CRA confirms that the issuer of registered debentures can satisfy its T5 obligations through its paying agent issuing T5s to the brokers who hold the debentures

If the issuer of debentures which have been registered in the names of brokers pays interest to a paying agent, it does not issue T5s to the paying agent as that agent is paying the interest on the issuer's behalf rather than receiving interest on behalf of beneficial owners of the interest. However, it or the paying agent (but not both) must issue T5s to the brokers who, in turn, issue T5s to their clients.

Neal Armstrong. Summary of 15 August 2014 T.I. 2014-0532941E5 under Reg. 201(1).