Hey! It looks like there is a bug report for this, thank you for pointing it out! We linked the bug report to this thread so you will be notified when it is fixed. In the meantime, we have found that setting the column to a specific type instead of Auto tends to have much more reliable sorting. Hope that helps!
Thanks, yes setting the String type solves the issue.
Here this is mostly for newcomers to Retool that expect it to work properly by Default. In our case this was one of our end customer that reported this problem.