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It appears to be working now. I re-generated the cert and it is publishing to WSUS. Now sure what the problem was with the first one...

We don't have a proxy. We do have a web filter but watching the monitor, it is allowing traffic out to digicert. When I run a tracert to that address it appears to timeout after it leaves my network at the hop for lag-115.ear2.chicago2.level3.net. This makes me think that digicert has ping blocked on their end so a ping test wouldn't do much good in diagnosing a connection to their servers. Are you able to ping digicert and receive a reply?

Certificate appears to be imported correctly. (See attached)
I am not able to ping timestamp.digicert.com - Getting Request timed out.

30 Day trial user here. Installed everything according to documentation. When running the Publishing Service Sync by clicking button on Sync Schedule tab I get this error.
Here is a few lines from the log:

Starting download for: http://armdl.adobe.com/pub/adobe/reader/win/Acrobat2017/1701130152/AcroRdr2017Upd1701130152_MUI.msp   Downloader   11/6/2019 8:27:11 AM   6 (0x0006)
Finished downloading file: [http://armdl.adobe.com/pub/adobe/reader/win/Acrobat2017/1701130152/AcroRdr2017Upd1701130152_MUI.msp] Average speed: 29.64 MB/s (62 MB)   Downloader   11/6/2019 8:27:13 AM   22 (0x0016)
Successfully downloaded the update   Downloader   11/6/2019 8:27:13 AM   6 (0x0006)
Digest of downloaded update 3aZy4l3CWZrj/TIFpxJPgfF4ZGg= matches the digest from the catalog 3aZy4l3CWZrj/TIFpxJPgfF4ZGg=   Worker   11/6/2019 8:27:13 AM   6 (0x0006)
Calling WSUS API to publish an update to WSUS this can take a few minutes for large updates   Worker   11/6/2019 8:27:13 AM   6 (0x0006)
An error occurred while publishing an update to WSUS: Failed to sign package; error was: 2148081670   Worker   11/6/2019 8:28:07 AM   6 (0x0006)
Starting download for: http://armdl.adobe.com/pub/adobe/reader/win/Acrobat2015/1500630505/AcroRdr2015Upd1500630505_MUI.msp   Downloader   11/6/2019 8:28:07 AM   6 (0x0006)
Finished downloading file: [http://armdl.adobe.com/pub/adobe/reader/win/Acrobat2015/1500630505/AcroRdr2015Upd1500630505_MUI.msp] Average speed: 23.21 MB/s (46 MB)   Downloader   11/6/2019 8:28:09 AM   17 (0x0011)
Successfully downloaded the update   Downloader   11/6/2019 8:28:09 AM   6 (0x0006)
Digest of downloaded update JegJchGI62xG3CFylbmo/QUNP6U= matches the digest from the catalog JegJchGI62xG3CFylbmo/QUNP6U=   Worker   11/6/2019 8:28:09 AM   6 (0x0006)
Calling WSUS API to publish an update to WSUS this can take a few minutes for large updates   Worker   11/6/2019 8:28:09 AM   6 (0x0006)
An error occurred while publishing an update to WSUS: Failed to sign package; error was: 2148081670   Worker   11/6/2019 8:28:48 AM   6 (0x0006)
Starting download for: http://armdl.adobe.com/pub/adobe/acrobat/win/AcrobatDC/1902120049/AcrobatDCUpd1902120049.msp   Downloader   11/6/2019 8:28:48 AM   6 (0x0006)
Finished downloading file: [http://armdl.adobe.com/pub/adobe/acrobat/win/AcrobatDC/1902120049/AcrobatDCUpd1902120049.msp] Average speed: 32.33 MB/s (370 MB)   Downloader   11/6/2019 8:28:59 AM   26 (0x001A)
Successfully downloaded the update   Downloader   11/6/2019 8:28:59 AM   6 (0x0006)
Digest of downloaded update A6kYicKDK+qL9ODzFBxg3kAOV7E= matches the digest from the catalog A6kYicKDK+qL9ODzFBxg3kAOV7E=   Worker   11/6/2019 8:29:02 AM   6 (0x0006)
Calling WSUS API to publish an update to WSUS this can take a few minutes for large updates   Worker   11/6/2019 8:29:02 AM   6 (0x0006)