I recently have been trying to set up SSL in SharePoint 2013. It has been working just fine using a wildcard cert, host headers, and binding to All Unassigned. However, I now have a need for another cert in the mix, so I can't have two different certs on All Unassigned and need to instead bind to IP Addresses.
The trouble is that every SharePoint web app generates a 404 if it's IIS site is assigned to an IP address. Works fine All Unassigned, always 404 when on an IP.
I tested creating a plain IIS site without SharePoint. Works fine in all cases, no 404 for either All Unassigned and binding to an IP.
I tested shutting down a SharePoint IIS and using it's host name on the plain IIS site, so I know it's not a DNS issue... the host name works just fine and routes properly to the proper IIS site, "All Unassigned" or bound to an IP address.
I tested this all without SSL as well. SSL isn't the culprit either. The same exact behavior happens to just the SharePoint sites configured for regular HTTP. Works All Unassigned, always 404s when bound to an IP address.
When the 404 happens, the SharePoint ULS logs show:
Reached maximum number of failed machines based on ping results for this routing group Mapping URI https://myhostname to https://myserversname
Since the ULS logs show "anything", I know the request is making it through IIS and into SharePoint, thus this must be a SharePoint issue.
I'm stumped. Haven't found any mention of this issue anywhere after spending hours hitting search engines, trying here, Stack Overflow, etc. I even tried reproducing this in one of my development SharePoint 2013 virtual machines, but everything worked as exptected. No 404s when messing with IP Address bindings. I just recently did this same thing to a clients SharePoint 2010 server, and again, everything worked just as expected. All IP address bound IIS sites fully accessible. It only seems to be this one particular SharePoint 2013 installation on this one particular server.
Hoping someone has some insight into the issue. I have yet to find any documented case of this happening. I've been messing with the hostnames in DNS, IIS bindings on this server, IIS bindings on other servers, creating test sites using the same hostnames and IP bindings, etc. for days now, and in every case the issue does not happen on any other server but this one specific installation of SharePoint.