It is time you posted:

    - Full logs detailing the processing of the message in question
    - Full configuration details:


After adding extensive debugging logs for this request I realized this is my 
mistake.
Postfix is sending the non-expanded virtual alias to the milter during the DATA 
stage.

The issue was a flaw in my perl, where i had:

  foreach my $recipient (@{$ctx->recipients}) {
    $recipient = $changes;
  }

I did not realize that created a pointer and not a copy. After adjusting to:

  my @recipientsCopy = @{$ctx->recipients};
  foreach my $recipient (@recipientsCopy) {
    $recipient = $changes;
  }

The $ctx->recipients is now protected from loop mutations and the alias remains 
during all of DATA.

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