Symptoms:
DHCP Discover: Broadbact message: Ethernet II, Src: VMware_82:13:08 (##:##:##:##:##:08), Dst: Broadcast (##:##:##:##:##:ff)
Dynamic Host Configuration Protocol (Discover)
Message type: Boot Request (1)
Hardware type: Ethernet (0x01)
Hardware address length: 6
Hops: 0
Transaction ID: 0x14f11746
Seconds elapsed: 0
Bootp flags: 0x8000, Broadcast flag (Broadcast)
1... .... .... .... = Broadcast flag: Broadcast <----------- Broadcast flag set to 1.
.000 0000 0000 0000 = Reserved flags: 0x0000
Client IP address: 0.0.0.0
Your (client) IP address: 0.0.0.0
Next server IP address: 0.0.0.0
Relay agent IP address: 0.0.0.0
Client MAC address: VMware_82:13:08 (##:##:##:##:##:08)
Client hardware address padding: 00000000000000000000
Server host name not given
Boot file name not given
Magic cookie: DHCP
Option: (53) DHCP Message Type (Discover)
Option: (116) DHCP Auto-Configuration
Option: (61) Client identifier
Option: (12) Host Name
Option: (60) Vendor class identifier
Option: (55) Parameter Request List
Option: (255) End
Therefore the reply coming from the DHCP Relay is not a broadcast one.
DHCP Offer received on the Windows VM: Ethernet II, Src: ##:##:##:##:##:52 (##:##:##:##:##:52), Dst: VMware_82:13:08 (##:##:##:##:##:08)
Even if the flag was set to Broadcast 1:
Dynamic Host Configuration Protocol (Offer)
Message type: Boot Reply (2)
Hardware type: Ethernet (0x01)
Hardware address length: 6
Hops: 0
Transaction ID: 0x14f11746
Seconds elapsed: 0
Bootp flags: 0x8000, Broadcast flag (Broadcast)
1... .... .... .... = Broadcast flag: Broadcast <----------- Broadcast flag set to 1.
.000 0000 0000 0000 = Reserved flags: 0x0000
Client IP address: 0.0.0.0
Your (client) IP address: 10.38.0.248
Next server IP address: 0.0.0.0
Relay agent IP address: 0.0.0.0
Client MAC address: VMware_82:13:08 (##:##:##:##:##:08)
Client hardware address padding: 00000000000000000000
Server host name not given
Boot file name not given
Magic cookie: DHCP
Option: (53) DHCP Message Type (Offer)
Option: (54) DHCP Server Identifier (10.38.0.200)
Option: (51) IP Address Lease Time
Option: (1) Subnet Mask (255.255.255.0)
Option: (3) Router
Option: (255) End
Padding: 000000000000000000000000000000000000000000000000…