Raising & lowering the main in a blow

[Normanby]

Hello Folks,
I'm still new to investigator ownership and i have a question about the main sail.
This is my first boat without a topping lift, and with roller-furling boom. When i raised the main sail in the driveway this morning (preparitory to a long weekend on the Gippsland Lakes this weekend) it wouldn't go up without the aft end of the boom supported with a clip onto the backstay. That was fine for the driveway with no wind, but i worry that i'll be trying to raise or lower the main on the water in wind. If the boom is secured to the backstay, will the boat stay pointed into the wind?
My old boat never did, and i had to let the boom swing, held up by the topping lift, while i hauled away.
It just seems dangerous to have the boom firmly held fore and aft in case the boat moves side-on to the wind while the raising or lowering is happening.
Am i missing something?
Cheers,
Matt

[Yara50]

Matt
You need a proper topping lift. I have changed the title of a previous post (BTW Greg, thanks for the compliment), to topping lifts so you can see how to do it.

Perhaps you also need to lubricate the slides if you have some.

Heaving to, and hoisting in the shelter of the jib is another option. As is motoring dead into the wind.