As the battery degrades, you have less and less additional charge after a regular charge. Plus the GOM isn't a great way to judge anything (unfortunately, Toyota/Tesla didn't give us a real battery level gauge). My understanding is that once the battery has degraded beyond a certain point, there essentially is no extended charge left.
What you can try is to do a regular charge, then change the setting to extended and see how long it charges after that. But if the car is set to extended, you're getting whatever extended charge is available. On the plus side, if you keep your speed down, 102 miles shouldn't be out of reach, but always have a backup plan (know where public charging is) when pushing the car's range.