On Wed, Sep 11, 2019 at 08:14:45AM +0200, Konstantinos Dalamagkidis wrote: > In my git configuration, I have an includeif section for work > related repositories that configures the user and sendemail > sections. What kind of includeIf are you using? Does it work with an unconditional include? This seems to work for me: $ git config --global include.path one $ git config --file ~/one sendemail.smtpserver one.example.com $ git send-email --dry-run -1 --to nobody | grep ^Server Server: one.example.com $ git config --global includeIf.gitdir:$PWD/.path two $ git config --file ~/two sendemail.smtpserver two.example.com $ git send-email --dry-run -1 --to nobody | grep ^Server Server: two.example.com I.e. both unconditional and gitdir includes work for me. If you do something similar, what output do you get? > I can verify that the configuration is read correctly by git: > > % git config --get-regex "sendemail.*" > sendemail.smtpencryption tls > sendemail.smtpserver smtp.office365.com > sendemail.smtpserverport 587 > sendemail.smtpuser dalamagkidis@xxxxxxxx Thanks for this output. That rules out that "git config" is somehow misbehaving in a way that normal internal config lookups wouldn't. The rest of git-config should behave the same, but you could also try: git config --get sendemail.smtpserver which is what send-email will actually run (you can run send-email with GIT_TRACE=1 to see the full set of commands if you want to try them manually). -Peff