v2.55.0.windows.5 installer always bundles OpenSSH, also overwrites previously saved choice of ExternalOpenSSH

[matthew-e-brown]

Existing issues matching what you're seeing

• I was not able to find an open or closed issue matching what I'm seeing

Git for Windows version

git version 2.55.0.windows.5
cpu: x86_64
built from commit: 32c4f7689275d233577576630e1ac5b7eb354eb0
sizeof-long: 4
sizeof-size_t: 8
shell-path: D:/git-sdk-64-build-installers/usr/bin/sh
rust: disabled
feature: fsmonitor--daemon
gettext: enabled
libcurl: 8.21.0
OpenSSL: OpenSSL 3.5.7 9 Jun 2026
zlib: 1.3.2
SHA-1: SHA1_DC
SHA-256: SHA256_BLK
default-ref-format: files
default-hash: sha1

Windows version

Both Windows 11 and Windows 10

Windows CPU architecture

x86_64 (64-bit)

Additional Windows version information

• Windows 11: Microsoft Windows [Version 10.0.26200.9168]
• Windows 10: Microsoft Windows [Version 10.0.19045.7663]

Options set during installation

Editor Option: VIM
Custom Editor Path:
Default Branch Option: main
Path Option: Cmd
SSH Option: OpenSSH
Tortoise Option: false
CURL Option: OpenSSL
CRLF Option: CRLFCommitAsIs
Bash Terminal Option: MinTTY
Git Pull Behavior Option: Merge
Use Credential Manager: Enabled
Performance Tweaks FSCache: Enabled
Enable Symlinks: Disabled
Enable FSMonitor: Disabled

Other interesting things

I have a third-party SSH agent running that listens on the named OpenSSH pipe, \\.\pipe\openssh-ssh-agent (specifically the 1Password SSH Agent). After updating to 2.55.0.windows.5, ssh could suddenly no longer see my agent running.

After some searching (see my comment on #6373), I discovered that C:\Program Files\Git\usr\bin suddenly included a bunch of extra SSH stuff which was not there before, despite me having selected "Use external SSH" during my original installation (though this does not appear in the install-options.txt above; you're just going to have to trust me when I say that I did select "Use external SSH"; see investigation below):

[Matthew@MATT-FW13 ~] $ ls /usr/bin | grep ssh
ssh.exe*
ssh-add.exe*
ssh-agent.exe*
ssh-copy-id*
ssh-keygen.exe*
ssh-keyscan.exe*
ssh-pageant.exe*

I thought I might try to re-install Git Bash, but when I did so, I was not even given the option to use an external SSH.

My investigation

Following this discussion comment, I believe that the issue comes down to this section of the installer script:

(*
 * Create a custom page for using (Tortoise)Plink or a self-supplied OpenSSH instead of bundled OpenSSH
 * if at least one PuTTY session is found in the Registry or an OpenSSH binary is found on the PATH.
 *)

if (RegGetSubkeyNames(HKEY_CURRENT_USER,'Software\SimonTatham\PuTTY\Sessions',PuTTYSessions) and (GetArrayLength(PuTTYSessions)>0)) or
   (FileSearch('ssh.exe', GetEnv('PATH')) <> '') then begin
    SSHChoicePage:=CreatePage(PrevPageID,'Choosing the SSH executable','Which Secure Shell client program would you like Git to use?',TabOrder,Top,Left);

// ...

I don't have PuTTY installed, and I never have; but I do have ssh.exe on my PATH (specifically, %SYSTEMROOT%\System32\OpenSSH is on my system PATH, not my user PATH):

PS C:\Users\Matthew> where.exe ssh.exe
C:\Windows\System32\OpenSSH\ssh.exe

So, specifically, I believe the problem comes down to FileSearch('ssh.exe', GetEnv('PATH')). It appears that, in the new installer, this function fails to locate ssh.exe on the system path for some reason. Maybe this has something to do with the move to a 64-bit installer? Anyways, the else branch of that check sets SSHChoicePage to NIL, which means that:

1. This block, to delete the files from OpenSSH, never runs:

   #ifdef DELETE_OPENSSH_FILES
       if (SSHChoicePage<>NIL) and (RdbSSH[GS_ExternalOpenSSH].Checked) then begin
           WizardForm.StatusLabel.Caption:='Removing bundled Git OpenSSH binaries';
           if not DeleteOpenSSHFiles() then
               LogError('Failed to remove OpenSSH file(s)');
       end;
   #endif

2. This block, later in the script, overwrites the previously selected ExternalOpenSSH with the default OpenSSH:

   // Git SSH options.
   Data:='';
   Data2:='false';
   if (SSHChoicePage=NIL) or RdbSSH[GS_OpenSSH].Checked then begin
       Data:='OpenSSH';
   end else if RdbSSH[GS_ExternalOpenSSH].Checked then begin
       Data:='ExternalOpenSSH'
   end else if RdbSSH[GS_Plink].Checked then begin
       Data:='Plink';
       RecordChoice(PreviousDataKey,'Plink Path',EdtPlink.Text);
       if TortoisePlink.Checked then
           Data2:='true';
   end;
   RecordChoice(PreviousDataKey,'SSH Option',Data);
   RecordChoice(PreviousDataKey,'Tortoise Option',Data2);

Unless I am mistaken, the second point means that, even if this issue is resolved, running that fixed installer with "only show new options" ticked will not be able to detect that the user had previously selected ExternalOpenSSH.

Terminal/shell

Git Bash in Windows Terminal.

Commands that trigger the issue

1. Verify that C:\Windows\System32\OpenSSH is on the system-level PATH (not the user-level PATH; though I'm not sure if it makes a difference), and that ssh.exe lives there (where.exe ssh). (NB: I am not sure if this issue occurs with other external SSH installations other than the one from System32).
2. Verify that HKEY_CURRENT_USER\SOFTWARE\SimonTatham\PuTTY does not appear in the Windows Registry.
3. Install or downgrade to v2.55.0.windows.4 and select "Use external SSH": 1. Run the Git-2.55.0.4-64-bit.exe installer from the previous release.
   2. Untick "Only show new options."
   3. Click through the installer and, when prompted, select "Use external SSH".
4. Verify that ssh points to C:\Windows\System32\OpenSSH\ssh.exe:
   1. Open Git Bash.
   2. Verify that where.exe ssh displays only the one instance of ssh.exe.
   3. Verify that ls /usr/bin | grep ssh does not include any of the ssh*.exe files from OpenSSH (should only display ssh-pageant.exe).
5. Upgrade to v2.55.0.windows.5:
   1. Run the Git-2.55.0.5-64-bit.exe installer from the latest release.
   2. Click through the installation wizard either with or without "Only show new options."
6. Check whether or not ssh points to C:\Windows\System32\OpenSSH\ssh.exe (repeat step 3).

Expected behaviour

After upgrading to v2.55.0.windows.5:

1. Running where.exe ssh should display only the external SSH program in C:\Windows\System32\OpenSSH\ssh.exe. Other OpenSSH files (ssh-add.exe, ssh-copy-id.exe, etc.) should not appear in C:\Program Files\Git\usr\bin.

2. Additionally, if run without "Only show new options," then the "Choosing the SSH executable" page should appear during installation (between "Adjusting your PATH environment" and "Choosing HTTPS transport backend"). The page should have the "Use external OpenSSH" option available, and it should be selected by default.

3. Furthermore, re-running Git-2.55.0.4-64-bit.exe without "Only show new options" should have "Use external SSH" selected by default when the "Choosing the SSH executable" page appears; re-running it with "Only show new options" should install v2.55.0.windows.4 without the bundled SSH included in C:\Program Files\Git\usr\bin.

Actual behaviour

After upgrading to v2.55.0.windows.5:

1. Running where.exe now displays C:\Program Files\Git\usr\bin\ssh.exe above C:\Windows\System32\OpenSSH\ssh.exe. Other OpenSSH files appear in C:\Program Files\Git\usr\bin.

2. Additionally, if the installer was run without "Only show new options," then the "Choosing the SSH executable" page never appears.

3. Finally, when re-running Git-2.55.0.4-64-bit.exe without "Only show new options," the "Choosing the SSH executable" page now defaults to "Use bundled OpenSSH"; re-running it with "Only show new options" installs v2.55.0.windows.4 with the bundled SSH included in C:\Program Files\Git\usr\bin.

Repository

No response