Winston and I both replied directly to Steve’s post. Winston’s post shows the

so I’m wondering what I might have done differently?

is it a functionality difference between these two buttons? one is more of a direct reply vs addition to the thread?
Yes, the blue box is general reply-to-the-thread and the no-background button in a post is reply-to-the-post. I make sure to use that one when I’m answering directly. I just used the Reply button at the end of your post and don’t get the “1 Replies” flag on your post… weird but not the end of the world, mostly just a Friday musing.
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