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Skruf
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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.

Skruf
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