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Last weekend I put our 95' 252 (Volvo Penta 7.4 GI DP) in the water and it struggled to start. Usually it fires right up. It ran fine until time to navigate home. Then it had the same issues. Would crank for a long time before starting. This weekend it had the same problem but the ramp wasn't busy so was able to spend some time with it to determine what's happening. When I go to start it, you don't hear the fuel pump prime when you turn on the key. If I crank it for a bit then shut it off multiple times it will finally prime and fire right up. So, we got it started and headed out. There were no further issues the multiple times we started it out on the water. On the ride home it flat out died at cruise speed and would not start. While a friendly boater towed us in I tried to start it a few times and finally it started only to die after a couple of minutes while in gear at idle.

Looking for ideas where to start? Could this simply be a filter issue or a much larger problem such as a fuel pump?

Not sure if that has a separate fuel pump relay or not. But check for it. The signal comes from the ecu so you may have a bad one also. Check your fuel pressure also. If you had a scan tool you could watch the signals getting turned on and off.

Time to measure fuel pressures.
What is the full model number of your engine?

Throttle body or MFI?