diff --git a/Sources/Sentry/include/SentryFileManager.h b/Sources/Sentry/include/SentryFileManager.h
index b66a8f81e5..1bdfef4b0b 100644
--- a/Sources/Sentry/include/SentryFileManager.h
+++ b/Sources/Sentry/include/SentryFileManager.h
@@ -15,6 +15,12 @@ NS_ASSUME_NONNULL_BEGIN
 @class SentryOptions;
 @class SentrySession;
 
+#if SENTRY_TEST || SENTRY_TEST_CI
+BOOL isErrorPathTooLong(NSError *error);
+
+BOOL createDirectoryIfNotExists(NSString *path, NSError **error);
+#endif // SENTRY_TEST || SENTRY_TEST_CI
+
 NS_SWIFT_NAME(SentryFileManager)
 @interface SentryFileManager : NSObject
 SENTRY_NO_INIT
diff --git a/Tests/SentryTests/Helper/SentryFileManagerTests.swift b/Tests/SentryTests/Helper/SentryFileManagerTests.swift
index 81df321cae..c07f024a32 100644
--- a/Tests/SentryTests/Helper/SentryFileManagerTests.swift
+++ b/Tests/SentryTests/Helper/SentryFileManagerTests.swift
@@ -1,3 +1,5 @@
+// swiftlint:disable file_length
+
 @testable import Sentry
 import SentryTestUtils
 import XCTest
@@ -723,6 +725,132 @@ class SentryFileManagerTests: XCTestCase {
         try "garbage".write(to: URL(fileURLWithPath: sut.timezoneOffsetFilePath), atomically: true, encoding: .utf8)
         XCTAssertNil(sut.readTimezoneOffset())
     }
+
+    func testIsErrorPathTooLong_underlyingErrorsAvailableAndMultipleErrorsGiven_shouldUseErrorInUserInfo() throws {
+        // -- Arrange --
+        guard #available(macOS 11.0, iOS 14.5, watchOS 7.4, tvOS 14.5, *) else {
+            throw XCTSkip("This test is only for macOS 11 and above")
+        }
+        // When accessing via `underlyingErrors`, the first result is the error set with `NSUnderlyingErrorKey`.
+        // This test asserts if that behavior changes.
+        let error = NSError(domain: NSCocoaErrorDomain, code: 1, userInfo: [
+            NSMultipleUnderlyingErrorsKey: [
+                NSError(domain: NSCocoaErrorDomain, code: 2, userInfo: nil)
+            ],
+            NSUnderlyingErrorKey: NSError(domain: NSPOSIXErrorDomain, code: Int(ENAMETOOLONG), userInfo: nil)
+        ])
+        // -- Act --
+        let result = isErrorPathTooLong(error)
+        // -- Assert --
+        XCTAssertTrue(result)
+    }
+
+    func testIsErrorPathTooLong_underlyingErrorsAvailableAndMultipleErrorsEmpty_shouldUseErrorInUserInfo() throws {
+        // -- Arrange --
+        guard #available(macOS 11.0, iOS 14.5, watchOS 7.4, tvOS 14.5, *) else {
+            throw XCTSkip("Test is disabled for this OS version")
+        }
+        // When accessing via `underlyingErrors`, the first result is the error set with `NSUnderlyingErrorKey`.
+        // This test asserts if that behavior changes.
+        let error = NSError(domain: NSCocoaErrorDomain, code: 1, userInfo: [
+            NSMultipleUnderlyingErrorsKey: [],
+            NSUnderlyingErrorKey: NSError(domain: NSPOSIXErrorDomain, code: Int(ENAMETOOLONG), userInfo: nil)
+        ])
+        // -- Act --
+        let result = isErrorPathTooLong(error)
+        // -- Assert --
+        XCTAssertTrue(result)
+    }
+
+    func testIsErrorPathTooLong_underlyingErrorsAvailableAndMultipleErrorsNotSet_shouldUseErrorInUserInfo() throws {
+        // -- Arrange --
+        guard #available(macOS 11.0, iOS 14.5, watchOS 7.4, tvOS 14.5, *) else {
+            throw XCTSkip("Test is disabled for this OS version")
+        }
+        // When accessing via `underlyingErrors`, the first result is the error set with `NSUnderlyingErrorKey`.
+        // This test asserts if that behavior changes.
+        let error = NSError(domain: NSCocoaErrorDomain, code: 1, userInfo: [
+            NSUnderlyingErrorKey: NSError(domain: NSPOSIXErrorDomain, code: Int(ENAMETOOLONG), userInfo: nil)
+        ])
+        // -- Act --
+        let result = isErrorPathTooLong(error)
+        // -- Assert --
+        XCTAssertTrue(result)
+    }
+
+    func testIsErrorPathTooLong_underlyingErrorsAvailableAndOnlyMultipleErrorsGiven_shouldUseErrorFirstError() throws {
+        // -- Arrange --
+        guard #available(macOS 11.0, iOS 14.5, watchOS 7.4, tvOS 14.5, *) else {
+            throw XCTSkip("Test is disabled for this OS version")
+        }
+        // When accessing via `underlyingErrors`, the first result is the error set with `NSUnderlyingErrorKey`.
+        // This test asserts if that behavior changes.
+        let error = NSError(domain: NSCocoaErrorDomain, code: 1, userInfo: [
+            NSMultipleUnderlyingErrorsKey: [
+                NSError(domain: NSPOSIXErrorDomain, code: Int(ENAMETOOLONG), userInfo: nil),
+                NSError(domain: NSCocoaErrorDomain, code: 2, userInfo: nil)
+            ]
+        ])
+        // -- Act --
+        let result = isErrorPathTooLong(error)
+        // -- Assert --
+        XCTAssertTrue(result)
+    }
+
+    func testIsErrorPathTooLong_underlyingErrorsNotAvailableAndErrorNotInUserInfo_shouldNotCheckError() throws {
+        // -- Arrange --
+        guard #unavailable(macOS 11.0, iOS 14.5, watchOS 7.4, tvOS 14.5) else {
+            throw XCTSkip("Test is disabled for this OS version")
+        }
+        // When accessing via `underlyingErrors`, the first result is the error set with `NSUnderlyingErrorKey`.
+        // This test asserts if that behavior changes.
+        let error = NSError(domain: NSCocoaErrorDomain, code: 1, userInfo: [:])
+        // -- Act --
+        let result = isErrorPathTooLong(error)
+        // -- Assert --
+        XCTAssertFalse(result)
+    }
+
+    func testIsErrorPathTooLong_underlyingErrorsNotAvailableAndNonErrorInUserInfo_shouldNotCheckError() throws {
+        // -- Arrange --
+        guard #unavailable(macOS 11.0, iOS 14.5, watchOS 7.4, tvOS 14.5) else {
+            throw XCTSkip("Test is disabled for this OS version")
+        }
+        // When accessing via `underlyingErrors`, the first result is the error set with `NSUnderlyingErrorKey`.
+        // This test asserts if that behavior changes.
+        let error = NSError(domain: NSCocoaErrorDomain, code: 1, userInfo: [
+            NSUnderlyingErrorKey: "This is not an error"
+        ])
+        // -- Act --
+        let result = isErrorPathTooLong(error)
+        // -- Assert --
+        XCTAssertFalse(result)
+    }
+
+    func testIsErrorPathTooLong_underlyingErrorsNotAvailableAndErrorInUserInfo_shouldNotCheckError() throws {
+        // -- Arrange --
+        guard #unavailable(macOS 11.0, iOS 14.5, watchOS 7.4, tvOS 14.5) else {
+            throw XCTSkip("Test is disabled for this OS version")
+        }
+        // When accessing via `underlyingErrors`, the first result is the error set with `NSUnderlyingErrorKey`.
+        // This test asserts if that behavior changes.
+        let error = NSError(domain: NSCocoaErrorDomain, code: 1, userInfo: [
+            NSUnderlyingErrorKey: NSError(domain: NSPOSIXErrorDomain, code: Int(ENAMETOOLONG), userInfo: nil)
+        ])
+        // -- Act --
+        let result = isErrorPathTooLong(error)
+        // -- Assert --
+        XCTAssertTrue(result)
+    }
+
+    func testIsErrrorPathTooLong_errorIsEnameTooLong_shouldReturnTrue() throws {
+        // -- Arrange --
+        let error = NSError(domain: NSPOSIXErrorDomain, code: Int(ENAMETOOLONG), userInfo: nil)
+        // -- Act --
+        let result = isErrorPathTooLong(error)
+        // -- Assert --
+        XCTAssertTrue(result)
+    }
 }
 
 #if os(iOS) || os(macOS) || targetEnvironment(macCatalyst)