diff --git a/ee/debug/checkups/checkups.go b/ee/debug/checkups/checkups.go
index 71c3886c0..9979bc93d 100644
--- a/ee/debug/checkups/checkups.go
+++ b/ee/debug/checkups/checkups.go
@@ -233,7 +233,7 @@ func RunDoctor(ctx context.Context, k types.Knapsack, w io.Writer) {
 	warningCheckups := []string{}
 
 	for _, c := range checkupsFor(k, doctorSupported) {
-		ctx, cancel := context.WithTimeout(context.TODO(), 10*time.Second)
+		ctx, cancel := context.WithTimeout(context.TODO(), 20*time.Second)
 		defer cancel()
 
 		doctorCheckup(ctx, c, w)
diff --git a/ee/debug/checkups/osquery.go b/ee/debug/checkups/osquery.go
index a00fea65a..c7db0c879 100644
--- a/ee/debug/checkups/osquery.go
+++ b/ee/debug/checkups/osquery.go
@@ -77,7 +77,7 @@ func (o *osqueryCheckup) interactive(ctx context.Context) error {
 	out, err := cmd.CombinedOutput()
 	o.executionTimes[cmd.String()] = fmt.Sprintf("%d ms", time.Now().UnixMilli()-startTime)
 	if err != nil {
-		return fmt.Errorf("running %s interactive: err %w, output %s", launcherPath, err, string(out))
+		return fmt.Errorf("running %s interactive: err %w, output %s; ctx err: %+v", launcherPath, err, string(out), cmdCtx.Err())
 	}
 
 	return nil