"Remember me" (aka "Trust this Device") is a red herring for me in nearly every case.
I suspect this is partly due to my pervasive use of IPv6; both my Android device and Windows receive IPv6 allocations on my home WiFi. The device fingerprinting that providers use seems to be fooled when the IPv6 Interface ID changes, even if the /64 is identical. So according to their algorithms, my device is perpetually new and untrusted.
Live.com always always pops a dialog to ask me whether I wish to remain logged in; I never remain logged in, but the dialog constantly asks and there's no way for me to dismiss it permanently.
The only time I've seen "Remember me" work properly is when it sets a cookie with my username and does nothing else. Since I use a password manager, I have no use for remembering my username, and in fact it disrupts my flow and presents an unnecessary leak of credential information.
I suspect this is partly due to my pervasive use of IPv6; both my Android device and Windows receive IPv6 allocations on my home WiFi. The device fingerprinting that providers use seems to be fooled when the IPv6 Interface ID changes, even if the /64 is identical. So according to their algorithms, my device is perpetually new and untrusted.
Live.com always always pops a dialog to ask me whether I wish to remain logged in; I never remain logged in, but the dialog constantly asks and there's no way for me to dismiss it permanently.
The only time I've seen "Remember me" work properly is when it sets a cookie with my username and does nothing else. Since I use a password manager, I have no use for remembering my username, and in fact it disrupts my flow and presents an unnecessary leak of credential information.