diff --git a/mercurial/context.py b/mercurial/context.py
--- a/mercurial/context.py
+++ b/mercurial/context.py
@@ -1968,6 +1968,19 @@
         self._repo.wwrite(self._path, data, flags,
                           backgroundclose=backgroundclose)
 
+    def clearunknown(self):
+        """Removes conflicting items in the working directory (and creates any
+        missing parent directories) so that ``write()`` can be called
+        successfully.
+        """
+        if self._repo.wvfs.isdir(self._path) and not self._repo.wvfs.islink(
+                self._path):
+            self._repo.wvfs.removedirs(self._path)
+
+        dirname = os.path.dirname(self._path)
+        if not self._repo.wvfs.isdir(dirname):
+            self._repo.wvfs.makedirs(dirname)
+
     def setflags(self, l, x):
         self._repo.wvfs.setflags(self._path, l, x)
 
diff --git a/mercurial/merge.py b/mercurial/merge.py
--- a/mercurial/merge.py
+++ b/mercurial/merge.py
@@ -1150,9 +1150,7 @@
                 except OSError as e:
                     if e.errno != errno.ENOENT:
                         raise
-
-            if repo.wvfs.isdir(f) and not repo.wvfs.islink(f):
-                repo.wvfs.removedirs(f)
+            wctx[f].clearunknown()
             wctx[f].write(fctx(f).data(), flags, backgroundclose=True)
             if i == 100:
                 yield i, f