diff --git a/bpkg_manager/subproc.py b/bpkg_manager/subproc.py
index 3eae60e..f0112ba 100644
--- a/bpkg_manager/subproc.py
+++ b/bpkg_manager/subproc.py
@@ -137,6 +137,9 @@ def _install(pipe_to_blender, pkgpath: pathlib.Path, dest: pathlib.Path):
     """Extracts/moves package at `pkgpath` to `dest`"""
     import zipfile
 
+    log = logging.getLogger('%s.install' % __name__)
+
+    log.debug("Starting installation")
     pipe_to_blender.send(Progress(0.0))
 
     if not pkgpath.is_file():
@@ -155,13 +158,27 @@ def _install(pipe_to_blender, pkgpath: pathlib.Path, dest: pathlib.Path):
 
     # check to see if the file is in compressed format (.zip)
     if zipfile.is_zipfile(pkgpath):
+        log.debug("Package is zipfile")
         try:
             file_to_extract = zipfile.ZipFile(str(pkgpath), 'r')
         except Exception as err:
+            # TODO HACK: see if it makes sense to make a single InstallError class which inherits from both Exception and SubprocError
+            # It sounds weird, but it could avoid the need for duplication here; create a new InstallError with the right message,
+            # then send it to blender and also raise it.
             pipe_to_blender.send(InstallError("Failed to read zip file: %s" % err))
             raise InstallException from err
 
-        conflicts = [f for f in file_to_extract.namelist() if (dest / f).exists()]
+        def root_files(filelist: list) -> list:
+            """Some string parsing to get a list of the root contents of a zip from its namelist"""
+            rootlist = []
+            for f in filelist:
+                # Get all names which have no path separators (root level files)
+                # or have a single path separator at the end (root level directories).
+                if len(f.rstrip('/').split('/')) == 1:
+                    rootlist.append(f)
+            return rootlist
+
+        conflicts = [f for f in root_files(file_to_extract.namelist()) if (dest / f).exists()]
         if len(conflicts) > 0:
             # TODO: handle this better than just dumping a list of all files
             pipe_to_blender.send(FileConflictError("Installation would overwrite: %s" % conflicts, conflicts))
@@ -174,6 +191,7 @@ def _install(pipe_to_blender, pkgpath: pathlib.Path, dest: pathlib.Path):
             raise InstallException from err
 
     else:
+        log.debug("Package is pyfile")
         dest_file = (dest / pkgpath.name)
 
         if dest_file.exists():
@@ -190,6 +208,7 @@ def _install(pipe_to_blender, pkgpath: pathlib.Path, dest: pathlib.Path):
 
     try:
         pkgpath.unlink()
+        log.debug("Removed cached package: %s", pkgpath)
     except Exception as err:
         pipe_to_blender.send(SubprocWarning("Failed to remove package from cache: %s" % err))
         raise InstallException from err