diff --git a/test/tools/ossfuzz/SolidityGenerator.cpp b/test/tools/ossfuzz/SolidityGenerator.cpp
index e7ccf0cbc..0d71a8516 100644
--- a/test/tools/ossfuzz/SolidityGenerator.cpp
+++ b/test/tools/ossfuzz/SolidityGenerator.cpp
@@ -518,10 +518,15 @@ string WhileStmtGenerator::visit()
 	pair<SolidityTypePtr, string> boolTypeName = {boolType, {}};
 	auto expression = exprGen.rLValueOrLiteral(boolTypeName);
 	solAssert(expression.has_value(), "");
-	whileStmt << indentation()
-		         << "while ("
-		         << expression.value().second
-		         << ")\n";
+	bool doWhile = uRandDist()->probable(2);
+	if (doWhile)
+		whileStmt << indentation()
+			<< "do\n";
+	else
+		whileStmt << indentation()
+			<< "while ("
+			<< expression.value().second
+			<< ")\n";
 	// Make sure block stmt generator does not output an unchecked block
 	mutator->generator<BlockStmtGenerator>()->unchecked(false);
 	ostringstream whileBlock;
@@ -529,6 +534,11 @@ string WhileStmtGenerator::visit()
 	if (whileBlock.str().empty())
 		whileBlock << indentation() << "{ }\n";
 	whileStmt << whileBlock.str();
+	if (doWhile)
+		whileStmt << indentation()
+			<< "while ("
+			<< expression.value().second
+			<< ")\n";
 	return whileStmt.str();
 }
 
diff --git a/test/tools/ossfuzz/SolidityGenerator.h b/test/tools/ossfuzz/SolidityGenerator.h
index 6323ada3c..35649f25a 100644
--- a/test/tools/ossfuzz/SolidityGenerator.h
+++ b/test/tools/ossfuzz/SolidityGenerator.h
@@ -30,6 +30,7 @@
 #include <memory>
 #include <random>
 #include <set>
+#include <stack>
 #include <variant>
 
 #include <range/v3/algorithm/all_of.hpp>
@@ -525,7 +526,7 @@ struct TestState
 		numFunctions(0),
 		indentationLevel(0),
 		insideContract(false),
-		loopState(false, false)
+		loopState({false})
 	{}
 	/// Adds @param _path to @name sourceUnitPaths updates
 	/// @name currentSourceUnitPath.
@@ -652,16 +653,15 @@ struct TestState
 	}
 	void enterLoop()
 	{
-		loopState.wasLoop = loopState.inLoop;
-		loopState.inLoop = true;
+		loopState.push(true);
 	}
 	void exitLoop()
 	{
-		loopState.inLoop = loopState.wasLoop;
+		loopState.pop();
 	}
 	bool inLoop()
 	{
-		return loopState.inLoop;
+		return loopState.top();
 	}
 	~TestState()
 	{
@@ -703,7 +703,7 @@ struct TestState
 	/// Contract scope
 	bool insideContract;
 	/// Loop state
-	LoopState loopState;
+	std::stack<bool> loopState;
 	/// Source name prefix
 	std::string const sourceUnitNamePrefix = "su";
 	/// Contract name prefix