Unfortunately there are APC550's and then there are different APC550's - in fact I am right now distinctly less than happy with APC over the way they have chosen to change their software, but that's another story.
APC has several different product lines - SmartUPS & BackUPS are the most common, they do not use the same communication protocols, and in fact, there appear to be differences in the communication protocols used by different versions of the different lines as well - so that software that works with one SmartUPS will not necessarily work with another.
For safety's sake - I would power the DNS-323 and the PC from a power source other than the UPS (the wall outlet if you have stable utility power), find a load at least 80% of the UPS' capacity - if it's a 350VA UPS something like a 200W lamp (lower can work, it will just take longer to reach a low battery), connect it to the UPS and then unplug the UPS and let it run on battery whilst monitoring the DNS-323 status page.
What you should see is the status change from online to on battery, and then the battery status should reduce - this may or may not be reported, depending on the UPS, the SmartUPS should report it, I don't think the BackUPS do - and at some point the UPS will send the low battery alert, which should cause the DNS-323 to power off.
Ideally the DNS-323 should shutdown a minute or so before the UPS turns off - if the UPS turns off before the DNS-323 does (or the UPS turns off and the DNS-323 doesn't) then you know the test failed.