We just had this issue occur now on our wireless network
For my test computer I moved it to a network with DHCP on the switch instead of a Microsoft DHCP server and the issue still occurred there. So it's definitely something with either the network or endpoint. Since it's spread across several types of endpoint I'm leaning toward the network. I'm opening a case with that vendor to troubleshoot further.
They will get a 169.x.x.x address after the timeout occurs. The test PC will have a valid IP address. Then after a quick reboot it will timeout.
PortFast is already enabled on our switchports.
We just had this issue occur now on our wireless network
For my test computer I moved it to a network with DHCP on the switch instead of a Microsoft DHCP server and the issue still occurred there. So it's definitely something with either the network or endpoint. Since it's spread across several types of endpoint I'm leaning toward the network. I'm opening a case with that vendor to troubleshoot further.