How would using a proxy masquerading as SMTP be any more viable in this situation than a proxy masquerading as HTTPS?
> Your next best bet is probably tunneling over DNS with Iodine or something similar.
DNS typically does not involve bidirectional transfer of large volumes of encrypted traffic. Doing this over DNS would stick out like a sore thumb to anyone doing traffic analysis, whereas this is exactly what you'd expect to see over HTTPS.
> Many internal DNS servers resolve external host names.
Sure, but the internal DNS in this scenario would typically be either forwarding external DNS requests to an outside resolver determined by its own configuration, or is itself hosting a full DNS table. How would you be able to use your own proxy masquerading as DNS in this situation?