Exchange OWA Access Error 500

Sometime happen strange things. In the past days I faced a really weird issue with a migration from Exchange 2010 to Exchange 2016 for a customer.

I was at the point in which Exchange 2016 should be inserted as frontend server for all communications: all the load balancer Kemp (LAN and DMZ) was switched and all the checks was ok.
SMTP, ActiveSync, Outlook Anywhere, Autodiscover ECP and OWA was ok and the authentication between servers works fine. SMTP mail flow inbound and outbound moved to brand new servers.  I also tested some mailbox migration and access to OWA and ECP.

That’s was fine, mailbox migration time! Customer’s IT responsible start to migrate some test mailbox before start a massive migration and after a couple of day they had problem to access to Outlook Web Access.  It’s my turn to check which is the problem.

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Rebuild Exchange Content Index

Sometimes happen that Exchange Database Content Index switch from Healthy to Fail. The first behaviors the users experiences is a fail on Search in their Outlook client (even if on Premises and Outlook Web Access).

Usually this fail go unnoticed when everything else is working fine however they will eventually begin to cause problems if you have a Database Availability Group (DAG) in place, for example by preventing database switchovers, thus it’s a good practice to monitor the status.
To achieve monitoring, I’m using a specific powershell sensor when customers have active Monitoring Services (in my case Peassler PRTG), otherwise here you could download an usefull script provided by Paul Cunningham to use as your needs. Read More