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I drove my 46 clipper yesterday about 50 miles and when I stopped my battery did not have enough charge to turn the starter. I suspect that there is an issue with the charging system. When I jumped the car it started right up. I am looking for advice on how to troubleshoot this problem to determine if its the generator, wiring, or regulator. Thanks in advance.

If your charging system failed, it should have been apparent to you while you were driving by observing the ammeter. What was it telling you during the drive?

Assuming your ammeter confirms that the charging system is not functioning and the wiring is intact, I suggest first just doing the standard test as described regularly on this site, and elsewhere. Using a short jumper wire, ground the Field terminal of the regulator, increase engine speed a bit above fast idle, and observe the ammeter. If it goes to full or near-full charge, then the generator is functioning and the regulator is suspect. If no charge, then the generator has failed. Do not leave the jumper connected for any longer than is required for the test.

If the ammeter is not functional, do the test with the headlights on, or a voltmeter on the battery, or both. That the generator is charging will be shown by the headlights getting much brighter and/or the voltage at the battery increasing to greater than 7 volts as you increase engine speed with the Field grounded.