This is a direct issue with the Rogers network and their policy on how they handle caller ID from remote networks. As explained by one of our upstream providers:
Calls from analogue lines on the MTSallstream network displays name and number on Rogers cell phone. Calls that are originating from other sources (such as pri/sip etc) which have a different method of generating name display are discarded by Rogers gateway switch. I worked with Rogers and confirmed by Rogers trace that name was being passed along. I also spoke with Bell IXC and they stated that this was a known problem with Rogers. They spent several weeks troubleshooting this with them. Unfortunately, there is nothing more I can do with this issue.