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Why would a 1988 Volvo 240 overdrive only work after long drive of around 2 hours or more?

The automatic transmission fluid may be low. When the fluid is low, it can cause the transmission to overheat, which can lead to the overdrive not working. Checking the fluid level and adding more if necessary can resolve this issue.

Another possible cause is a faulty overdrive solenoid. The overdrive solenoid is responsible for engaging the overdrive gear, and if it is faulty, it can prevent the overdrive from working. Replacing the overdrive solenoid can fix this problem.

Finally, a faulty overdrive relay could also be the cause. The overdrive relay is responsible for supplying power to the overdrive solenoid, and if it is faulty, it can prevent the overdrive from working. Replacing the overdrive relay can resolve this issue.