diff --git a/locales/en-US.yml b/locales/en-US.yml
index f44c3d1842..a70eb2406f 100644
--- a/locales/en-US.yml
+++ b/locales/en-US.yml
@@ -1227,6 +1227,8 @@ publishTimelinesDescription: "If enabled, the Local and Global timelines will be
   on {url} even when signed out."
 noAltTextWarning: "Some attached file(s) have no description. Did you forget to write?"
 showNoAltTextWarning: "Show a warning if you attempt to post files without a description"
+showAddFileDescriptionAtFirstPost: "Automatically open a form to write a description when you
+  attempt to post files without a description"
 
 _emojiModPerm:
   unauthorized: "None"
diff --git a/locales/zh-CN.yml b/locales/zh-CN.yml
index c8579a4c1a..1be460f7f0 100644
--- a/locales/zh-CN.yml
+++ b/locales/zh-CN.yml
@@ -2054,6 +2054,7 @@ searchRangeDescription: "如果您要过滤时间段，请按以下格式输入
 messagingUnencryptedInfo: "Firefish 上的聊天没有经过端到端加密，请不要在聊天中分享您的敏感信息。"
 noAltTextWarning: 有些附件没有描述。您是否忘记写描述了？
 showNoAltTextWarning: 当您尝试发布没有描述的帖子附件时显示警告
+showAddFileDescriptionAtFirstPost: 当您首次尝试发布没有描述的帖子附件时自动弹出添加描述页面
 autocorrectNoteLanguage: 当帖子语言不符合自动检测的结果的时候显示警告
 incorrectLanguageWarning: "看上去您帖子使用的语言是{detected}，但您选择的语言是{current}。\n要改为以{detected}发帖吗？"
 noteEditHistory: "帖子编辑历史"
diff --git a/packages/client/src/components/MkPostForm.vue b/packages/client/src/components/MkPostForm.vue
index 582da6c6d4..5850fdf498 100644
--- a/packages/client/src/components/MkPostForm.vue
+++ b/packages/client/src/components/MkPostForm.vue
@@ -318,6 +318,8 @@ import XNoteSimple from "@/components/MkNoteSimple.vue";
 import XNotePreview from "@/components/MkNotePreview.vue";
 import XPostFormAttaches from "@/components/MkPostFormAttaches.vue";
 import XPollEditor from "@/components/MkPollEditor.vue";
+import XCheatSheet from "@/components/MkCheatSheetDialog.vue";
+import XMediaCaption from "@/components/MkMediaCaption.vue";
 import { host, url } from "@/config";
 import { erase, unique } from "@/scripts/array";
 import { extractMentions } from "@/scripts/extract-mentions";
@@ -334,7 +336,6 @@ import { getAccounts, openAccountMenu as openAccountMenu_ } from "@/account";
 import { me } from "@/me";
 import { uploadFile } from "@/scripts/upload";
 import { deepClone } from "@/scripts/clone";
-import XCheatSheet from "@/components/MkCheatSheetDialog.vue";
 import preprocess from "@/scripts/preprocess";
 import { vibrate } from "@/scripts/vibrate";
 import { langmap } from "@/scripts/langmap";
@@ -508,6 +509,8 @@ const hashtags = computed(
 	defaultStore.makeGetterSetter("postFormHashtags"),
 ) as Ref<string | null>;
 
+let isFirstPostAttempt = true;
+
 watch(text, () => {
 	checkMissingMention();
 });
@@ -1022,6 +1025,46 @@ function deleteDraft() {
 	localStorage.setItem("drafts", JSON.stringify(draftData));
 }
 
+/**
+ * @returns whether the file is described
+ */
+function openFileDescriptionWindow(file: entities.DriveFile) {
+	return new Promise<boolean>((resolve, reject) => {
+		os.popup(
+			XMediaCaption,
+			{
+				title: i18n.ts.describeFile,
+				input: {
+					placeholder: i18n.ts.inputNewDescription,
+					default: file.comment !== null ? file.comment : "",
+				},
+				image: file,
+			},
+			{
+				done: (result) => {
+					if (!result || result.canceled) {
+						resolve(false);
+						return;
+					}
+					const comment = result.result?.length === 0 ? null : result.result;
+					os.api("drive/files/update", {
+						fileId: file.id,
+						comment,
+					})
+						.then(() => {
+							resolve(true);
+							file.comment = comment ?? null;
+						})
+						.catch((err: unknown) => {
+							reject(err);
+						});
+				},
+			},
+			"closed",
+		);
+	});
+}
+
 async function post() {
 	// For text that is too short, the false positive rate may be too high, so we don't show alarm.
 	if (defaultStore.state.autocorrectNoteLanguage && text.value.length > 10) {
@@ -1056,6 +1099,24 @@ async function post() {
 		}
 	}
 
+	if (
+		defaultStore.state.showAddFileDescriptionAtFirstPost &&
+		files.value.some((f) => f.comment == null || f.comment.length === 0)
+	) {
+		if (isFirstPostAttempt) {
+			for (const file of files.value) {
+				if (file.comment == null || file.comment.length === 0) {
+					const described = await openFileDescriptionWindow(file);
+					if (!described) {
+						return;
+					}
+				}
+			}
+			isFirstPostAttempt = false;
+			return;
+		}
+	}
+
 	if (
 		defaultStore.state.showNoAltTextWarning &&
 		files.value.some((f) => f.comment == null || f.comment.length === 0)
@@ -1064,12 +1125,22 @@ async function post() {
 		const { canceled } = await os.confirm({
 			type: "warning",
 			text: i18n.ts.noAltTextWarning,
-			okText: i18n.ts.goBack,
+			okText: i18n.ts.describeFile,
 			cancelText: i18n.ts.toPost,
 			isPlaintext: true,
 		});
 
-		if (!canceled) return;
+		if (!canceled) {
+			for (const file of files.value) {
+				if (file.comment == null || file.comment.length === 0) {
+					const described = await openFileDescriptionWindow(file);
+					if (!described) {
+						return;
+					}
+				}
+			}
+			return;
+		}
 	}
 
 	const processedText = preprocess(text.value);
diff --git a/packages/client/src/pages/settings/general.vue b/packages/client/src/pages/settings/general.vue
index 15e1172169..bc21efc132 100644
--- a/packages/client/src/pages/settings/general.vue
+++ b/packages/client/src/pages/settings/general.vue
@@ -124,6 +124,9 @@
 			<FormSwitch v-model="showNoAltTextWarning" class="_formBlock">{{
 				i18n.ts.showNoAltTextWarning
 			}}</FormSwitch>
+			<FormSwitch v-model="showAddFileDescriptionAtFirstPost" class="_formBlock">{{
+				i18n.ts.showAddFileDescriptionAtFirstPost
+			}}</FormSwitch>
 			<FormSwitch v-model="autocorrectNoteLanguage" class="_formBlock">{{
 				i18n.ts.autocorrectNoteLanguage
 			}}</FormSwitch>
@@ -533,6 +536,9 @@ const pullToRefreshThreshold = computed(
 const showNoAltTextWarning = computed(
 	defaultStore.makeGetterSetter("showNoAltTextWarning"),
 );
+const showAddFileDescriptionAtFirstPost = computed(
+	defaultStore.makeGetterSetter("showAddFileDescriptionAtFirstPost"),
+);
 const autocorrectNoteLanguage = computed(
 	defaultStore.makeGetterSetter("autocorrectNoteLanguage"),
 );
diff --git a/packages/client/src/pages/settings/preferences-backups.vue b/packages/client/src/pages/settings/preferences-backups.vue
index 73e098c4ea..15ff5de402 100644
--- a/packages/client/src/pages/settings/preferences-backups.vue
+++ b/packages/client/src/pages/settings/preferences-backups.vue
@@ -125,6 +125,7 @@ const defaultStoreSaveKeys: (keyof (typeof defaultStore)["state"])[] = [
 	"enablePullToRefresh",
 	"pullToRefreshThreshold",
 	"showNoAltTextWarning",
+	"showAddFileDescriptionAtFirstPost",
 	"autocorrectNoteLanguage",
 ];
 const coldDeviceStorageSaveKeys: (keyof typeof ColdDeviceStorage.default)[] = [
diff --git a/packages/client/src/store.ts b/packages/client/src/store.ts
index 29393123c0..0adc4e76db 100644
--- a/packages/client/src/store.ts
+++ b/packages/client/src/store.ts
@@ -442,6 +442,10 @@ export const defaultStore = markRaw(
 			where: "account",
 			default: true,
 		},
+		showAddFileDescriptionAtFirstPost: {
+			where: "account",
+			default: false,
+		},
 		autocorrectNoteLanguage: {
 			where: "account",
 			default: true,