diff --git a/lib/python/pyflyby/_file.py b/lib/python/pyflyby/_file.py
index 51e4b2ba..1546cb0d 100644
--- a/lib/python/pyflyby/_file.py
+++ b/lib/python/pyflyby/_file.py
@@ -48,7 +48,7 @@ def __new__(cls, arg):
     def _from_filename(cls, filename: str):
         if not isinstance(filename, str):
             raise TypeError
-        filename = str(filename)
+        filename = os.path.abspath(filename)
         if not filename:
             raise UnsafeFilenameError("(empty string)")
         # we only allow filename with given character set
@@ -58,7 +58,7 @@ def _from_filename(cls, filename: str):
         if re.search("(^|/)~", filename):
             raise UnsafeFilenameError(filename)
         self = object.__new__(cls)
-        self._filename = os.path.abspath(filename)
+        self._filename =  filename
         return self
 
     def __str__(self):
diff --git a/lib/python/pyflyby/_importdb.py b/lib/python/pyflyby/_importdb.py
index 832cc803..d8d851b5 100644
--- a/lib/python/pyflyby/_importdb.py
+++ b/lib/python/pyflyby/_importdb.py
@@ -9,6 +9,8 @@
 import re
 import sys
 
+from pathlib import Path
+
 from   typing                   import Any, Dict, Tuple, Union, List
 
 from   pyflyby._file            import (Filename, UnsafeFilenameError,
@@ -201,6 +203,8 @@ class ImportDB:
     mandatory_imports: ImportSet
     canonical_imports: ImportMap
 
+    _default_cache: Dict[Any, Any] = {}
+
     def __new__(cls, *args):
         if len(args) != 1:
             raise TypeError
@@ -213,7 +217,6 @@ def __new__(cls, *args):
 
     
 
-    _default_cache: Dict[Any, Any] = {}
 
     @classmethod
     def clear_default_cache(cls):
@@ -224,24 +227,22 @@ def clear_default_cache(cls):
         cached results.  Existing ImportDB instances are not affected by this
         call.
         """
-        if cls._default_cache:
-            if logger.debug_enabled:
-                allpyfiles = set()
-                for tup in cls._default_cache:
-                    if tup[0] != 2:
-                        continue
-                    for tup2 in tup[1:]:
-                        for f in tup2:
-                            assert isinstance(f, Filename)
-                            if f.ext == '.py':
-                                allpyfiles.add(f)
-                nfiles = len(allpyfiles)
-                logger.debug("ImportDB: Clearing default cache of %d files",
-                             nfiles)
-            cls._default_cache.clear()
+        if logger.debug_enabled:
+            allpyfiles = set()
+            for tup in cls._default_cache:
+                if tup[0] != 2:
+                    continue
+                for tup2 in tup[1:]:
+                    for f in tup2:
+                        assert isinstance(f, Filename)
+                        if f.ext == ".py":
+                            allpyfiles.add(f)
+            nfiles = len(allpyfiles)
+            logger.debug("ImportDB: Clearing default cache of %d files", nfiles)
+        cls._default_cache.clear()
 
     @classmethod
-    def get_default(cls, target_filename: Union[Filename, str]):
+    def get_default(cls, target_filename: Union[Filename, str], /):
         """
         Return the default import library for the given target filename.
 
@@ -258,7 +259,7 @@ def get_default(cls, target_filename: Union[Filename, str]):
         :rtype:
           `ImportDB`
         """
-        # We're going to canonicalize target_filenames in a number of steps.
+        # We're going to canonicalize target_filename in a number of steps.
         # At each step, see if we've seen the input so far.  We do the cache
         # checking incrementally since the steps involve syscalls.  Since this
         # is going to potentially be executed inside the IPython interactive
@@ -267,25 +268,55 @@ def get_default(cls, target_filename: Union[Filename, str]):
         # been touched, and if so, return new data.  Check file timestamps at
         # most once every 60 seconds.
         cache_keys:List[Tuple[Any,...]] = []
-        if target_filename:
-            if isinstance(target_filename, str):
-                target_filename = Filename(target_filename)
-        target_filename = target_filename or Filename(".")
-        assert isinstance(target_filename, Filename)
+        if target_filename is None:
+            target_filename = "."
+
+        if isinstance(target_filename, Filename):
+            target_filename = str(target_filename)
+
+        assert isinstance(target_filename, str), (
+            target_filename,
+            type(target_filename),
+        )
+
+        target_path = Path(target_filename).resolve()
+
+        parents: List[Path]
+        if not target_path.is_dir():
+            parents = [target_path]
+        else:
+            parents = []
+
+        # filter safe parents
+        safe_parent = None
+        for p in parents + list(target_path.parents):
+            try:
+                safe_parent = Filename(str(p))
+                break
+            except UnsafeFilenameError:
+                pass
+        if safe_parent is None:
+            raise ValueError("No know path are safe")
+
+        target_dirname = safe_parent
+
         if target_filename.startswith("/dev"):
-            target_filename = Filename(".")
-        target_dirname:Filename = target_filename
-        # TODO: with StatCache
-        while True:
-            cache_keys.append((1,
-                               target_dirname,
-                               os.getenv("PYFLYBY_PATH"),
-                               os.getenv("PYFLYBY_KNOWN_IMPORTS_PATH"),
-                               os.getenv("PYFLYBY_MANDATORY_IMPORTS_PATH")))
             try:
-                return cls._default_cache[cache_keys[-1]]
-            except KeyError:
+                target_dirname = Filename(".")
+            except UnsafeFilenameError:
                 pass
+        # TODO: with StatCache
+        while True:
+            key = (
+                1,
+                target_dirname,
+                os.getenv("PYFLYBY_PATH"),
+                os.getenv("PYFLYBY_KNOWN_IMPORTS_PATH"),
+                os.getenv("PYFLYBY_MANDATORY_IMPORTS_PATH"),
+            )
+            cache_keys.append(key)
+            if key in cls._default_cache:
+                return cls._default_cache[key]
             if target_dirname.isdir:
                 break
             target_dirname = target_dirname.dir