This has been my experience. I managed to switch to working remotely 100% by saying "I need to move to another town, either I start working remotely or I'll need to switch jobs". My boss wanted me to say, but not enough was done (by anyone, me included) to really make it work. I wasn't let go, they were still happy with me, but I decided to leave after about half a year, even though there were definitely aspects of working remotely that I loved.