diff --git a/wgengine/watchdog.go b/wgengine/watchdog.go
index 432d869dd..46260221f 100644
--- a/wgengine/watchdog.go
+++ b/wgengine/watchdog.go
@@ -8,10 +8,12 @@
 package wgengine
 
 import (
+	"fmt"
 	"log"
 	"net/netip"
 	"runtime/pprof"
 	"strings"
+	"sync"
 	"time"
 
 	"tailscale.com/envknob"
@@ -38,21 +40,49 @@ func NewWatchdog(e Engine) Engine {
 		return e
 	}
 	return &watchdogEngine{
-		wrap:    e,
-		logf:    log.Printf,
-		fatalf:  log.Fatalf,
-		maxWait: 45 * time.Second,
+		wrap:     e,
+		logf:     log.Printf,
+		fatalf:   log.Fatalf,
+		maxWait:  45 * time.Second,
+		inFlight: make(map[inFlightKey]time.Time),
 	}
 }
 
+type inFlightKey struct {
+	op  string
+	ctr uint64
+}
+
 type watchdogEngine struct {
 	wrap    Engine
 	logf    func(format string, args ...any)
 	fatalf  func(format string, args ...any)
 	maxWait time.Duration
+
+	// Track the start time(s) of in-flight operations
+	inFlightMu  sync.Mutex
+	inFlight    map[inFlightKey]time.Time
+	inFlightCtr uint64
 }
 
 func (e *watchdogEngine) watchdogErr(name string, fn func() error) error {
+	// Track all in-flight operations so we can print more useful error
+	// messages on watchdog failure
+	e.inFlightMu.Lock()
+	key := inFlightKey{
+		op:  name,
+		ctr: e.inFlightCtr,
+	}
+	e.inFlightCtr++
+	e.inFlight[key] = time.Now()
+	e.inFlightMu.Unlock()
+
+	defer func() {
+		e.inFlightMu.Lock()
+		defer e.inFlightMu.Unlock()
+		delete(e.inFlight, key)
+	}()
+
 	errCh := make(chan error)
 	go func() {
 		errCh <- fn()
@@ -66,6 +96,22 @@ func (e *watchdogEngine) watchdogErr(name string, fn func() error) error {
 		buf := new(strings.Builder)
 		pprof.Lookup("goroutine").WriteTo(buf, 1)
 		e.logf("wgengine watchdog stacks:\n%s", buf.String())
+
+		// Collect the list of in-flight operations for debugging.
+		var (
+			b   []byte
+			now = time.Now()
+		)
+		e.inFlightMu.Lock()
+		for k, t := range e.inFlight {
+			dur := now.Sub(t).Round(time.Millisecond)
+			b = fmt.Appendf(b, "in-flight[%d]: name=%s duration=%v start=%s\n", k.ctr, k.op, dur, t.Format(time.RFC3339Nano))
+		}
+		e.inFlightMu.Unlock()
+
+		// Print everything as a single string to avoid log
+		// rate limits.
+		e.logf("wgengine watchdog in-flight:\n%s", b)
 		e.fatalf("wgengine: watchdog timeout on %s", name)
 		return nil
 	}
diff --git a/wgengine/watchdog_test.go b/wgengine/watchdog_test.go
index 277767837..cf950b866 100644
--- a/wgengine/watchdog_test.go
+++ b/wgengine/watchdog_test.go
@@ -6,6 +6,7 @@ package wgengine
 
 import (
 	"fmt"
+	"regexp"
 	"runtime"
 	"strings"
 	"testing"
@@ -68,9 +69,15 @@ func TestWatchdog(t *testing.T) {
 
 		select {
 		case <-fatalCalled:
-			if !strings.Contains(logBuf.String(), "goroutine profile: total ") {
-				t.Errorf("fatal called without watchdog stacks, got: %s", logBuf.String())
+			logs := logBuf.String()
+			if !strings.Contains(logs, "goroutine profile: total ") {
+				t.Errorf("fatal called without watchdog stacks, got: %s", logs)
 			}
+			re := regexp.MustCompile(`(?m)^\s*in-flight\[\d+\]: name=RequestStatus duration=.* start=.*$`)
+			if !re.MatchString(logs) {
+				t.Errorf("fatal called without in-flight list, got: %s", logs)
+			}
+
 			// expected
 		case <-time.After(3 * time.Second):
 			t.Fatalf("watchdog failed to fire")