Steps to Reproduce:

1. Place repeat command block at the bottom and conditional chain command block at the top
2. Set the following command in the bottom command block:

   RUA (Repeat, Unconditional, and Always Active):
   /execute as @e[name=diamond] at @s run kill

3. Set the following command in the top command block:

   CCA (Chain, Conditional, and Always Active) and DITs (Delay in Ticks): 40
   /say Hello

4. Drop diamond

Expected Results:
"Hello" will appear in chat after 40 ticks, or 2 seconds

Observed Results:
"Hello" will appear in chat immediately

Note:
It seems doesn't happen if it's placed on top of command block; neither chain nor repeat

Video (Attention: This is old):
https://drive.google.com/file/d/1RNwFDFu6hxT6_mkSagiyXBx0LDvK4UgO/view?usp=sharing