refactor: extract _detect_file_drop() + add 28 tests

Extract the inline file-drop detection logic into a standalone
_detect_file_drop() function at module level for testability. The main
loop now calls this function instead of inlining the logic.

Tests cover:
- Slash commands still route correctly (/help, /quit, /xyz)
- Image paths auto-detected (.png, .jpg, .gif, etc.)
- Non-image files detected (.py, .txt, Makefile, etc.)
- Backslash-escaped spaces from macOS drag-and-drop
- Trailing user text preserved as remainder
- Edge cases: directories, symlinks, no-extension files
- Non-string input, empty strings, nonexistent paths

cli.py

@@ -830,6 +830,63 @@ def _cprint(text: str):
     _pt_print(_PT_ANSI(text))
 
 
+# ---------------------------------------------------------------------------
+# File-drop detection — extracted as a pure function for testability.
+# ---------------------------------------------------------------------------
+
+_IMAGE_EXTENSIONS = frozenset({
+    '.png', '.jpg', '.jpeg', '.gif', '.webp',
+    '.bmp', '.tiff', '.tif', '.svg', '.ico',
+})
+
+
+def _detect_file_drop(user_input: str) -> "dict | None":
+    """Detect if *user_input* is a dragged/pasted file path, not a slash command.
+
+    When a user drags a file into the terminal, macOS pastes the absolute path
+    (e.g. ``/Users/roland/Desktop/file.png``) which starts with ``/`` and would
+    otherwise be mistaken for a slash command.
+
+    Returns a dict on match::
+
+        {
+            "path": Path,          # resolved file path
+            "is_image": bool,      # True when suffix is a known image type
+            "remainder": str,      # any text after the path
+        }
+
+    Returns ``None`` when the input is not a real file path.
+    """
+    if not isinstance(user_input, str) or not user_input.startswith("/"):
+        return None
+
+    # Walk the string absorbing backslash-escaped spaces ("\ ").
+    raw = user_input
+    pos = 0
+    while pos < len(raw):
+        ch = raw[pos]
+        if ch == '\\' and pos + 1 < len(raw) and raw[pos + 1] == ' ':
+            pos += 2  # skip escaped space
+        elif ch == ' ':
+            break
+        else:
+            pos += 1
+
+    first_token_raw = raw[:pos]
+    first_token = first_token_raw.replace('\\ ', ' ')
+    drop_path = Path(first_token)
+
+    if not drop_path.exists() or not drop_path.is_file():
+        return None
+
+    remainder = raw[pos:].strip()
+    return {
+        "path": drop_path,
+        "is_image": drop_path.suffix.lower() in _IMAGE_EXTENSIONS,
+        "remainder": remainder,
+    }
+
+
 class ChatConsole:
     """Rich Console adapter for prompt_toolkit's patch_stdout context.
 
@@ -7556,48 +7613,23 @@ class HermesCLI:
                         user_input, submit_images = user_input
                     
                     # Check for commands — but detect dragged/pasted file paths first.
-                    # When a user drags a file into the terminal, macOS pastes the
+                    # See _detect_file_drop() for details.
-                    # absolute path (e.g. /Users/roland/Desktop/file.png) which
+                    _file_drop = _detect_file_drop(user_input) if isinstance(user_input, str) else None
-                    # starts with "/" and would otherwise be mistaken for a slash
+                    if _file_drop:
-                    # command.  We detect this by checking if the first token is a
+                        _drop_path = _file_drop["path"]
-                    # real filesystem path.
+                        _remainder = _file_drop["remainder"]
-                    _is_file_drop = False
+                        if _file_drop["is_image"]:
-                    if isinstance(user_input, str) and user_input.startswith("/"):
+                            submit_images.append(_drop_path)
-                        # Extract the first whitespace-delimited token as a path candidate.
+                            user_input = _remainder or f"[User attached image: {_drop_path.name}]"
-                        # Dragged paths may have backslash-escaped spaces, so also try
+                            _cprint(f"  📎 Auto-attached image: {_drop_path.name}")
-                        # unescaping.  Walk forward absorbing "\ " sequences.
+                        else:
-                        _raw = user_input
+                            _cprint(f"  📄 Detected file: {_drop_path.name}")
-                        _pos = 0
+                            user_input = (
-                        while _pos < len(_raw):
+                                f"[User attached file: {_drop_path}]"
-                            ch = _raw[_pos]
+                                + (f"\n{_remainder}" if _remainder else "")
-                            if ch == '\\' and _pos + 1 < len(_raw) and _raw[_pos + 1] == ' ':
+                            )
-                                _pos += 2  # skip escaped space
-                            elif ch == ' ':
-                                break
-                            else:
-                                _pos += 1
-                        _first_token_raw = _raw[:_pos]
-                        _first_token = _first_token_raw.replace('\\ ', ' ')
-                        _drop_path = Path(_first_token)
-                        if _drop_path.exists() and _drop_path.is_file():
-                            _is_file_drop = True
-                            _IMAGE_EXTS = {'.png', '.jpg', '.jpeg', '.gif', '.webp',
-                                           '.bmp', '.tiff', '.tif', '.svg', '.ico'}
-                            _remainder = _raw[_pos:].strip()
-                            if _drop_path.suffix.lower() in _IMAGE_EXTS:
-                                submit_images.append(_drop_path)
-                                user_input = _remainder or f"[User attached image: {_drop_path.name}]"
-                                _cprint(f"  📎 Auto-attached image: {_drop_path.name}")
-                            else:
-                                # Non-image file — mention it in the chat message so
-                                # the agent can read_file / analyze it.
-                                _cprint(f"  📄 Detected file: {_drop_path.name}")
-                                user_input = (
-                                    f"[User attached file: {_drop_path}]"
-                                    + (f"\n{_remainder}" if _remainder else "")
-                                )
 
-                    if not _is_file_drop and isinstance(user_input, str) and user_input.startswith("/"):
+                    if not _file_drop and isinstance(user_input, str) and user_input.startswith("/"):
                         _cprint(f"\n⚙️  {user_input}")
                         if not self.process_command(user_input):
                             self._should_exit = True

tests/test_cli_file_drop.py

@@ -0,0 +1,176 @@
+"""Tests for _detect_file_drop — file path detection that prevents
+dragged/pasted absolute paths from being mistaken for slash commands."""
+
+import os
+import tempfile
+from pathlib import Path
+
+import pytest
+
+from cli import _detect_file_drop
+
+
+# ---------------------------------------------------------------------------
+# Fixtures
+# ---------------------------------------------------------------------------
+
+@pytest.fixture()
+def tmp_image(tmp_path):
+    """Create a temporary .png file and return its path."""
+    img = tmp_path / "screenshot.png"
+    img.write_bytes(b"\x89PNG\r\n\x1a\n")  # minimal PNG header
+    return img
+
+
+@pytest.fixture()
+def tmp_text(tmp_path):
+    """Create a temporary .py file and return its path."""
+    f = tmp_path / "main.py"
+    f.write_text("print('hello')\n")
+    return f
+
+
+@pytest.fixture()
+def tmp_image_with_spaces(tmp_path):
+    """Create a file whose name contains spaces (like macOS screenshots)."""
+    img = tmp_path / "Screenshot 2026-04-01 at 7.25.32 PM.png"
+    img.write_bytes(b"\x89PNG\r\n\x1a\n")
+    return img
+
+
+# ---------------------------------------------------------------------------
+# Tests: returns None for non-file inputs
+# ---------------------------------------------------------------------------
+
+class TestNonFileInputs:
+    def test_regular_slash_command(self):
+        assert _detect_file_drop("/help") is None
+
+    def test_unknown_slash_command(self):
+        assert _detect_file_drop("/xyz") is None
+
+    def test_slash_command_with_args(self):
+        assert _detect_file_drop("/config set key value") is None
+
+    def test_empty_string(self):
+        assert _detect_file_drop("") is None
+
+    def test_non_slash_input(self):
+        assert _detect_file_drop("hello world") is None
+
+    def test_non_string_input(self):
+        assert _detect_file_drop(42) is None
+
+    def test_nonexistent_path(self):
+        assert _detect_file_drop("/nonexistent/path/to/file.png") is None
+
+    def test_directory_not_file(self, tmp_path):
+        """A directory path should not be treated as a file drop."""
+        assert _detect_file_drop(str(tmp_path)) is None
+
+
+# ---------------------------------------------------------------------------
+# Tests: image file detection
+# ---------------------------------------------------------------------------
+
+class TestImageFileDrop:
+    def test_simple_image_path(self, tmp_image):
+        result = _detect_file_drop(str(tmp_image))
+        assert result is not None
+        assert result["path"] == tmp_image
+        assert result["is_image"] is True
+        assert result["remainder"] == ""
+
+    def test_image_with_trailing_text(self, tmp_image):
+        user_input = f"{tmp_image} analyze this please"
+        result = _detect_file_drop(user_input)
+        assert result is not None
+        assert result["path"] == tmp_image
+        assert result["is_image"] is True
+        assert result["remainder"] == "analyze this please"
+
+    @pytest.mark.parametrize("ext", [".png", ".jpg", ".jpeg", ".gif", ".webp",
+                                      ".bmp", ".tiff", ".tif", ".svg", ".ico"])
+    def test_all_image_extensions(self, tmp_path, ext):
+        img = tmp_path / f"test{ext}"
+        img.write_bytes(b"fake")
+        result = _detect_file_drop(str(img))
+        assert result is not None
+        assert result["is_image"] is True
+
+    def test_uppercase_extension(self, tmp_path):
+        img = tmp_path / "photo.JPG"
+        img.write_bytes(b"fake")
+        result = _detect_file_drop(str(img))
+        assert result is not None
+        assert result["is_image"] is True
+
+
+# ---------------------------------------------------------------------------
+# Tests: non-image file detection
+# ---------------------------------------------------------------------------
+
+class TestNonImageFileDrop:
+    def test_python_file(self, tmp_text):
+        result = _detect_file_drop(str(tmp_text))
+        assert result is not None
+        assert result["path"] == tmp_text
+        assert result["is_image"] is False
+        assert result["remainder"] == ""
+
+    def test_non_image_with_trailing_text(self, tmp_text):
+        user_input = f"{tmp_text} review this code"
+        result = _detect_file_drop(user_input)
+        assert result is not None
+        assert result["is_image"] is False
+        assert result["remainder"] == "review this code"
+
+
+# ---------------------------------------------------------------------------
+# Tests: backslash-escaped spaces (macOS drag-and-drop)
+# ---------------------------------------------------------------------------
+
+class TestEscapedSpaces:
+    def test_escaped_spaces_in_path(self, tmp_image_with_spaces):
+        r"""macOS drags produce paths like /path/to/my\ file.png"""
+        escaped = str(tmp_image_with_spaces).replace(' ', '\\ ')
+        result = _detect_file_drop(escaped)
+        assert result is not None
+        assert result["path"] == tmp_image_with_spaces
+        assert result["is_image"] is True
+
+    def test_escaped_spaces_with_trailing_text(self, tmp_image_with_spaces):
+        escaped = str(tmp_image_with_spaces).replace(' ', '\\ ')
+        user_input = f"{escaped} what is this?"
+        result = _detect_file_drop(user_input)
+        assert result is not None
+        assert result["path"] == tmp_image_with_spaces
+        assert result["remainder"] == "what is this?"
+
+
+# ---------------------------------------------------------------------------
+# Tests: edge cases
+# ---------------------------------------------------------------------------
+
+class TestEdgeCases:
+    def test_path_with_no_extension(self, tmp_path):
+        f = tmp_path / "Makefile"
+        f.write_text("all:\n\techo hi\n")
+        result = _detect_file_drop(str(f))
+        assert result is not None
+        assert result["is_image"] is False
+
+    def test_path_that_looks_like_command_but_is_file(self, tmp_path):
+        """A file literally named 'help' inside a directory starting with /."""
+        f = tmp_path / "help"
+        f.write_text("not a command\n")
+        result = _detect_file_drop(str(f))
+        assert result is not None
+        assert result["is_image"] is False
+
+    def test_symlink_to_file(self, tmp_image, tmp_path):
+        link = tmp_path / "link.png"
+        link.symlink_to(tmp_image)
+        result = _detect_file_drop(str(link))
+        assert result is not None
+        assert result["is_image"] is True