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I'm using Sourcetree with openssh on Win10. When I have only one ssh key added everything works like expected. I can push to my remote repos and it also works after restarting Sourcetree. Some of my keys are with a password and after starting Sourcetree, the command prompt pops up asking me to enter the password for the key.
As soon as I add another ssh-key, it only works until I restart Sourcetree. Before restarting it works, but after restarting there is only a quick flash of the command prompt, and then I cannot not push to any repo with either key.
I just get the popup that I need to add a key. Even though the keys are already listed in Options -> SSH key (separated by ;).
Outside of Sourcetree (e.g. in Git Bash) it always works.