diff --git a/src/rebar_file_utils.erl b/src/rebar_file_utils.erl
index e3e7858c4..2a782f059 100644
--- a/src/rebar_file_utils.erl
+++ b/src/rebar_file_utils.erl
@@ -150,6 +150,25 @@ cp_r_win32({false, Source},{false, Dest}) ->
     %% from file to file
     {ok,_} = file:copy(Source, Dest),
     ok;
+cp_r_win32({true, SourceDir}, {false, DestDir}) ->
+    case filelib:is_regular(DestDir) of
+        true ->
+            %% From directory to file? This shouldn't happen
+            {error, lists:flatten(
+                      io_lib:format("Cannot copy dir (~p) to file (~p)\n",
+                                    [SourceDir, DestDir]))};
+        false ->
+            %% Specifying a target directory that doesn't currently exist.
+            %% So let's attempt to create this directory
+            case filelib:ensure_dir(filename:join(DestDir, "dummy")) of
+                ok ->
+                    ok = xcopy_win32(SourceDir, DestDir);
+                {error, Reason} ->
+                    {error, lists:flatten(
+                              io_lib:format("Unable to create dir ~p: ~p\n",
+                                            [DestDir, Reason]))}
+            end
+    end;
 cp_r_win32(Source,Dest) ->
     Dst = {filelib:is_dir(Dest), Dest},
     lists:foreach(fun(Src) ->