diff --git a/src/module/system/check/dialog.ts b/src/module/system/check/dialog.ts
index 6e7952687f5..71342cac7a9 100644
--- a/src/module/system/check/dialog.ts
+++ b/src/module/system/check/dialog.ts
@@ -185,7 +185,7 @@ export class CheckModifiersDialog extends Application {
         // Toggle show dialog default
         const toggle = htmlQuery<HTMLInputElement>(html, "input[data-action=change-show-default]");
         toggle?.addEventListener("click", async () => {
-            await game.user.setFlag("pf2e", "settings.showCheckDialogs", toggle.checked);
+            await game.user.update({ "flags.pf2e.settings.showCheckDialogs": toggle.checked });
         });
     }
 
diff --git a/src/module/system/damage/dialog.ts b/src/module/system/damage/dialog.ts
index 330fe6685e4..795ecf139c3 100644
--- a/src/module/system/damage/dialog.ts
+++ b/src/module/system/damage/dialog.ts
@@ -341,7 +341,7 @@ class DamageModifierDialog extends Application {
         // Toggle show dialog default
         const toggle = htmlQuery<HTMLInputElement>(html, "input[data-action=change-show-default]");
         toggle?.addEventListener("click", async () => {
-            await game.user.setFlag("pf2e", "settings.showDamageDialogs", toggle.checked);
+            await game.user.update({ "flags.pf2e.settings.showDamageDialogs": toggle.checked });
         });
     }