I pointed out in May 2016 that automatic updates were broken in Debian Jessie.
I came across a post on Ximions blog yesterday explaining the reason why.
A subsequent post claims that the issue was fixed at some point, but also mentions that many people using Jessie have never received automatic updates- which was true for me: running Jessie until last week, I never saw an automatic update notification.
The update also states that automatic updates are working in Debian Stretch.
A while back I posted about how I'd seen automatic update notifications in Debian Testing (Stretch) on my old laptop, and how updates are now carried out offline.
Last week I updated my current laptop to Stretch- but I haven't seen any update notifications yet.
Important to note that Stretch is still in Testing, but I do hope automatic updates are going to work in Stretch.
I've also blogged about how Bluetooth file transfer from an Android phone to Debian Jessie was broken.
Despite having seen this work previously in Testing, I've had no luck getting this to work in Debian Stretch recently- either on the computer it originally worked on, or my laptop recently updated to Stretch.
I will keep an eye on these issues as updates arrive to Stretch and report if I see these features start to work.