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I was able to do it, Now, I cant anymore.
I have this message: Assign up to 1 person to this issue. If I select somebody else, alan345 will be removed
Is it a premium feature now?
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You could assign the issue to one of them and @-mention the GitHub usernames of the others, which will subscribe them to updates for that issue. If you have groups of people who will often be assigned together, you could also create teams within an organization to mention them all at once.
With pull requests you can invite other people to review your work and give you feedback. Once a pull request is open, you can discuss your code with other developers. Most Git hosting platforms allow other users to add comments and suggest changes during that process.
On GitHub.com, navigate to the main page of the repository. Under your repository name, click Issues or Pull requests. Select the checkbox next to the items you want to assign to someone.
Answer from Github:
With the recent updates, if you are using GitHub Free, then you will only be able to have a single assignee for issues or pull requests:
https://help.github.com/en/github/getting-started-with-github/faq-about-changes-to-githubs-plans#if-i-downgrade-from-github-team-or-a-legacy-plan-to-github-free-what-features-will-i-lose
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