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HAProxy 2.2 with Exchange 2019 - Continious password prompt

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Hello,

i’m a bit stuck setting up my HAProxy reverse proxe in combination with Exchange.

I have several webservers but only 1 public IP so i opted for HAProxy as reverse Proxy.

All my websites work except for the Exchange 2019 - Outlook connection.

When i fire up outlook from an external connection i continuously get prompted for a password.
Internally (or when i configure my hosts file to point to the reverse-proxy) everything works great.

I’m a bit at a loss what the problem could be.
I’ve stripped my config file to remove my public address etc. and i removed the other sites/acl’s.
Can you please take a look at my config and tell me how i f-ed up? :slight_smile:

Here is my cfg file: https://pastebin.com/Gk56CmCn

Thanks in advance for any advise :slight_smile:

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