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If I push each commit separately activity section in the pull request will display user updated the pull request with n commits, but if I push all commits at once just the last commit will be displayed which can be misleading.
Hi @jovan_petrovic and welcome to the community.
This is indeed a bug, we have a ticket in our issue tracker about this:
I would suggest selecting the link This affects my team in that issue to indicate that you are affected by this bug. You can also select the Start watching this issue link if you'd like to get notified via email on updates.
Our development team tracks bugs in that issue tracker and will post an update there when this is fixed. Please note though that we don't provide ETAs and bug fixing is implemented as per our policy here.