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Unable to Sign in when using a Checkpoint Firewall

If you use a Checkpoint firewall and are unable to sign into Skype for Business after checking all the necessary Outbound Firewall ports, the issue is likely to be with the built-in rule for TCP Port 5061, which is designed for SIP.

Define a new rule as a regular rule, ensuring you open TCP Port 5061 and do no use the built-in rule.

The default rule strips the TLS traffic and sends the packets un-encrypted.

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