Changing WSUS location

Yes. You need to check: Specify intranet Microsoft update service location
This is under Computer Config/Policies/Admin Templates/Windows Components/Windows Update

I have that GPO in place already and updated the location. Do I need to set-up an "intranet" location or does WSUS do that for me during install and I simply need to tell it http://server?

Yes - you need to use http://server for intranet location under the GPO.  To test it quickly - use systinternals PsExec with elevated priviliges.

Find a client pc that needs an update and make sure you policy is updated using:  gupdate /force.

1.  Login to client machine using psexec \\clientpc cmd to open command line
2.  Execute update by running wuauclt.exe -   example:  wuauclt /resetauthorization /detectnow
3.  Allow some time for update to occur.
4.  Then execute:  wuauclt /reportnow
5.  On WSUS server you will see client report in after it has completed.

I have tried two machines. One virtual and one metal. Neither are checking in.
Any other thoughts? Perhaps my initial set-up?

Here are few things I check.

1. Check client windowsupdate.log at C:\Windows\WindowsUpdate.log
     Here is sample I ran for you on a client pc using  'wuauclt.exe /detectnow /updatenow /reportnow'

2014-10-30      08:41:53:099       344      cb4      AU      Triggering AU detection through DetectNow API
2014-10-30      08:41:53:099       344      cb4      AU      Triggering Online detection (non-interactive)
2014-10-30      08:41:53:099       344      8b4      AU      #############
2014-10-30      08:41:53:099       344      8b4      AU      ## START ##  AU: Search for updates
2014-10-30      08:41:53:099       344      8b4      AU      #########
2014-10-30      08:41:53:114       344      8b4      AU      <<## SUBMITTED ## AU: Search for updates [CallId = {2B22EEDC-A72F-46B4-9B21-7F0C042F0001}]
2014-10-30      08:41:53:114       344      d60      Agent      *************
2014-10-30      08:41:53:114       344      d60      Agent      ** START **  Agent: Finding updates [CallerId = AutomaticUpdates]
2014-10-30      08:41:53:114       344      d60      Agent      *********
2014-10-30      08:41:53:114       344      d60      Agent        * Online = Yes; Ignore download priority = No
2014-10-30      08:41:53:114       344      d60      Agent        * Criteria = "IsInstalled=0 and DeploymentAction='Installation' or IsPresent=1 and DeploymentAction='Uninstallation' or IsInstalled=1 and DeploymentAction='Installation' and RebootRequired=1 or IsInstalled=0 and DeploymentAction='Uninstallation' and RebootRequired=1"
2014-10-30      08:41:53:114       344      d60      Agent        * ServiceID = {3DA21691-E39D-4DA6-8A4B-B43877BCB1B7} Managed
2014-10-30      08:41:53:114       344      d60      Agent        * Search Scope = {Machine}
2014-10-30      08:41:53:457       344      d60      Setup      Checking for agent SelfUpdate
2014-10-30      08:41:53:457       344      d60      Setup      Client version: Core: 7.6.7600.256  Aux: 7.6.7600.256
2014-10-30      08:41:53:457       344      d60      Misc      Validating signature for C:\Windows\SoftwareDistribution\SelfUpdate\wuident.cab:
2014-10-30      08:41:53:457       344      d60      Misc       Microsoft signed: Yes
2014-10-30      08:41:56:078       344      d60      Misc      Validating signature for C:\Windows\SoftwareDistribution\SelfUpdate\wuident.cab:
2014-10-30      08:41:56:078       344      d60      Misc       Microsoft signed: Yes
2014-10-30      08:41:56:094       344      d60      Misc      Validating signature for C:\Windows\SoftwareDistribution\SelfUpdate\wsus3setup.cab:
2014-10-30      08:41:56:094       344      d60      Misc       Microsoft signed: Yes
2014-10-30      08:41:56:109       344      d60      Misc      Validating signature for C:\Windows\SoftwareDistribution\SelfUpdate\wsus3setup.cab:
2014-10-30      08:41:56:109       344      d60      Misc       Microsoft signed: Yes
2014-10-30      08:41:56:125       344      d60      Setup      Determining whether a new setup handler needs to be downloaded
2014-10-30      08:41:56:125       344      d60      Setup      SelfUpdate handler is not found.  It will be downloaded
2014-10-30      08:41:56:125       344      d60      Setup      Evaluating applicability of setup package "WUClient-SelfUpdate-ActiveX~31bf3856ad364e35~amd64~~7.6.7600.256"
2014-10-30      08:41:57:560       344      d60      Setup      Setup package "WUClient-SelfUpdate-ActiveX~31bf3856ad364e35~amd64~~7.6.7600.256" is already installed.
2014-10-30      08:41:57:560       344      d60      Setup      Evaluating applicability of setup package "WUClient-SelfUpdate-Aux-TopLevel~31bf3856ad364e35~amd64~~7.6.7600.256"
2014-10-30      08:41:57:576       344      d60      Setup      Setup package "WUClient-SelfUpdate-Aux-TopLevel~31bf3856ad364e35~amd64~~7.6.7600.256" is already installed.
2014-10-30      08:41:57:576       344      d60      Setup      Evaluating applicability of setup package "WUClient-SelfUpdate-Core-TopLevel~31bf3856ad364e35~amd64~~7.6.7600.256"
2014-10-30      08:41:57:591       344      d60      Setup      Setup package "WUClient-SelfUpdate-Core-TopLevel~31bf3856ad364e35~amd64~~7.6.7600.256" is already installed.
2014-10-30      08:41:57:591       344      d60      Setup      SelfUpdate check completed.  SelfUpdate is NOT required.
2014-10-30      08:42:04:471       344      d60      PT      +++++++++++  PT: Synchronizing server updates  +++++++++++
2014-10-30      08:42:04:471       344      d60      PT        + ServiceId = {3DA21691-E39D-4DA6-8A4B-B43877BCB1B7}, Server URL = http://kdcserver1.kdc.corp.local/ClientWebService/client.asmx
2014-10-30      08:42:04:580       344      d60      PT      WARNING: Cached cookie has expired or new PID is available
2014-10-30      08:42:04:580       344      d60      PT      Initializing simple targeting cookie, clientId = 8a8cb24f-8a9b-44b9-a171-72085f8a1c55, target group = , DNS name = kodakscanner.kdc.corp.local
2014-10-30      08:42:04:580       344      d60      PT        Server URL = http://kdcserver1.kdc.corp.local/SimpleAuthWebService/SimpleAuth.asmx
2014-10-30      08:42:15:859       344      d60      PT      +++++++++++  PT: Synchronizing extended update info  +++++++++++
2014-10-30      08:42:15:859       344      d60      PT        + ServiceId = {3DA21691-E39D-4DA6-8A4B-B43877BCB1B7}, Server URL = http://kdcserver1.kdc.corp.local/ClientWebService/client.asmx
2014-10-30      08:42:17:715       344      d60      Agent        * Added update {1263C625-EC7E-4D70-A153-A449BD118EF1}.200 to search result
2014-10-30      08:42:17:715       344      d60      Agent        * Found 1 updates and 77 categories in search; evaluated appl. rules of 1554 out of 2763 deployed entities
2014-10-30      08:42:17:871       344      d60      Agent      *********
2014-10-30      08:42:17:871       344      d60      Agent      **  END  **  Agent: Finding updates [CallerId = AutomaticUpdates]
2014-10-30      08:42:17:871       344      d60      Agent      *************
2014-10-30      08:42:17:903       344      ac4      AU      >>##  RESUMED  ## AU: Search for updates [CallId = {2B22EEDC-A72F-46B4-9B21-7F0C042F0001}]
2014-10-30      08:42:17:903       344      ac4      AU        # 1 updates detected
2014-10-30      08:42:17:918       344      ac4      AU      #########
2014-10-30      08:42:17:918       344      ac4      AU      ##  END  ##  AU: Search for updates [CallId = {2B22EEDC-A72F-46B4-9B21-7F0C042F0001}]
2014-10-30      08:42:17:918       344      ac4      AU      #############
2014-10-30      08:42:17:918       344      ac4      AU      Successfully wrote event for AU health state:0
2014-10-30      08:42:17:918       344      ac4      AU      Featured notifications is disabled.
2014-10-30      08:42:17:918       344      ac4      AU      AU setting next detection timeout to 2014-10-31 11:42:18
2014-10-30      08:42:17:918       344      ac4      AU      Setting AU scheduled install time to 2014-10-31 08:00:00
2014-10-30      08:42:17:918       344      ac4      AU      Successfully wrote event for AU health state:0
2014-10-30      08:42:17:918       344      ac4      AU      Auto-approving update for download, updateId = {1263C625-EC7E-4D70-A153-A449BD118EF1}.200, ForUx=0, IsOwnerUx=0, HasDeadline=0, IsMinor=1
2014-10-30      08:42:17:918       344      ac4      AU      Auto-approved 1 update(s) for download (NOT for Ux)
2014-10-30      08:42:17:918       344      ac4      AU      #############
2014-10-30      08:42:17:918       344      ac4      AU      ## START ##  AU: Download updates
2014-10-30      08:42:17:918       344      ac4      AU      #########
2014-10-30      08:42:17:918       344      ac4      AU        # Approved updates = 1
2014-10-30      08:42:17:918       344      d60      DnldMgr      *************
2014-10-30      08:42:17:918       344      d60      DnldMgr      ** START **  DnldMgr: Downloading updates [CallerId = AutomaticUpdates]
2014-10-30      08:42:17:918       344      d60      DnldMgr      *********
2014-10-30      08:42:17:918       344      d60      DnldMgr        * Call ID = {9544DC9C-D92F-412B-9A14-244D8A42CB11}
2014-10-30      08:42:17:918       344      d60      DnldMgr        * Priority = 2, Interactive = 0, Owner is system = 1, Explicit proxy = 0, Proxy session id = -1, ServiceId = {3DA21691-E39D-4DA6-8A4B-B43877BCB1B7}
2014-10-30      08:42:17:918       344      d60      DnldMgr        * Updates to download = 1
2014-10-30      08:42:17:918       344      d60      Agent        *   Title = Definition Update for Windows Defender - KB915597 (Definition 1.187.850.0)
2014-10-30      08:42:17:934       344      d60      Agent        *   UpdateId = {1263C625-EC7E-4D70-A153-A449BD118EF1}.200
2014-10-30      08:42:17:934       344      d60      Agent        *     Bundles 1 updates:
2014-10-30      08:42:17:934       344      d60      Agent        *       {5783244D-0AEE-496D-BD93-DA32C6E971D0}.200
2014-10-30      08:42:17:949       344      ac4      AU      AU initiated download, updateId = {1263C625-EC7E-4D70-A153-A449BD118EF1}.200, callId = {9544DC9C-D92F-412B-9A14-244D8A42CB11}
2014-10-30      08:42:17:949       344      ac4      AU      Setting AU scheduled install time to 2014-10-31 08:00:00
2014-10-30      08:42:17:949       344      ac4      AU      Successfully wrote event for AU health state:0
2014-10-30      08:42:17:965       344      d60      DnldMgr      ***********  DnldMgr: New download job [UpdateId = {5783244D-0AEE-496D-BD93-DA32C6E971D0}.200]  ***********
2014-10-30      08:42:20:321       344      d60      DnldMgr        * BITS job initialized, JobId = {2A15AAB9-DB07-460E-AAA3-34C2681532EF}
2014-10-30      08:42:20:430       344      d60      DnldMgr        * Downloading from http://wsus.ds.download.windowsupdate.com/d/msdownload/update/software/defu/2014/10/mpas-d_bd_1.187.710.0_fdf9222f8947a9ff3400db77d28a31e2f5fea3de.exe to C:\Windows\SoftwareDistribution\Download\654ab75d339ce61c0a23dc06712ed32f\fdf9222f8947a9ff3400db77d28a31e2f5fea3de (full file).
2014-10-30      08:42:20:586       344      ac4      AU      AU setting pending client directive to 'Download Progress'
2014-10-30      08:42:20:586       344      d60      Agent      *********
2014-10-30      08:42:20:586       344      d60      Agent      **  END  **  Agent: Downloading updates [CallerId = AutomaticUpdates]
2014-10-30      08:42:20:586       344      d60      Agent      *************
2014-10-30      08:42:20:633       344      ac4      AU      Successfully wrote event for AU health state:0
2014-10-30      08:42:20:633       344      ac4      AU        # Pending download calls = 1
2014-10-30      08:42:20:633       344      ac4      AU      <<## SUBMITTED ## AU: Download updates
2014-10-30      08:42:20:633       344      ac4      AU      Successfully wrote event for AU health state:0
2014-10-30      08:42:22:879       344      d60      Report      REPORT EVENT: {E1B3DEBF-FC84-4488-9A3A-96DC18D4C7C8}      2014-10-30 08:42:17:871-0700      1      147      101      {00000000-0000-0000-0000-000000000000}      0      0      AutomaticUpdates      Success      Software Synchronization      Windows Update Client successfully detected 1 updates.
2014-10-30      08:42:22:879       344      d60      Report      REPORT EVENT: {7C9E4688-3874-4314-86FF-F197F5F8A58B}      2014-10-30 08:42:17:871-0700      1      156      101      {00000000-0000-0000-0000-000000000000}      0      0      AutomaticUpdates      Success      Pre-Deployment Check      Reporting client status.
2014-10-30      08:42:22:879       344      d60      Report      CWERReporter finishing event handling. (00000000)
2014-10-30      08:42:35:593       344      8b4      AU      Launched new AU client for directive 'Download Progress', session id = 0x2
2014-10-30      08:42:36:935       344      12d8      DnldMgr      BITS job {2A15AAB9-DB07-460E-AAA3-34C2681532EF} completed successfully
2014-10-30      08:42:37:013       344      12d8      Misc      Validating signature for C:\Windows\SoftwareDistribution\Download\654ab75d339ce61c0a23dc06712ed32f\fdf9222f8947a9ff3400db77d28a31e2f5fea3de:
2014-10-30      08:42:37:028       344      12d8      Misc       Microsoft signed: Yes
2014-10-30      08:42:37:059       344      12d8      DnldMgr        Download job bytes total = 324856, bytes transferred = 324856
2014-10-30      08:42:37:059       344      12d8      DnldMgr      ***********  DnldMgr: New download job [UpdateId = {5783244D-0AEE-496D-BD93-DA32C6E971D0}.200]  ***********
2014-10-30      08:42:37:059       344      12d8      DnldMgr        * All files for update were already downloaded and are valid.
2014-10-30      08:42:37:075       344      ac4      AU      >>##  RESUMED  ## AU: Download update [UpdateId = {1263C625-EC7E-4D70-A153-A449BD118EF1}, succeeded]
2014-10-30      08:42:37:075       344      ac4      AU      #########
2014-10-30      08:42:37:075       344      ac4      AU      ##  END  ##  AU: Download updates
2014-10-30      08:42:37:075       344      ac4      AU      #############
2014-10-30      08:42:37:075       344      ac4      AU      Setting AU scheduled install time to 2014-10-31 08:00:00
2014-10-30      08:42:37:075       344      ac4      AU      Successfully wrote event for AU health state:0
2014-10-30      08:42:37:075       344      ac4      AU      Auto-approving update for install, updateId = {1263C625-EC7E-4D70-A153-A449BD118EF1}.200, ForUx=0, IsOwnerUx=0, HasDeadline=0, IsMinor=1
2014-10-30      08:42:37:075       344      ac4      AU      Auto-approved 1 update(s) for install (NOT for Ux), installType=2
2014-10-30      08:42:37:075       344      ac4      AU      #############
2014-10-30      08:42:37:075       344      ac4      AU      ## START ##  AU: Install updates
2014-10-30      08:42:37:075       344      ac4      AU      #########
2014-10-30      08:42:37:075       344      ac4      AU        # Initiating minor updates install
2014-10-30      08:42:37:075       344      ac4      AU        # Approved updates = 1
2014-10-30      08:42:37:075       344      ac4      AU      <<## SUBMITTED ## AU: Install updates / installing updates [CallId = {39E26501-FD41-4115-9C44-E72E9B5CA6B9}]
2014-10-30      08:42:37:075       344      1128      Agent      *************
2014-10-30      08:42:37:075       344      1128      Agent      ** START **  Agent: Installing updates [CallerId = AutomaticUpdates]
2014-10-30      08:42:37:075       344      1128      Agent      *********
2014-10-30      08:42:37:075       344      1128      Agent        * Updates to install = 1
2014-10-30      08:42:37:075       344      1128      Agent        *   Title = Definition Update for Windows Defender - KB915597 (Definition 1.187.850.0)
2014-10-30      08:42:37:075       344      1128      Agent        *   UpdateId = {1263C625-EC7E-4D70-A153-A449BD118EF1}.200
2014-10-30      08:42:37:075       344      1128      Agent        *     Bundles 1 updates:
2014-10-30      08:42:37:075       344      1128      Agent        *       {5783244D-0AEE-496D-BD93-DA32C6E971D0}.200
2014-10-30      08:42:37:075       344      ac4      AU      Successfully wrote event for AU health state:0
2014-10-30      08:42:37:091       344      8b4      AU      AU received handle event
2014-10-30      08:42:37:153       344      1128      DnldMgr      Preparing update for install, updateId = {5783244D-0AEE-496D-BD93-DA32C6E971D0}.200.
2014-10-30      08:42:37:184      3412      1b0      Misc      ===========  Logging initialized (build: 7.6.7600.256, tz: -0700)  ===========
2014-10-30      08:42:37:184      3412      1b0      Misc        = Process: C:\Windows\system32\wuauclt.exe
2014-10-30      08:42:37:184      3412      1b0      Misc        = Module: C:\Windows\system32\wuaueng.dll
2014-10-30      08:42:37:184      3412      1b0      Handler      :::::::::::::
2014-10-30      08:42:37:184      3412      1b0      Handler      :: START ::  Handler: Command Line Install
2014-10-30      08:42:37:184      3412      1b0      Handler      :::::::::
2014-10-30      08:42:37:184      3412      1b0      Handler        : Updates to install = 1
2014-10-30      08:42:42:083       344      d60      Report      REPORT EVENT: {4D1C6EA3-DD64-4A53-92CD-D06F03B75674}      2014-10-30 08:42:37:075-0700      1      162      101      {1263C625-EC7E-4D70-A153-A449BD118EF1}      200      0      AutomaticUpdates      Success      Content Download      Download succeeded.
2014-10-30      08:42:42:083       344      d60      Report      REPORT EVENT: {4AEFB762-D250-4744-997F-89ECA2C0201A}      2014-10-30 08:42:37:075-0700      1      188      102      {00000000-0000-0000-0000-000000000000}      0      0      AutomaticUpdates      Success      Content Install      Installation Ready: The following updates are downloaded and ready for installation. This computer is currently scheduled to install these updates on ‎Friday, ‎October ‎31, ‎2014 at 1:00 AM:  - Definition Update for Windows Defender - KB915597 (Definition 1.187.850.0)
2014-10-30      08:42:42:083       344      d60      Report      CWERReporter finishing event handling. (00000000)
2014-10-30      08:42:44:594      3412      1b0      Handler        : Command line install completed. Return code = 0x00000000, Result = Succeeded, Reboot required = false
2014-10-30      08:42:44:594      3412      1b0      Handler      :::::::::
2014-10-30      08:42:44:594      3412      1b0      Handler      ::  END  ::  Handler: Command Line Install
2014-10-30      08:42:44:594      3412      1b0      Handler      :::::::::::::
2014-10-30      08:42:44:641       344      ac4      AU      >>##  RESUMED  ## AU: Installing update [UpdateId = {1263C625-EC7E-4D70-A153-A449BD118EF1}, succeeded]
2014-10-30      08:42:44:859       344      1128      Agent      *********
2014-10-30      08:42:44:859       344      1128      Agent      **  END  **  Agent: Installing updates [CallerId = AutomaticUpdates]
2014-10-30      08:42:44:859       344      1128      Agent      *************
2014-10-30      08:42:44:859       344      ac4      AU      Install call completed.
2014-10-30      08:42:44:859       344      ac4      AU        # WARNING: Install call completed, reboot required = No, error = 0x00000000
2014-10-30      08:42:44:859       344      ac4      AU      #########
2014-10-30      08:42:44:859       344      ac4      AU      ##  END  ##  AU: Installing updates [CallId = {39E26501-FD41-4115-9C44-E72E9B5CA6B9}]
2014-10-30      08:42:44:859       344      ac4      AU      #############
2014-10-30      08:42:44:859       344      ac4      AU      Install complete for all calls, reboot NOT needed
2014-10-30      08:42:44:859       344      ac4      AU      Setting AU scheduled install time to 2014-10-31 08:00:00
2014-10-30      08:42:44:859       344      ac4      AU      Successfully wrote event for AU health state:0
2014-10-30      08:42:44:875       344      ac4      AU      Successfully wrote event for AU health state:0
2014-10-30      08:42:44:875       344      ac4      AU      Triggering Offline detection (non-interactive)
2014-10-30      08:42:44:875       344      8b4      AU      #############
2014-10-30      08:42:44:875       344      8b4      AU      ## START ##  AU: Search for updates
2014-10-30      08:42:44:875       344      8b4      AU      #########
2014-10-30      08:42:44:875       344      8b4      AU      <<## SUBMITTED ## AU: Search for updates [CallId = {99DA7C7E-CA19-433A-B5F9-9192F47A63D0}]
2014-10-30      08:42:44:875       344      d60      Agent      *************
2014-10-30      08:42:44:875       344      d60      Agent      ** START **  Agent: Finding updates [CallerId = AutomaticUpdates]
2014-10-30      08:42:44:875       344      d60      Agent      *********
2014-10-30      08:42:44:875       344      d60      Agent        * Online = No; Ignore download priority = No
2014-10-30      08:42:44:875       344      d60      Agent        * Criteria = "IsInstalled=0 and DeploymentAction='Installation' or IsPresent=1 and DeploymentAction='Uninstallation' or IsInstalled=1 and DeploymentAction='Installation' and RebootRequired=1 or IsInstalled=0 and DeploymentAction='Uninstallation' and RebootRequired=1"
2014-10-30      08:42:44:875       344      d60      Agent        * ServiceID = {3DA21691-E39D-4DA6-8A4B-B43877BCB1B7} Managed
2014-10-30      08:42:44:875       344      d60      Agent        * Search Scope = {Machine}
2014-10-30      08:42:54:984       344      d60      Agent        * Found 0 updates and 77 categories in search; evaluated appl. rules of 1339 out of 2763 deployed entities
2014-10-30      08:42:54:999       344      d60      Agent      *********
2014-10-30      08:42:54:999       344      d60      Agent      **  END  **  Agent: Finding updates [CallerId = AutomaticUpdates]
2014-10-30      08:42:54:999       344      d60      Agent      *************
2014-10-30      08:42:55:031       344      d60      Report      REPORT EVENT: {92BA9FA6-968B-4038-99B7-DA1E91BC6834}      2014-10-30 08:42:44:641-0700      1      183      101      {1263C625-EC7E-4D70-A153-A449BD118EF1}      200      0      AutomaticUpdates      Success      Content Install      Installation Successful: Windows successfully installed the following update: Definition Update for Windows Defender - KB915597 (Definition 1.187.850.0)
2014-10-30      08:42:55:031       344      ac4      AU      >>##  RESUMED  ## AU: Search for updates [CallId = {99DA7C7E-CA19-433A-B5F9-9192F47A63D0}]
2014-10-30      08:42:55:031       344      ac4      AU        # 0 updates detected
2014-10-30      08:42:55:031       344      ac4      AU      #########
2014-10-30      08:42:55:031       344      ac4      AU      ##  END  ##  AU: Search for updates [CallId = {99DA7C7E-CA19-433A-B5F9-9192F47A63D0}]
2014-10-30      08:42:55:031       344      ac4      AU      #############
2014-10-30      08:42:55:031       344      ac4      AU      Featured notifications is disabled.
2014-10-30      08:42:55:031       344      d60      Report      CWERReporter finishing event handling. (00000000)
2014-10-30      08:42:55:031       344      ac4      AU      Setting AU scheduled install time to 2014-10-31 08:00:00
2014-10-30      08:42:55:031       344      ac4      AU      Successfully wrote event for AU health state:0
2014-10-30      08:42:55:031       344      ac4      AU      Successfully wrote event for AU health state:0
2014-10-30      08:43:00:038       344      d60      Report      CWERReporter finishing event handling. (00000000)
2014-10-30      08:45:18:020       344      d60      Report      Uploading 4 events using cached cookie, reporting URL = http://kdcserver1.kdc.corp.local/ReportingWebService/ReportingWebService.asmx
2014-10-30      08:45:18:036       344      d60      Report      Reporter successfully uploaded 4 events.
2014-10-30      09:36:37:476       344      8b4      AU      AU setting next sqm report timeout to 2014-10-31 16:36:37


2. Log will contain information showing the time you launched a manual update to contact WSUS.
3. Firewall not blocking access to WSUS service.
4. Run wireshark and manually launch 'wuauclt /detectnow /reportnow'  and see if you are communicating.

This is helpful. Here is the bottom of the report. Any initial thoughts before I look at error codes?

2014-10-30      14:04:24:490      1148      2e7c      PT      WARNING: Cached cookie has expired or new PID is available
2014-10-30      14:04:24:490      1148      2e7c      PT      Initializing simple targeting cookie, clientId = 77b1a98a-268d-4834-b10b-2fb901c65328, target group = , DNS name = it-pc.domain.com
2014-10-30      14:04:24:490      1148      2e7c      PT        Server URL = http://192.168.1.121/SimpleAuthWebService/SimpleAuth.asmx
2014-10-30      14:04:24:495      1148      2e7c      PT      WARNING: GetAuthorizationCookie failure, error = 0x80244019, soap client error = 10, soap error code = 0, HTTP status code = 404
2014-10-30      14:04:24:495      1148      2e7c      PT      WARNING: Failed to initialize Simple Targeting Cookie: 0x80244019
2014-10-30      14:04:24:495      1148      2e7c      PT      WARNING: PopulateAuthCookies failed: 0x80244019
2014-10-30      14:04:24:495      1148      2e7c      PT      WARNING: RefreshCookie failed: 0x80244019
2014-10-30      14:04:24:495      1148      2e7c      PT      WARNING: RefreshPTState failed: 0x80244019
2014-10-30      14:04:24:495      1148      2e7c      PT      WARNING: PTError: 0x80244019
2014-10-30      14:04:24:495      1148      2e7c      Report      WARNING: Reporter failed to upload events with hr = 80244019

If using psexec from WSUS server you will need to use:  psexec \\pclient wuauclt /detectnow /updatenow /reportnow.

If on PC then run cmd in elevated mode and use:  wuauclt /detectnow /updatenow /reportnow

404 error suggests that the HTTP page is missing

Is  IIS installed?
Port blocked?

Please See:

https://social.technet.microsoft.com/Forums/en-US/2f837dc3-65d2-40f5-b1fa-d2df50839541/clients-not-registering-with-wsus-servercompletely-out-of-ideas?forum=winserverwsus

WARNING: GetAuthorizationCookie failure, error = 0x80244019, soap client error = 10, soap error code = 0, HTTP status code = 404

Much better view on this. Here is what came up. I am going to try changing the IP address of WSUS back to name within GPO. Any other thoughts on what you see below. It looks like I am missing something pretty fundamental here...

2014-10-30      14:44:32:917      1148      1200      AU      #############
2014-10-30      14:44:32:917      1148      1200      AU      ## START ##  AU: Search for updates
2014-10-30      14:44:32:917      1148      1200      AU      #########
2014-10-30      14:44:32:919      1148      1200      AU      <<## SUBMITTED ## AU: Search for updates [CallId = {4CD11EE8-8141-48AA-A400-ED467D2BEA1C}]
2014-10-30      14:44:32:919      1148      1cf4      Agent      *************
2014-10-30      14:44:32:919      1148      1cf4      Agent      ** START **  Agent: Finding updates [CallerId = AutomaticUpdates]
2014-10-30      14:44:32:919      1148      1cf4      Agent      *********
2014-10-30      14:44:32:919      1148      1cf4      Agent        * Online = Yes; Ignore download priority = No
2014-10-30      14:44:32:919      1148      1cf4      Agent        * Criteria = "IsInstalled=0 and DeploymentAction='Installation' or IsPresent=1 and DeploymentAction='Uninstallation' or IsInstalled=1 and DeploymentAction='Installation' and RebootRequired=1 or IsInstalled=0 and DeploymentAction='Uninstallation' and RebootRequired=1"
2014-10-30      14:44:32:919      1148      1cf4      Agent        * ServiceID = {3DA21691-E39D-4DA6-8A4B-B43877BCB1B7} Managed
2014-10-30      14:44:32:919      1148      1cf4      Agent        * Search Scope = {Machine}
2014-10-30      14:44:32:945      1148      1cf4      Setup      Checking for agent SelfUpdate
2014-10-30      14:44:32:946      1148      1cf4      Setup      Client version: Core: 7.6.7600.256  Aux: 7.6.7600.256
2014-10-30      14:44:32:949      1148      1cf4      Misc      WARNING: WinHttp: SendRequestToServerForFileInformation failed with 0x80190194
2014-10-30      14:44:32:949      1148      1cf4      Misc      WARNING: WinHttp: ShouldFileBeDownloaded failed with 0x80190194
2014-10-30      14:44:32:949      1148      1cf4      Misc      WARNING: DownloadFileInternal failed for http://192.168.1.121/selfupdate/wuident.cab: error 0x80190194
2014-10-30      14:44:32:949      1148      1cf4      Setup      WARNING: SelfUpdate check failed to download package information, error = 0x80244019
2014-10-30      14:44:32:949      1148      1cf4      Setup      FATAL: SelfUpdate check failed, err = 0x80244019
2014-10-30      14:44:32:950      1148      1cf4      Agent        * WARNING: Skipping scan, self-update check returned 0x80244019
2014-10-30      14:44:32:958      1148      1cf4      Agent        * WARNING: Exit code = 0x80244019
2014-10-30      14:44:32:958      1148      1cf4      Agent      *********
2014-10-30      14:44:32:958      1148      1cf4      Agent      **  END  **  Agent: Finding updates [CallerId = AutomaticUpdates]
2014-10-30      14:44:32:958      1148      1cf4      Agent      *************
2014-10-30      14:44:32:958      1148      1cf4      Agent      WARNING: WU client failed Searching for update with error 0x80244019
2014-10-30      14:44:32:958      1148      2730      AU      >>##  RESUMED  ## AU: Search for updates [CallId = {4CD11EE8-8141-48AA-A400-ED467D2BEA1C}]
2014-10-30      14:44:32:958      1148      2730      AU        # WARNING: Search callback failed, result = 0x80244019
2014-10-30      14:44:32:958      1148      2730      AU        # WARNING: Failed to find updates with error code 80244019
2014-10-30      14:44:32:958      1148      2730      AU      #########
2014-10-30      14:44:32:958      1148      2730      AU      ##  END  ##  AU: Search for updates [CallId = {4CD11EE8-8141-48AA-A400-ED467D2BEA1C}]
2014-10-30      14:44:32:958      1148      2730      AU      #############
2014-10-30      14:44:32:959      1148      2730      AU      Successfully wrote event for AU health state:0
2014-10-30      14:44:32:959      1148      2730      AU      AU setting next detection timeout to 2014-10-31 00:44:32
2014-10-30      14:44:32:959      1148      2730      AU      Setting AU scheduled install time to 2014-10-31 08:00:00
2014-10-30      14:44:32:959      1148      2730      AU      Successfully wrote event for AU health state:0
2014-10-30      14:44:32:960      1148      2730      AU      Successfully wrote event for AU health state:0
2014-10-30      14:44:37:949      1148      1cf4      Report      REPORT EVENT: {EAE2396F-3149-4E9E-B082-65284C692CD3}      2014-10-30 14:44:32:949-0500      1      148      101      {D67661EB-2423-451D-BF5D-13199E37DF28}      1      80244019      SelfUpdate      Failure      Software Synchronization      Windows Update Client failed to detect with error 0x80244019.
2014-10-30      14:44:37:961      1148      1cf4      Report      CWERReporter::HandleEvents - WER report upload completed with status 0x8
2014-10-30      14:44:37:962      1148      1cf4      Report      WER Report sent: 7.6.7600.256 0x80244019 D67661EB-2423-451D-BF5D-13199E37DF28 Scan 101 Managed
2014-10-30      14:44:37:962      1148      1cf4      Report      CWERReporter finishing event handling. (00000000)

Sorry, missed your previous message before responding.
Yes, IIS is installed and I've completely turned off the firewall on the server too.

I will check our link out as well...

OH MY GOD! It was the port number. And unfortunately I didn't remove all the users and computers within group policy so I just created an hour long network storm while everyone's machines decided to check in with WSUS. AUGH!

Hope I still have a job tomorrow. That was one brutal hour.

I added the port number and machines checked in!

Way to go Mark!