diff --git a/src/Analyser/TypeSpecifier.php b/src/Analyser/TypeSpecifier.php
index 334b96f68e..e66e992c03 100644
--- a/src/Analyser/TypeSpecifier.php
+++ b/src/Analyser/TypeSpecifier.php
@@ -742,11 +742,15 @@ public function specifyTypesInCondition(
 				if ($types->shouldOverwrite()) {
 					$result = $result->setAlwaysOverwriteTypes();
 				}
-				return $result->setNewConditionalExpressionHolders(array_merge(
+				$leftNormalizedForHolders = $leftTypesForHolders->normalize($scope);
+				$rightNormalizedForHolders = $rightTypesForHolders->normalize($rightScope);
+				return $result->setNewConditionalExpressionHolders($this->mergeHolders(
 					$this->processBooleanNotSureConditionalTypes($scope, $leftTypesForHolders, $rightTypesForHolders, $rightScope),
 					$this->processBooleanNotSureConditionalTypes($scope, $rightTypesForHolders, $leftTypesForHolders, $scope),
 					$this->processBooleanSureConditionalTypes($scope, $leftTypesForHolders, $rightTypesForHolders, $rightScope),
 					$this->processBooleanSureConditionalTypes($scope, $rightTypesForHolders, $leftTypesForHolders, $scope),
+					$this->processBooleanSureConditionalTypes($scope, $leftNormalizedForHolders, $rightNormalizedForHolders, $rightScope),
+					$this->processBooleanSureConditionalTypes($scope, $rightNormalizedForHolders, $leftNormalizedForHolders, $scope),
 				))->setRootExpr($expr);
 			}
 
@@ -795,11 +799,15 @@ public function specifyTypesInCondition(
 				if ($types->shouldOverwrite()) {
 					$result = $result->setAlwaysOverwriteTypes();
 				}
-				return $result->setNewConditionalExpressionHolders(array_merge(
+				$leftNormalizedForHolders = $leftTypes->normalize($scope);
+				$rightNormalizedForHolders = $rightTypes->normalize($rightScope);
+				return $result->setNewConditionalExpressionHolders($this->mergeHolders(
 					$this->processBooleanNotSureConditionalTypes($scope, $leftTypes, $rightTypes, $rightScope),
 					$this->processBooleanNotSureConditionalTypes($scope, $rightTypes, $leftTypes, $scope),
 					$this->processBooleanSureConditionalTypes($scope, $leftTypes, $rightTypes, $rightScope),
 					$this->processBooleanSureConditionalTypes($scope, $rightTypes, $leftTypes, $scope),
+					$this->processBooleanSureConditionalTypes($scope, $leftNormalizedForHolders, $rightNormalizedForHolders, $rightScope),
+					$this->processBooleanSureConditionalTypes($scope, $rightNormalizedForHolders, $leftNormalizedForHolders, $scope),
 				))->setRootExpr($expr);
 			}
 
@@ -2123,6 +2131,26 @@ private function processBooleanSureConditionalTypes(Scope $scope, SpecifiedTypes
 		return [];
 	}
 
+	/**
+	 * @param array<string, ConditionalExpressionHolder[]> ...$arrays
+	 * @return array<string, ConditionalExpressionHolder[]>
+	 */
+	private function mergeHolders(array ...$arrays): array
+	{
+		$result = [];
+		foreach ($arrays as $array) {
+			foreach ($array as $exprString => $holders) {
+				if (!isset($result[$exprString])) {
+					$result[$exprString] = $holders;
+				} else {
+					$result[$exprString] = array_merge($result[$exprString], $holders);
+				}
+			}
+		}
+
+		return $result;
+	}
+
 	private function isTrackableExpression(Expr $expr): bool
 	{
 		if ($expr instanceof Expr\Variable) {
diff --git a/tests/PHPStan/Analyser/nsrt/bug-3385.php b/tests/PHPStan/Analyser/nsrt/bug-3385.php
new file mode 100644
index 0000000000..c3015451aa
--- /dev/null
+++ b/tests/PHPStan/Analyser/nsrt/bug-3385.php
@@ -0,0 +1,134 @@
+<?php
+
+namespace Bug3385;
+
+use function PHPStan\Testing\assertType;
+
+class Greeter
+{
+	public function sayHello(): string
+	{
+		return 'hello';
+	}
+
+	public function isEqualTo(Greeter $otherGreeter): bool
+	{
+		return $this->sayHello() === $otherGreeter->sayHello();
+	}
+}
+
+function threeGuards(?Greeter $a, ?Greeter $b): bool
+{
+	if ($a === null && $b !== null) {
+		return true;
+	}
+
+	if ($a !== null && $b === null) {
+		return true;
+	}
+
+	if ($a === null && $b === null) {
+		return false;
+	}
+
+	assertType('Bug3385\Greeter', $a);
+	assertType('Bug3385\Greeter', $b);
+
+	return $a->isEqualTo($b);
+}
+
+function threeGuardsReversed(?Greeter $a, ?Greeter $b): bool
+{
+	if ($b !== null && $a === null) {
+		return true;
+	}
+
+	if ($b === null && $a !== null) {
+		return true;
+	}
+
+	if ($b === null && $a === null) {
+		return false;
+	}
+
+	assertType('Bug3385\Greeter', $a);
+	assertType('Bug3385\Greeter', $b);
+
+	return $a->isEqualTo($b);
+}
+
+function orCombined(?Greeter $a, ?Greeter $b): bool
+{
+	if (($a === null && $b !== null) || ($a !== null && $b === null)) {
+		return true;
+	}
+
+	if ($a === null && $b === null) {
+		return false;
+	}
+
+	assertType('Bug3385\Greeter', $a);
+	assertType('Bug3385\Greeter', $b);
+
+	return $a->isEqualTo($b);
+}
+
+function twoGuardsSuffice(?Greeter $a, ?Greeter $b): bool
+{
+	if ($a === null && $b !== null) {
+		return true;
+	}
+
+	if ($b === null) {
+		return false;
+	}
+
+	assertType('Bug3385\Greeter', $a);
+	assertType('Bug3385\Greeter', $b);
+
+	return $a->isEqualTo($b);
+}
+
+function nestedAlreadyWorks(?Greeter $a, ?Greeter $b): bool
+{
+	if ($a === null) {
+		if ($b === null) {
+			return false;
+		}
+		return true;
+	}
+
+	if ($b === null) {
+		return true;
+	}
+
+	assertType('Bug3385\Greeter', $a);
+	assertType('Bug3385\Greeter', $b);
+
+	return $a->isEqualTo($b);
+}
+
+function orTruthyConditionalHolder(?Greeter $a, ?Greeter $b): bool
+{
+	if ($a === null || $b !== null) {
+		if ($b === null) {
+			assertType('null', $a);
+		}
+	}
+
+	return true;
+}
+
+function orTruthyConditionalHolderCross(?Greeter $a, ?Greeter $b): bool
+{
+	if ($a !== null || $b !== null) {
+		if ($a === null) {
+			assertType('Bug3385\Greeter', $b);
+		}
+		if ($b === null) {
+			assertType('Bug3385\Greeter', $a);
+		}
+	}
+
+	return true;
+}