Dell Digital Delivery

I'm using a freshly imaged copy of Windows 10, version 1903 and trying to get Dell Digital Delivery to work. It keeps erroring out saying it can't connect to the internet, but following the troubleshooting page I'm able to get to the link it mentions without issue. I'm getting a strange HTTPS error in the logs, but my Google skills are not finding much related. Anyone else seen this kind of error?

2019-09-23 14:19:02,776 [4] INFO Service Started; Client Version: 3.5.2000.0; OS: WIN10; Service Tag: XXXXXXXX; BIOS SystemId: 05BD; Thread UI: en-US; Installed UI: en-US [OnStart]
2019-09-23 14:19:02,869 [4] INFO Debug Logging: 0 / Test Server Services: 0 / Test Server DAWS: 0 / FSUIF: 0 [OnStart]
2019-09-23 14:19:03,104 [4] INFO Settings file is owned by BUILTIN\Administrators [DoFileSystemCleanup]
2019-09-23 14:19:03,104 [4] INFO Service Initializing. [InitializeService]
2019-09-23 14:19:03,104 [4] INFO Network status: Connected; Not Configured; Not Offline; Modem not Connected; LAN Connected; No Proxy; RAS. [InitializeService]
2019-09-23 14:19:03,119 [4] INFO The OS is WT so using OOBEComplete API [SystemOobeIsInProgress]
2019-09-23 14:19:03,119 [4] INFO isOobeCompleteResult : 1 [SystemOobeIsInProgress]
2019-09-23 14:19:03,807 [4] INFO Getting configuration for '_upgradePath2'. [GetAppConfigString]
2019-09-23 14:19:04,322 [4] ERROR Error getting/processing App Config: An error occurred while making the HTTP request to https://cloud.dell.com/ClientServices/Client.svc/v1/Client/Config?r=_upgradePath2. This could be due to the fact that the server certificate is not configured properly with HTTP.SYS in the HTTPS case. This could also be caused by a mismatch of the security binding between the client and the server.

Server stack trace:
at System.ServiceModel.Channels.HttpChannelUtilities.ProcessGetResponseWebException(WebException webException, HttpWebRequest request, HttpAbortReason abortReason)
at System.ServiceModel.Channels.HttpChannelFactory`1.HttpRequestChannel.HttpChannelRequest.WaitForReply(TimeSpan timeout)
at System.ServiceModel.Channels.RequestChannel.Request(Message message, TimeSpan timeout)
at System.ServiceModel.Dispatcher.RequestChannelBinder.Request(Message message, TimeSpan timeout)
at System.ServiceModel.Channels.ServiceChannel.Call(String action, Boolean oneway, ProxyOperationRuntime operation, Object[] ins, Object[] outs, TimeSpan timeout)
at System.ServiceModel.Channels.ServiceChannelProxy.InvokeService(IMethodCallMessage methodCall, ProxyOperationRuntime operation)
at System.ServiceModel.Channels.ServiceChannelProxy.Invoke(IMessage message)

Exception rethrown at [0]:
at System.Runtime.Remoting.Proxies.RealProxy.HandleReturnMessage(IMessage reqMsg, IMessage retMsg)
at System.Runtime.Remoting.Proxies.RealProxy.PrivateInvoke(MessageData& msgData, Int32 type)
at Dell.CDA.ClientServices.Contracts.IClientSupport.GetRegionalConfig(String Region)
at Dell.Svdc.WebApps.Fulfillment.Client.DellItServicesConnection.GetAppConfigString()
at Dell.Svdc.WebApps.Fulfillment.Client.DellItServicesConnection.GetAppConfig()
at Dell.ClientFulfillmentService.ClientFulfillmentService.RetrieveAppConfig() [RetrieveAppConfig]
2019-09-23 14:19:04,322 [4] ERROR AppConfig not processed [ProcessAppConfig]
2019-09-23 14:19:04,338 [4] INFO Checking EULA status. [InitializeService]
2019-09-23 14:19:04,338 [5] WARN Unable to retrieving setting 'IsCommercial': Specified cast is not valid. [GetSetting]
2019-09-23 14:19:04,338 [5] WARN Not logging event because DAWS logging not explicitly enabled in the registry. [LogEventToDawsAndWait]
2019-09-23 14:19:04,447 [4] INFO Loaded unencrypted (new format) settings. [LoadSettingsFromXml]
2019-09-23 14:19:04,479 [4] INFO Slow Polling Mode is OFF; Polling Interval is 300 minutes. [Initialize]
2019-09-23 14:19:04,494 [4] INFO Initializing Download Manager [Initialize]
2019-09-23 14:19:09,478 [4] INFO Receiver Started [InitializeService]