I am asking that it be configurable as to how many retries are allowed
(eg how many E=691 R=1) before a no retries failed authentication
message (E=691 R=0) is sent.


Ah gotcha. Thanks for the detail!

As Alan has suggested in his other email, you can change the "MS-CHAP-Error" in the post-auth section:

post-auth {
  Post-Auth-Type REJECT {
    if (reply:MS-CHAP-Error =~ /E=691 R=1/) {
      update reply {
        MS-CHAP-Error := "E=691 R=0"
      }
    }
  }
}


If a no retries failed authentication message (E=691 R=0) is sent I
believe that that the apple device to re-prompt the user to update the
password.

...but I'm not sure this will work.

The reason being, if you're using wireless you're probably using PEAP/MS-CHAP. This is actually EAP-PEAP outer, and EAP-MSCHAP inner - that is, it is *not* raw mschap inside the tunnel.

The FreeRadius EAP-MSCHAP (rlm_eap_mschap) has a hardcoded error message:

E=691 R=0

...ignoring any errors the "mschap" module might have generated.

So in theory at least, FreeRadius is already doing what you want for EAP-MSCHAP, and changing it won't help.
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