Trust the community! My question has been answered by GeekWisdom! Did you ever encounter the same problem?
This is the twitter question that started it all, (and why I started this blog on wordpress.com)

So I setup this very WordPress blog just to test this out myself, and it turns out, dang it, no matter what I try, neither the categories nor tags will automatically become hashtags when the ‘twitter share’ button is pressed.
I found this link https://wordpress.com/forums/topic/add-wp-blog-tags-to-twitter-posts-as-hashtags – which seems to suggest it is a feature that has been asked for for some time.
WordPress.com the free version, also does not appear to allow embedding of JavaScript, or installation of plugins without using a paid ‘business account’. So those options seem to be a no-go as well.
With the free account, one small workaround is to put one hash tag at the end of the post title. If you do this, at least that one hashtag is added to the share.
If this still does…
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