diff --git a/src/libcommonserver/io/iohelper.cpp b/src/libcommonserver/io/iohelper.cpp
index cb8fd8de8..a653afc1a 100644
--- a/src/libcommonserver/io/iohelper.cpp
+++ b/src/libcommonserver/io/iohelper.cpp
@@ -63,6 +63,7 @@ IoError IoHelper::stdError2ioError(int error) noexcept {
         case static_cast<int>(std::errc::is_a_directory):
             return IoErrorIsADirectory;
         case static_cast<int>(std::errc::no_such_file_or_directory):
+        case static_cast<int>(std::errc::not_a_directory):  // Occurs in particular when converting a bundle into a single file
             return IoErrorNoSuchFileOrDirectory;
         case static_cast<int>(std::errc::no_space_on_device):
             return IoErrorDiskFull;
diff --git a/test/libcommonserver/io/testcheckifpathexists.cpp b/test/libcommonserver/io/testcheckifpathexists.cpp
index ad1a2636e..b5d24434d 100644
--- a/test/libcommonserver/io/testcheckifpathexists.cpp
+++ b/test/libcommonserver/io/testcheckifpathexists.cpp
@@ -454,6 +454,17 @@ void TestIo::testCheckIfPathExistsWithSameNodeIdAllBranches() {
 
         _testObj->resetFunctions();
     }
+
+    // Checking existence of a subdirectory inside a directory that have been deleted and replaced with a file with the same name
+    // ex: conversion of a bundle into a single file (macOS)
+    {
+        const SyncPath path = _localTestDirPath / "test_pictures/picture-1.jpg/A";
+        bool exists = false;
+        IoError ioError = IoErrorUnknown;
+        CPPUNIT_ASSERT(_testObj->checkIfPathExists(path, exists, ioError));
+        CPPUNIT_ASSERT(!exists);
+        CPPUNIT_ASSERT_EQUAL(IoErrorNoSuchFileOrDirectory, ioError);
+    }
 }