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WMS Unable to Pull Image from D90D7

Very frustrating. So I have recently upgraded our server from WDM to WMS 1.4 and I am having issues doing anything that interacts with the WMS Local Repository. My current setup is trying to pull an image from one D90D7 that I have customized for our other machines, and put it onto our WMS local repository. Every time I try to pull, it gets stuck at "Failed to connect to WMS Repository... Error 105 - Please check network connection/authentication".

I have done everything from updating our WDA to latest version, the Merlin OS to 4.0.1, reimaged the device after wiping it. The only difference is that the WMS Server is running on a different port than default (443) as it was impossible to run the Web Server without changing the port.

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