diff --git a/src/libraries/System.Diagnostics.Process/src/System/Diagnostics/AsyncStreamReader.cs b/src/libraries/System.Diagnostics.Process/src/System/Diagnostics/AsyncStreamReader.cs
index fbfd3a6baaae8a..a4b1640a2f743b 100644
--- a/src/libraries/System.Diagnostics.Process/src/System/Diagnostics/AsyncStreamReader.cs
+++ b/src/libraries/System.Diagnostics.Process/src/System/Diagnostics/AsyncStreamReader.cs
@@ -24,6 +24,11 @@ internal sealed class AsyncStreamReader : IDisposable
     {
         private const int DefaultBufferSize = 1024;  // Byte buffer size
 
+        /// <summary>
+        /// Default timeout in milliseconds to wait for redirected streams to complete after the process exits.
+        /// </summary>
+        private const int StreamDrainDefaultTimeoutMs = 300;
+
         private readonly Stream _stream;
         private readonly Decoder _decoder;
         private readonly byte[] _byteBuffer;
@@ -253,7 +258,29 @@ private bool FlushMessageQueue(bool rethrowInNewThread)
             }
         }
 
-        internal Task EOF => _readToBufferTask ?? Task.CompletedTask;
+        internal void CancelDueToProcessExit()
+        {
+            Task? task = _readToBufferTask;
+            if (task is not null && !task.Wait(StreamDrainDefaultTimeoutMs))
+            {
+                _cts.Cancel();
+                task.GetAwaiter().GetResult();
+            }
+        }
+
+        internal async Task CancelDueToProcessExitAsync(CancellationToken cancellationToken)
+        {
+            Task? task = _readToBufferTask;
+            if (task is not null)
+            {
+                Task completed = await Task.WhenAny(task, Task.Delay(StreamDrainDefaultTimeoutMs, cancellationToken)).ConfigureAwait(false);
+                if (completed != task)
+                {
+                    _cts.Cancel();
+                    await task.ConfigureAwait(false);
+                }
+            }
+        }
 
         public void Dispose()
         {
diff --git a/src/libraries/System.Diagnostics.Process/src/System/Diagnostics/Process.Unix.cs b/src/libraries/System.Diagnostics.Process/src/System/Diagnostics/Process.Unix.cs
index f26a8f70ffba74..61d89baf60c8b5 100644
--- a/src/libraries/System.Diagnostics.Process/src/System/Diagnostics/Process.Unix.cs
+++ b/src/libraries/System.Diagnostics.Process/src/System/Diagnostics/Process.Unix.cs
@@ -205,10 +205,10 @@ private bool WaitForExitCore(int milliseconds)
             bool exited = GetWaitState().WaitForExit(milliseconds);
             Debug.Assert(exited || milliseconds != Timeout.Infinite);
 
-            if (exited && milliseconds == Timeout.Infinite) // if we have a hard timeout, we cannot wait for the streams
+            if (exited)
             {
-                _output?.EOF.GetAwaiter().GetResult();
-                _error?.EOF.GetAwaiter().GetResult();
+                _output?.CancelDueToProcessExit();
+                _error?.CancelDueToProcessExit();
             }
 
             return exited;
diff --git a/src/libraries/System.Diagnostics.Process/src/System/Diagnostics/Process.Windows.cs b/src/libraries/System.Diagnostics.Process/src/System/Diagnostics/Process.Windows.cs
index f073bd1e8d54f5..98f028802aef5c 100644
--- a/src/libraries/System.Diagnostics.Process/src/System/Diagnostics/Process.Windows.cs
+++ b/src/libraries/System.Diagnostics.Process/src/System/Diagnostics/Process.Windows.cs
@@ -176,11 +176,10 @@ private bool WaitForExitCore(int milliseconds)
             }
             finally
             {
-                // If we have a hard timeout, we cannot wait for the streams
-                if (milliseconds == Timeout.Infinite)
+                if (_signaled)
                 {
-                    _output?.EOF.GetAwaiter().GetResult();
-                    _error?.EOF.GetAwaiter().GetResult();
+                    _output?.CancelDueToProcessExit();
+                    _error?.CancelDueToProcessExit();
                 }
 
                 handle?.Dispose();
diff --git a/src/libraries/System.Diagnostics.Process/src/System/Diagnostics/Process.cs b/src/libraries/System.Diagnostics.Process/src/System/Diagnostics/Process.cs
index 4218596c129644..4f3d3abccf01f6 100644
--- a/src/libraries/System.Diagnostics.Process/src/System/Diagnostics/Process.cs
+++ b/src/libraries/System.Diagnostics.Process/src/System/Diagnostics/Process.cs
@@ -1527,7 +1527,7 @@ public async Task WaitForExitAsync(CancellationToken cancellationToken = default
                 // exception up to the user
                 if (HasExited)
                 {
-                    await WaitUntilOutputEOF(cancellationToken).ConfigureAwait(false);
+                    await CancelStreamReadersDueToProcessExitAsync(cancellationToken).ConfigureAwait(false);
                     return;
                 }
 
@@ -1554,24 +1554,24 @@ public async Task WaitForExitAsync(CancellationToken cancellationToken = default
                     }
                 }
 
-                // Wait until output streams have been drained
-                await WaitUntilOutputEOF(cancellationToken).ConfigureAwait(false);
+                // Cancel stream readers after process exit with a default timeout
+                await CancelStreamReadersDueToProcessExitAsync(cancellationToken).ConfigureAwait(false);
             }
             finally
             {
                 Exited -= handler;
             }
 
-            async Task WaitUntilOutputEOF(CancellationToken cancellationToken)
+            async Task CancelStreamReadersDueToProcessExitAsync(CancellationToken cancellationToken)
             {
                 if (_output is not null)
                 {
-                    await _output.EOF.WaitAsync(cancellationToken).ConfigureAwait(false);
+                    await _output.CancelDueToProcessExitAsync(cancellationToken).ConfigureAwait(false);
                 }
 
                 if (_error is not null)
                 {
-                    await _error.EOF.WaitAsync(cancellationToken).ConfigureAwait(false);
+                    await _error.CancelDueToProcessExitAsync(cancellationToken).ConfigureAwait(false);
                 }
             }
         }
diff --git a/src/libraries/System.Diagnostics.Process/tests/ProcessWaitingTests.cs b/src/libraries/System.Diagnostics.Process/tests/ProcessWaitingTests.cs
index 8ef602113be272..e1d48347386651 100644
--- a/src/libraries/System.Diagnostics.Process/tests/ProcessWaitingTests.cs
+++ b/src/libraries/System.Diagnostics.Process/tests/ProcessWaitingTests.cs
@@ -671,5 +671,61 @@ public async Task WaitForExitAsync_NotDirected_ThrowsInvalidOperationException()
             var process = new Process();
             await Assert.ThrowsAsync<InvalidOperationException>(() => process.WaitForExitAsync());
         }
+
+        [ConditionalTheory(typeof(RemoteExecutor), nameof(RemoteExecutor.IsSupported))]
+        [InlineData("WaitForExit")]
+        [InlineData("WaitForExitInt")]
+        [InlineData("WaitForExitTimeSpan")]
+        [InlineData("WaitForExitAsync")]
+        public async Task WaitForExit_WithGrandChildProcess_DoesNotHang(string waitMethod)
+        {
+            Process child = CreateProcess(() =>
+            {
+                using Process grandChild = CreateProcess(SleepForEightHours);
+                grandChild.Start();
+                Console.WriteLine(grandChild.Id);
+
+                return RemoteExecutor.SuccessExitCode;
+            });
+            child.StartInfo.RedirectStandardOutput = true;
+            child.Start();
+
+            string grandChildPidStr = await child.StandardOutput.ReadLineAsync();
+            int grandChildPid = int.Parse(grandChildPidStr);
+
+            var stopwatch = Stopwatch.StartNew();
+
+            switch (waitMethod)
+            {
+                case "WaitForExit":
+                    child.WaitForExit();
+                    break;
+                case "WaitForExitInt":
+                    Assert.True(child.WaitForExit(WaitInMS));
+                    break;
+                case "WaitForExitTimeSpan":
+                    Assert.True(child.WaitForExit(TimeSpan.FromMilliseconds(WaitInMS)));
+                    break;
+                case "WaitForExitAsync":
+                    await child.WaitForExitAsync();
+                    break;
+            }
+
+            stopwatch.Stop();
+            Assert.True(stopwatch.Elapsed.TotalSeconds < 2, $"WaitForExit took {stopwatch.Elapsed.TotalSeconds:F1}s, expected < 2s");
+
+            try
+            {
+                Process.GetProcessById(grandChildPid).Kill();
+            }
+            catch (Exception) { }
+        }
+
+        private static int SleepForEightHours()
+        {
+            Thread.Sleep(TimeSpan.FromHours(8));
+
+            return RemoteExecutor.SuccessExitCode;
+        }
     }
 }