Yep, definitely learnt that the hard way! I've got one foot in the Championship now so I'd be looking to upgrade him anyway, although he would've been a useful backup.
On FM, I've made offers for players who had their contracts expiring, but as soon as I made the offer, their parent club triggered the extension so my offer became effectively null and void. Had this been an optional extension, I would've done the same.
However, this wasn't an option, it was an automatic extension based on appearances and survival. If he's able to sign a pre-contract elsewhere before the extension is applied, which makes the automatic extension redundant, maybe this needs to be rephrased.
Will do. I'm now mathematically safe and the player has made 25 appearances, but I think these are only applied well after the season finishes anyway, around June if I'm not mistaken. I'm expecting him to leave though, based on the previous replies.