It could also be that he is going through a growth spurt atm so his milk demand has increased? And maybe attempting some cluster feeding to up the supply maybe?
Yeah I wondered if it's a growth spurt too... Ah interesting, did you eventually get a milk supply when pumping after the bedtime feed? I have it during the night (3am) but it would be nice to sleep as soon as he does! And yes, I need to remember hydration!
Your milk supply is stabilising around now. Unless you have an undiagnosed health issue it is very unlikely your milk is drying up. Babies around this age are changing and their old hunger cues, sometimes are no longer hunger cues but just exploring I recommend following a decent lactation consultant online, there is so much misinformation in the media and they can break it down to what’s actually real v made up. I like Lucy Webber https://www.instagram.com/lucywebberfeedingsupport_ibclc?igsh=MWc5czlueHg3Z3Zycg==
In the evening and night the supply naturally goes down. One way I used to manage it was to feed and pump at night after feeding for bed. To try and increase demand. Also hydration during day is way more important than I ever realised. Coconut water was a good way to get the job done