diff --git a/client/ios_handler/in_process_intermediate_dump_handler_test.cc b/client/ios_handler/in_process_intermediate_dump_handler_test.cc
index 90f76d58..27179bb3 100644
--- a/client/ios_handler/in_process_intermediate_dump_handler_test.cc
+++ b/client/ios_handler/in_process_intermediate_dump_handler_test.cc
@@ -89,6 +89,18 @@ class InProcessIntermediateDumpHandlerTest : public testing::Test {
   const auto& path() const { return path_; }
   auto writer() const { return writer_.get(); }
 
+#if TARGET_OS_SIMULATOR
+  // macOS 14.0 is 23A344, macOS 13.6.5 is 22G621, so if the first two
+  // characters in the kern.osversion are > 22, this build will reproduce the
+  // simulator bug in crbug.com/328282286
+  bool IsMacOSVersion143OrGreaterAndiOS16OrLess() {
+    if (__builtin_available(iOS 17, *)) {
+      return false;
+    }
+    return std::stoi(system_data_.Build().substr(0, 2)) > 22;
+  }
+#endif
+
  private:
   std::unique_ptr<internal::IOSIntermediateDumpWriter> writer_;
   internal::IOSSystemDataCollector system_data_;
@@ -125,6 +137,15 @@ TEST_F(InProcessIntermediateDumpHandlerTest, TestSystem) {
 }
 
 TEST_F(InProcessIntermediateDumpHandlerTest, TestAnnotations) {
+#if TARGET_OS_SIMULATOR
+  // This test will fail on older (<iOS17 simulators) when running on macOS 14.3
+  // or newer due to a bug in Simulator. crbug.com/328282286
+  if (IsMacOSVersion143OrGreaterAndiOS16OrLess()) {
+    // For TearDown.
+    ASSERT_TRUE(LoggingRemoveFile(path()));
+    return;
+  }
+#endif
   // This is “leaked” to crashpad_info.
   crashpad::SimpleStringDictionary* simple_annotations =
       new crashpad::SimpleStringDictionary();
diff --git a/test/ios/crash_type_xctest.mm b/test/ios/crash_type_xctest.mm
index 8d4038db..1b3b5671 100644
--- a/test/ios/crash_type_xctest.mm
+++ b/test/ios/crash_type_xctest.mm
@@ -14,6 +14,7 @@
 
 #import <XCTest/XCTest.h>
 #include <objc/runtime.h>
+#include <sys/sysctl.h>
 
 #include <vector>
 
@@ -24,6 +25,34 @@
 #include "util/mach/exception_types.h"
 #include "util/mach/mach_extensions.h"
 
+namespace {
+
+#if TARGET_OS_SIMULATOR
+// macOS 14.0 is 23A344, macOS 13.6.5 is 22G621, so if the first two characters
+// in the kern.osversion are > 22, this build will reproduce the simulator bug
+// in crbug.com/328282286
+bool IsMacOSVersion143OrGreaterAndiOS16OrLess() {
+  if (__builtin_available(iOS 17, *)) {
+    return false;
+  }
+
+  size_t buf_len;
+  static constexpr char name[] = "kern.osversion";
+  if (sysctlbyname(name, nullptr, &buf_len, nullptr, 0) != 0) {
+    return false;
+  }
+
+  std::string build(buf_len - 1, '\0');
+  if (sysctlbyname(name, &build[0], &buf_len, nullptr, 0) != 0) {
+    return false;
+  }
+
+  return std::stoi(build.substr(0, 2)) > 22;
+}
+#endif
+
+}  // namespace
+
 @interface CPTestTestCase : XCTestCase {
   XCUIApplication* app_;
   CPTestSharedObject* rootObject_;
@@ -317,6 +346,14 @@
 #endif
 
 - (void)testCrashWithAnnotations {
+#if TARGET_OS_SIMULATOR
+  // This test will fail on older (<iOS17 simulators) when running on macOS 14.3
+  // or newer due to a bug in Simulator. crbug.com/328282286
+  if (IsMacOSVersion143OrGreaterAndiOS16OrLess()) {
+    return;
+  }
+#endif
+
   [rootObject_ crashWithAnnotations];
   [self verifyCrashReportException:EXC_SOFT_SIGNAL];
   NSNumber* report_exception;