diff --git a/libraries/tools/kotlin-gradle-plugin-integration-tests/src/test/kotlin/org/jetbrains/kotlin/gradle/native/NativeXcodeSimulatorTestsIT.kt b/libraries/tools/kotlin-gradle-plugin-integration-tests/src/test/kotlin/org/jetbrains/kotlin/gradle/native/NativeXcodeSimulatorTestsIT.kt
new file mode 100644
index 00000000000..d43d50c4b83
--- /dev/null
+++ b/libraries/tools/kotlin-gradle-plugin-integration-tests/src/test/kotlin/org/jetbrains/kotlin/gradle/native/NativeXcodeSimulatorTestsIT.kt
@@ -0,0 +1,28 @@
+/*
+ * Copyright 2010-2023 JetBrains s.r.o. and Kotlin Programming Language contributors.
+ * Use of this source code is governed by the Apache 2.0 license that can be found in the license/LICENSE.txt file.
+ */
+
+package org.jetbrains.kotlin.gradle.native
+
+import org.gradle.util.GradleVersion
+import org.jetbrains.kotlin.gradle.testbase.*
+import org.junit.jupiter.api.DisplayName
+import org.junit.jupiter.api.condition.EnabledOnOs
+import org.junit.jupiter.api.condition.OS
+
+@DisplayName("tests for the K/N simulator test infrastructure")
+@NativeGradlePluginTests
+@EnabledOnOs(OS.MAC)
+class NativeXcodeSimulatorTestsIT : KGPBaseTest() {
+    @DisplayName("iOS simulator test with an https request fails with default settings")
+    @GradleTest
+    fun checkSimulatorTestFailsInStandaloneMode(gradleVersion: GradleVersion) {
+        project("native-test-ios-https-request", gradleVersion) {
+            buildAndFail("check") {
+                // that's an Apple's issue that we expect to fail the build
+                assertOutputContains("The certificate for this server is invalid. You might be connecting to a server that is pretending to be ")
+            }
+        }
+    }
+}
\ No newline at end of file
diff --git a/libraries/tools/kotlin-gradle-plugin-integration-tests/src/test/resources/testProject/native-test-ios-https-request/build.gradle.kts b/libraries/tools/kotlin-gradle-plugin-integration-tests/src/test/resources/testProject/native-test-ios-https-request/build.gradle.kts
new file mode 100644
index 00000000000..4ea483b7d41
--- /dev/null
+++ b/libraries/tools/kotlin-gradle-plugin-integration-tests/src/test/resources/testProject/native-test-ios-https-request/build.gradle.kts
@@ -0,0 +1,12 @@
+plugins {
+    id("org.jetbrains.kotlin.multiplatform")
+}
+
+repositories {
+    mavenLocal()
+    mavenCentral()
+}
+
+kotlin {
+    iosSimulatorArm64()
+}
diff --git a/libraries/tools/kotlin-gradle-plugin-integration-tests/src/test/resources/testProject/native-test-ios-https-request/src/iosSimulatorArm64Test/kotlin/tests.kt b/libraries/tools/kotlin-gradle-plugin-integration-tests/src/test/resources/testProject/native-test-ios-https-request/src/iosSimulatorArm64Test/kotlin/tests.kt
new file mode 100644
index 00000000000..5cdd5b87863
--- /dev/null
+++ b/libraries/tools/kotlin-gradle-plugin-integration-tests/src/test/resources/testProject/native-test-ios-https-request/src/iosSimulatorArm64Test/kotlin/tests.kt
@@ -0,0 +1,26 @@
+/*
+ * Copyright 2010-2023 JetBrains s.r.o. and Kotlin Programming Language contributors.
+ * Use of this source code is governed by the Apache 2.0 license that can be found in the license/LICENSE.txt file.
+ */
+
+import kotlinx.cinterop.*
+import platform.Foundation.*
+import kotlin.test.*
+
+@Test
+fun fooTest() {
+    println("foo")
+}
+
+@Test
+fun request() {
+    val response = memScoped {
+        val request = NSURLRequest(NSURL(string = "https://cache-redirector.jetbrains.com/"))
+        val responseRef = alloc<ObjCObjectVar<NSURLResponse?>>()
+        val errorRef = alloc<ObjCObjectVar<NSError?>>()
+        NSURLConnection.sendSynchronousRequest(request, responseRef.ptr, errorRef.ptr) ?:
+        throw Error(errorRef.value?.toString() ?: "")
+        responseRef.value!! as NSHTTPURLResponse
+    }
+    kotlin.test.assertEquals(200, response.statusCode)
+}
\ No newline at end of file