Thank you for filling out a Git bug report! Please answer the following questions to help us understand your issue. What did you do before the bug happened? (Steps to reproduce your issue) cd '/'; cd '/'; rm --force --recursive -- './test_git'; mkdir "$_"; cd "$_"; mkdir --parents -- './server1' './server2' './server3' './server4' './server5' './server6' './client'; git -C './client' init './repo' git -C './client/repo' remote --verbose git -C './client/repo' config list --local --show-scope --show-origin git -C './client/repo' remote add server 'file://'"$(realpath './server1/repo.git')" git -C './client/repo' config set --local --append 'remote.server.url' 'file://'"$(realpath './server2/repo.git')" git -C './client/repo' config set --local --append 'remote.server.pushurl' 'file://'"$(realpath './server3/repo.git')" git -C './client/repo' config set --local --append 'remote.server.pushurl' 'file://'"$(realpath './server4/repo.git')" git -C './client/repo' config set --local --append 'url.scheme1://authority1/path1/.insteadOf' 'file://'"$(realpath './')"'/' git -C './client/repo' config set --local --append 'url.scheme2://authority2/path2/.pushInsteadOf' 'file://'"$(realpath './')"'/' git -C './client/repo' remote --verbose git -C './client/repo' config list --local --show-scope --show-origin git -C './client/repo' remote get-url server git -C './client/repo' remote get-url --all server git -C './client/repo' remote get-url --push server git -C './client/repo' remote get-url --push --all server git -C './client/repo' remote set-url server 'file://'"$(realpath './server5/repo.git')" git -C './client/repo' remote set-url server 'file://'"$(realpath './server5/repo.git')" 'server' git -C './client/repo' remote set-url server 'file://'"$(realpath './server5/repo.git')" 'server2' git -C './client/repo' remote set-url server --push 'file://'"$(realpath './server6/repo.git')" git -C './client/repo' remote set-url server --push 'file://'"$(realpath './server6/repo.git')" 'server' git -C './client/repo' remote set-url server --push 'file://'"$(realpath './server6/repo.git')" 'server4' git -C './client/repo' remote --verbose git -C './client/repo' config list --local --show-scope --show-origin git -C './client/repo' remote get-url server git -C './client/repo' remote get-url --all server git -C './client/repo' remote get-url --push server git -C './client/repo' remote get-url --push --all server What did you expect to happen? (Expected behavior) https://git-scm.com/docs/git-remote says: if <oldurl> is given, sets first URL for remote <name> that matches regex <oldurl> to <newurl>. if no <oldurl> is given, sets first URL to <newurl>. so these commands should not fail: git -C './client/repo' remote set-url server 'file://'"$(realpath './server5/repo.git')" git -C './client/repo' remote set-url server 'file://'"$(realpath './server5/repo.git')" 'server' git -C './client/repo' remote set-url server --push 'file://'"$(realpath './server6/repo.git')" git -C './client/repo' remote set-url server --push 'file://'"$(realpath './server6/repo.git')" 'server' What happened instead? (Actual behavior) these commands fail: git -C './client/repo' remote set-url server 'file://'"$(realpath './server5/repo.git')" git -C './client/repo' remote set-url server 'file://'"$(realpath './server5/repo.git')" 'server' git -C './client/repo' remote set-url server --push 'file://'"$(realpath './server6/repo.git')" git -C './client/repo' remote set-url server --push 'file://'"$(realpath './server6/repo.git')" 'server' What's different between what you expected and what actually happened? Anything else you want to add: Please review the rest of the bug report below. You can delete any lines you don't wish to share. [System Info] git version: git version 2.46.0.windows.1 cpu: x86_64 built from commit: 2e6a859ffc0471f60f79c1256f766042b0d5d17d sizeof-long: 4 sizeof-size_t: 8 shell-path: D:/git-sdk-64-build-installers/usr/bin/sh feature: fsmonitor--daemon libcurl: 8.9.0 OpenSSL: OpenSSL 3.2.2 4 Jun 2024 zlib: 1.3.1 uname: Windows 10.0 22631 compiler info: gnuc: 14.1 libc info: no libc information available $SHELL (typically, interactive shell): C:\Program Files\Git\usr\bin\bash.exe [Enabled Hooks] not run from a git repository - no hooks to show