diff --git a/src/Analyser/TypeSpecifier.php b/src/Analyser/TypeSpecifier.php
index 9f7a86eb4a..06eb10dbfb 100644
--- a/src/Analyser/TypeSpecifier.php
+++ b/src/Analyser/TypeSpecifier.php
@@ -734,7 +734,13 @@ public function specifyTypesInCondition(
 			$leftTypes = $this->specifyTypesInCondition($scope, $expr->left, $context)->setRootExpr($expr);
 			$rightScope = $scope->filterByTruthyValue($expr->left);
 			$rightTypes = $this->specifyTypesInCondition($rightScope, $expr->right, $context)->setRootExpr($expr);
-			$types = $context->true() ? $leftTypes->unionWith($rightTypes) : $leftTypes->normalize($scope)->intersectWith($rightTypes->normalize($rightScope));
+			if ($context->true()) {
+				$types = $leftTypes->unionWith($rightTypes);
+			} else {
+				$leftNormalized = $this->propagateArrayDimFetchToParentArray($leftTypes->normalize($scope), $scope);
+				$rightNormalized = $this->propagateArrayDimFetchToParentArray($rightTypes->normalize($rightScope), $rightScope);
+				$types = $leftNormalized->intersectWith($rightNormalized);
+			}
 			if ($context->false()) {
 				$leftTypesForHolders = $leftTypes;
 				$rightTypesForHolders = $rightTypes;
@@ -788,7 +794,9 @@ public function specifyTypesInCondition(
 				) {
 					$types = $leftTypes->normalize($scope);
 				} else {
-					$types = $leftTypes->normalize($scope)->intersectWith($rightTypes->normalize($rightScope));
+					$leftNormalized = $this->propagateArrayDimFetchToParentArray($leftTypes->normalize($scope), $scope);
+					$rightNormalized = $this->propagateArrayDimFetchToParentArray($rightTypes->normalize($rightScope), $rightScope);
+					$types = $leftNormalized->intersectWith($rightNormalized);
 					$types = $this->augmentBooleanOrTruthyWithConditionalHolders($scope, $rightScope, $expr, $types);
 				}
 			} else {
@@ -2076,6 +2084,56 @@ private function augmentBooleanOrTruthyWithConditionalHolders(MutatingScope $sco
 		return $types;
 	}
 
+	private function propagateArrayDimFetchToParentArray(SpecifiedTypes $normalizedTypes, Scope $scope): SpecifiedTypes
+	{
+		$additionalSureTypes = [];
+		$sureTypes = $normalizedTypes->getSureTypes();
+		foreach ($sureTypes as $exprString => [$expr, $type]) {
+			if (
+				!$expr instanceof Expr\ArrayDimFetch
+				|| $expr->dim === null
+				|| !$expr->var instanceof Expr\Variable
+			) {
+				continue;
+			}
+			$dimType = $scope->getType($expr->dim)->toArrayKey();
+			$constantDimType = null;
+			if ($dimType instanceof ConstantIntegerType) {
+				$constantDimType = $dimType;
+			} else {
+				$constantStrings = $dimType->getConstantStrings();
+				if (count($constantStrings) === 1) {
+					$constantDimType = $constantStrings[0];
+				}
+			}
+			if ($constantDimType === null) {
+				continue;
+			}
+			$varExprString = $this->exprPrinter->printExpr($expr->var);
+			if (isset($sureTypes[$varExprString]) || isset($additionalSureTypes[$varExprString])) {
+				continue;
+			}
+			$varType = $scope->getType($expr->var);
+			if ($varType instanceof MixedType || $varType->isArray()->no()) {
+				continue;
+			}
+			$narrowedVarType = TypeCombinator::intersect($varType, new HasOffsetValueType($constantDimType, $type));
+			if ($narrowedVarType instanceof NeverType) {
+				continue;
+			}
+			$additionalSureTypes[$varExprString] = [$expr->var, $narrowedVarType];
+		}
+
+		if ($additionalSureTypes === []) {
+			return $normalizedTypes;
+		}
+
+		return new SpecifiedTypes(
+			$sureTypes + $additionalSureTypes,
+			$normalizedTypes->getSureNotTypes(),
+		);
+	}
+
 	/**
 	 * @return array<string, ConditionalExpressionHolder[]>
 	 */
diff --git a/tests/PHPStan/Analyser/nsrt/bug-14566.php b/tests/PHPStan/Analyser/nsrt/bug-14566.php
new file mode 100644
index 0000000000..d4202a29e7
--- /dev/null
+++ b/tests/PHPStan/Analyser/nsrt/bug-14566.php
@@ -0,0 +1,80 @@
+<?php declare(strict_types = 1);
+
+namespace Bug14566;
+
+use function PHPStan\Testing\assertType;
+
+/**
+ * @param array{}|array{hi: 'hello'}|array{hi: array{0: 42, 1?: 42}} $test
+ */
+function foo(array $test): void {
+	if (isset($test['hi']) && is_string($test['hi'])) {
+		return;
+	}
+	assertType("array{}|array{hi: array{0: 42, 1?: 42}}", $test);
+}
+
+/**
+ * @param array{}|array{hi: 'hello'}|array{hi: array{0: 42, 1?: 42}} $test
+ */
+function fooElse(array $test): void {
+	if (isset($test['hi']) && is_string($test['hi'])) {
+		assertType("array{hi: 'hello'}", $test);
+	} else {
+		assertType("array{}|array{hi: array{0: 42, 1?: 42}}", $test);
+	}
+}
+
+/**
+ * @param array{}|array{hi: 'hello'}|array{hi: array{0: 42, 1?: 42}} $test
+ */
+function fooIsArray(array $test): void {
+	if (isset($test['hi']) && is_array($test['hi'])) {
+		return;
+	}
+	assertType("array{}|array{hi: 'hello'}", $test);
+}
+
+/**
+ * @param array{}|array{hi: 'hello'}|array{hi: int} $test
+ */
+function fooIsInt(array $test): void {
+	if (isset($test['hi']) && is_int($test['hi'])) {
+		return;
+	}
+	assertType("array{}|array{hi: 'hello'}", $test);
+}
+
+class Foo {}
+
+/**
+ * @param array{}|array{hi: Foo}|array{hi: 'hello'} $test
+ */
+function fooInstanceof(array $test): void {
+	if (isset($test['hi']) && $test['hi'] instanceof Foo) {
+		return;
+	}
+	assertType("array{}|array{hi: 'hello'}", $test);
+}
+
+/**
+ * @param array{}|array{hi: 'hello'}|array{hi: 'world'} $test
+ */
+function fooStrictComparison(array $test): void {
+	if (isset($test['hi']) && $test['hi'] === 'hello') {
+		return;
+	}
+	assertType("array{}|array{hi: 'world'}", $test);
+}
+
+/**
+ * BooleanOr truthy: logically equivalent to falsy branch of && version
+ * @param array{}|array{hi: 'hello'}|array{hi: array{0: 42, 1?: 42}} $test
+ */
+function fooBooleanOr(array $test): void {
+	if (!isset($test['hi']) || !is_string($test['hi'])) {
+		assertType("array{}|array{hi: array{0: 42, 1?: 42}}", $test);
+	} else {
+		assertType("array{hi: 'hello'}", $test);
+	}
+}