Office 365 Single Sign Out with ISA or TMG as the ADFS Proxy

Over the last year I’ve spent a decent chunk of my time shaping and delivering Identity and Access Management workshops for Office 365 projects at Content and Code. This is generally underpinned by Active Directory Federation Services v2.0 (ADFS). In fact I don’t think we’ve done a single Office 365 project without it. Along the way I’ve become acquainted with many of the nuances of the sign on and sign out experiences as they differ across Office 365 services, client applications and different (valid) network perimeter technologies. In this post I will mainly focus on the security implications of publishing ADFS through ISA or TMG Reverse Proxies in the place of ADFS Proxy servers. In the majority of our engagements we’ve considered this option (potentially allowing our clients to consolidate infrastructure) since ISA, TMG or similar Reverse Proxies are commonly deployed. Yet we need to evaluate with full awareness of how ADFS operates without a Claims-aware Reverse Proxy such as the ADFS Proxy. This gets pretty technical, so I’m assuming some high-level familiarity with ADFS, Reverse Proxies and Office 365.

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