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Whitelisting outlook client for Office 365 Access


We are trying to whitelist Outlook (client) for O365 Access. I've tried using User-Agent, and it works fine for authenticated clients. However if someone walks away from their PC for about 10 minutes and the session is lost, they need to close and re-open outlook for it to reconnect properly. How do we allow constant access to O365 resources while still targeting outlook?

The User-Agent string shows in properties in tracing, but when it does the matching of the ruleset the field is blank.

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