Hi Devin,
You may be hitting this;
Call Transfer Blocking
Transfers to all numbers except those on local phones are automatically blocked by default. During configuration, you can allow transfers to nonlocal numbers. In Cisco Unified CME 4.0 and later versions, you can prevent individual phones from transferring calls to numbers that are globally enabled for transfer. This ensures that individual phones do not incur toll charges by transferring calls outside the Cisco Unified CME system. Call transfer blocking can be configured for individual phones or configured as part of a template that is applied to a set of phones.
Another way to eliminate toll charges on call transfers is to limit the number of digits that phone users can dial when transferring calls. For example, if you specify a maximum of eight digits in the configuration, users who are transferring calls can dial one digit for external access and seven digits more, which is generally enough for a local number but not a long-distance number. In most locations, this plan will limit transfers to nontoll destinations. Long-distance calls, which typically require ten digits or more, will not be allowed. This configuration is only necessary when global transfer to numbers outside the Cisco Unified CME system has been enabled using the transfer-pattern (telephony-service) command. Transfers to numbers outside the Cisco Unified CME system are not permitted by default.
http://www.cisco.com/en/US/docs/voice_ip_comm/cucme/admin/configuration/guide/cmetrans.html#wp1102688
Hope this helps!
Rob
