I find it far more effective to make friends with and be kind to that employee, and then describe how I know it isn't their fault but this one aspect of the thing that their company does really sucks, right? They're then able to carry that specific complaint from one of their best customers up the chain.

There are a thousand reasons why someone might be miserable, might resign or ask for a raise, but at the next monthly meeting or whatever opportunity they have for receiving suggestions, an employee who actually likes you will be more likely to speak up and get something done.

This has worked for me at least in the B2B space, where I'm affecting one of 50 state applications engineers or something like that. I'm aware that this isn't exactly the same as the federal government that employs like 3 million people, but the principle is the same.

If you got on Karen's good side, she might grouse with you that sending and receiving faxes is archaic, that mail is slow, agree that printed paper's not that accommodating to blind people, and acknowledge that it's cruel and wasteful to ask people to prove their chronic, incurable disabilities every year under threat of taking away their benefits through these platforms. You could work together and laugh about how funny it would be to communicate the real costs and hardships with her supervisors if you literally faxed 1,200 pages of a PDF, wearing through multiple toner cartridges and reams of paper, generating a box that she could drop on the table with a "thud" to emphasize that they should stop doing that.

That might create change, especially if it happens for multiple employees multiple times a day.

Making a bureaucrat miserable because they have a lot of paperwork to do is not going to create change.

Indeed, if you're nice they might take your side. If you're an asshole, that's a lot less likely.