diff --git a/src/libraries/Common/src/Interop/Windows/Kernel32/Interop.CreateProcess.cs b/src/libraries/Common/src/Interop/Windows/Kernel32/Interop.CreateProcess.cs
index ac2f7dca331b06..4a1fcb5ccee46d 100644
--- a/src/libraries/Common/src/Interop/Windows/Kernel32/Interop.CreateProcess.cs
+++ b/src/libraries/Common/src/Interop/Windows/Kernel32/Interop.CreateProcess.cs
@@ -58,6 +58,7 @@ internal struct STARTUPINFO
         }
 
         internal const int PROC_THREAD_ATTRIBUTE_HANDLE_LIST = 0x00020002;
+        internal const int CREATE_BREAKAWAY_FROM_JOB = 0x01000000;
         internal const int EXTENDED_STARTUPINFO_PRESENT = 0x00080000;
 
         [StructLayout(LayoutKind.Sequential)]
diff --git a/src/libraries/Common/src/Interop/Windows/Kernel32/Interop.JobObjects.cs b/src/libraries/Common/src/Interop/Windows/Kernel32/Interop.JobObjects.cs
index 3fd311578a3c92..b23709e05917b8 100644
--- a/src/libraries/Common/src/Interop/Windows/Kernel32/Interop.JobObjects.cs
+++ b/src/libraries/Common/src/Interop/Windows/Kernel32/Interop.JobObjects.cs
@@ -21,6 +21,7 @@ public SafeJobHandle() : base(true) { }
         internal static partial SafeJobHandle CreateJobObjectW(IntPtr lpJobAttributes, IntPtr lpName);
 
         internal const uint JOB_OBJECT_LIMIT_KILL_ON_JOB_CLOSE = 0x00002000;
+        internal const uint JOB_OBJECT_LIMIT_BREAKAWAY_OK = 0x00000800;
 
         internal enum JOBOBJECTINFOCLASS
         {
diff --git a/src/libraries/System.Diagnostics.Process/src/Microsoft/Win32/SafeHandles/SafeProcessHandle.Windows.cs b/src/libraries/System.Diagnostics.Process/src/Microsoft/Win32/SafeHandles/SafeProcessHandle.Windows.cs
index c3f772c26c4a39..1d8525da6e2c41 100644
--- a/src/libraries/System.Diagnostics.Process/src/Microsoft/Win32/SafeHandles/SafeProcessHandle.Windows.cs
+++ b/src/libraries/System.Diagnostics.Process/src/Microsoft/Win32/SafeHandles/SafeProcessHandle.Windows.cs
@@ -98,7 +98,7 @@ private static bool TryOpenCore(int processId, [NotNullWhen(true)] out SafeProce
         private static unsafe Interop.Kernel32.SafeJobHandle CreateKillOnParentExitJob()
         {
             Interop.Kernel32.JOBOBJECT_EXTENDED_LIMIT_INFORMATION limitInfo = default;
-            limitInfo.BasicLimitInformation.LimitFlags = Interop.Kernel32.JOB_OBJECT_LIMIT_KILL_ON_JOB_CLOSE;
+            limitInfo.BasicLimitInformation.LimitFlags = Interop.Kernel32.JOB_OBJECT_LIMIT_KILL_ON_JOB_CLOSE | Interop.Kernel32.JOB_OBJECT_LIMIT_BREAKAWAY_OK;
 
             Interop.Kernel32.SafeJobHandle jobHandle = Interop.Kernel32.CreateJobObjectW(IntPtr.Zero, IntPtr.Zero);
             if (jobHandle.IsInvalid || !Interop.Kernel32.SetInformationJobObject(
diff --git a/src/libraries/System.Diagnostics.Process/tests/ProcessHandlesTests.Windows.cs b/src/libraries/System.Diagnostics.Process/tests/ProcessHandlesTests.Windows.cs
index d7188e0f63297a..6054c93e430e32 100644
--- a/src/libraries/System.Diagnostics.Process/tests/ProcessHandlesTests.Windows.cs
+++ b/src/libraries/System.Diagnostics.Process/tests/ProcessHandlesTests.Windows.cs
@@ -159,6 +159,85 @@ public unsafe void StartWithCallback_CreateProcess_CanRedirectOutput()
             Assert.Equal(0, process.ExitCode);
         }
 
+        [ConditionalTheory(typeof(RemoteExecutor), nameof(RemoteExecutor.IsSupported))]
+        [InlineData(true)]
+        [InlineData(false)]
+        public unsafe void ChildProcess_CanBreakAwayFromJob(bool killOnParentExit)
+        {
+            using Process process = CreateProcess(() =>
+            {
+                using (Process grandChild = CreateProcess(() =>
+                {
+                    return RemoteExecutor.SuccessExitCode;
+                }))
+                {
+                    ProcessStartInfo grandChildStartInfo = grandChild.StartInfo;
+
+                    using Process started = WindowsProcessStartArguments.Start(grandChildStartInfo, (WindowsProcessStartArguments args) =>
+                    {
+                        Interop.Kernel32.STARTUPINFOEX startupInfoEx = default;
+                        Interop.Kernel32.PROCESS_INFORMATION processInfo = default;
+                        Interop.Kernel32.SECURITY_ATTRIBUTES unused_SecAttrs = default;
+
+                        startupInfoEx.StartupInfo.cb = sizeof(Interop.Kernel32.STARTUPINFOEX);
+                        startupInfoEx.StartupInfo.hStdInput = args.StandardInput;
+                        startupInfoEx.StartupInfo.hStdOutput = args.StandardOutput;
+                        startupInfoEx.StartupInfo.hStdError = args.StandardError;
+                        startupInfoEx.StartupInfo.dwFlags = Interop.Advapi32.StartupInfoOptions.STARTF_USESTDHANDLES;
+
+                        int creationFlags = Interop.Kernel32.CREATE_BREAKAWAY_FROM_JOB | Interop.Kernel32.EXTENDED_STARTUPINFO_PRESENT;
+                        if (args.EnvironmentVariables != null)
+                        {
+                            creationFlags |= Interop.Advapi32.StartupInfoOptions.CREATE_UNICODE_ENVIRONMENT;
+                        }
+
+                        if (!Interop.Kernel32.CreateProcess(
+                            null,
+                            args.Arguments,
+                            ref unused_SecAttrs,
+                            ref unused_SecAttrs,
+                            bInheritHandles: true,
+                            creationFlags,
+                            args.EnvironmentVariables,
+                            null,
+                            &startupInfoEx,
+                            &processInfo
+                        ))
+                        {
+                            throw new Win32Exception();
+                        }
+
+                        Interop.Kernel32.CloseHandle(processInfo.hThread);
+
+                        return processInfo.hProcess;
+                    });
+
+                    try
+                    {
+                        Assert.True(started.WaitForExit(WaitInMS));
+                        return started.ExitCode;
+                    }
+                    finally
+                    {
+                        started.Kill();
+                    }
+                }
+            });
+
+            process.StartInfo.KillOnParentExit = killOnParentExit;
+            process.Start();
+
+            try
+            {
+                Assert.True(process.WaitForExit(WaitInMS));
+                Assert.Equal(RemoteExecutor.SuccessExitCode, process.ExitCode);
+            }
+            finally
+            {
+                process.Kill();
+            }
+        }
+
         private unsafe int RunWithInvalidHandles(ProcessStartInfo startInfo)
         {
             const nint INVALID_HANDLE_VALUE = -1;