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MacOS Mail.app behaviour
I think I've finally figured it out! Up until now, I've experienced what appeared to be random selection of a From address whe sending a message. Now I see that it's based on what message I have selected in my mailbox. Which, you know... is still kinda random - I'd rather it always default to my main email address, leaving me with the option to use the Hartwell bookings address.

A little more background: In the preferences for Mail.app, you can specify multiple addresses in the Email Address field, separated by commas. Mine is set to "nathan_jones.id.au, bookings_hartwellplayers.org.au". Then when I compose a new message, the Account field shows one of the two. It's nice to now understand why the bookings address keeps showing up, even if it is a bit annoying.