Nah, he isn't.
He's made the ridiculous assumption that it's ok to change faulty software.
As we all know (and as so elegantly elucidated by Edsger Djikstra) software never fails, it's just that we don't know when it succeeds.
Also, on a slightly less philosophical note, I have to question the OP. First of all you do NOT have to understand the problem, you have to establish what it really is, not what you think it is, not what the person reporting it thinks it is, and definitely not what their manager thinks it is. There's no point understanding a problem if it's not the one being experienced.
Going straight to the horse's mouth is the only way to deal with a problem. Discuss with and interview (if necessary) the person who is experiencing the problem. Only they know what they're experiencing, their manager is an interfering irrelevance.
It sort of reminds me of the junior officer on the radio to the commander in chief, requesting assistance. The general in his nice comfy bunker say "Our charts show no enemy activity near you, what are you moaning about?" The very junior officer says "General, I don't give a **** about your charts, listen to this" and then holds the mouthpiece up. The whine of bullets, the shouts of wounded and the whistle (and subsequent crump) of artillery shells are heard. The officer tells the general to send help because regardless of charts, they're being slaughtered.
The second item, making a plan seems equally daft to me. Suppose you believe that you've correctly determined the real problem, and not what you (or anyone else) thought it was. You then carry out a test, to determine whether or not the fix you have devised solves the problem. If it doesn't you try something else. Planning stuff, when reality can bite you one the bum at any instant is just daft. You don't plan how to put out a conflagration, you first of all get as many tenders to the fire as possible to contain it. Then and only then can you plan how best to extinguish it.
If the problem is that a thermonuclear device will detonate in 10 minutes, planning is just idiotic. Stop the countdown timer, and stop it now! Until that's done, any and all plans are irrelevant.
Ooh, do I sound like someone in IT who's been shafted so often now, that he's a bit hypersensitive to faults being reported, now let me see, how did that happen.....
Regards
T