&quot;Proactive&quot; desktop support is very common in larger organizations where the time needed to personally dispatch a technician to each user in meatspace would be prohibitive. Usually such remote proactive support is initiated with the user&#x27;s direct approval.<p>In my opinion the &quot;consenting adults&quot; principle applies here: it doesn&#x27;t hurt to ask for a user&#x27;s permission, and if they agree, it&#x27;s not creepy. If they don&#x27;t agree, no harm is done.<p>One last thing: you&#x27;re right to worry about scalability. High-touch support is fundamentally not scalable (someone please prove me wrong!), which is why you see companies like Google providing automated &quot;support&quot; that makes customers feel alienated and not valued.