It turns out the main problem was not SSl at all. Since my setup involves a Remote blob store, i need Libraries added for this on my webservers. Reference https://technet.microsoft.com/en-us/library/ff629463.aspx

I downloaded the Library(it says sql 2008 but seems to work on 2014 too) and ran these in PowerShell:

1 time on 1st web server: msiexec /qn /lvx* rbs_install_log.txt /i RBS_amd64.msi TRUSTSERVERCERTIFICATE=true FILEGROUP=PRIMARY DBNAME="WSS_Content" DBINSTANCE="DBInstanceName" FILESTREAMFILEGROUP=RBSFilestreamProvider FILESTREAMSTORENAME=FilestreamProvider_1

1 time for every other webservers: msiexec /qn /lvx* rbs_install_log.txt /i RBS_amd64.msi DBNAME="WSS_Content" DBINSTANCE="DBInstanceName" ADDLOCAL=Client,Docs,Maintainer,ServerScript,FilestreamClient,FilestreamServer

You can find info about these commands in the referenced link about RBS and SharePoint.

It turns out the main problem was not SSl at all. Since my setup involves a Remote blob store, i need Libraries added for this on my webservers. Reference https://technet.microsoft.com/en-us/library/ff629463.aspx

I downloaded the Library(it says sql 2008 but seems to work on 2014 too) and ran these in PowerShell:

1 time on 1st web server:

msiexec /qn /lvx* rbs_install_log.txt /i RBS_amd64.msi TRUSTSERVERCERTIFICATE=true FILEGROUP=PRIMARY DBNAME="WSS_Content" DBINSTANCE="DBInstanceName" FILESTREAMFILEGROUP=RBSFilestreamProvider FILESTREAMSTORENAME=FilestreamProvider_1

1 time for every other webservers:

msiexec /qn /lvx* rbs_install_log.txt /i RBS_amd64.msi DBNAME="WSS_Content" DBINSTANCE="DBInstanceName" ADDLOCAL=Client,Docs,Maintainer,ServerScript,FilestreamClient,FilestreamServer

You can find info about these commands in the referenced link about RBS and SharePoint.