I am 100% ok with WN charging the difference in fare when it's done at the start of a trip. I've seen people pay big $$ (and have done so myself) when I got to the airport very early, or need to be at a meeting in the AM instead of my originally booked time. If WN relented on this rule, then we'd have to give something BIG to make up for it (like no more free bags or no-show fees).

I've gotten this for free when on standard RR 1.0 awards or full fare but never on WGA.

My letter to WN basically said that "If I have a connection, and weather/flight delays make me late, I miss the connection and take a later flight, but if I arrive early enough for an earlier connection with NO checked bag, please extend the same in reverse as a courtesy." Then the agent keys it in as customer courtesy (already an option), or, to prevent abuse, picks (confirmed that inbound origin flight arrived early).

In the days of RR 1.0, I didn't care, and likely already had booked the connection as 2 one way segments. (sometimes with dangerous connection times, my record was a negative 5 minute connection that yes, I made).

PS: As luck would have it, my original connecting flight posted as 20 minutes late a minute or two after the earlier flight pushed back. I think the 20minute late mark is normally grounds for a free flight time change.