I don't believe this is a WIM issue as you're using the identical image file across the two servers. I am suspecting that the short filename / path (8.3 file system) is not implemented with v9.5 (new WinPE image based on Win8 has this disabled by default).
During your provisioning stage where you prep your disk prior to applying the WIM to the partition, execute this format command;
FORMAT <your windows destination drive> /FS:NTFS /Q /S:ENABLE /Y
The command will re-enable short filename system on the partition. Apply your image after the format and carry on as you would normally and see if this has resolved your issue.
I've added an Enhancement Request to have the 8.3 filesystem as an optional checkbox under the Provisioning Template action to resolve this issue to support legacy apps.