diff --git a/app/javascript/mastodon/actions/bookmark_categories.js b/app/javascript/mastodon/actions/bookmark_categories.js
index 9fa2ffc9f2..b6f82b49c8 100644
--- a/app/javascript/mastodon/actions/bookmark_categories.js
+++ b/app/javascript/mastodon/actions/bookmark_categories.js
@@ -1,6 +1,10 @@
+import { bookmarkCategoryNeeded } from 'mastodon/initial_state';
+import { makeGetStatus } from 'mastodon/selectors';
+
 import api, { getLinks } from '../api';
 
 import { importFetchedStatuses } from './importer';
+import { unbookmark } from './interactions';
 
 export const BOOKMARK_CATEGORY_FETCH_REQUEST = 'BOOKMARK_CATEGORY_FETCH_REQUEST';
 export const BOOKMARK_CATEGORY_FETCH_SUCCESS = 'BOOKMARK_CATEGORY_FETCH_SUCCESS';
@@ -330,7 +334,17 @@ export const addToBookmarkCategoryAdder = bookmarkCategoryId => (dispatch, getSt
 };
 
 export const removeFromBookmarkCategoryAdder = bookmarkCategoryId => (dispatch, getState) => {
-  dispatch(removeFromBookmarkCategory(bookmarkCategoryId, getState().getIn(['bookmarkCategoryAdder', 'statusId'])));
+  if (bookmarkCategoryNeeded) {
+    const categories = getState().getIn(['bookmarkCategoryAdder', 'bookmarkCategories', 'items']);
+    if (categories && categories.count() <= 1) {
+      const status = makeGetStatus()(getState(), { id: getState().getIn(['bookmarkCategoryAdder', 'statusId']) });
+      dispatch(unbookmark(status));
+    } else {
+      dispatch(removeFromBookmarkCategory(bookmarkCategoryId, getState().getIn(['bookmarkCategoryAdder', 'statusId'])));
+    }
+  } else {
+    dispatch(removeFromBookmarkCategory(bookmarkCategoryId, getState().getIn(['bookmarkCategoryAdder', 'statusId'])));
+  }
 };
 
 export function expandBookmarkCategoryStatuses(bookmarkCategoryId) {
diff --git a/app/javascript/mastodon/components/status_action_bar.jsx b/app/javascript/mastodon/components/status_action_bar.jsx
index cd647cb379..7c6f3d1bd3 100644
--- a/app/javascript/mastodon/components/status_action_bar.jsx
+++ b/app/javascript/mastodon/components/status_action_bar.jsx
@@ -12,7 +12,7 @@ import { PERMISSION_MANAGE_USERS, PERMISSION_MANAGE_FEDERATION } from 'mastodon/
 
 import DropdownMenuContainer from '../containers/dropdown_menu_container';
 import EmojiPickerDropdown from '../features/compose/containers/emoji_picker_dropdown_container';
-import { me } from '../initial_state';
+import { bookmarkCategoryNeeded, me } from '../initial_state';
 
 import { IconButton } from './icon_button';
 
@@ -166,13 +166,21 @@ class StatusActionBar extends ImmutablePureComponent {
   };
 
   handleBookmarkClick = () => {
-    this.props.onBookmark(this.props.status);
+    if (bookmarkCategoryNeeded) {
+      this.handleBookmarkCategoryAdderClick();
+    } else {
+      this.props.onBookmark(this.props.status);
+    }
   };
 
   handleBookmarkCategoryAdderClick = () => {
     this.props.onBookmarkCategoryAdder(this.props.status);
   };
 
+  handleBookmarkClickOriginal = () => {
+    this.props.onBookmark(this.props.status);
+  };
+
   handleDeleteClick = () => {
     this.props.onDelete(this.props.status, this.context.router.history);
   };
@@ -305,7 +313,7 @@ class StatusActionBar extends ImmutablePureComponent {
         menu.push({ text: intl.formatMessage(messages.reference), action: this.handleReference });
       }
 
-      menu.push({ text: intl.formatMessage(status.get('bookmarked') ? messages.removeBookmark : messages.bookmark), action: this.handleBookmarkClick });
+      menu.push({ text: intl.formatMessage(status.get('bookmarked') ? messages.removeBookmark : messages.bookmark), action: this.handleBookmarkClickOriginal });
       menu.push({ text: intl.formatMessage(messages.bookmarkCategory), action: this.handleBookmarkCategoryAdderClick });
 
       if (writtenByMe && pinnableStatus) {
diff --git a/app/javascript/mastodon/features/status/components/action_bar.jsx b/app/javascript/mastodon/features/status/components/action_bar.jsx
index 7831b02922..c5980461e9 100644
--- a/app/javascript/mastodon/features/status/components/action_bar.jsx
+++ b/app/javascript/mastodon/features/status/components/action_bar.jsx
@@ -12,7 +12,7 @@ import { PERMISSION_MANAGE_USERS, PERMISSION_MANAGE_FEDERATION } from 'mastodon/
 
 import { IconButton } from '../../../components/icon_button';
 import DropdownMenuContainer from '../../../containers/dropdown_menu_container';
-import { me } from '../../../initial_state';
+import { bookmarkCategoryNeeded, me } from '../../../initial_state';
 import EmojiPickerDropdown from '../../compose/containers/emoji_picker_dropdown_container';
 
 const messages = defineMessages({
@@ -107,7 +107,11 @@ class ActionBar extends PureComponent {
   };
 
   handleBookmarkClick = (e) => {
-    this.props.onBookmark(this.props.status, e);
+    if (bookmarkCategoryNeeded) {
+      this.props.onBookmarkCategoryAdder(this.props.status);
+    } else {
+      this.props.onBookmark(this.props.status, e);
+    }
   };
 
   handleDeleteClick = () => {
diff --git a/app/javascript/mastodon/features/status/index.jsx b/app/javascript/mastodon/features/status/index.jsx
index 8d88308923..cf4c2bd6ce 100644
--- a/app/javascript/mastodon/features/status/index.jsx
+++ b/app/javascript/mastodon/features/status/index.jsx
@@ -63,7 +63,7 @@ import {
 import ColumnHeader from '../../components/column_header';
 import { textForScreenReader, defaultMediaVisibility } from '../../components/status';
 import StatusContainer from '../../containers/status_container';
-import { boostModal, deleteModal } from '../../initial_state';
+import { bookmarkCategoryNeeded, boostModal, deleteModal } from '../../initial_state';
 import { makeGetStatus, makeGetPictureInPicture } from '../../selectors';
 import Column from '../ui/components/column';
 import { attachFullscreenListener, detachFullscreenListener, isFullscreen } from '../ui/util/fullscreen';
@@ -367,6 +367,11 @@ class Status extends ImmutablePureComponent {
   };
 
   handleBookmarkClick = (status) => {
+    if (bookmarkCategoryNeeded) {
+      this.handleBookmarkCategoryAdderClick(status);
+      return;
+    }
+    
     if (status.get('bookmarked')) {
       this.props.dispatch(unbookmark(status));
     } else {
diff --git a/app/javascript/mastodon/initial_state.js b/app/javascript/mastodon/initial_state.js
index c171c56d99..fd8e514f98 100644
--- a/app/javascript/mastodon/initial_state.js
+++ b/app/javascript/mastodon/initial_state.js
@@ -50,6 +50,7 @@
  * @property {boolean} auto_play_gif
  * @property {boolean} activity_api_enabled
  * @property {string} admin
+ * @property {boolean} bookmark_category_needed
  * @property {boolean=} boost_modal
  * @property {boolean=} delete_modal
  * @property {boolean=} disable_swiping
@@ -113,6 +114,7 @@ const getMeta = (prop) => initialState?.meta && initialState.meta[prop];
 
 export const activityApiEnabled = getMeta('activity_api_enabled');
 export const autoPlayGif = getMeta('auto_play_gif');
+export const bookmarkCategoryNeeded = getMeta('bookmark_category_needed');
 export const boostModal = getMeta('boost_modal');
 export const deleteModal = getMeta('delete_modal');
 export const disableSwiping = getMeta('disable_swiping');
diff --git a/app/javascript/mastodon/reducers/bookmark_categories.js b/app/javascript/mastodon/reducers/bookmark_categories.js
index 561dea1824..86df1e6565 100644
--- a/app/javascript/mastodon/reducers/bookmark_categories.js
+++ b/app/javascript/mastodon/reducers/bookmark_categories.js
@@ -20,7 +20,14 @@ import {
 
 const initialState = ImmutableMap();
 
-const normalizeBookmarkCategory = (state, category) => state.set(category.id, fromJS(category));
+const normalizeBookmarkCategory = (state, category) => {
+  const old = state.get(category.id);
+  state = state.set(category.id, fromJS(category));
+  if (old) {
+    state = state.setIn([category.id, 'items'], old.get('items'));
+  }
+  return state;
+};
 
 const normalizeBookmarkCategories = (state, bookmarkCategories) => {
   bookmarkCategories.forEach(bookmarkCategory => {
diff --git a/app/javascript/mastodon/reducers/bookmark_category_adder.js b/app/javascript/mastodon/reducers/bookmark_category_adder.js
index 05148d3336..c47ecb3b40 100644
--- a/app/javascript/mastodon/reducers/bookmark_category_adder.js
+++ b/app/javascript/mastodon/reducers/bookmark_category_adder.js
@@ -9,6 +9,9 @@ import {
   BOOKMARK_CATEGORY_EDITOR_ADD_SUCCESS,
   BOOKMARK_CATEGORY_EDITOR_REMOVE_SUCCESS,
 } from '../actions/bookmark_categories';
+import {
+  UNBOOKMARK_SUCCESS,
+} from '../actions/interactions';
 
 const initialState = ImmutableMap({
   statusId: null,
@@ -42,6 +45,8 @@ export default function bookmarkCategoryAdderReducer(state = initialState, actio
     return state.updateIn(['bookmarkCategories', 'items'], bookmarkCategory => bookmarkCategory.unshift(action.bookmarkCategoryId));
   case BOOKMARK_CATEGORY_EDITOR_REMOVE_SUCCESS:
     return state.updateIn(['bookmarkCategories', 'items'], bookmarkCategory => bookmarkCategory.filterNot(item => item === action.bookmarkCategoryId));
+  case UNBOOKMARK_SUCCESS:
+    return action.status.get('id') === state.get('statusId') ? state.setIn(['bookmarkCategories', 'items'], ImmutableList()) : state;
   default:
     return state;
   }
diff --git a/app/models/concerns/has_user_settings.rb b/app/models/concerns/has_user_settings.rb
index b602081988..dfb37c3517 100644
--- a/app/models/concerns/has_user_settings.rb
+++ b/app/models/concerns/has_user_settings.rb
@@ -31,6 +31,10 @@ module HasUserSettings
     settings['web.enable_login_privacy']
   end
 
+  def setting_bookmark_category_needed
+    settings['web.bookmark_category_needed']
+  end
+
   def setting_hide_recent_emojis
     settings['web.hide_recent_emojis']
   end
diff --git a/app/models/user_settings.rb b/app/models/user_settings.rb
index 40c146f596..32bfa563cd 100644
--- a/app/models/user_settings.rb
+++ b/app/models/user_settings.rb
@@ -42,6 +42,7 @@ class UserSettings
     setting :use_blurhash, default: true
     setting :use_pending_items, default: false
     setting :use_system_font, default: false
+    setting :bookmark_category_needed, default: false
     setting :disable_swiping, default: false
     setting :delete_modal, default: true
     setting :enable_login_privacy, default: false
diff --git a/app/serializers/initial_state_serializer.rb b/app/serializers/initial_state_serializer.rb
index 06e1bf2393..063c17e57d 100644
--- a/app/serializers/initial_state_serializer.rb
+++ b/app/serializers/initial_state_serializer.rb
@@ -52,6 +52,7 @@ class InitialStateSerializer < ActiveModel::Serializer
       store[:use_blurhash]      = object.current_account.user.setting_use_blurhash
       store[:use_pending_items] = object.current_account.user.setting_use_pending_items
       store[:show_trends]       = Setting.trends && object.current_account.user.setting_trends
+      store[:bookmark_category_needed] = object.current_account.user.setting_bookmark_category_needed
     else
       store[:auto_play_gif] = Setting.auto_play_gif
       store[:display_media] = Setting.display_media
diff --git a/app/views/settings/preferences/appearance/show.html.haml b/app/views/settings/preferences/appearance/show.html.haml
index bc16bf9da1..c01d9a8311 100644
--- a/app/views/settings/preferences/appearance/show.html.haml
+++ b/app/views/settings/preferences/appearance/show.html.haml
@@ -40,6 +40,9 @@
     .fields-group
       = ff.input :'web.hide_recent_emojis', wrapper: :with_label, kmyblue: true, label: I18n.t('simple_form.labels.defaults.setting_hide_recent_emojis'), hint: false
 
+    .fields-group
+      = ff.input :'web.bookmark_category_needed', wrapper: :with_label, kmyblue: true, label: I18n.t('simple_form.labels.defaults.setting_bookmark_category_needed'), hint: I18n.t('simple_form.hints.defaults.setting_bookmark_category_needed')
+
     %h4= t 'appearance.discovery'
 
     .fields-group
diff --git a/config/locales/simple_form.en.yml b/config/locales/simple_form.en.yml
index 148e8a109f..88d9ded9d5 100644
--- a/config/locales/simple_form.en.yml
+++ b/config/locales/simple_form.en.yml
@@ -61,6 +61,7 @@ en:
         scopes: Which APIs the application will be allowed to access. If you select a top-level scope, you don't need to select individual ones.
         setting_aggregate_reblogs: Do not show new boosts for posts that have been recently boosted (only affects newly-received boosts)
         setting_always_send_emails: Normally e-mail notifications won't be sent when you are actively using Mastodon
+        setting_bookmark_category_needed: When removing from all category, unbookmarked automatically
         setting_default_sensitive: Sensitive media is hidden by default and can be revealed with a click
         setting_display_media_default: Hide media marked as sensitive
         setting_display_media_hide_all: Always hide media
@@ -218,6 +219,7 @@ en:
         setting_always_send_emails: Always send e-mail notifications
         setting_auto_play_gif: Auto-play animated GIFs
         setting_bio_markdown: Enable profile markdown
+        setting_bookmark_category_needed: Category selection needed when registering bookmark on web
         setting_boost_modal: Show confirmation dialog before boosting
         setting_default_language: Posting language
         setting_default_privacy: Posting privacy
diff --git a/config/locales/simple_form.ja.yml b/config/locales/simple_form.ja.yml
index 4617d6c849..05e27f62a3 100644
--- a/config/locales/simple_form.ja.yml
+++ b/config/locales/simple_form.ja.yml
@@ -60,6 +60,7 @@ ja:
         setting_send_without_domain_blocks: 管理人が同人コンテンツの配送にふさわしくないと判断したサーバーに、制限に関係なく全ての投稿を配送します。ただし何が起きても自己責任になります
         setting_aggregate_reblogs: 最近ブーストされた投稿が新たにブーストされても表示しません (設定後受信したものにのみ影響)
         setting_always_send_emails: 通常、Mastodon からメール通知は行われません。
+        setting_bookmark_category_needed: すべてのカテゴリから削除したとき、ブックマークが自動で外れるようになります
         setting_boost_modal: ブーストの公開範囲が指定できるようになります
         setting_default_sensitive: 閲覧注意状態のメディアはデフォルトでは内容が伏せられ、クリックして初めて閲覧できるようになります
         setting_disallow_unlisted_public_searchability: この設定を有効にすると、未収載投稿と検索範囲「全て」は両立できず不特定多数からの検索が不可になります。Fedibirdと同じ挙動になります
@@ -227,6 +228,7 @@ ja:
         setting_always_send_emails: 常にメール通知を送信する
         setting_auto_play_gif: アニメーションGIFを自動再生する
         setting_bio_markdown: プロフィールのMarkdownを有効にする
+        setting_bookmark_category_needed: Webでブックマーク時にカテゴリの選択を必須にする
         setting_boost_modal: ブーストする前に確認ダイアログを表示する
         setting_default_language: 投稿する言語
         setting_default_privacy: 投稿の公開範囲