Yes, people in Heaven have some idea of what’s going on here. They may not know or pay attention to everything that’s happening (like the time you slipped ice into your brother’s pillowcase). But the martyrs in Revelation 6 knew that God hadn’t yet brought judgment on those who killed them, so it’s likely that they knew many other things about what’s happening on earth.
At the very least, if they aren’t seeing events, people in Heaven are told about events on Earth. For example, there’s the time when Babylon (a name that represents an evil world power) is brought down. An angel points to Earth and says, “Rejoice over her, O heaven! Rejoice, saints and apostles and prophets! God has judged her for the way she treated you” (Revelation 18:20, NIV)
When Moses and Elijah appeared on the mountain with Jesus, they spoke “about his exodus from this world, which was about to be fulfilled in Jerusalem” (Luke 9:31). They seemed to know what was up with Jesus: how he’d have to die soon. (And surely they returned to Heaven remembering what they’d discussed with Jesus on earth.)
Hebrews 12:1 tells us we are surrounded by a “huge cloud of witnesses,” the believers who’ve died and are now with Jesus in Heaven. They seem to be cheering us on from Heaven.
Jesus, who is in Heaven, definitely knows what’s up, especially with his people. (See chapters 2 and 3 of Revelation.) Isn’t it great to discover Jesus knows everything, sees everything, is in control, and is never taken by surprise? For one thing, it means that he’ll never find out something about us a million years from now and say, “If I’d known you did that, I’d never have let you into Heaven!!” Jesus has seen us at our worst and still loves us. And in Heaven he’ll see to it that we’ll always be at our best—and that’s how we’ll always want to be.