The Curious Case of TCP/9808
Posted on September 23, 2018 by Richard Brynteson in Skype for Business
Sometimes a mystery is so satisfying once you have solved it. Check out this amazing story from co-worker and amazing guy Mitch Steiner.
The Scene: A typical day in Ops
Ops engineer: Oh, I just got an alert that the default certificate on one of our enterprise pools is about to expire. Time to create a change request for the upcoming maintenance window and get it replaced.
Act 1 Scene 1
(Two days later , during the weekly maintenance window)
Our trusty ops engineer , having filed the proper change request and obtaining an approval, creates a CSR , submits it to his internal PKI and generates a new default certificate. He launches the deployment wizard, imports his certificate , and assigns it to the proper usages ( server default , internal and external web services).
No errors were found, and all appears working as expected.
Following his organization’s pre defined best practices (trust but verify!) , our ops engineer now runs through his certificate replacement checklist.
He grabs his trusty DigiCert utility for windows , and proceeds to verify that the new certificate is being presented on the known ports ( 5061, 443, 4443). To accomplish this, he launches the tool on the enterprise pool server , selects tools and clicks “check install” in the certificate installation checker section. He sets his server address to localhost , sets the SSL mode to direct and checks each port , verifying the new “valid to” date and serial number match the newly provisioned certificate (Exhibit A is shown below)