Usually after offering a player out on TransferRoom, that option is greyed out for a few days, and clubs may come back with offers after those few days.
However, after you accept a bid for a player and try and offer them out on TransferRoom at a higher price, the "Offer via TransferRoom" option will no longer be greyed out after you "Continue" once. It seems that there is no actual offer that goes out, because you don't get any notification about no clubs being interested via TransferRoom as you normally would, or any new bids that come in after those few days.
I am quite certain that this issue did not occur before the Winter Update.
Usually after offering a player out on TransferRoom, that option is greyed out for a few days, and clubs may come back with offers after those few days. However, after you accept a bid for a player and try and offer them out on TransferRoom at a higher price, the "Offer via TransferRoom" option will no longer be greyed out after you "Continue" once. It seems that there is no actual offer that goes out, because you don't get any notification about no clubs being interested via TransferRoom as you normally would, or any new bids that come in after those few days. I am quite certain that this issue did not occur before the Winter Update.