clipsy 1.8.0__tar.gz → 1.9.0__tar.gz

{clipsy-1.8.0/src/clipsy.egg-info → clipsy-1.9.0}/PKG-INFO

@@ -1,6 +1,6 @@
 Metadata-Version: 2.4
 Name: clipsy
-Version: 1.8.0
+Version: 1.9.0
 Summary: Lightweight clipboard history manager for macOS
 Author-email: Brendan Conrad <brendan.conrad@gmail.com>
 License: MIT
@@ -46,6 +46,8 @@ A lightweight clipboard history manager for macOS. Runs as a menu bar icon — n
 - **Image thumbnails** — Visual previews for copied images in the menu
 - **Sensitive data masking** — Auto-detects API keys, passwords, SSNs, credit cards, private keys, and tokens; displays masked previews with 🔒 icon
 - **Search** — Full-text search across all clipboard entries (SQLite FTS5)
+- **Rich text preservation** — Preserves RTF and HTML formatting when re-copying from history (e.g., bold, italic, links from web pages)
+- **Pin favorites** — Option-click to pin up to 5 frequently-used snippets (sensitive data cannot be pinned)
 - **Click to re-copy** — Click any entry in the menu to put it back on your clipboard
 - **Deduplication** — Copying the same content twice bumps it to the top instead of creating a duplicate
 - **Auto-purge** — Keeps the most recent 500 entries, automatically cleans up old ones
@@ -103,11 +105,15 @@ Then just use your Mac normally. Every time you copy something, it shows up in t
 ├── ──────────────────
 ├── Search...
 ├── ──────────────────
+├── 📌 Pinned ►
+│   ├── "my-api-endpoint.com/v1..."
+│   └── "SELECT * FROM users..."
+├── ──────────────────
 ├── "Meeting notes for Q3 plan..."
 ├── "https://github.com/example..."
 ├── 🔒 "password=••••••••"
 ├── [thumbnail] "[Image: 1920x1080]"
-├── ... (up to 10 items)
+├── ... (up to 10 items, configurable)
 ├── ──────────────────
 ├── Clear History
 ├── ──────────────────
@@ -116,6 +122,8 @@ Then just use your Mac normally. Every time you copy something, it shows up in t
 └── Quit Clipsy
 ```
 
+**Tip:** Hold **Option (⌥)** while clicking an entry to pin/unpin it.
+
 ## Commands
 
 ```bash
@@ -125,6 +133,17 @@ clipsy uninstall  # Remove from login items
 clipsy run        # Run in foreground (for debugging)
 ```
 
+## Configuration
+
+| Variable | Default | Range | Description |
+|----------|---------|-------|-------------|
+| `CLIPSY_MENU_DISPLAY_COUNT` | `10` | 5–50 | Number of entries shown in the menu |
+
+```bash
+# Example: show 20 entries in the menu
+export CLIPSY_MENU_DISPLAY_COUNT=20
+```
+
 ## Data Storage
 
 All data is stored in `~/.local/share/clipsy/`:

{clipsy-1.8.0 → clipsy-1.9.0}/README.md

@@ -15,6 +15,8 @@ A lightweight clipboard history manager for macOS. Runs as a menu bar icon — n
 - **Image thumbnails** — Visual previews for copied images in the menu
 - **Sensitive data masking** — Auto-detects API keys, passwords, SSNs, credit cards, private keys, and tokens; displays masked previews with 🔒 icon
 - **Search** — Full-text search across all clipboard entries (SQLite FTS5)
+- **Rich text preservation** — Preserves RTF and HTML formatting when re-copying from history (e.g., bold, italic, links from web pages)
+- **Pin favorites** — Option-click to pin up to 5 frequently-used snippets (sensitive data cannot be pinned)
 - **Click to re-copy** — Click any entry in the menu to put it back on your clipboard
 - **Deduplication** — Copying the same content twice bumps it to the top instead of creating a duplicate
 - **Auto-purge** — Keeps the most recent 500 entries, automatically cleans up old ones
@@ -72,11 +74,15 @@ Then just use your Mac normally. Every time you copy something, it shows up in t
 ├── ──────────────────
 ├── Search...
 ├── ──────────────────
+├── 📌 Pinned ►
+│   ├── "my-api-endpoint.com/v1..."
+│   └── "SELECT * FROM users..."
+├── ──────────────────
 ├── "Meeting notes for Q3 plan..."
 ├── "https://github.com/example..."
 ├── 🔒 "password=••••••••"
 ├── [thumbnail] "[Image: 1920x1080]"
-├── ... (up to 10 items)
+├── ... (up to 10 items, configurable)
 ├── ──────────────────
 ├── Clear History
 ├── ──────────────────
@@ -85,6 +91,8 @@ Then just use your Mac normally. Every time you copy something, it shows up in t
 └── Quit Clipsy
 ```
 
+**Tip:** Hold **Option (⌥)** while clicking an entry to pin/unpin it.
+
 ## Commands
 
 ```bash
@@ -94,6 +102,17 @@ clipsy uninstall  # Remove from login items
 clipsy run        # Run in foreground (for debugging)
 ```
 
+## Configuration
+
+| Variable | Default | Range | Description |
+|----------|---------|-------|-------------|
+| `CLIPSY_MENU_DISPLAY_COUNT` | `10` | 5–50 | Number of entries shown in the menu |
+
+```bash
+# Example: show 20 entries in the menu
+export CLIPSY_MENU_DISPLAY_COUNT=20
+```
+
 ## Data Storage
 
 All data is stored in `~/.local/share/clipsy/`:

{clipsy-1.8.0 → clipsy-1.9.0}/pyproject.toml

@@ -4,7 +4,7 @@ build-backend = "setuptools.build_meta"
 
 [project]
 name = "clipsy"
-version = "1.8.0"
+version = "1.9.0"
 description = "Lightweight clipboard history manager for macOS"
 readme = "README.md"
 license = {text = "MIT"}

{clipsy-1.8.0 → clipsy-1.9.0}/src/clipsy/__init__.py

@@ -1,2 +1,2 @@
-__version__ = "1.8.0"
+__version__ = "1.9.0"
 __app_name__ = "Clipsy"

{clipsy-1.8.0 → clipsy-1.9.0}/src/clipsy/app.py

@@ -5,7 +5,7 @@ from pathlib import Path
 import rumps
 
 from clipsy import __version__
-from clipsy.config import DB_PATH, IMAGE_DIR, MENU_DISPLAY_COUNT, POLL_INTERVAL, REDACT_SENSITIVE, THUMBNAIL_SIZE
+from clipsy.config import DB_PATH, IMAGE_DIR, MAX_PINNED_ENTRIES, MENU_DISPLAY_COUNT, POLL_INTERVAL, REDACT_SENSITIVE, THUMBNAIL_SIZE
 from clipsy.models import ClipboardEntry, ContentType
 from clipsy.monitor import ClipboardMonitor
 from clipsy.storage import StorageManager
@@ -34,10 +34,24 @@ class ClipsyApp(rumps.App):
             None,  # separator
         ]
 
-        entries = self._storage.get_recent(limit=MENU_DISPLAY_COUNT)
         self._entry_ids.clear()
 
-        if not entries:
+        # Add pinned submenu if there are pinned entries
+        pinned_entries = self._storage.get_pinned()
+        if pinned_entries:
+            pinned_menu = rumps.MenuItem("📌 Pinned")
+            for entry in pinned_entries:
+                pinned_menu.add(self._create_entry_menu_item(entry))
+            pinned_menu.add(None)  # separator
+            pinned_menu.add(rumps.MenuItem("Clear Pinned", callback=self._on_clear_pinned))
+            self.menu.add(pinned_menu)
+            self.menu.add(None)  # separator
+
+        entries = self._storage.get_recent(limit=MENU_DISPLAY_COUNT)
+        # Filter out pinned entries from recent list
+        entries = [e for e in entries if not e.pinned]
+
+        if not entries and not pinned_entries:
             self.menu.add(rumps.MenuItem("(No clipboard history)", callback=None))
         else:
             for entry in entries:
@@ -118,6 +132,17 @@ class ClipsyApp(rumps.App):
         if entry is None:
             return
 
+        # Check if Option key is held (for pin toggle)
+        try:
+            from AppKit import NSAlternateKeyMask, NSEvent
+
+            modifier_flags = NSEvent.modifierFlags()
+            if modifier_flags & NSAlternateKeyMask:
+                self._on_pin_toggle(entry)
+                return
+        except Exception:
+            pass  # If we can't check modifiers, proceed with normal copy
+
         try:
             from AppKit import NSPasteboard, NSPasteboardTypePNG, NSPasteboardTypeString
             from Foundation import NSData
@@ -161,6 +186,32 @@ class ClipsyApp(rumps.App):
         except Exception:
             logger.exception("Error copying entry to clipboard")
 
+    def _on_pin_toggle(self, entry: ClipboardEntry) -> None:
+        """Toggle pin status for an entry."""
+        if entry.pinned:
+            # Unpin
+            self._storage.toggle_pin(entry.id)
+            rumps.notification("Clipsy", "", "Unpinned", sound=False)
+        else:
+            # Check if we can pin (not sensitive, under limit)
+            if entry.is_sensitive:
+                rumps.notification("Clipsy", "", "Cannot pin sensitive data", sound=False)
+                return
+
+            if self._storage.count_pinned() >= MAX_PINNED_ENTRIES:
+                rumps.notification("Clipsy", "", f"Maximum {MAX_PINNED_ENTRIES} pinned items", sound=False)
+                return
+
+            self._storage.toggle_pin(entry.id)
+            rumps.notification("Clipsy", "", "Pinned", sound=False)
+
+        self._refresh_menu()
+
+    def _on_clear_pinned(self, _sender) -> None:
+        """Clear all pinned entries."""
+        self._storage.clear_pinned()
+        self._refresh_menu()
+
     def _on_search(self, _sender) -> None:
         response = rumps.Window(
             message="Search clipboard history:",

{clipsy-1.8.0 → clipsy-1.9.0}/src/clipsy/config.py

@@ -25,3 +25,4 @@ def _parse_menu_display_count() -> int:
 MENU_DISPLAY_COUNT = _parse_menu_display_count()
 THUMBNAIL_SIZE = (32, 32)  # pixels, for menu icon display
 REDACT_SENSITIVE = True  # mask sensitive data in preview (API keys, passwords, etc.)
+MAX_PINNED_ENTRIES = 5  # maximum number of pinned entries allowed

{clipsy-1.8.0 → clipsy-1.9.0}/src/clipsy/storage.py

@@ -211,6 +211,21 @@ class StorageManager:
         row = self._conn.execute("SELECT COUNT(*) as cnt FROM clipboard_entries").fetchone()
         return row["cnt"]
 
+    def get_pinned(self) -> list[ClipboardEntry]:
+        rows = self._conn.execute(
+            "SELECT * FROM clipboard_entries WHERE pinned = 1 ORDER BY created_at DESC"
+        ).fetchall()
+        return [self._row_to_entry(r) for r in rows]
+
+    def count_pinned(self) -> int:
+        row = self._conn.execute("SELECT COUNT(*) as cnt FROM clipboard_entries WHERE pinned = 1").fetchone()
+        return row["cnt"]
+
+    def clear_pinned(self) -> None:
+        """Unpin all pinned entries."""
+        self._conn.execute("UPDATE clipboard_entries SET pinned = 0 WHERE pinned = 1")
+        self._conn.commit()
+
     def close(self) -> None:
         self._conn.close()
 

{clipsy-1.8.0 → clipsy-1.9.0/src/clipsy.egg-info}/PKG-INFO

@@ -1,6 +1,6 @@
 Metadata-Version: 2.4
 Name: clipsy
-Version: 1.8.0
+Version: 1.9.0
 Summary: Lightweight clipboard history manager for macOS
 Author-email: Brendan Conrad <brendan.conrad@gmail.com>
 License: MIT
@@ -46,6 +46,8 @@ A lightweight clipboard history manager for macOS. Runs as a menu bar icon — n
 - **Image thumbnails** — Visual previews for copied images in the menu
 - **Sensitive data masking** — Auto-detects API keys, passwords, SSNs, credit cards, private keys, and tokens; displays masked previews with 🔒 icon
 - **Search** — Full-text search across all clipboard entries (SQLite FTS5)
+- **Rich text preservation** — Preserves RTF and HTML formatting when re-copying from history (e.g., bold, italic, links from web pages)
+- **Pin favorites** — Option-click to pin up to 5 frequently-used snippets (sensitive data cannot be pinned)
 - **Click to re-copy** — Click any entry in the menu to put it back on your clipboard
 - **Deduplication** — Copying the same content twice bumps it to the top instead of creating a duplicate
 - **Auto-purge** — Keeps the most recent 500 entries, automatically cleans up old ones
@@ -103,11 +105,15 @@ Then just use your Mac normally. Every time you copy something, it shows up in t
 ├── ──────────────────
 ├── Search...
 ├── ──────────────────
+├── 📌 Pinned ►
+│   ├── "my-api-endpoint.com/v1..."
+│   └── "SELECT * FROM users..."
+├── ──────────────────
 ├── "Meeting notes for Q3 plan..."
 ├── "https://github.com/example..."
 ├── 🔒 "password=••••••••"
 ├── [thumbnail] "[Image: 1920x1080]"
-├── ... (up to 10 items)
+├── ... (up to 10 items, configurable)
 ├── ──────────────────
 ├── Clear History
 ├── ──────────────────
@@ -116,6 +122,8 @@ Then just use your Mac normally. Every time you copy something, it shows up in t
 └── Quit Clipsy
 ```
 
+**Tip:** Hold **Option (⌥)** while clicking an entry to pin/unpin it.
+
 ## Commands
 
 ```bash
@@ -125,6 +133,17 @@ clipsy uninstall  # Remove from login items
 clipsy run        # Run in foreground (for debugging)
 ```
 
+## Configuration
+
+| Variable | Default | Range | Description |
+|----------|---------|-------|-------------|
+| `CLIPSY_MENU_DISPLAY_COUNT` | `10` | 5–50 | Number of entries shown in the menu |
+
+```bash
+# Example: show 20 entries in the menu
+export CLIPSY_MENU_DISPLAY_COUNT=20
+```
+
 ## Data Storage
 
 All data is stored in `~/.local/share/clipsy/`:

{clipsy-1.8.0 → clipsy-1.9.0}/tests/test_app.py

@@ -238,3 +238,80 @@ class TestRichTextRestoration:
         assert entry.rtf_data is None
         assert entry.html_data is None
         assert entry.text_content == "plain text"
+
+
+class TestPinningBehavior:
+    """Test pinning-related behavior at the app level."""
+
+    def test_pinned_entries_not_in_recent_list(self, storage, make_entry):
+        id1 = storage.add_entry(make_entry("pinned entry", content_hash="h1"))
+        id2 = storage.add_entry(make_entry("regular entry", content_hash="h2"))
+        storage.toggle_pin(id1)
+
+        recent = storage.get_recent()
+        pinned = storage.get_pinned()
+
+        # Filter recent like app.py does
+        recent_unpinned = [e for e in recent if not e.pinned]
+
+        assert len(pinned) == 1
+        assert pinned[0].id == id1
+        assert all(e.id != id1 for e in recent_unpinned)
+
+    def test_cannot_pin_sensitive_entry(self, storage, make_entry):
+        from clipsy.models import ClipboardEntry, ContentType
+        from datetime import datetime
+
+        sensitive_entry = ClipboardEntry(
+            id=None,
+            content_type=ContentType.TEXT,
+            text_content="password=secret123",
+            image_path=None,
+            preview="password=secret123",
+            content_hash="sensitive_hash",
+            byte_size=20,
+            created_at=datetime.now(),
+            is_sensitive=True,
+            masked_preview="password=••••••••",
+        )
+        entry_id = storage.add_entry(sensitive_entry)
+        entry = storage.get_entry(entry_id)
+
+        # The entry is sensitive
+        assert entry.is_sensitive is True
+
+        # Simulate app-level check: sensitive entries should not be pinned
+        # This mimics what _on_pin_toggle does
+        if entry.is_sensitive:
+            can_pin = False
+        else:
+            can_pin = True
+
+        assert can_pin is False
+
+    def test_max_pinned_limit(self, storage, make_entry):
+        from clipsy.config import MAX_PINNED_ENTRIES
+
+        # Pin up to the limit
+        for i in range(MAX_PINNED_ENTRIES):
+            entry_id = storage.add_entry(make_entry(f"entry {i}", content_hash=f"hash_{i}"))
+            storage.toggle_pin(entry_id)
+
+        assert storage.count_pinned() == MAX_PINNED_ENTRIES
+
+        # App should check this before allowing another pin
+        at_limit = storage.count_pinned() >= MAX_PINNED_ENTRIES
+        assert at_limit is True
+
+    def test_clear_pinned_clears_all(self, storage, make_entry):
+        id1 = storage.add_entry(make_entry("entry 1", content_hash="h1"))
+        id2 = storage.add_entry(make_entry("entry 2", content_hash="h2"))
+        storage.toggle_pin(id1)
+        storage.toggle_pin(id2)
+
+        assert storage.count_pinned() == 2
+
+        storage.clear_pinned()
+
+        assert storage.count_pinned() == 0
+        assert storage.get_pinned() == []

{clipsy-1.8.0 → clipsy-1.9.0}/tests/test_monitor.py

@@ -1,3 +1,6 @@
+import importlib
+import sys
+import types as stdlib_types
 from unittest.mock import MagicMock, patch
 
 import pytest
@@ -82,6 +85,29 @@ class TestCheckClipboard:
         assert monitor.check_clipboard() is False
         assert storage.count() == 0
 
+    def test_empty_text_returns_no_entry(self, monitor, mock_pasteboard, storage):
+        mock_pasteboard.changeCount.return_value = 1
+        mock_pasteboard.types.return_value = ["public.utf8-plain-text"]
+        mock_pasteboard.stringForType_.return_value = ""
+
+        with patch("clipsy.monitor.NSPasteboardTypeString", "public.utf8-plain-text"):
+            assert monitor.check_clipboard() is False
+
+        assert storage.count() == 0
+
+    def test_oversized_text_skipped(self, monitor, mock_pasteboard, storage):
+        mock_pasteboard.changeCount.return_value = 1
+        mock_pasteboard.types.return_value = ["public.utf8-plain-text"]
+        mock_pasteboard.stringForType_.return_value = "x" * 2_000_000
+
+        with (
+            patch("clipsy.monitor.NSPasteboardTypeString", "public.utf8-plain-text"),
+            patch("clipsy.monitor.MAX_TEXT_SIZE", 1_000_000),
+        ):
+            assert monitor.check_clipboard() is False
+
+        assert storage.count() == 0
+
     def test_none_types_no_crash(self, monitor, mock_pasteboard):
         mock_pasteboard.changeCount.return_value = 1
         mock_pasteboard.types.return_value = None
@@ -108,6 +134,21 @@ class TestFileClipboard:
         assert entries[0].content_type == ContentType.FILE
         assert "document.pdf" in entries[0].preview
 
+    def test_empty_filenames_returns_no_entry(self, monitor, mock_pasteboard, storage):
+        mock_pasteboard.changeCount.return_value = 1
+        mock_pasteboard.types.return_value = ["NSFilenamesPboardType"]
+        mock_pasteboard.propertyListForType_.return_value = None
+
+        with (
+            patch("clipsy.monitor.NSPasteboardTypeString", "public.utf8-plain-text"),
+            patch("clipsy.monitor.NSPasteboardTypePNG", "public.png"),
+            patch("clipsy.monitor.NSPasteboardTypeTIFF", "public.tiff"),
+            patch("clipsy.monitor.NSFilenamesPboardType", "NSFilenamesPboardType"),
+        ):
+            assert monitor.check_clipboard() is False
+
+        assert storage.count() == 0
+
     def test_multiple_files(self, monitor, mock_pasteboard, storage):
         mock_pasteboard.changeCount.return_value = 1
         mock_pasteboard.types.return_value = ["NSFilenamesPboardType"]
@@ -470,3 +511,29 @@ class TestRichTextClipboard:
         entries = storage.get_recent()
         assert len(entries) == 1
         assert entries[0].rtf_data is None
+
+
+class TestImportFallbacks:
+    def test_rtf_and_html_import_fallback(self):
+        import clipsy.monitor as monitor_mod
+
+        real_appkit = sys.modules["AppKit"]
+
+        fake_appkit = stdlib_types.ModuleType("AppKit")
+        for attr in (
+            "NSPasteboard",
+            "NSPasteboardTypePNG",
+            "NSPasteboardTypeTIFF",
+            "NSPasteboardTypeString",
+            "NSFilenamesPboardType",
+        ):
+            setattr(fake_appkit, attr, getattr(real_appkit, attr))
+
+        try:
+            sys.modules["AppKit"] = fake_appkit
+            importlib.reload(monitor_mod)
+            assert monitor_mod.NSPasteboardTypeRTF == "public.rtf"
+            assert monitor_mod.NSPasteboardTypeHTML == "public.html"
+        finally:
+            sys.modules["AppKit"] = real_appkit
+            importlib.reload(monitor_mod)

{clipsy-1.8.0 → clipsy-1.9.0}/tests/test_storage.py

@@ -389,6 +389,74 @@ class TestRichTextEntries:
         assert results[0].rtf_data == rtf_bytes
 
 
+class TestPinnedEntries:
+    def test_get_pinned_empty(self, storage):
+        assert storage.get_pinned() == []
+
+    def test_get_pinned_returns_pinned_entries(self, storage, make_entry):
+        id1 = storage.add_entry(make_entry("entry 1"))
+        id2 = storage.add_entry(make_entry("entry 2", content_hash="hash2"))
+        storage.toggle_pin(id1)
+
+        pinned = storage.get_pinned()
+        assert len(pinned) == 1
+        assert pinned[0].id == id1
+        assert pinned[0].pinned is True
+
+    def test_count_pinned(self, storage, make_entry):
+        assert storage.count_pinned() == 0
+
+        id1 = storage.add_entry(make_entry("entry 1"))
+        id2 = storage.add_entry(make_entry("entry 2", content_hash="hash2"))
+        storage.toggle_pin(id1)
+        storage.toggle_pin(id2)
+
+        assert storage.count_pinned() == 2
+
+    def test_toggle_pin_on_and_off(self, storage, make_entry):
+        entry_id = storage.add_entry(make_entry("test"))
+
+        # Pin
+        result = storage.toggle_pin(entry_id)
+        assert result is True
+        assert storage.get_entry(entry_id).pinned is True
+
+        # Unpin
+        result = storage.toggle_pin(entry_id)
+        assert result is False
+        assert storage.get_entry(entry_id).pinned is False
+
+    def test_pinned_entries_ordered_by_created_at(self, storage, make_entry):
+        import time
+
+        id1 = storage.add_entry(make_entry("older", content_hash="h1"))
+        time.sleep(0.01)
+        id2 = storage.add_entry(make_entry("newer", content_hash="h2"))
+        storage.toggle_pin(id1)
+        storage.toggle_pin(id2)
+
+        pinned = storage.get_pinned()
+        assert len(pinned) == 2
+        assert pinned[0].id == id2  # newer first
+        assert pinned[1].id == id1
+
+    def test_clear_pinned(self, storage, make_entry):
+        id1 = storage.add_entry(make_entry("entry 1"))
+        id2 = storage.add_entry(make_entry("entry 2", content_hash="hash2"))
+        id3 = storage.add_entry(make_entry("entry 3", content_hash="hash3"))
+        storage.toggle_pin(id1)
+        storage.toggle_pin(id2)
+
+        assert storage.count_pinned() == 2
+
+        storage.clear_pinned()
+
+        assert storage.count_pinned() == 0
+        assert storage.get_entry(id1).pinned is False
+        assert storage.get_entry(id2).pinned is False
+        assert storage.get_entry(id3).pinned is False  # was never pinned
+
+
 class TestRichTextMigration:
     def test_migrate_adds_rtf_and_html_columns(self, tmp_path):
         """Test that migration adds rtf_data and html_data to old databases."""

{clipsy-1.8.0 → clipsy-1.9.0}/tests/test_utils.py

@@ -148,3 +148,66 @@ class TestCreateThumbnail:
         # Thumbnail should be a valid PNG
         thumb_data = thumb_file.read_bytes()
         assert thumb_data.startswith(b"\x89PNG")
+
+    def test_tiff_representation_fails(self, tmp_path):
+        mock_original = MagicMock()
+        mock_resized = MagicMock()
+        mock_resized.TIFFRepresentation.return_value = None
+
+        mock_nsimage_cls = MagicMock()
+        mock_nsimage_cls.alloc.return_value.initWithContentsOfFile_.return_value = mock_original
+        mock_nsimage_cls.alloc.return_value.initWithSize_.return_value = mock_resized
+
+        with patch.dict("sys.modules", {"AppKit": MagicMock(NSImage=mock_nsimage_cls)}):
+            result = create_thumbnail("/fake.png", str(tmp_path / "thumb.png"))
+
+        assert result is False
+
+    def test_bitmap_rep_fails(self, tmp_path):
+        mock_original = MagicMock()
+        mock_resized = MagicMock()
+        mock_resized.TIFFRepresentation.return_value = MagicMock()
+
+        mock_nsimage_cls = MagicMock()
+        mock_nsimage_cls.alloc.return_value.initWithContentsOfFile_.return_value = mock_original
+        mock_nsimage_cls.alloc.return_value.initWithSize_.return_value = mock_resized
+
+        mock_bitmap_cls = MagicMock()
+        mock_bitmap_cls.imageRepWithData_.return_value = None
+
+        with patch.dict("sys.modules", {"AppKit": MagicMock(NSImage=mock_nsimage_cls, NSBitmapImageRep=mock_bitmap_cls)}):
+            result = create_thumbnail("/fake.png", str(tmp_path / "thumb.png"))
+
+        assert result is False
+
+    def test_png_data_fails(self, tmp_path):
+        mock_original = MagicMock()
+        mock_resized = MagicMock()
+        mock_resized.TIFFRepresentation.return_value = MagicMock()
+
+        mock_bitmap_rep = MagicMock()
+        mock_bitmap_rep.representationUsingType_properties_.return_value = None
+
+        mock_nsimage_cls = MagicMock()
+        mock_nsimage_cls.alloc.return_value.initWithContentsOfFile_.return_value = mock_original
+        mock_nsimage_cls.alloc.return_value.initWithSize_.return_value = mock_resized
+
+        mock_bitmap_cls = MagicMock()
+        mock_bitmap_cls.imageRepWithData_.return_value = mock_bitmap_rep
+
+        with patch.dict("sys.modules", {"AppKit": MagicMock(NSImage=mock_nsimage_cls, NSBitmapImageRep=mock_bitmap_cls)}):
+            result = create_thumbnail("/fake.png", str(tmp_path / "thumb.png"))
+
+        assert result is False
+
+    def test_exception_returns_false(self, tmp_path):
+        mock_original = MagicMock()
+        mock_original.drawInRect_.side_effect = RuntimeError("boom")
+
+        mock_nsimage_cls = MagicMock()
+        mock_nsimage_cls.alloc.return_value.initWithContentsOfFile_.return_value = mock_original
+
+        with patch.dict("sys.modules", {"AppKit": MagicMock(NSImage=mock_nsimage_cls)}):
+            result = create_thumbnail("/fake.png", str(tmp_path / "thumb.png"))
+
+        assert result is False