bingo!
so your DHCP configuration is wrong
As stated at the very beginning of this long thread (or perhaps in the one you deleted), you are trying to implement to much complex set up in regard to your technical skill (for the time being. No doubt you will improve
)
You should rather go for basic DHCP configuration, ensure everything fine then move to the next step, adding - under control - more features.
Anyway, we are not going to investigate this right now.
To make it short:
- what is your client OS (I previously made assumption that it is Windows but I might be wrong)?
- in order to check wpad auto-discovery, could you please "rename" your client as
whatveryouwant.msserver01.lan and test auto-discovery?
Then we (or perhaps someone else
) will deal with DHCP conf.
BTW what's this habit to not use domain name when describing devices name?