Time to Leave Alerts not working

While continuing to do research on this issue, I also found reference to what Apple Support recommended to me: reset the phone to factory settings and set it up as a new phone: Settings > General >Reset > Erase all content & settings. But Apple didn't supply the reason why: the notification culprit is the data from your previous/old phone. It’s not a hardware fault, it’s something with the notification setting in the restore from backup that is causing the problem. Don't know if that is true or not, but if it is, I don't think the solution is worth the loss of this functionality.

Have you tried using the Reminder app?

• Add a location: Tap , then choose where you want to be reminded—for example, when you arrive home or get into a car with a Bluetooth connection to your iPhone.
• Note: To receive location-based reminders, you must allow Reminders to use your precise location. Go to Settings  > Privacy > Location Services, turn on Location Services, tap Reminders, choose While Using the App, then turn on Precise Location.

I found this in a different Discussion thread: Settings -> General -> Reset -> Reset Location & Privacy. I tried it on my work iPhone (iPhone SE) but it didn't work. Maybe it will work for you?

OK, that is very interesting! I upgraded from an iPhone 11 to an iPhone 12 when IOS 14 was released. So I had to do a restore from iCloud backup to move all my data to the new phone. If you just did a software update from IOS 13 to IOS 14 on an existing iPhone, this "explanation" is not justified. I will definitely be calling back on my case and mention this to Apple Support.

You may have already tried this but I did have some success with getting Time To Leave to work, but not consistently. The idea came from the other issue I was tracking with AppleCarPlay which is related to the bluetooth not recognizing that AppleCarPlay has disconnected, and it doesn't get resolved until the phone is rebooted.

So I started to think that maybe iOS 14 is having a problem identifying which map to use to identify my current location and determine how long it will take me to get to my destination, as I have Apple Maps and Google maps installed on my phone and both have Location settings set to While Using the App. Even though Google Maps was not "opened" on my phone, I changed the location setting for Google Maps to Never. I also found the Time To Leave would only work when I had a secondary reminder set on the event.

So in my test, I had a reminder of 30 minutes Before, as well as Time to Leave set on the event. In this test, I received a notification 30 minutes before, a time to leave notification warning me in advance how long it would take me to get to my destination, and a final notification telling me to Leave Now to make it to my destination. Problem solved? Not completely. I was so happy that it worked that I set up a second test on the same day, at a different time and at a different location. This time I had a secondary notification for an hour before as well as Time to Leave. I only received the notification an hour before on this test. The mystery continues ...

I think that was my suggestion. It solved the problem for me briefly, but then it came back. I’m almost at the point where setting the phone up as new sounds appealing.

I have Waze as well and I note that it is also hit or miss with time to leave notifications. Wondering if something changed with location services in iOS 14 because this was fine up through iOS 13.

I am also a Waze user and I didn't have Time to Leave set up in that app until I started trouble shooting this issue. After setup, I did a test event and I got the Time To Leave notification. Great! So I did a second test - and nothing. So the same thing occurs regardless if I use Waze or Apple's TTL functionality. I thought maybe having Waze open was confusing the phone as to which app to send the notification to, so I did a test where Waze was closed. First test worked successfully; second, nothing. So then I did a "reboot" (volume up button, volume down button, hold side button until the screen goes blank). As soon as I opened the phone, the second test notification fired. So something is getting 'locked' after a successful TTL notification, and the "reboot" releases or resets it.

I am also having an issue with my Apple Watch not ringing when I receive a phone call. It turns out the issue is with AppleCarPlay. After a successful connection, the AppleCarPlay wifi connection is not "disconnecting" when you turn off the car. It only drops if you "reboot" your phone. 

[Edited by Moderator]

All of a sudden I had a Time To Leave alert work for me today. For an appointment I made weeks ago. I didn't play with any settings or configurations - except!... I did receive a Carrier Setting Update from my cellular provider because 5G service has started in my area. So I started overthinking ... is this the culprit as to why this feature stopped working? This feature stopped working for me when I switched from an iPhone 11 to an iPhone 12 - which was built for 5G service. I'd be interested to know if anyone else may have updated their carrier settings recently and found this feature is now working.

Spoke too soon. In the past few days, the alerts have not been working 🤷🏻‍♂️