diff --git a/src/libraries/System.Diagnostics.Process/src/System/Diagnostics/ProcessManager.Win32.cs b/src/libraries/System.Diagnostics.Process/src/System/Diagnostics/ProcessManager.Win32.cs
index 18243a75c56702..0fdb798af5334e 100644
--- a/src/libraries/System.Diagnostics.Process/src/System/Diagnostics/ProcessManager.Win32.cs
+++ b/src/libraries/System.Diagnostics.Process/src/System/Diagnostics/ProcessManager.Win32.cs
@@ -131,7 +131,14 @@ private static ProcessModuleCollection GetModules(int processId, bool firstModul
 
                 var modules = new ProcessModuleCollection(firstModuleOnly ? 1 : modulesCount);
 
-                char[] chars = ArrayPool<char>.Shared.Rent(1024);
+#if RELEASE
+                int minimumLength = Interop.Kernel32.MAX_PATH;
+#else
+                // use a smaller value to ensure that at least for DEBUG builds
+                // we test the code path that rents a bigger array from ArrayPool
+                int minimumLength = Interop.Kernel32.MAX_PATH / 4;
+#endif
+                char[]? chars = ArrayPool<char>.Shared.Rent(minimumLength);
                 try
                 {
                     for (int i = 0; i < modulesCount; i++)
@@ -171,14 +178,29 @@ private static ProcessModuleCollection GetModules(int processId, bool firstModul
 
                         module.ModuleName = new string(chars, 0, length);
 
-                        length = Interop.Kernel32.GetModuleFileNameEx(processHandle, moduleHandle, chars, chars.Length);
+                        while (true)
+                        {
+                            length = Interop.Kernel32.GetModuleFileNameEx(processHandle, moduleHandle, chars, chars.Length);
+                            if (length == chars.Length)
+                            {
+                                minimumLength = chars.Length * 2;
+                                char[] toReturn = chars;
+                                chars = null;
+                                ArrayPool<char>.Shared.Return(toReturn);
+                                chars = ArrayPool<char>.Shared.Rent(minimumLength);
+                                continue;
+                            }
+
+                            break;
+                        }
+
                         if (length == 0)
                         {
                             HandleLastWin32Error();
                             continue;
                         }
 
-                        module.FileName = (length >= 4 && chars[0] == '\\' && chars[1] == '\\' && chars[2] == '?' && chars[3] == '\\') ?
+                        module.FileName = chars.AsSpan().StartsWith(@"\\?\") ?
                             new string(chars, 4, length - 4) :
                             new string(chars, 0, length);
 
@@ -187,7 +209,10 @@ private static ProcessModuleCollection GetModules(int processId, bool firstModul
                 }
                 finally
                 {
-                    ArrayPool<char>.Shared.Return(chars);
+                    if (chars != null)
+                    {
+                        ArrayPool<char>.Shared.Return(chars);
+                    }
                 }
 
                 return modules;
diff --git a/src/libraries/System.Diagnostics.Process/tests/ProcessModuleTests.cs b/src/libraries/System.Diagnostics.Process/tests/ProcessModuleTests.cs
index 2631cb8b1a3dcb..b8f7d8f6ae0844 100644
--- a/src/libraries/System.Diagnostics.Process/tests/ProcessModuleTests.cs
+++ b/src/libraries/System.Diagnostics.Process/tests/ProcessModuleTests.cs
@@ -92,32 +92,36 @@ public void ModulesAreDisposedWhenProcessIsDisposed()
             Assert.Equal(expectedCount, disposedCount);
         }
 
-        [ActiveIssue("https://github.com/dotnet/runtime/pull/335059")]
+        [SkipOnMono("Assembly.LoadFile used the way this test is implemented fails on Mono")]
         [ConditionalFact(typeof(PathFeatures), nameof(PathFeatures.AreAllLongPathsAvailable))]
         [PlatformSpecific(TestPlatforms.Windows)]
         public void LongModuleFileNamesAreSupported()
         {
-            // To be able to test Long Path support for ProcessModule.FileName we need a .dll that has a path >= 260 chars.
+            // To be able to test Long Path support for ProcessModule.FileName we need a .dll that has a path > 260 chars.
             // Since Long Paths support can be disabled (see the ConditionalFact attribute usage above),
             // we just copy "LongName.dll" from bin to a temp directory with a long name and load it from there.
             // Loading from new path is possible because the type exposed by the assembly is not referenced in any explicit way.
             const string libraryName = "LongPath.dll";
+            const int minPathLength = 261;
 
             string testBinPath = Path.GetDirectoryName(typeof(ProcessModuleTests).Assembly.Location);
             string libraryToCopy = Path.Combine(testBinPath, libraryName);
             Assert.True(File.Exists(libraryToCopy), $"{libraryName} was not present in bin folder '{testBinPath}'");
 
-            string directoryWithLongName = Path.Combine(TestDirectory, new string('a', Math.Max(1, 261 - TestDirectory.Length)));
+            string directoryWithLongName = Path.Combine(TestDirectory, new string('a', Math.Max(1, minPathLength - TestDirectory.Length)));
             Directory.CreateDirectory(directoryWithLongName);
 
             string longNamePath = Path.Combine(directoryWithLongName, libraryName);
-            Assert.True(longNamePath.Length > 260);
+            Assert.True(longNamePath.Length > minPathLength);
 
             File.Copy(libraryToCopy, longNamePath);
+            Assert.True(File.Exists(longNamePath));
 
             Assembly loaded = Assembly.LoadFile(longNamePath);
+            Assert.Equal(longNamePath, loaded.Location);
 
-            Assert.Contains(Process.GetCurrentProcess().Modules.Cast<ProcessModule>(), module => module.FileName == longNamePath);
+            ProcessModule[] longPathModules = Process.GetCurrentProcess().Modules.Cast<ProcessModule>().Where(module => module.FileName.Contains(libraryName)).ToArray();
+            Assert.Contains(longPathModules, module => module.FileName == longNamePath);
         }
     }
 }