Nate, my father had a similar situation with his 1998 diesel this past winter. It turned out to be a severely clogged pre-filter. The shop changed both the main and pre-filters and the problem has never returned.

Might be worth checking if you don't know when it was last done.

Good luck.

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1998 W210 diesel (wiped out by a texter)
Baum spring compressor "for rent"