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@baldur as an adjacent point, these situations are also good times to make small references to #FreeSoftware. Especially when the user is being frustrated by an #AntiFeature.

"It's annoying they didn't think about this use case"
"This tool is mainly useful, it's a shame we can't change this one thing"

https://media.libreplanet.org/u/libreplanet/m/questions-are-the-answer-how-to-have-deeper-conversations-with-anyone-about-free-software-philosophy/

Of course, when to do this is very context dependent. But, every so often, highlighting why software doesn't work the way *they* want can be a good springboard.