Troubleshooting

“No route found between these points; drew a straight line.” Apple Maps has no route between the two points: water, private land, or no cycling directions in that region. Move the point onto a road or path, or try another mode. The straight leg still counts.

My point jumped onto the road. With a routing mode on, taps and dragged points land on the nearest path. For an exact spot, choose Straight Lines for that leg, or type the coordinates in the points table.

“The way back along roads retraces your route, so the area closes with a straight line.” The only way back was the way you came. Add a tap partway round to steer the route.

“The outline crosses itself; the area is not meaningful.” Two edges cross, usually from points tapped out of order. Tap Show where to zoom to the red ✕, then drag the points into order or delete the stray one.

Tapping the map adds nothing. You are in Select; a hint says “Choose Add Points to draw on the map.” If you tapped inside another shape in Add Points, that shape was selected instead.

“Your location is not available. Check Location Services for Geo Measure.” Turn location on for Geo Measure in Settings › Privacy & Security › Location Services, or on the Mac in System Settings › Privacy & Security › Location Services.

“… has no areas, paths or circles that Geo Measure can show.” The imported file has nothing to measure, such as a GPX with only waypoints.