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I found my issue after a ton of searching. This thread (https://social.technet.microsoft.com/Forums/ie/en-US/a1246f62-6a8a-482b-9323-7e02dfeab196/wds-tftp-errorcode-1460?forum=winserversetup) had the answer. I was getting a TFTP error 1460 which is a timeout and it turns out that a limitation in the block size for files being transferred via TFTP was what caused my issue. This seems like the kind of thing that others would run into so I will post the actual change. On the PXE Boot DP/MP you need to make a change to the following registry key and then restart the Windows Deployment Service in the Services MMC snap in. Location:HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\services\WDSServer\Providers\WDSTFTPName: MaximumBlockSize Type: (REG_DWORD) Value range: 512–1456 Base: (Decimal) I have experimented with 512 and 1024 block sizes and they both seem to work however my guess is that 1024 will produce faster results when imaging. I am pulling my first image for Windows 10 using PXE Boot but unfortunately I don't have a local DP setup to handle the files so the whole process is being strung out through my WAN. I hope to get a test DP in my location later today so that further testing can move along much faster.