diff --git a/src/backend/common/ConfigManager.ts b/src/backend/common/ConfigManager.ts
index 43f37c3112..1d3d56ea7a 100644
--- a/src/backend/common/ConfigManager.ts
+++ b/src/backend/common/ConfigManager.ts
@@ -123,6 +123,20 @@ const migrations: [string, (store: Record<string, unknown>) => unknown][] = [
       return config;
     },
   ],
+  [
+    ">=0.17",
+    (config) => {
+      // 書き出し先のディレクトリが空文字の場合書き出し先固定を無効化する
+      // FIXME: 勝手に書き換えるのは少し不親切なので、ダイアログで書き換えたことを案内する
+      const savingSetting = config.savingSetting as ConfigType["savingSetting"];
+      if (
+        savingSetting.fixedExportEnabled &&
+        savingSetting.fixedExportDir === ""
+      ) {
+        savingSetting.fixedExportEnabled = false;
+      }
+    },
+  ],
 ];
 
 export type Metadata = {
diff --git a/src/components/Dialog/SettingDialog.vue b/src/components/Dialog/SettingDialog.vue
index 2333a86ea8..826386ac89 100644
--- a/src/components/Dialog/SettingDialog.vue
+++ b/src/components/Dialog/SettingDialog.vue
@@ -470,7 +470,7 @@
                       flat
                       color="primary"
                       icon="folder_open"
-                      @click="openFileExplore"
+                      @click="selectFixedExportDir()"
                     >
                       <QTooltip :delay="500" anchor="bottom left">
                         フォルダ選択
@@ -1011,7 +1011,7 @@
 </template>
 
 <script setup lang="ts">
-import { computed, ref } from "vue";
+import { computed, ref, watchEffect } from "vue";
 import FileNamePatternDialog from "./FileNamePatternDialog.vue";
 import { useStore } from "@/store";
 import {
@@ -1289,17 +1289,35 @@ const outputSamplingRate = computed({
   },
 });
 
-const openFileExplore = async () => {
-  const path = await window.backend.showSaveDirectoryDialog({
+const openFileExplore = () => {
+  return window.backend.showSaveDirectoryDialog({
     title: "書き出し先のフォルダを選択",
   });
-  if (path) {
-    store.dispatch("SET_SAVING_SETTING", {
-      data: { ...savingSetting.value, fixedExportDir: path },
-    });
+};
+
+const selectFixedExportDir = async () => {
+  const path = await openFileExplore();
+  if (path != undefined) {
+    handleSavingSettingChange("fixedExportDir", path);
   }
 };
 
+// 書き出し先を固定を有効にしたときに書き出し先が未選択の場合は自動的にダイアログを表示する
+watchEffect(async () => {
+  if (
+    savingSetting.value.fixedExportEnabled &&
+    savingSetting.value.fixedExportDir === ""
+  ) {
+    const path = await openFileExplore();
+    if (path != undefined) {
+      handleSavingSettingChange("fixedExportDir", path);
+    } else {
+      // キャンセルした場合書き出し先の固定を無効化する
+      handleSavingSettingChange("fixedExportEnabled", false);
+    }
+  }
+});
+
 const [splitTextWhenPaste, changeSplitTextWhenPaste] =
   useRootMiscSetting("splitTextWhenPaste");