Yes ! you are absolutely right. I also didn't got 1GB Extra against my wife's ₹149/- recharge (had done ₹99 + ₹149*3 during March & ₹303 in April for Summer Surprise). After the Summer Surprise got over on 19th July the ₹149 recharge got activated for 28 days (till 16th August) instead of ₹303 as expected and ₹149*2 & ₹303 is showing queued under My Statement. So the recharges are getting activated chronologically as was the order of recharges.
I remember that 1GB extra for ₹149 was announced later after 25th March so who ever recharged after that may get it directly whereas other users who ever recharged before that may have to approach customer care to get it added manually (Software glitch as pointed out by you).
See my wife's recharge history below and the Plan balance info also - 1GB extra is shown against my third ₹149 recharge which is done after 25th March & not against my earlier recharges.
Further Jio did announce to pass on the extra benefit (current validity) for ₹303/₹309 or higher candidates but neglected ₹149 users (could have increased either bonus data or validity). Seems they want to discourage ₹149/- customers.
Update (21st July) : Called customer service today morning and was assured that my case is escalated & 1GB extra will be added to my account in 48 hours. Let's see.