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Two new batteries a year ago. New alternator about 4 years ago. Have tested neither, but here's the issue:

In this 90+ degree weather the engine groans like it's a very cold day without having the heater plugged in, or the battery is weak. Then when I try the second time it's got a little more spunk but still doesn't start. It takes 4 to 5 cycles to start and each time she turns over much better than the previous attempt.

I'll have the batteries and alternator checked out tomorrow, but any hunches?
 

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The starter is your likely culprit. One other possibility is that one battery is isolated due to a bad ground or other connection. The test for that would be to put a voltmeter across one battery at a time and watch for voltage drop when someone cranks the truck. They should drop the same amount. You could also put the voltmeter between the positive terminal of each battery. The voltage should be zero and should stay that way when someone cranks it.
 
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Helpful going forward ...... Get a plug in digital volt meter. Plug it into your 12V lighter or power inside the cab. Leave it plugged in full time. Then you can tell what your voltage is, when and how much your alternator is charging. Like an ongoing basic charging health check up. Helps take some guess workout of issues like you are having.
 

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^^^ what Oneof6 said. There’s room on the dash to permanently install if you buy one of the mini volt meters. I also put a rocker switch right above mine as I have it wired into constant power / key off. And for night time driving I can turn it off to reduce glare from the LED.
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White '99.5 F250 SD XLT 4x2, 7.3PSD, 6spd, SuperCab, Short Bed - purchased Oct'05
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Helpful going forward ...... Get a plug in digital volt meter. Plug it into your 12V lighter or power inside the cab. Leave it plugged in full time. Then you can tell what your voltage is, when and how much your alternator is charging. Like an ongoing basic charging health check up. Helps take some guess workout of issues like you are having.
Yes, great advice. I put one in mine a couple of years ago. It shows voltage and has a USB port.
 

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Two new batteries a year ago. New alternator about 4 years ago. Have tested neither, but here's the issue:

In this 90+ degree weather the engine groans like it's a very cold day without having the heater plugged in, or the battery is weak. Then when I try the second time it's got a little more spunk but still doesn't start. It takes 4 to 5 cycles to start and each time she turns over much better than the previous attempt.

I'll have the batteries and alternator checked out tomorrow, but any hunches?
Starter…….mine lasted 180K.. do research on replacement, rebuilt Ford has the best requirements. Rock Auto the best price.
 

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+1 for starter. My '99 had so much trouble I actually carry a spare starter around with me.
 

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Plus a voltmeter is one of the options on a Scan-Gauge-2.
 

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Starter maybe, but don't rule out the battery cables either especially if they are the original cables.
 

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Starter maybe, but don't rule out the battery cables either especially if they are the original cables.
+1 on that. Check all your connections first. If jumping it off helps, that may indicate bad batteries OR bad connections. If jumping doesn't help, it's more likely the starter.
 

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If you do buy a new starter, I recommend the DENSO 228000-8420. I've had one on my 7.3 for about 8 years now and it's fantastic.
 
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