is arranged to not panic even in the presence
+	// of a concurrent map update. The runtime is responsible for
+	// yelling loudly if that happens. See issue 33275.
+	n := mapValue.Len()
+	key := make([]reflect.Value, 0, n)
+	value := make([]reflect.Value, 0, n)
+	iter := mapValue.MapRange()
+	for iter.Next() {
+		key = append(key, iter.Key())
+		value = append(value, iter.Value())
+	}
+	sorted := &sortedMap{
+		Key:   key,
+		Value: value,
+	}
+	sort.Stable(sorted)
+	return sorted
+}
+
+// compare compares two values of the same type. It returns -1, 0, 1
+// according to whether a > b (1), a == b (0), or a < b (-1).
+// If the types differ, it returns -1.
+// See the comment on Sort for the comparison rules.
+func compare(aVal, bVal reflect.Value) int {
+	aType, bType := aVal.Type(), bVal.Type()
+	if aType != bType {
+		return -1 // No good answer possible, but don't return 0: they're not equal.
+	}
+	switch aVal.Kind() {
+	case reflect.Int, reflect.Int8, reflect.Int16, reflect.Int32, reflect.Int64:
+		a, b := aVal.Int(), bVal.Int()
+		switch {
+		case a < b:
+			return -1
+		case a > b:
+			return 1
+		default:
+			return 0
+		}
+	case reflect.Uint, reflect.Uint8, reflect.Uint16, reflect.Uint32, reflect.Uint64, reflect.Uintptr:
+		a, b := aVal.Uint(), bVal.Uint()
+		switch {
+		case a < b:
+			return -1
+		case a > b:
+			return 1
+		default:
+			return 0
+		}
+	case reflect.String:
+		a, b := aVal.String(), bVal.String()
+		switch {
+		case a < b:
+			return -1
+		case a > b:
+			return 1
+		default:
+			return 0
+		}
+	case reflect.Float32, reflect.Float64:
+		return floatCompare(aVal.Float(), bVal.Float())
+	case reflect.Complex64, reflect.Complex128:
+		a, b := aVal.Complex(), bVal.Complex()
+		if c := floatCompare(real(a), real(b)); c != 0 {
+			return c
+		}
+		return floatCompare(imag(a), imag(b))
+	case reflect.Bool:
+		a, b := aVal.Bool(), bVal.Bool()
+		switch {
+		case a == b:
+			return 0
+		case a:
+			return 1
+		default:
+			return -1
+		}
+	case reflect.Ptr:
+		a, b := aVal.Pointer(), bVal.Pointer()
+		switch {
+		case a < b:
+			return -1
+		case a > b:
+			return 1
+		default:
+			return 0
+		}
+	case reflect.Chan:
+		if c, ok := nilCompare(aVal, bVal); ok {
+			return c
+		}
+		ap, bp := aVal.Pointer(), bVal.Pointer()
+		switch {
+		case ap < bp:
+			return -1
+		case ap > bp:
+			return 1
+		default:
+			return 0
+		}
+	case reflect.Struct:
+		for i := 0; i < aVal.NumField(); i++ {
+			if c := compare(aVal.Field(i), bVal.Field(i)); c != 0 {
+				return c
+			}
+		}
+		return 0
+	case reflect.Array:
+		for i := 0; i < aVal.Len(); i++ {
+			if c := compare(aVal.Index(i), bVal.Index(i)); c != 0 {
+				return c
+			}
+		}
+		return 0
+	case reflect.Interface:
+		if c, ok := nilCompare(aVal, bVal); ok {
+			return c
+		}
+		c := compare(reflect.ValueOf(aVal.Elem().Type()), reflect.ValueOf(bVal.Elem().Type()))
+		if c != 0 {
+			return c
+		}
+		return compare(aVal.Elem(), bVal.Elem())
+	default:
+		// Certain types cannot appear as keys (maps, funcs, slices), but be explicit.
+		panic("bad type in compare: " + aType.String())
+	}
+}
+
+// nilCompare checks whether either value is nil. If not, the boolean is false.
+// If either value is nil, the boolean is true and the integer is the comparison
+// value. The comparison is defined to be 0 if both are nil, otherwise the one
+// nil value compares low. Both arguments must represent a chan, func,
+// interface, map, pointer, or slice.
+func nilCompare(aVal, bVal reflect.Value) (int, bool) {
+	if aVal.IsNil() {
+		if bVal.IsNil() {
+			return 0, true
+		}
+		return -1, true
+	}
+	if bVal.IsNil() {
+		return 1, true
+	}
+	return 0, false
+}
+
+// floatCompare compares two floating-point values. NaNs compare low.
+func floatCompare(a, b float64) int {
+	switch {
+	case isNaN(a):
+		return -1 // No good answer if b is a NaN so don't bother checking.
+	case isNaN(b):
+		return 1
+	case a < b:
+		return -1
+	case a > b:
+		return 1
+	}
+	return 0
+}
+
+func isNaN(a float64) bool {
+	return a != a
+}
diff --git a/wgengine/userspace.go b/wgengine/userspace.go
index d75647cd4..6859904e6 100644
--- a/wgengine/userspace.go
+++ b/wgengine/userspace.go
@@ -26,6 +26,7 @@
 	"github.com/tailscale/wireguard-go/wgcfg"
 	"go4.org/mem"
 	"tailscale.com/control/controlclient"
+	"tailscale.com/internal/deepprint"
 	"tailscale.com/ipn/ipnstate"
 	"tailscale.com/net/interfaces"
 	"tailscale.com/tailcfg"
@@ -488,17 +489,13 @@ func (e *userspaceEngine) pinger(peerKey wgcfg.Key, ips []wgcfg.IP) {
 	p.run(ctx, peerKey, ips, srcIP)
 }
 
-// configSignatures returns string signatures for the given configs.
-// The exact strings should be considered opaque; the only guarantee is that
-// if cfg or routerCfg change, so do their signatures.
-func configSignatures(cfg *wgcfg.Config, routerCfg *router.Config) (configSig, engineSig string, err error) {
-	// TODO(apenwarr): get rid of uapi stuff for in-process comms
-	uapi, err := cfg.ToUAPI()
-	if err != nil {
-		return "", "", err
+func updateSig(last *string, v interface{}) (changed bool) {
+	sig := deepprint.Hash(v)
+	if *last != sig {
+		*last = sig
+		return true
 	}
-
-	return uapi, fmt.Sprintf("%v", routerCfg), nil
+	return false
 }
 
 func (e *userspaceEngine) Reconfig(cfg *wgcfg.Config, routerCfg *router.Config) error {
@@ -529,17 +526,11 @@ func (e *userspaceEngine) Reconfig(cfg *wgcfg.Config, routerCfg *router.Config)
 	}
 	e.mu.Unlock()
 
-	ec, rc, err := configSignatures(cfg, routerCfg)
-	if err != nil {
-		return err
-	}
-	engineChanged := ec != e.lastEngineSig
-	routerChanged := rc != e.lastRouterSig
+	engineChanged := updateSig(&e.lastEngineSig, cfg)
+	routerChanged := updateSig(&e.lastRouterSig, routerCfg)
 	if !engineChanged && !routerChanged {
 		return ErrNoChanges
 	}
-	e.lastEngineSig = ec
-	e.lastRouterSig = rc
 	e.lastCfg = cfg.Copy()
 
 	if engineChanged {