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How to split 443 traffic between 365 and cloud proxy?

We have an Exchange Hybrid recently setup. We have a conditional access rule which will trigger depending on the source IP of an Outlook client. The issue is that our default route for 443 (which Outlook uses) is to route everything via a cloud proxy called Zscaler, but we want to exclude and bypass the cloud proxy for anything that Outlook routes to behind the scenes. There are many exclusions recommended by MS, and a lot that contain wild card URL's, however firewall routes don't allow wildcards, and also 365 sites are always changing.

Any suggestions?
ExchangeOutlookMicrosoft 365

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Seth Simmons
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Seth Simmons
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No comment has been added to this question in more than 21 days, so it is now classified as abandoned.

I have recommended this question be closed as follows:

Accept: 'DEMAN-BARCELO (MVP) Thierry' (https:#a43294313)

If you feel this question should be closed differently, post an objection and the moderators will review all objections and close it as they feel fit. If no one objects, this question will be closed automatically the way described above.

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Exchange is the server side of a collaborative application product that is part of the Microsoft Server infrastructure. Exchange's major features include email, calendaring, contacts and tasks, support for mobile and web-based access to information, and support for data storage.

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