Decouple bookmark folders from library folders, add move-aware save + submenu pickers everywhere

Bookmark folders and library folders used to share identity through
_db.get_folders() — the same string was both a row in favorite_folders
and a directory under saved_dir. They look like one concept but they're
two stores, and the cross-bleed produced a duplicate-on-move bug and
made "Save to Library" silently re-file the bookmark too.

Now they're independent name spaces:
  - library_folders() in core.config reads filesystem subdirs of
    saved_dir; the source of truth for every Save-to-Library menu
  - find_library_files(post_id) walks the library shallowly and is the
    new "is this saved?" / delete primitive
  - bookmark folders stay DB-backed and are only used for bookmark
    organization (filter combo, Move to Folder)
  - delete_from_library no longer takes a folder hint — walks every
    library folder by post id and deletes every match (also cleans up
    duplicates left by the old save-to-folder copy bug)
  - _save_to_library is move-aware: if the post is already in another
    library folder, atomic Path.rename() into the destination instead
    of re-copying from cache (the duplicate bug fix)
  - bookmark "Move to Folder" no longer also calls _copy_to_library;
    Save to Library no longer also calls move_bookmark_to_folder
  - settings export/import unchanged; favorite_folders table preserved
    so no migration

UI additions:
  - Library tab right-click: Move to Folder submenu (single + multi),
    uses Path.rename for atomic moves
  - Bookmarks tab: − Folder button next to + Folder for deleting the
    selected bookmark folder (DB-only, library filesystem untouched)
  - Browse tab right-click: "Bookmark" replaced with "Bookmark as"
    submenu when not yet bookmarked (Unfiled / folders / + New); flat
    "Remove Bookmark" when already bookmarked
  - Embedded preview Bookmark button: same submenu shape via new
    bookmark_to_folder signal + set_bookmark_folders_callback
  - Popout Bookmark button: same shape — works in both browse and
    bookmarks tab modes
  - Popout Save button: Save-to-Library submenu via new save_to_folder
    + unsave_requested signals (drops save_toggle_requested + the
    _save_toggle_from_popout indirection)
  - Popout in library mode: Save button stays visible as Unsave; the
    rest of the toolbar (Bookmark / BL Tag / BL Post) is hidden

State plumbing:
  - _update_fullscreen_state mirrors the embedded preview's
    _is_bookmarked / _is_saved instead of re-querying DB+filesystem,
    eliminating the popout state drift during async bookmark adds
  - Library tab Save button reads "Unsave" the entire time; Save
    button width bumped 60→75 so the label doesn't clip on tight themes
  - Embedded preview tracks _is_bookmarked alongside _is_saved so the
    new Bookmark-as submenu can flip to a flat unbookmark when active

Naming:
  - "Unsorted" renamed to "Unfiled" everywhere user-facing — library
    Unfiled and bookmarks Unfiled now share one label. Internal
    comparison in library.py:_scan_files updated to match the combo.

booru_viewer/core/cache.py

@@ -435,16 +435,27 @@ def is_cached(url: str, dest_dir: Path | None = None) -> bool:
 
 
 def delete_from_library(post_id: int, folder: str | None = None) -> bool:
-    """Delete a saved image from the library. Returns True if a file was deleted."""
+    """Delete every saved copy of `post_id` from the library.
-    from .config import saved_dir, saved_folder_dir
+
-    search_dir = saved_folder_dir(folder) if folder else saved_dir()
+    Returns True if at least one file was deleted.
-    from .config import MEDIA_EXTENSIONS
+
-    for ext in MEDIA_EXTENSIONS:
+    The `folder` argument is kept for back-compat with existing call sites
-        path = search_dir / f"{post_id}{ext}"
+    but is now ignored — we walk every library folder by post id and delete
-        if path.exists():
+    all matches. This is what makes the "bookmark folder ≠ library folder"
+    separation work: a bookmark no longer needs to know which folder its
+    library file lives in. It also cleans up duplicates left by the old
+    pre-fix "save to folder = copy" bug in a single Unsave action.
+    """
+    from .config import find_library_files
+    matches = find_library_files(post_id)
+    deleted = False
+    for path in matches:
+        try:
             path.unlink()
-            return True
+            deleted = True
-    return False
+        except OSError:
+            pass
+    return deleted
 
 
 def cache_size_bytes(include_thumbnails: bool = True) -> int:

booru_viewer/core/config.py

@@ -109,6 +109,46 @@ def db_path() -> Path:
     return data_dir() / "booru.db"
 
 
+def library_folders() -> list[str]:
+    """List library folder names — direct subdirectories of saved_dir().
+
+    The library is filesystem-truth: a folder exists iff there is a real
+    directory on disk. There is no separate DB list of folder names. This
+    is the source the "Save to Library → folder" menus everywhere should
+    read from. Bookmark folders (DB-backed) are a different concept.
+    """
+    root = saved_dir()
+    if not root.is_dir():
+        return []
+    return sorted(d.name for d in root.iterdir() if d.is_dir())
+
+
+def find_library_files(post_id: int) -> list[Path]:
+    """Return all library files matching `post_id` across every folder.
+
+    The library has a flat shape: root + one level of subdirectories.
+    We walk it shallowly (one iterdir of root + one iterdir per subdir)
+    looking for any media file whose stem equals str(post_id). Used by:
+    - "is this post saved?" badges (any match → yes)
+    - delete_from_library (delete every match — handles duplicates left
+      by the old save-to-folder copy bug in a single click)
+    - the move-aware _save_to_library / library "Move to Folder" actions
+    """
+    matches: list[Path] = []
+    root = saved_dir()
+    if not root.is_dir():
+        return matches
+    stem = str(post_id)
+    for entry in root.iterdir():
+        if entry.is_file() and entry.stem == stem and entry.suffix.lower() in MEDIA_EXTENSIONS:
+            matches.append(entry)
+        elif entry.is_dir():
+            for sub in entry.iterdir():
+                if sub.is_file() and sub.stem == stem and sub.suffix.lower() in MEDIA_EXTENSIONS:
+                    matches.append(sub)
+    return matches
+
+
 # Defaults
 DEFAULT_THUMBNAIL_SIZE = (200, 200)
 DEFAULT_PAGE_SIZE = 40

booru_viewer/gui/app.py

@@ -512,6 +512,7 @@ class BooruApp(QMainWindow):
         self._preview.open_in_default.connect(self._open_preview_in_default)
         self._preview.open_in_browser.connect(self._open_preview_in_browser)
         self._preview.bookmark_requested.connect(self._bookmark_from_preview)
+        self._preview.bookmark_to_folder.connect(self._bookmark_to_folder_from_preview)
         self._preview.save_to_folder.connect(self._save_from_preview)
         self._preview.unsave_requested.connect(self._unsave_from_preview)
         self._preview.blacklist_tag_requested.connect(self._blacklist_tag_from_popout)
@@ -519,7 +520,13 @@ class BooruApp(QMainWindow):
         self._preview.navigate.connect(self._navigate_preview)
         self._preview.play_next_requested.connect(self._on_video_end_next)
         self._preview.fullscreen_requested.connect(self._open_fullscreen_preview)
-        self._preview.set_folders_callback(self._db.get_folders)
+        # Library folders come from the filesystem (subdirs of saved_dir),
+        # not the bookmark folders DB table — those are separate concepts.
+        from ..core.config import library_folders
+        self._preview.set_folders_callback(library_folders)
+        # Bookmark folders feed the toolbar Bookmark-as submenu, sourced
+        # from the DB so it stays in sync with the bookmarks tab combo.
+        self._preview.set_bookmark_folders_callback(self._db.get_folders)
         self._fullscreen_window = None
         # Wide enough that the preview toolbar (Bookmark, Save, BL Tag,
         # BL Post, [stretch], Popout) has room to lay out all five buttons
@@ -748,10 +755,18 @@ class BooruApp(QMainWindow):
         self._library_view._grid.clear_selection()
         self._preview._current_post = None
         self._preview._current_site_id = None
-        self._preview.update_bookmark_state(False)
-        self._preview.update_save_state(False)
-        # Show/hide preview toolbar buttons per tab
         is_library = index == 2
+        self._preview.update_bookmark_state(False)
+        # On the library tab the Save button is the only toolbar action
+        # left visible (Bookmark / BL Tag / BL Post are hidden a few lines
+        # down). Library files are saved by definition, so the button
+        # should read "Unsave" the entire time the user is in that tab —
+        # forcing the state to True here makes that true even before the
+        # user clicks anything (the toolbar might already be showing old
+        # media from the previous tab; this is fine because the same media
+        # is also in the library if it was just saved).
+        self._preview.update_save_state(is_library)
+        # Show/hide preview toolbar buttons per tab
         self._preview._bookmark_btn.setVisible(not is_library)
         self._preview._bl_tag_btn.setVisible(not is_library)
         self._preview._bl_post_btn.setVisible(not is_library)
@@ -1030,20 +1045,24 @@ class BooruApp(QMainWindow):
         # Clear loading after a brief delay so scroll signals don't re-trigger
         QTimer.singleShot(100, self._clear_loading)
 
-        from ..core.config import saved_dir, saved_folder_dir
+        from ..core.config import saved_dir
         from ..core.cache import cached_path_for, cache_dir
         site_id = self._site_combo.currentData()
 
-        # Pre-scan saved directories once instead of per-post exists() calls
+        # Pre-scan the library once into a flat post-id set so the per-post
+        # check below is O(1). Folders are filesystem-truth — walk every
+        # subdir of saved_dir() rather than consulting the bookmark folder
+        # list (which used to leak DB state into library detection).
         _sd = saved_dir()
         _saved_ids: set[int] = set()
-        if _sd.exists():
+        if _sd.is_dir():
-            _saved_ids = {int(f.stem) for f in _sd.iterdir() if f.is_file() and f.stem.isdigit()}
+            for entry in _sd.iterdir():
-        _folder_saved: dict[str, set[int]] = {}
+                if entry.is_file() and entry.stem.isdigit():
-        for folder in self._db.get_folders():
+                    _saved_ids.add(int(entry.stem))
-            d = saved_folder_dir(folder)
+                elif entry.is_dir():
-            if d.exists():
+                    for sub in entry.iterdir():
-                _folder_saved[folder] = {int(f.stem) for f in d.iterdir() if f.is_file() and f.stem.isdigit()}
+                        if sub.is_file() and sub.stem.isdigit():
+                            _saved_ids.add(int(sub.stem))
 
         # Pre-fetch bookmarks for the site once and project to a post-id set
         # so the per-post check below is an O(1) membership test instead of
@@ -1062,14 +1081,9 @@ class BooruApp(QMainWindow):
             # Bookmark status (DB)
             if post.id in _bookmarked_ids:
                 thumb.set_bookmarked(True)
-            # Saved status (filesystem) — independent of bookmark
+            # Saved status (filesystem) — _saved_ids already covers both
-            saved = post.id in _saved_ids
+            # the unsorted root and every library subdirectory.
-            if not saved:
+            thumb.set_saved_locally(post.id in _saved_ids)
-                for folder_name, folder_ids in _folder_saved.items():
-                    if post.id in folder_ids:
-                        saved = True
-                        break
-            thumb.set_saved_locally(saved)
             # Set drag path from cache
             cached = cached_path_for(post.file_url)
             if cached.name in _cached_names:
@@ -1366,61 +1380,39 @@ class BooruApp(QMainWindow):
         if self._fullscreen_window and self._fullscreen_window.isVisible():
             self._preview._video_player.stop()
             self._fullscreen_window.set_media(path, info)
-            # Show/hide action buttons based on current tab
+            # Bookmark / BL Tag / BL Post hidden on the library tab (no
-            show = self._stack.currentIndex() != 2
+            # site/post id to act on for local-only files). Save stays
-            self._fullscreen_window._bookmark_btn.setVisible(show)
+            # visible — it acts as Unsave for the library file currently
-            self._fullscreen_window._save_btn.setVisible(show)
+            # being viewed, matching the embedded preview's library mode.
-            self._fullscreen_window._bl_tag_btn.setVisible(show)
+            show_full = self._stack.currentIndex() != 2
-            self._fullscreen_window._bl_post_btn.setVisible(show)
+            self._fullscreen_window._bookmark_btn.setVisible(show_full)
-            if show:
+            self._fullscreen_window._save_btn.setVisible(True)
+            self._fullscreen_window._bl_tag_btn.setVisible(show_full)
+            self._fullscreen_window._bl_post_btn.setVisible(show_full)
             self._update_fullscreen_state()
 
     def _update_fullscreen_state(self) -> None:
-        """Update popout button states for the current post."""
+        """Update popout button states by mirroring the embedded preview.
+
+        The embedded preview is the canonical owner of bookmark/save
+        state — every code path that bookmarks, unsaves, navigates, or
+        loads a post calls update_bookmark_state / update_save_state on
+        it. Re-querying the DB and filesystem here used to drift out of
+        sync with the embedded preview during async bookmark adds and
+        immediately after tab switches; mirroring eliminates the gap and
+        is one source of truth instead of two.
+        """
         if not self._fullscreen_window:
             return
-        from ..core.config import saved_dir, saved_folder_dir, MEDIA_EXTENSIONS
+        self._fullscreen_window.update_state(
-        site_id = self._site_combo.currentData()
+            self._preview._is_bookmarked,
-
+            self._preview._is_saved,
-        if self._stack.currentIndex() == 1:
-            # Bookmarks view
-            grid = self._bookmarks_view._grid
-            favs = self._bookmarks_view._bookmarks
-            idx = grid.selected_index
-            if 0 <= idx < len(favs):
-                fav = favs[idx]
-                saved = False
-                if fav.folder:
-                    saved = any(
-                        (saved_folder_dir(fav.folder) / f"{fav.post_id}{ext}").exists()
-                        for ext in MEDIA_EXTENSIONS
         )
-                else:
-                    saved = any(
-                        (saved_dir() / f"{fav.post_id}{ext}").exists()
-                        for ext in MEDIA_EXTENSIONS
-                    )
-                self._fullscreen_window.update_state(True, saved)
-                self._fullscreen_window.set_post_tags(
-                    fav.tag_categories or {}, (fav.tags or "").split()
-                )
-            else:
-                self._fullscreen_window.update_state(False, False)
-        else:
-            post = None
-            idx = self._grid.selected_index
-            if 0 <= idx < len(self._posts):
-                post = self._posts[idx]
-            elif self._preview._current_post:
         post = self._preview._current_post
-            if post:
+        if post is not None:
-                s_id = self._preview._current_site_id or site_id
+            self._fullscreen_window.set_post_tags(
-                bookmarked = bool(s_id and self._db.is_bookmarked(s_id, post.id))
+                post.tag_categories or {}, post.tag_list
-                saved = self._is_post_saved(post.id)
+            )
-                self._fullscreen_window.update_state(bookmarked, saved)
-                self._fullscreen_window.set_post_tags(post.tag_categories, post.tag_list)
-            else:
-                self._fullscreen_window.update_state(False, False)
 
     def _on_image_done(self, path: str, info: str) -> None:
         self._dl_progress.hide()
@@ -1552,15 +1544,10 @@ class BooruApp(QMainWindow):
             self._update_fullscreen(fav.cached_path, info)
             return
 
-        # Try saved library
+        # Try saved library — walk by post id; the file may live in any
-        from ..core.config import saved_dir, saved_folder_dir
+        # library folder regardless of which bookmark folder fav is in.
-        search_dirs = [saved_dir()]
+        from ..core.config import find_library_files
-        if fav.folder:
+        for path in find_library_files(fav.post_id):
-            search_dirs.insert(0, saved_folder_dir(fav.folder))
-        for d in search_dirs:
-            for ext in MEDIA_EXTENSIONS:
-                path = d / f"{fav.post_id}{ext}"
-                if path.exists():
             self._set_preview_media(str(path), info)
             self._update_fullscreen(str(path), info)
             return
@@ -1917,20 +1904,14 @@ class BooruApp(QMainWindow):
             )
 
     def _is_post_saved(self, post_id: int) -> bool:
-        """Check if a post is saved in the library (any folder)."""
+        """Check if a post is saved in the library (any folder).
-        from ..core.config import saved_dir, saved_folder_dir, MEDIA_EXTENSIONS
+
-        _sd = saved_dir()
+        Walks the library by post id rather than consulting the bookmark
-        if _sd.exists():
+        folder list — library folders are filesystem-truth now, and a
-            for ext in MEDIA_EXTENSIONS:
+        post can be in any folder regardless of bookmark state.
-                if (_sd / f"{post_id}{ext}").exists():
+        """
-                    return True
+        from ..core.config import find_library_files
-        for folder in self._db.get_folders():
+        return bool(find_library_files(post_id))
-            d = saved_folder_dir(folder)
-            if d.exists():
-                for ext in MEDIA_EXTENSIONS:
-                    if (d / f"{post_id}{ext}").exists():
-                        return True
-        return False
 
     def _get_preview_post(self):
         """Get the post currently shown in the preview, from grid or stored ref."""
@@ -1970,12 +1951,61 @@ class BooruApp(QMainWindow):
         if self._stack.currentIndex() == 1:
             self._bookmarks_view.refresh()
 
+    def _bookmark_to_folder_from_preview(self, folder: str) -> None:
+        """Bookmark the current preview post into a specific bookmark folder.
+
+        Triggered by the toolbar Bookmark-as submenu, which only shows
+        when the post is not yet bookmarked — so this method only handles
+        the create path, never the move/remove paths. Empty string means
+        Unfiled. Brand-new folder names get added to the DB folder list
+        first so the bookmarks tab combo immediately shows them.
+        """
+        post, idx = self._get_preview_post()
+        if not post:
+            return
+        site_id = self._preview._current_site_id or self._site_combo.currentData()
+        if not site_id:
+            return
+        target = folder if folder else None
+        if target and target not in self._db.get_folders():
+            try:
+                self._db.add_folder(target)
+            except ValueError as e:
+                self._status.showMessage(f"Invalid folder name: {e}")
+                return
+        if idx >= 0:
+            # In the grid — go through _toggle_bookmark so the grid
+            # thumbnail's bookmark badge updates via _on_bookmark_done.
+            self._toggle_bookmark(idx, target)
+        else:
+            # Preview-only post (e.g. opened from the bookmarks tab while
+            # browse is empty). Inline the add — no grid index to update.
+            from ..core.cache import cached_path_for
+            cached = cached_path_for(post.file_url)
+            self._db.add_bookmark(
+                site_id=site_id, post_id=post.id,
+                file_url=post.file_url, preview_url=post.preview_url or "",
+                tags=post.tags, rating=post.rating, score=post.score,
+                source=post.source,
+                cached_path=str(cached) if cached.exists() else None,
+                folder=target,
+                tag_categories=post.tag_categories,
+            )
+            where = target or "Unfiled"
+            self._status.showMessage(f"Bookmarked #{post.id} to {where}")
+        self._preview.update_bookmark_state(True)
+        self._update_fullscreen_state()
+        # Refresh bookmarks tab if visible so the new entry appears.
+        if self._stack.currentIndex() == 1:
+            self._bookmarks_view.refresh()
+
     def _save_from_preview(self, folder: str) -> None:
         post, idx = self._get_preview_post()
         if post:
             target = folder if folder else None
-            if folder and folder not in self._db.get_folders():
+            # _save_to_library calls saved_folder_dir() which mkdir's the
-                self._db.add_folder(folder)
+            # target directory itself — no need to register it in the
+            # bookmark folders DB table (those are unrelated now).
             self._save_to_library(post, target)
             # State updates happen in _on_bookmark_done after async save completes
 
@@ -1983,25 +2013,10 @@ class BooruApp(QMainWindow):
         post, idx = self._get_preview_post()
         if not post:
             return
+        # delete_from_library now walks every library folder by post id
+        # and deletes every match in one call — no folder hint needed.
         from ..core.cache import delete_from_library
-        # Check all folders for saved files
+        deleted = delete_from_library(post.id)
-        from ..core.config import saved_dir, saved_folder_dir, MEDIA_EXTENSIONS
-        deleted = False
-        # Try unsorted
-        _sd = saved_dir()
-        for ext in MEDIA_EXTENSIONS:
-            p = _sd / f"{post.id}{ext}"
-            if p.exists():
-                p.unlink()
-                deleted = True
-        # Try all folders
-        for folder in self._db.get_folders():
-            d = saved_folder_dir(folder)
-            for ext in MEDIA_EXTENSIONS:
-                p = d / f"{post.id}{ext}"
-                if p.exists():
-                    p.unlink()
-                    deleted = True
         if deleted:
             self._status.showMessage(f"Removed #{post.id} from library")
             self._preview.update_save_state(False)
@@ -2023,12 +2038,6 @@ class BooruApp(QMainWindow):
             self._status.showMessage(f"#{post.id} not in library")
         self._update_fullscreen_state()
 
-    def _save_toggle_from_popout(self) -> None:
-        if self._fullscreen_window and self._fullscreen_window._is_saved:
-            self._unsave_from_preview()
-        else:
-            self._save_from_preview("")
-
     def _blacklist_tag_from_popout(self, tag: str) -> None:
         reply = QMessageBox.question(
             self, "Blacklist Tag",
@@ -2103,9 +2112,21 @@ class BooruApp(QMainWindow):
         self._fullscreen_window = FullscreenPreview(grid_cols=cols, show_actions=show_actions, monitor=monitor, parent=self)
         self._fullscreen_window.navigate.connect(self._navigate_fullscreen)
         self._fullscreen_window.play_next_requested.connect(self._on_video_end_next)
+        # Save signals are always wired — even in library mode, the
+        # popout's Save button is the only toolbar action visible (acting
+        # as Unsave for the file being viewed), and it has its own
+        # Save-to-Library submenu shape that matches the embedded preview.
+        from ..core.config import library_folders
+        self._fullscreen_window.set_folders_callback(library_folders)
+        self._fullscreen_window.save_to_folder.connect(self._save_from_preview)
+        self._fullscreen_window.unsave_requested.connect(self._unsave_from_preview)
         if show_actions:
             self._fullscreen_window.bookmark_requested.connect(self._bookmark_from_preview)
-            self._fullscreen_window.save_toggle_requested.connect(self._save_toggle_from_popout)
+            # Same Bookmark-as flow as the embedded preview — popout reuses
+            # the existing handler since both signals carry just a folder
+            # name and read the post from self._preview._current_post.
+            self._fullscreen_window.set_bookmark_folders_callback(self._db.get_folders)
+            self._fullscreen_window.bookmark_to_folder.connect(self._bookmark_to_folder_from_preview)
             self._fullscreen_window.blacklist_tag_requested.connect(self._blacklist_tag_from_popout)
             self._fullscreen_window.blacklist_post_requested.connect(self._blacklist_post_from_popout)
         self._fullscreen_window.closed.connect(self._on_fullscreen_closed)
@@ -2131,7 +2152,9 @@ class BooruApp(QMainWindow):
                     pass
             sv.media_ready.connect(_seek_when_ready)
         self._fullscreen_window.set_media(path, info)
-        if show_actions:
+        # Always sync state — the save button is visible in both modes
+        # (library mode = only Save shown, browse/bookmarks = full toolbar)
+        # so its Unsave label needs to land before the user sees it.
         self._update_fullscreen_state()
 
     def _on_fullscreen_closed(self) -> None:
@@ -2205,12 +2228,14 @@ class BooruApp(QMainWindow):
         menu.addSeparator()
         save_as = menu.addAction("Save As...")
 
-        # Save to Library submenu
+        # Save to Library submenu — folders come from the library
+        # filesystem, not the bookmark folder DB.
+        from ..core.config import library_folders
         save_lib_menu = menu.addMenu("Save to Library")
-        save_lib_unsorted = save_lib_menu.addAction("Unsorted")
+        save_lib_unsorted = save_lib_menu.addAction("Unfiled")
         save_lib_menu.addSeparator()
         save_lib_folders = {}
-        for folder in self._db.get_folders():
+        for folder in library_folders():
             a = save_lib_menu.addAction(folder)
             save_lib_folders[id(a)] = folder
         save_lib_menu.addSeparator()
@@ -2223,7 +2248,29 @@ class BooruApp(QMainWindow):
         copy_url = menu.addAction("Copy Image URL")
         copy_tags = menu.addAction("Copy Tags")
         menu.addSeparator()
-        fav_action = menu.addAction("Remove Bookmark" if self._is_current_bookmarked(index) else "Bookmark")
+
+        # Bookmark action: when not yet bookmarked, offer "Bookmark as"
+        # with a submenu of bookmark folders so the user can file the
+        # new bookmark in one click. Bookmark folders come from the DB
+        # (separate name space from library folders). When already
+        # bookmarked, the action collapses to a flat "Remove Bookmark"
+        # — re-filing an existing bookmark belongs in the bookmarks tab
+        # right-click menu's "Move to Folder" submenu.
+        fav_action = None
+        bm_folder_actions: dict[int, str] = {}
+        bm_unfiled = None
+        bm_new = None
+        if self._is_current_bookmarked(index):
+            fav_action = menu.addAction("Remove Bookmark")
+        else:
+            fav_menu = menu.addMenu("Bookmark as")
+            bm_unfiled = fav_menu.addAction("Unfiled")
+            fav_menu.addSeparator()
+            for folder in self._db.get_folders():
+                a = fav_menu.addAction(folder)
+                bm_folder_actions[id(a)] = folder
+            fav_menu.addSeparator()
+            bm_new = fav_menu.addAction("+ New Folder...")
         menu.addSeparator()
         bl_menu = menu.addMenu("Blacklist Tag")
         if post.tag_categories:
@@ -2252,8 +2299,12 @@ class BooruApp(QMainWindow):
             from PySide6.QtWidgets import QInputDialog, QMessageBox
             name, ok = QInputDialog.getText(self, "New Folder", "Folder name:")
             if ok and name.strip():
+                # _save_to_library → saved_folder_dir() does the mkdir
+                # and the path-traversal check; we surface the same error
+                # message it would emit so a bad name is reported clearly.
                 try:
-                    self._db.add_folder(name.strip())
+                    from ..core.config import saved_folder_dir
+                    saved_folder_dir(name.strip())
                 except ValueError as e:
                     QMessageBox.warning(self, "Invalid Folder Name", str(e))
                     return
@@ -2271,8 +2322,25 @@ class BooruApp(QMainWindow):
         elif action == copy_tags:
             QApplication.clipboard().setText(post.tags)
             self._status.showMessage("Tags copied")
-        elif action == fav_action:
+        elif fav_action is not None and action == fav_action:
+            # Currently bookmarked → flat "Remove Bookmark" path.
             self._toggle_bookmark(index)
+        elif bm_unfiled is not None and action == bm_unfiled:
+            self._toggle_bookmark(index, None)
+        elif bm_new is not None and action == bm_new:
+            from PySide6.QtWidgets import QInputDialog, QMessageBox
+            name, ok = QInputDialog.getText(self, "New Bookmark Folder", "Folder name:")
+            if ok and name.strip():
+                # Bookmark folders are DB-managed; add_folder validates
+                # the name and is the same call the bookmarks tab uses.
+                try:
+                    self._db.add_folder(name.strip())
+                except ValueError as e:
+                    QMessageBox.warning(self, "Invalid Folder Name", str(e))
+                    return
+                self._toggle_bookmark(index, name.strip())
+        elif id(action) in bm_folder_actions:
+            self._toggle_bookmark(index, bm_folder_actions[id(action)])
         elif self._is_child_of_menu(action, bl_menu):
             tag = action.text()
             self._db.add_blacklisted_tag(tag)
@@ -2361,9 +2429,10 @@ class BooruApp(QMainWindow):
         fav_all = menu.addAction(f"Bookmark All ({count})")
 
         save_menu = menu.addMenu(f"Save All to Library ({count})")
-        save_unsorted = save_menu.addAction("Unsorted")
+        save_unsorted = save_menu.addAction("Unfiled")
         save_folder_actions = {}
-        for folder in self._db.get_folders():
+        from ..core.config import library_folders
+        for folder in library_folders():
             a = save_menu.addAction(folder)
             save_folder_actions[id(a)] = folder
         save_menu.addSeparator()
@@ -2388,7 +2457,8 @@ class BooruApp(QMainWindow):
             name, ok = QInputDialog.getText(self, "New Folder", "Folder name:")
             if ok and name.strip():
                 try:
-                    self._db.add_folder(name.strip())
+                    from ..core.config import saved_folder_dir
+                    saved_folder_dir(name.strip())
                 except ValueError as e:
                     QMessageBox.warning(self, "Invalid Folder Name", str(e))
                     return
@@ -2404,13 +2474,9 @@ class BooruApp(QMainWindow):
             site_id = self._site_combo.currentData()
             if site_id:
                 from ..core.cache import delete_from_library
-                from ..core.config import saved_dir, saved_folder_dir
                 for post in posts:
-                    # Delete from unsorted library
+                    # Single call now walks every library folder by post id.
-                    delete_from_library(post.id, None)
+                    delete_from_library(post.id)
-                    # Delete from all folders
-                    for folder in self._db.get_folders():
-                        delete_from_library(post.id, folder)
                     self._db.remove_bookmark(site_id, post.id)
                 for idx in indices:
                     if 0 <= idx < len(self._grid._thumbs):
@@ -2451,7 +2517,7 @@ class BooruApp(QMainWindow):
 
     def _bulk_save(self, indices: list[int], posts: list[Post], folder: str | None) -> None:
         site_id = self._site_combo.currentData()
-        where = folder or "Unsorted"
+        where = folder or "Unfiled"
         self._status.showMessage(f"Saving {len(posts)} to {where}...")
 
         async def _do():
@@ -2568,19 +2634,74 @@ class BooruApp(QMainWindow):
             self._status.showMessage("Image not cached yet — double-click to download first")
 
     def _save_to_library(self, post: Post, folder: str | None) -> None:
-        """Download and save image to the library folder structure."""
+        """Save (or relocate) an image in the library folder structure.
-        from ..core.config import saved_dir, saved_folder_dir
+
+        If the post is already saved somewhere in the library, the existing
+        file is renamed into the target folder rather than re-downloading.
+        This is what makes "Save to Library → SomeFolder" act like a move
+        when the post is already in Unfiled (or another folder), instead
+        of producing a duplicate. rename() is atomic on the same filesystem
+        so a crash mid-move can never leave both copies behind.
+        """
+        from ..core.config import saved_dir, saved_folder_dir, MEDIA_EXTENSIONS
 
         self._status.showMessage(f"Saving #{post.id} to library...")
 
-        async def _save():
+        # Resolve destination synchronously — saved_folder_dir() does
+        # the path-traversal check and may raise ValueError. Surface
+        # that error here rather than from inside the async closure.
         try:
-                path = await download_image(post.file_url)
-                ext = Path(path).suffix
             if folder:
                 dest_dir = saved_folder_dir(folder)
             else:
                 dest_dir = saved_dir()
+        except ValueError as e:
+            self._status.showMessage(f"Invalid folder name: {e}")
+            return
+        dest_resolved = dest_dir.resolve()
+
+        # Look for an existing copy of this post anywhere in the library.
+        # The library is shallow (root + one level of subdirectories) so
+        # this is cheap — at most one iterdir per top-level entry.
+        existing: Path | None = None
+        root = saved_dir()
+        if root.is_dir():
+            stem = str(post.id)
+            for entry in root.iterdir():
+                if entry.is_file() and entry.stem == stem and entry.suffix.lower() in MEDIA_EXTENSIONS:
+                    existing = entry
+                    break
+                if entry.is_dir():
+                    for sub in entry.iterdir():
+                        if sub.is_file() and sub.stem == stem and sub.suffix.lower() in MEDIA_EXTENSIONS:
+                            existing = sub
+                            break
+                    if existing is not None:
+                        break
+
+        async def _save():
+            try:
+                if existing is not None:
+                    # Already in the library — relocate instead of re-saving.
+                    if existing.parent.resolve() != dest_resolved:
+                        target = dest_dir / existing.name
+                        if target.exists():
+                            # Destination already has a file with the same
+                            # name (matched by post id, so it's the same
+                            # post). Drop the source to collapse the
+                            # duplicate rather than leaving both behind.
+                            existing.unlink()
+                        else:
+                            try:
+                                existing.rename(target)
+                            except OSError:
+                                # Cross-device rename — fall back to copy+unlink.
+                                import shutil as _sh
+                                _sh.move(str(existing), str(target))
+                else:
+                    # Not in the library yet — pull from cache and copy in.
+                    path = await download_image(post.file_url)
+                    ext = Path(path).suffix
                     dest = dest_dir / f"{post.id}{ext}"
                     if not dest.exists():
                         import shutil
@@ -2607,7 +2728,7 @@ class BooruApp(QMainWindow):
                     source=post.source, file_url=post.file_url,
                 )
 
-                where = folder or "Unsorted"
+                where = folder or "Unfiled"
                 self._signals.bookmark_done.emit(
                     self._grid.selected_index,
                     f"Saved #{post.id} to {where}"
@@ -2837,7 +2958,14 @@ class BooruApp(QMainWindow):
 
     # -- Bookmarks --
 
-    def _toggle_bookmark(self, index: int) -> None:
+    def _toggle_bookmark(self, index: int, folder: str | None = None) -> None:
+        """Toggle the bookmark state of post at `index`.
+
+        When `folder` is given and the post is not yet bookmarked, the
+        new bookmark is filed under that bookmark folder. The folder
+        arg is ignored when removing — bookmark folder membership is
+        moot if the bookmark itself is going away.
+        """
         post = self._posts[index]
         site_id = self._site_combo.currentData()
         if not site_id:
@@ -2865,9 +2993,11 @@ class BooruApp(QMainWindow):
                         score=post.score,
                         source=post.source,
                         cached_path=str(path),
+                        folder=folder,
                         tag_categories=post.tag_categories,
                     )
-                    self._signals.bookmark_done.emit(index, f"Bookmarked #{post.id}")
+                    where = folder or "Unfiled"
+                    self._signals.bookmark_done.emit(index, f"Bookmarked #{post.id} to {where}")
                 except Exception as e:
                     self._signals.bookmark_error.emit(str(e))
 
@@ -2875,7 +3005,7 @@ class BooruApp(QMainWindow):
 
     def _on_bookmark_done(self, index: int, msg: str) -> None:
         self._status.showMessage(f"{len(self._posts)} results — {msg}")
-        # Detect batch operations (e.g. "Saved 3/10 to Unsorted") — skip heavy updates
+        # Detect batch operations (e.g. "Saved 3/10 to Unfiled") — skip heavy updates
         is_batch = "/" in msg and any(c.isdigit() for c in msg.split("/")[0][-2:])
         thumbs = self._grid._thumbs
         if 0 <= index < len(thumbs):

booru_viewer/gui/bookmarks.py

@@ -71,12 +71,28 @@ class BookmarksView(QWidget):
         top.addWidget(self._folder_combo)
 
         manage_btn = QPushButton("+ Folder")
-        manage_btn.setToolTip("New folder")
+        manage_btn.setToolTip("New bookmark folder")
         manage_btn.setFixedWidth(75)
         manage_btn.setStyleSheet(_btn_style)
         manage_btn.clicked.connect(self._new_folder)
         top.addWidget(manage_btn)
 
+        # Delete the currently-selected bookmark folder. Disabled when
+        # the combo is on a virtual entry (All Bookmarks / Unfiled).
+        # This only removes the DB row — bookmarks in that folder become
+        # Unfiled (per remove_folder's UPDATE … SET folder = NULL). The
+        # library filesystem is untouched: bookmark folders and library
+        # folders are independent name spaces.
+        self._delete_folder_btn = QPushButton("− Folder")
+        self._delete_folder_btn.setToolTip("Delete the selected bookmark folder")
+        self._delete_folder_btn.setFixedWidth(75)
+        self._delete_folder_btn.setStyleSheet(_btn_style)
+        self._delete_folder_btn.clicked.connect(self._delete_folder)
+        top.addWidget(self._delete_folder_btn)
+        self._folder_combo.currentTextChanged.connect(
+            self._update_delete_folder_enabled
+        )
+
         self._search_input = QLineEdit()
         self._search_input.setPlaceholderText("Search bookmarks by tag")
         # Enter still triggers an immediate search.
@@ -120,6 +136,39 @@ class BookmarksView(QWidget):
         if idx >= 0:
             self._folder_combo.setCurrentIndex(idx)
         self._folder_combo.blockSignals(False)
+        self._update_delete_folder_enabled()
+
+    def _update_delete_folder_enabled(self, *_args) -> None:
+        """Enable the delete-folder button only on real folder rows."""
+        text = self._folder_combo.currentText()
+        self._delete_folder_btn.setEnabled(text not in ("", "All Bookmarks", "Unfiled"))
+
+    def _delete_folder(self) -> None:
+        """Delete the currently-selected bookmark folder.
+
+        Bookmarks filed under it become Unfiled (remove_folder UPDATEs
+        favorites.folder = NULL before DELETE FROM favorite_folders).
+        Library files on disk are unaffected — bookmark folders and
+        library folders are separate concepts after the decoupling.
+        """
+        name = self._folder_combo.currentText()
+        if name in ("", "All Bookmarks", "Unfiled"):
+            return
+        reply = QMessageBox.question(
+            self,
+            "Delete Bookmark Folder",
+            f"Delete bookmark folder '{name}'?\n\n"
+            f"Bookmarks in this folder will become Unfiled. "
+            f"Library files on disk are not affected.",
+            QMessageBox.StandardButton.Yes | QMessageBox.StandardButton.No,
+        )
+        if reply != QMessageBox.StandardButton.Yes:
+            return
+        self._db.remove_folder(name)
+        # Drop back to All Bookmarks so the now-orphan filter doesn't
+        # leave the combo on a missing row.
+        self._folder_combo.setCurrentText("All Bookmarks")
+        self.refresh()
 
     def refresh(self, search: str | None = None) -> None:
         self._refresh_folders()
@@ -145,22 +194,12 @@ class BookmarksView(QWidget):
         self._count_label.setText(f"{len(self._bookmarks)} bookmarks")
         thumbs = self._grid.set_posts(len(self._bookmarks))
 
-        from ..core.config import saved_dir, saved_folder_dir, MEDIA_EXTENSIONS
+        from ..core.config import find_library_files
         for i, (fav, thumb) in enumerate(zip(self._bookmarks, thumbs)):
             thumb.set_bookmarked(True)
-            # Check if saved to library
+            # Library state is filesystem-truth and folder-agnostic now —
-            saved = False
+            # walk the library by post id, ignore the bookmark's folder.
-            if fav.folder:
+            thumb.set_saved_locally(bool(find_library_files(fav.post_id)))
-                saved = any(
-                    (saved_folder_dir(fav.folder) / f"{fav.post_id}{ext}").exists()
-                    for ext in MEDIA_EXTENSIONS
-                )
-            else:
-                saved = any(
-                    (saved_dir() / f"{fav.post_id}{ext}").exists()
-                    for ext in MEDIA_EXTENSIONS
-                )
-            thumb.set_saved_locally(saved)
             # Set cached path for drag-and-drop and copy
             if fav.cached_path and Path(fav.cached_path).exists():
                 thumb._cached_path = fav.cached_path
@@ -250,31 +289,22 @@ class BookmarksView(QWidget):
         menu.addSeparator()
         save_as = menu.addAction("Save As...")
 
-        # Save to Library submenu
+        # Save to Library submenu — folders come from the library
+        # filesystem, not the bookmark folder DB.
+        from ..core.config import library_folders, find_library_files
         save_lib_menu = menu.addMenu("Save to Library")
-        save_lib_unsorted = save_lib_menu.addAction("Unsorted")
+        save_lib_unsorted = save_lib_menu.addAction("Unfiled")
         save_lib_menu.addSeparator()
         save_lib_folders = {}
-        for folder in self._db.get_folders():
+        for folder in library_folders():
             a = save_lib_menu.addAction(folder)
             save_lib_folders[id(a)] = folder
         save_lib_menu.addSeparator()
         save_lib_new = save_lib_menu.addAction("+ New Folder...")
 
         unsave_lib = None
-        # Only show unsave if the post is saved locally
+        # Only show unsave if the post is actually on disk somewhere.
-        from ..core.config import saved_dir, saved_folder_dir, MEDIA_EXTENSIONS
+        if find_library_files(fav.post_id):
-        _saved = False
-        _sd = saved_dir()
-        if _sd.exists():
-            _saved = any((_sd / f"{fav.post_id}{ext}").exists() for ext in MEDIA_EXTENSIONS)
-        if not _saved:
-            for folder in self._db.get_folders():
-                d = saved_folder_dir(folder)
-                if d.exists() and any((d / f"{fav.post_id}{ext}").exists() for ext in MEDIA_EXTENSIONS):
-                    _saved = True
-                    break
-        if _saved:
             unsave_lib = menu.addAction("Unsave from Library")
         copy_file = menu.addAction("Copy File to Clipboard")
         copy_url = menu.addAction("Copy Image URL")
@@ -305,13 +335,16 @@ class BookmarksView(QWidget):
         elif action == save_lib_new:
             name, ok = QInputDialog.getText(self, "New Folder", "Folder name:")
             if ok and name.strip():
+                # Validate the name via saved_folder_dir() which mkdir's
+                # the library subdir and runs the path-traversal check.
+                # No DB folder write — bookmark folders are independent.
                 try:
-                    self._db.add_folder(name.strip())
+                    from ..core.config import saved_folder_dir
+                    saved_folder_dir(name.strip())
                 except ValueError as e:
                     QMessageBox.warning(self, "Invalid Folder Name", str(e))
                     return
                 self._copy_to_library(fav, name.strip())
-                self._db.move_bookmark_to_folder(fav.id, name.strip())
                 self.refresh()
         elif id(action) in save_lib_folders:
             folder_name = save_lib_folders[id(action)]
@@ -331,7 +364,10 @@ class BookmarksView(QWidget):
                     shutil.copy2(src, dest)
         elif action == unsave_lib:
             from ..core.cache import delete_from_library
-            if delete_from_library(fav.post_id, fav.folder):
+            # delete_from_library walks every library folder by post id
+            # now — no folder hint needed (and fav.folder wouldn't be
+            # accurate anyway after the bookmark/library separation).
+            if delete_from_library(fav.post_id):
                 self.refresh()
                 self.bookmarks_changed.emit()
         elif action == copy_file:
@@ -360,13 +396,14 @@ class BookmarksView(QWidget):
                 except ValueError as e:
                     QMessageBox.warning(self, "Invalid Folder Name", str(e))
                     return
+                # Pure bookmark organization: file the bookmark, don't
+                # touch the library filesystem. Save to Library is now a
+                # separate, explicit action.
                 self._db.move_bookmark_to_folder(fav.id, name.strip())
-                self._copy_to_library(fav, name.strip())
                 self.refresh()
         elif id(action) in folder_actions:
             folder_name = folder_actions[id(action)]
             self._db.move_bookmark_to_folder(fav.id, folder_name)
-            self._copy_to_library(fav, folder_name)
             self.refresh()
         elif action == remove_bookmark:
             self._db.remove_bookmark(fav.site_id, fav.post_id)
@@ -378,11 +415,28 @@ class BookmarksView(QWidget):
         if not favs:
             return
 
+        from ..core.config import library_folders
+
         menu = QMenu(self)
-        save_all = menu.addAction(f"Save All ({len(favs)}) to Library")
+
+        # Save All to Library submenu — folders are filesystem-truth.
+        # Conversion from a flat action to a submenu so the user can
+        # pick a destination instead of having "save all" silently use
+        # each bookmark's fav.folder (which was the cross-bleed bug).
+        save_lib_menu = menu.addMenu(f"Save All ({len(favs)}) to Library")
+        save_lib_unsorted = save_lib_menu.addAction("Unfiled")
+        save_lib_menu.addSeparator()
+        save_lib_folder_actions: dict[int, str] = {}
+        for folder in library_folders():
+            a = save_lib_menu.addAction(folder)
+            save_lib_folder_actions[id(a)] = folder
+        save_lib_menu.addSeparator()
+        save_lib_new = save_lib_menu.addAction("+ New Folder...")
+
         unsave_all = menu.addAction(f"Unsave All ({len(favs)}) from Library")
         menu.addSeparator()
 
+        # Move to Folder is bookmark organization — reads from the DB.
         move_menu = menu.addMenu(f"Move All ({len(favs)}) to Folder")
         move_none = move_menu.addAction("Unfiled")
         move_menu.addSeparator()
@@ -398,17 +452,32 @@ class BookmarksView(QWidget):
         if not action:
             return
 
-        if action == save_all:
+        def _save_all_into(folder_name: str | None) -> None:
             for fav in favs:
-                if fav.folder:
+                if folder_name:
-                    self._copy_to_library(fav, fav.folder)
+                    self._copy_to_library(fav, folder_name)
                 else:
                     self._copy_to_library_unsorted(fav)
             self.refresh()
+
+        if action == save_lib_unsorted:
+            _save_all_into(None)
+        elif action == save_lib_new:
+            name, ok = QInputDialog.getText(self, "New Folder", "Folder name:")
+            if ok and name.strip():
+                try:
+                    from ..core.config import saved_folder_dir
+                    saved_folder_dir(name.strip())
+                except ValueError as e:
+                    QMessageBox.warning(self, "Invalid Folder Name", str(e))
+                    return
+                _save_all_into(name.strip())
+        elif id(action) in save_lib_folder_actions:
+            _save_all_into(save_lib_folder_actions[id(action)])
         elif action == unsave_all:
             from ..core.cache import delete_from_library
             for fav in favs:
-                delete_from_library(fav.post_id, fav.folder)
+                delete_from_library(fav.post_id)
             self.refresh()
             self.bookmarks_changed.emit()
         elif action == move_none:
@@ -417,9 +486,9 @@ class BookmarksView(QWidget):
             self.refresh()
         elif id(action) in folder_actions:
             folder_name = folder_actions[id(action)]
+            # Bookmark organization only — Save to Library is separate.
             for fav in favs:
                 self._db.move_bookmark_to_folder(fav.id, folder_name)
-                self._copy_to_library(fav, folder_name)
             self.refresh()
         elif action == remove_all:
             for fav in favs:

booru_viewer/gui/library.py

@@ -19,6 +19,7 @@ from PySide6.QtWidgets import (
     QComboBox,
     QMenu,
     QMessageBox,
+    QInputDialog,
     QApplication,
 )
 
@@ -194,7 +195,7 @@ class LibraryView(QWidget):
         self._folder_combo.blockSignals(True)
         self._folder_combo.clear()
         self._folder_combo.addItem("All Files")
-        self._folder_combo.addItem("Unsorted")
+        self._folder_combo.addItem("Unfiled")
 
         root = saved_dir()
         if root.is_dir():
@@ -217,7 +218,7 @@ class LibraryView(QWidget):
 
         if folder_text == "All Files":
             return self._collect_recursive(root)
-        elif folder_text == "Unsorted":
+        elif folder_text == "Unfiled":
             return self._collect_top_level(root)
         else:
             sub = root / folder_text
@@ -347,6 +348,76 @@ class LibraryView(QWidget):
         if 0 <= index < len(self._files):
             self.file_activated.emit(str(self._files[index]))
 
+    def _move_files_to_folder(
+        self, files: list[Path], target_folder: str | None
+    ) -> None:
+        """Move library files into target_folder (None = Unfiled root).
+
+        Uses Path.rename for an atomic same-filesystem move. That matters
+        here because the bug we're fixing is "move produces a duplicate" —
+        a copy-then-delete sequence can leave both files behind if the
+        delete fails or the process is killed mid-step. rename() is one
+        syscall and either fully succeeds or doesn't happen at all. If
+        the rename crosses filesystems (rare — only if the user pointed
+        the library at a different mount than its parent), Python raises
+        OSError(EXDEV) and we fall back to shutil.move which copies-then-
+        unlinks; in that path the unlink failure is the only window for
+        a duplicate, and it's logged.
+        """
+        import shutil
+
+        try:
+            if target_folder:
+                dest_dir = saved_folder_dir(target_folder)
+            else:
+                dest_dir = saved_dir()
+        except ValueError as e:
+            QMessageBox.warning(self, "Invalid Folder Name", str(e))
+            return
+
+        dest_resolved = dest_dir.resolve()
+        moved = 0
+        skipped_same = 0
+        collisions: list[str] = []
+        errors: list[str] = []
+
+        for src in files:
+            if not src.exists():
+                continue
+            if src.parent.resolve() == dest_resolved:
+                skipped_same += 1
+                continue
+            target = dest_dir / src.name
+            if target.exists():
+                collisions.append(src.name)
+                continue
+            try:
+                src.rename(target)
+                moved += 1
+            except OSError:
+                # Cross-device move — fall back to copy + delete.
+                try:
+                    shutil.move(str(src), str(target))
+                    moved += 1
+                except Exception as e:
+                    log.warning("Failed to move %s → %s: %s", src, target, e)
+                    errors.append(f"{src.name}: {e}")
+
+        self.refresh()
+
+        if collisions:
+            sample = "\n".join(collisions[:10])
+            more = f"\n... and {len(collisions) - 10} more" if len(collisions) > 10 else ""
+            QMessageBox.warning(
+                self,
+                "Move Conflicts",
+                f"Skipped {len(collisions)} file(s) — destination already "
+                f"contains a file with the same name:\n\n{sample}{more}",
+            )
+        if errors:
+            sample = "\n".join(errors[:10])
+            QMessageBox.warning(self, "Move Errors", sample)
+
     def _on_context_menu(self, index: int, pos) -> None:
         if index < 0 or index >= len(self._files):
             return
@@ -361,6 +432,25 @@ class LibraryView(QWidget):
         menu.addSeparator()
         copy_file = menu.addAction("Copy File to Clipboard")
         copy_path = menu.addAction("Copy File Path")
+        menu.addSeparator()
+
+        # Move to Folder submenu — atomic rename, no copy step, so a
+        # crash mid-move can never leave a duplicate behind. The current
+        # location is included in the list (no-op'd in the move helper)
+        # so the menu shape stays predictable for the user.
+        move_menu = menu.addMenu("Move to Folder")
+        move_unsorted = move_menu.addAction("Unfiled")
+        move_menu.addSeparator()
+        move_folder_actions: dict[int, str] = {}
+        root = saved_dir()
+        if root.is_dir():
+            for entry in sorted(root.iterdir()):
+                if entry.is_dir():
+                    a = move_menu.addAction(entry.name)
+                    move_folder_actions[id(a)] = entry.name
+        move_menu.addSeparator()
+        move_new = move_menu.addAction("+ New Folder...")
+
         menu.addSeparator()
         delete_action = menu.addAction("Delete from Library")
 
@@ -372,6 +462,14 @@ class LibraryView(QWidget):
             QDesktopServices.openUrl(QUrl.fromLocalFile(str(filepath)))
         elif action == open_folder:
             QDesktopServices.openUrl(QUrl.fromLocalFile(str(filepath.parent)))
+        elif action == move_unsorted:
+            self._move_files_to_folder([filepath], None)
+        elif action == move_new:
+            name, ok = QInputDialog.getText(self, "New Folder", "Folder name:")
+            if ok and name.strip():
+                self._move_files_to_folder([filepath], name.strip())
+        elif id(action) in move_folder_actions:
+            self._move_files_to_folder([filepath], move_folder_actions[id(action)])
         elif action == copy_file:
             from PySide6.QtCore import QMimeData
             from PySide6.QtGui import QPixmap as _QP
@@ -403,13 +501,36 @@ class LibraryView(QWidget):
             return
 
         menu = QMenu(self)
+
+        move_menu = menu.addMenu(f"Move {len(files)} files to Folder")
+        move_unsorted = move_menu.addAction("Unfiled")
+        move_menu.addSeparator()
+        move_folder_actions: dict[int, str] = {}
+        root = saved_dir()
+        if root.is_dir():
+            for entry in sorted(root.iterdir()):
+                if entry.is_dir():
+                    a = move_menu.addAction(entry.name)
+                    move_folder_actions[id(a)] = entry.name
+        move_menu.addSeparator()
+        move_new = move_menu.addAction("+ New Folder...")
+
+        menu.addSeparator()
         delete_all = menu.addAction(f"Delete {len(files)} files from Library")
 
         action = menu.exec(pos)
         if not action:
             return
 
-        if action == delete_all:
+        if action == move_unsorted:
+            self._move_files_to_folder(files, None)
+        elif action == move_new:
+            name, ok = QInputDialog.getText(self, "New Folder", "Folder name:")
+            if ok and name.strip():
+                self._move_files_to_folder(files, name.strip())
+        elif id(action) in move_folder_actions:
+            self._move_files_to_folder(files, move_folder_actions[id(action)])
+        elif action == delete_all:
             reply = QMessageBox.question(
                 self, "Confirm", f"Delete {len(files)} files from library?",
                 QMessageBox.StandardButton.Yes | QMessageBox.StandardButton.No,

booru_viewer/gui/preview.py

@@ -38,7 +38,15 @@ class FullscreenPreview(QMainWindow):
     navigate = Signal(int)  # direction: -1/+1 for left/right, -cols/+cols for up/down
     play_next_requested = Signal()  # video ended in "Next" mode (wrap-aware)
     bookmark_requested = Signal()
-    save_toggle_requested = Signal()  # save or unsave depending on state
+    # Bookmark-as: emitted when the popout's Bookmark button submenu picks
+    # a bookmark folder. Empty string = Unfiled. Mirrors ImagePreview's
+    # signal so app.py routes both through _bookmark_to_folder_from_preview.
+    bookmark_to_folder = Signal(str)
+    # Save-to-library: same signal pair as ImagePreview so app.py reuses
+    # _save_from_preview / _unsave_from_preview for both. Empty string =
+    # Unfiled (root of saved_dir).
+    save_to_folder = Signal(str)
+    unsave_requested = Signal()
     blacklist_tag_requested = Signal(str)  # tag name
     blacklist_post_requested = Signal()
     privacy_requested = Signal()
@@ -89,16 +97,26 @@ class FullscreenPreview(QMainWindow):
         # short labels in narrow fixed slots.
         _tb_btn_style = "padding: 2px 6px;"
 
+        # Bookmark folders for the popout's Bookmark-as submenu — wired
+        # by app.py via set_bookmark_folders_callback after construction.
+        self._bookmark_folders_callback = None
+        self._is_bookmarked = False
+        # Library folders for the popout's Save-to-Library submenu —
+        # wired by app.py via set_folders_callback. Same shape as the
+        # bookmark folders callback above; library and bookmark folders
+        # are independent name spaces and need separate callbacks.
+        self._folders_callback = None
+
         self._bookmark_btn = QPushButton("Bookmark")
         self._bookmark_btn.setMaximumWidth(90)
         self._bookmark_btn.setStyleSheet(_tb_btn_style)
-        self._bookmark_btn.clicked.connect(self.bookmark_requested)
+        self._bookmark_btn.clicked.connect(self._on_bookmark_clicked)
         toolbar.addWidget(self._bookmark_btn)
 
         self._save_btn = QPushButton("Save")
         self._save_btn.setMaximumWidth(70)
         self._save_btn.setStyleSheet(_tb_btn_style)
-        self._save_btn.clicked.connect(self.save_toggle_requested)
+        self._save_btn.clicked.connect(self._on_save_clicked)
         toolbar.addWidget(self._save_btn)
         self._is_saved = False
 
@@ -117,8 +135,11 @@ class FullscreenPreview(QMainWindow):
         toolbar.addWidget(self._bl_post_btn)
 
         if not show_actions:
+            # Library mode: only the Save button stays — it acts as
+            # Unsave for the file currently being viewed. Bookmark and
+            # blacklist actions are meaningless on already-saved local
+            # files (no site/post id to bookmark, no search to filter).
             self._bookmark_btn.hide()
-            self._save_btn.hide()
             self._bl_tag_btn.hide()
             self._bl_post_btn.hide()
 
@@ -238,11 +259,91 @@ class FullscreenPreview(QMainWindow):
             self.blacklist_tag_requested.emit(action.text())
 
     def update_state(self, bookmarked: bool, saved: bool) -> None:
+        self._is_bookmarked = bookmarked
         self._bookmark_btn.setText("Unbookmark" if bookmarked else "Bookmark")
         self._bookmark_btn.setMaximumWidth(90 if bookmarked else 80)
         self._is_saved = saved
         self._save_btn.setText("Unsave" if saved else "Save")
 
+    def set_bookmark_folders_callback(self, callback) -> None:
+        """Wire the bookmark folder list source. Called once from app.py
+        right after the popout is constructed; matches the embedded
+        ImagePreview's set_bookmark_folders_callback shape.
+        """
+        self._bookmark_folders_callback = callback
+
+    def set_folders_callback(self, callback) -> None:
+        """Wire the library folder list source. Called once from app.py
+        right after the popout is constructed; matches the embedded
+        ImagePreview's set_folders_callback shape.
+        """
+        self._folders_callback = callback
+
+    def _on_save_clicked(self) -> None:
+        """Popout Save button — same shape as the embedded preview's
+        version. When already saved, emit unsave_requested for the existing
+        unsave path. When not saved, pop a menu under the button with
+        Unfiled / library folders / + New Folder, then emit the chosen
+        name through save_to_folder. app.py reuses _save_from_preview /
+        _unsave_from_preview to handle both signals.
+        """
+        if self._is_saved:
+            self.unsave_requested.emit()
+            return
+        menu = QMenu(self)
+        unfiled = menu.addAction("Unfiled")
+        menu.addSeparator()
+        folder_actions: dict[int, str] = {}
+        if self._folders_callback:
+            for folder in self._folders_callback():
+                a = menu.addAction(folder)
+                folder_actions[id(a)] = folder
+        menu.addSeparator()
+        new_action = menu.addAction("+ New Folder...")
+        action = menu.exec(self._save_btn.mapToGlobal(self._save_btn.rect().bottomLeft()))
+        if not action:
+            return
+        if action == unfiled:
+            self.save_to_folder.emit("")
+        elif action == new_action:
+            name, ok = QInputDialog.getText(self, "New Folder", "Folder name:")
+            if ok and name.strip():
+                self.save_to_folder.emit(name.strip())
+        elif id(action) in folder_actions:
+            self.save_to_folder.emit(folder_actions[id(action)])
+
+    def _on_bookmark_clicked(self) -> None:
+        """Popout Bookmark button — same shape as the embedded preview's
+        version. When already bookmarked, emits bookmark_requested for the
+        existing toggle/remove path. When not bookmarked, pops a menu under
+        the button with Unfiled / bookmark folders / + New Folder, then
+        emits the chosen name through bookmark_to_folder.
+        """
+        if self._is_bookmarked:
+            self.bookmark_requested.emit()
+            return
+        menu = QMenu(self)
+        unfiled = menu.addAction("Unfiled")
+        menu.addSeparator()
+        folder_actions: dict[int, str] = {}
+        if self._bookmark_folders_callback:
+            for folder in self._bookmark_folders_callback():
+                a = menu.addAction(folder)
+                folder_actions[id(a)] = folder
+        menu.addSeparator()
+        new_action = menu.addAction("+ New Folder...")
+        action = menu.exec(self._bookmark_btn.mapToGlobal(self._bookmark_btn.rect().bottomLeft()))
+        if not action:
+            return
+        if action == unfiled:
+            self.bookmark_to_folder.emit("")
+        elif action == new_action:
+            name, ok = QInputDialog.getText(self, "New Bookmark Folder", "Folder name:")
+            if ok and name.strip():
+                self.bookmark_to_folder.emit(name.strip())
+        elif id(action) in folder_actions:
+            self.bookmark_to_folder.emit(folder_actions[id(action)])
+
     def set_media(self, path: str, info: str = "") -> None:
         self._info_label.setText(info)
         ext = Path(path).suffix.lower()
@@ -1293,6 +1394,10 @@ class ImagePreview(QWidget):
     save_to_folder = Signal(str)
     unsave_requested = Signal()
     bookmark_requested = Signal()
+    # Bookmark-as: emitted when the user picks a bookmark folder from
+    # the toolbar's Bookmark button submenu. Empty string = Unfiled.
+    # Mirrors save_to_folder's shape so app.py can route it the same way.
+    bookmark_to_folder = Signal(str)
     blacklist_tag_requested = Signal(str)
     blacklist_post_requested = Signal()
     navigate = Signal(int)  # -1 = prev, +1 = next
@@ -1302,10 +1407,15 @@ class ImagePreview(QWidget):
     def __init__(self, parent: QWidget | None = None) -> None:
         super().__init__(parent)
         self._folders_callback = None
+        # Bookmark folders live in a separate name space (DB-backed); the
+        # toolbar Bookmark-as submenu reads them via this callback so the
+        # preview widget stays decoupled from the Database object.
+        self._bookmark_folders_callback = None
         self._current_path: str | None = None
         self._current_post = None  # Post object, set by app.py
         self._current_site_id = None  # site_id for the current post
         self._is_saved = False  # tracks library save state for context menu
+        self._is_bookmarked = False  # tracks bookmark state for the button submenu
         self._current_tags: dict[str, list[str]] = {}
         self._current_tag_list: list[str] = []
 
@@ -1333,11 +1443,14 @@ class ImagePreview(QWidget):
         self._bookmark_btn = QPushButton("Bookmark")
         self._bookmark_btn.setFixedWidth(100)
         self._bookmark_btn.setStyleSheet(_tb_btn_style)
-        self._bookmark_btn.clicked.connect(self.bookmark_requested)
+        self._bookmark_btn.clicked.connect(self._on_bookmark_clicked)
         tb.addWidget(self._bookmark_btn)
 
         self._save_btn = QPushButton("Save")
-        self._save_btn.setFixedWidth(60)
+        # 75 fits "Unsave" (6 chars) cleanly across every bundled theme.
+        # The previous 60 was tight enough that some themes clipped the
+        # last character on library files where the label flips to Unsave.
+        self._save_btn.setFixedWidth(75)
         self._save_btn.setStyleSheet(_tb_btn_style)
         self._save_btn.clicked.connect(self._on_save_clicked)
         tb.addWidget(self._save_btn)
@@ -1429,12 +1542,48 @@ class ImagePreview(QWidget):
         if action:
             self.blacklist_tag_requested.emit(action.text())
 
+    def _on_bookmark_clicked(self) -> None:
+        """Toolbar Bookmark button — mirrors the browse-tab Bookmark-as
+        submenu so the preview pane has the same one-click filing flow.
+
+        When the post is already bookmarked, the button collapses to a
+        flat unbookmark action (emits the same signal as before, the
+        existing toggle in app.py handles the removal). When not yet
+        bookmarked, a popup menu lets the user pick the destination
+        bookmark folder — the chosen name is sent through bookmark_to_folder
+        and app.py adds the folder + creates the bookmark.
+        """
+        if self._is_bookmarked:
+            self.bookmark_requested.emit()
+            return
+        menu = QMenu(self)
+        unfiled = menu.addAction("Unfiled")
+        menu.addSeparator()
+        folder_actions: dict[int, str] = {}
+        if self._bookmark_folders_callback:
+            for folder in self._bookmark_folders_callback():
+                a = menu.addAction(folder)
+                folder_actions[id(a)] = folder
+        menu.addSeparator()
+        new_action = menu.addAction("+ New Folder...")
+        action = menu.exec(self._bookmark_btn.mapToGlobal(self._bookmark_btn.rect().bottomLeft()))
+        if not action:
+            return
+        if action == unfiled:
+            self.bookmark_to_folder.emit("")
+        elif action == new_action:
+            name, ok = QInputDialog.getText(self, "New Bookmark Folder", "Folder name:")
+            if ok and name.strip():
+                self.bookmark_to_folder.emit(name.strip())
+        elif id(action) in folder_actions:
+            self.bookmark_to_folder.emit(folder_actions[id(action)])
+
     def _on_save_clicked(self) -> None:
         if self._save_btn.text() == "Unsave":
             self.unsave_requested.emit()
             return
         menu = QMenu(self)
-        unsorted = menu.addAction("Unsorted")
+        unsorted = menu.addAction("Unfiled")
         menu.addSeparator()
         folder_actions = {}
         if self._folders_callback:
@@ -1456,6 +1605,7 @@ class ImagePreview(QWidget):
             self.save_to_folder.emit(folder_actions[id(action)])
 
     def update_bookmark_state(self, bookmarked: bool) -> None:
+        self._is_bookmarked = bookmarked
         self._bookmark_btn.setText("Unbookmark" if bookmarked else "Bookmark")
         self._bookmark_btn.setFixedWidth(90 if bookmarked else 80)
 
@@ -1477,6 +1627,13 @@ class ImagePreview(QWidget):
     def set_folders_callback(self, callback) -> None:
         self._folders_callback = callback
 
+    def set_bookmark_folders_callback(self, callback) -> None:
+        """Wire the bookmark folder list source. Called once from app.py
+        with self._db.get_folders. Kept separate from set_folders_callback
+        because library and bookmark folders are independent name spaces.
+        """
+        self._bookmark_folders_callback = callback
+
     def set_image(self, pixmap: QPixmap, info: str = "") -> None:
         self._video_player.stop()
         self._image_viewer.set_image(pixmap, info)
@@ -1523,7 +1680,7 @@ class ImagePreview(QWidget):
         fav_action = menu.addAction("Bookmark")
 
         save_menu = menu.addMenu("Save to Library")
-        save_unsorted = save_menu.addAction("Unsorted")
+        save_unsorted = save_menu.addAction("Unfiled")
         save_menu.addSeparator()
         save_folder_actions = {}
         if self._folders_callback: