I recently started a job as a contractor. My boss wants a written daily report detailing what I will do today and what I did yesterday and how much time was spent on each item. The level of detail he wants is quite high. A lot of time is spent setting things up and trouble shooting random issues. For example, the video playback on videos I had to watch for work kept freezing. Yesterday I spent 30 minutes updating codecs and getting a new media player. Do these 30 minutes count towards "work" and should I include this in my daily report and invoice? What about the time spent installing and configuring new applications or troubleshooting old ones (like when Skype randomly stops working)? Another specific I'm wondering about, I'm required to take internal training to learn a system, does the time I take to organize notes count towards work?
That totally depends on your contract.
The way I see it, if I have to do it because of work, it is work. You want me to use skype? those skype troubles are billed. You have a shitty VPN client with stupid configuration? Those hours are billed. I spend 20 hours researching for nothing because the request was badly phrased? those hours are billed.
Of course, there is a line. A customer can assume that you have a PC with a working OS on it...
It is not standard to get super detailed on invoices. Depending on customer, how fine grained it is was different. From "development work" everyday in the project, and just how many hours that day, to which rough topics I worked that day. The invoice to your level of detail is super rare, and I would push back against it.
I would advise against asking your boss after the fact, that just opens up discussions. And it makes you exploitable because you show weakness. The greedy boss will try to define as much work as possible as not billable, while still expecting you to do it. Your boss might be different, just be wary of this.
If you are unsure, ask BEFORE you do it. And if he says no, dont do it. Will I be able to bill X? No -> Dont do it.