If the situation is about cherry-picking a commit that adds a new file F to a checkout of another commit that lacks the file F, I think the command is working exactly as designed. $ git init $ git commit -m 'initial' --allow-empty $ git tag initial $ date >file $ git add file $ git commit -m 'add file' $ git tag added $ git checkout -b second initial ... at this point we are back to the original state ... without 'file' $ >file ... the file is untracked with precious contents ... and the presence of it stops a cherry-pick that clobbers it $ git cherry-pick added error: The following untracked working tree files would be overwritten by merge: file Please move or remove them before you merge. Aborting fatal: cherry-pick failed Now continuing from the above, things get (slightly) interesting $ echo file >.gitignore $ git cherry-pick added This will replace "file" with the one from the "added" commit, and that is because the user marked that the "file" in the working tree is expendable. Files in a working tree controlled by git fall into one of three classes. Tracked files are those that are known to the index and appear in "git ls-files" output. Among the others, ignored files are those that .gitignore mechanism says are expendable. The rest are "untracked", possibly containing valuable contents that should not be lost as the user may choose to 'git add' them later. Not just cherry-pick but any merge-related operations, including "checkout", follow this semantics. Untracked files are kept, but ignored files are expendable and will be removed if they are in the way to complete the operation the user asks. $ rm .gitignore $ git checkout master error: The following untracked working tree files would be overwritten by checkout: file Please move or remove them before you switch branches. Aborting $ echo file >.gitignore $ git checkout master ... this should succeed, removing "file" whose contents were ... marked expendable. Of course, after switching to 'master' (or cherry-picking 'added'), the project now cares about the 'file'. After all, it bothered to add it to keep track of the changes to its contents. So it is recommended that you would adjust the contents of .gitignore so that it no longer is marked as expendable.