When a file is deleted from Git and replaced with a directory+file(s), git-stash has two unexpected behaviors. This is tested against versions 2.8.1 and 2.10.1: 1) Old file is removed from index and newly-added directory+file(s) are added to index. In this scenario, 'git stash' fails with the message: error: <directory>: is a directory - add individual files instead fatal: Unable to process path <directory> Cannot save the current work tree state The expected result would be that Git properly records the state currently stored in index. 2) Old file is removed and new-added directory+file(s) are present only in worktree, but not added to the index. In this scenario, 'git stash -u' works fine, but 'git stash apply' fails with the message: fatal: cannot create directory at '<directory>': File exists Could not restore untracked files from stash The expected result would be that Git removes 'file' and replaces with the untracked contents recorded in the original stash. It is worth noting that Git does properly handle the scenario where the stash operation of (1) is replaced with a commit to a temporary branch, so this quirk seems to be restricted to stashes only. I found a similar issue reported 22 April 2016 titled "possible bug of git stash deleting uncommitted files in corner case". The thread-view of the message is here: http://marc.info/?t=146132568600002&r=1&w=2 Here's a quick-and-dirty bash script to re-create all three scenarios (1, 2, and 'commit to branch'): ===== BEGIN stash-test.sh #!/bin/bash set -x export GIT_TRACE=1 setup() { repo=$1 # Prepare repo rm -rf $repo git init $repo cd $repo # Add initial file (symlink to external assets) ln -fs /external/dir dir git add dir git commit -m "Add symlink to /external/dir" # Replace symlink with local copy of assets rm dir mkdir -p dir touch dir/local_copy_of_dir_files } { ( setup stash-test-unstaged git stash -u git stash apply ) ( setup stash-test-staged git add . git stash ) ( setup stash-test-commit git add . git co -b stash-branch git commit -m "commit to branch instead of stash" ) } 2>&1 | tee stash-test.log ===== END stash-test.sh Thanks, -Alex Reed