An update to my last post. At the time BOS-ICN waitlist cleared in F, there was no award space available for my connecting ICN-SIN flight. However a couple of days later, KE did release economy space, making it possible to ticket the desired itinerary. I contacted KE by online chat. The agent consulted with "back office" and advised that I had two options... I could ticket just the BOS-ICN in F, and then if the waitlist cleared for ICN-SIN I could contact them and have the ticket reissued for BOS-ICN-SIN. Alternatively I could ticket BOS-ICN-SIN in F/Y and similarly contact them to change the ICN-SIN segment to J if the waitlist clears. I elected the 2nd option and asked the agent to secure the economy seats. They did that and advised that I would have to telephone to ticket as they cannot do ticketing over chat.
Before telephoning, I cleaned up the reservation by removing the other JFK/BOS waitlists, so itinerary only had the confirmed BOS-ICN-SIN and waitlist for ICN-SIN in J. You cannot ticket this online without canceling the ICN-SIN waitlists, so I telephoned.
Telephone agent confirmed skypass account that miles coming from, confirmed price, did a pretty thorough identity verification and then connected me to a ticketing agent. Ticketing agent finalized payment collection from credit card and issued tickets. And confirmed that I was still waitlisted for business on the ICN-SIN flight.
I have to say that the whole interaction, chat and telephone, was much more straight forward than I expected. All agents I worked with were well trained, understood what I wanted to do, and were very pleasant to talk with. Their telephone ticketing process does very thorough identity verification and payment collection (using e.g. secure system to collect some info rather than disclosing to a human agent). Their online chat times out after 4 minutes of inactivity, but the chat agent made sure I knew that and how to keep it alive if necessary. Well done Korean Air.
Now crossing my fingers that one of the two flights I waitlisted for J on ICN-SIN segment clears.