Hi Mirth, thanks for taking a look and testing. > Please could you add instructions how to test it? Sure, below you can find steps which can be used for testing. # requirement git-credentials-oauth installed # build patched git git clone https://git.kernel.org/pub/scm/git/git.git tmp_git cd tmp_git curl https://lore.kernel.org/git/20240225103413.9845-1-julian@xxxxxxxxxxxxxxx/raw |git am make # backup gitconfig mv ~/.gitconfig{,_backup} # create minimal gitconfig cat << EOF >> ~/.gitconfig [credential] helper = cache --timeout 7200 helper = oauth [credential "smtp://smtp.gmail.com:587"] oauthClientId = 406964657835-aq8lmia8j95dhl1a2bvharmfk3t1hgqj.apps.googleusercontent.com oauthClientSecret = kSmqreRr0qwBWJgbf5Y-PjSU oauthScopes = https://mail.google.com/ oauthAuthURL = https://accounts.google.com/o/oauth2/auth oauthTokenURL = https://oauth2.googleapis.com/token [user] email = you@xxxxxxxxxxx name = Your Name EOF # create email to send cat << EOF >> message.txt Subject: test email from git Hay from git EOF # update PATH to use patched git export PATH="${PWD}:${PATH}" # confirm you are using the correct git version, should look # something like `git version 2.48.0.rc2.32.g5adec67521` git --version git send-email \ --to=email@xxxxxxxxxxx \ --smtp-auth=XOAUTH2 \ --smtp-encryption=tls \ --smtp-server-port=587 \ --smtp-server=smtp.gmail.com \ --smtp-debug=1 \ --smtp-user=you@xxxxxxxxxxx \ message.txt # now the browser should open with the oauth flow. > Which servers have you tested? I've tested this with gmail using a consumer google account as well as a managed google account and with the office settings I've tested office365. > Looking at the debug information, it looks like the SMTP command "AUTH > XOAUTH2 <base64>" was corrupted by a space at column 241. Exactly one > base64 string should follow "AUTH XOAUTH2 ", no spaces. I can also see a space in the debug output, but the position depends on my terminal size, and it is not interfering with authentication in my case. I think it is caused by output formatting of the debug statement and not the source of the issue you are having. If you have a coded auth string you can use openssl client directly to test it. openssl s_client -starttls smtp -connect smtp.gmail.com:587 AUTH XOAUTH2 auth_sting If you have the xoauth2 access token you can create the auth string with echo -n -e "user=${EMAIL}\x01auth=Bearer ${TOKEN}\x01\x01" | base64 -w0 If that does not help, can you give me some more details on your setup? Then I'll try to reproduce the problem. I've tested the steps above on Arch Linux with Perl v5.40.0, and Ubuntu with Perl v5.38.2. Regards Julian