That would depend on the additional equipment and its configuration.
L3 switches can split your network into separate segments, and some switches labeled as "L2 plus", "smart L2" or similar may be hybrid L2/L3 switches with limited configuration options (so they may lack e.g. DHCP relay options).
When that happens, what are the corresponding DHCP activities in Pi-hole's log?
Also, please upload a debug log and post just the token URL that is generated after the log is uploaded by running the following command from the Pi-hole host terminal:
pihole -d
or do it through the Web interface:
Tools > Generate Debug Log