Is your Defender parked in a garage or otherwise blocked from signals when you park it? Many folks have discovered that if the Defender can't "phone home" or receive a signal, it won't pick up the updates. That's why the "long drives" usually kick it in. If so, try to connect the Defender to your home wifi (if it reaches your garage) before putting it to bed.

 

I haven't received an update yet but have only had the truck for about 2 weeks. I haven't tried every method just yet but I noticed there is a "reset connection" in the settings menu, have you hit that when in a good cell phone reception spot? Similarly, you can try this when connected to WiFi in your garage, which you said you've done already. I can't try it right now but I noticed the Defender is always showing 1 bar of Tmobile when I'm in 5 bar areas so I feel like there's something there.

 

Unfortunately the truck has to stay outside so I should be okay from that perspective. I am driving up to Boston this afternoon. That'll be about 3 hours so maybe, if the LR gods are in the mood, it'll download

I do wish there was a way to request it...... I'll stop whining now