well, it does exactly that…it progresses for 28 days/4 weeks and then resets back to start from day one…
it starts and resets on same day for everyone, so if you miss a day, you are not able to collect all rewards
your issue is that you probably believe it is personalized for each player…it is not, we all use the same 4 week time period starting from season start for claiming rewards…and if someone starts playing in middle of that 4 week period, he can’t claim all 28 rewards
as far i know (from previous seasons), that also means that it will again reset to day 1 with the server wipe in about a week
perhaps if you took a few minutes of your time to read a section about daily loot in the Guide part of HWS site, you would know that