Russia has just sent Syria the largest shipment of missiles between the two countries to date, the latest delivery between the two allies that could further change the stakes in the Middle East, U.S. officials told Fox News on Wednesday.

The shipment of 50 SS-21 short-range ballistic missiles arrived at the Syrian port of Tartus along the Mediterranean Sea in the past two days, the officials said.

“For someone winding down a war, that’s a big missile shipment,” one official said.

The SS-21, which comes in different types, has a range of roughly 100 miles. […]