diff --git a/src/libraries/System.Threading.Channels/src/System/Threading/Channels/BoundedChannel.cs b/src/libraries/System.Threading.Channels/src/System/Threading/Channels/BoundedChannel.cs
index 3f7a967a60a47..6e911a797121f 100644
--- a/src/libraries/System.Threading.Channels/src/System/Threading/Channels/BoundedChannel.cs
+++ b/src/libraries/System.Threading.Channels/src/System/Threading/Channels/BoundedChannel.cs
@@ -146,8 +146,15 @@ public override ValueTask<T> ReadAsync(CancellationToken cancellationToken)
                         }
                     }
 
-                    // Otherwise, queue the reader.
-                    var reader = new AsyncOperation<T>(parent._runContinuationsAsynchronously, cancellationToken);
+                    // Otherwise, queue a reader.  Note that in addition to checking whether synchronous continuations were requested,
+                    // we also check whether the supplied cancellation token can be canceled.  The writer calls UnregisterCancellation
+                    // while holding the lock, and if a callback needs to be unregistered and is currently running, it needs to wait
+                    // for that callback to complete so that the subsequent code knows it won't be contending with another thread
+                    // trying to complete the operation.  However, if we allowed a synchronous continuation from this operation, that
+                    // cancellation callback could end up running arbitrary code, including code that called back into the reader or
+                    // writer and tried to take the same lock held by the thread running UnregisterCancellation... deadlock.  As such,
+                    // we only allow synchronous continuations here if both a) the caller requested it and the token isn't cancelable.
+                    var reader = new AsyncOperation<T>(parent._runContinuationsAsynchronously | cancellationToken.CanBeCanceled, cancellationToken);
                     parent._blockedReaders.EnqueueTail(reader);
                     return reader.ValueTaskOfT;
                 }
@@ -193,8 +200,15 @@ public override ValueTask<bool> WaitToReadAsync(CancellationToken cancellationTo
                         }
                     }
 
-                    // Otherwise, queue a reader.
-                    var waiter = new AsyncOperation<bool>(parent._runContinuationsAsynchronously, cancellationToken);
+                    // Otherwise, queue a reader.  Note that in addition to checking whether synchronous continuations were requested,
+                    // we also check whether the supplied cancellation token can be canceled.  The writer calls UnregisterCancellation
+                    // while holding the lock, and if a callback needs to be unregistered and is currently running, it needs to wait
+                    // for that callback to complete so that the subsequent code knows it won't be contending with another thread
+                    // trying to complete the operation.  However, if we allowed a synchronous continuation from this operation, that
+                    // cancellation callback could end up running arbitrary code, including code that called back into the reader or
+                    // writer and tried to take the same lock held by the thread running UnregisterCancellation... deadlock.  As such,
+                    // we only allow synchronous continuations here if both a) the caller requested it and the token isn't cancelable.
+                    var waiter = new AsyncOperation<bool>(parent._runContinuationsAsynchronously | cancellationToken.CanBeCanceled, cancellationToken);
                     ChannelUtilities.QueueWaiter(ref _parent._waitingReadersTail, waiter);
                     return waiter.ValueTaskOfT;
                 }
diff --git a/src/libraries/System.Threading.Channels/tests/BoundedChannelTests.cs b/src/libraries/System.Threading.Channels/tests/BoundedChannelTests.cs
index ea27c1482901b..19c28a248fc8e 100644
--- a/src/libraries/System.Threading.Channels/tests/BoundedChannelTests.cs
+++ b/src/libraries/System.Threading.Channels/tests/BoundedChannelTests.cs
@@ -390,16 +390,18 @@ public async Task WaitToWriteAsync_AfterFullThenRead_ReturnsTrue()
         }
 
         [Theory]
-        [InlineData(false)]
-        [InlineData(true)]
-        public void AllowSynchronousContinuations_WaitToReadAsync_ContinuationsInvokedAccordingToSetting(bool allowSynchronousContinuations)
+        [MemberData(nameof(ThreeBools))]
+        public void AllowSynchronousContinuations_Reading_ContinuationsInvokedAccordingToSetting(bool allowSynchronousContinuations, bool cancelable, bool waitToReadAsync)
         {
             var c = Channel.CreateBounded<int>(new BoundedChannelOptions(1) { AllowSynchronousContinuations = allowSynchronousContinuations });
 
+            CancellationToken ct = cancelable ? new CancellationTokenSource().Token : CancellationToken.None;
+
             int expectedId = Environment.CurrentManagedThreadId;
-            Task r = c.Reader.WaitToReadAsync().AsTask().ContinueWith(_ =>
+            Task t = waitToReadAsync ? (Task)c.Reader.WaitToReadAsync(ct).AsTask() : c.Reader.ReadAsync(ct).AsTask();
+            Task r = t.ContinueWith(_ =>
             {
-                Assert.Equal(allowSynchronousContinuations, expectedId == Environment.CurrentManagedThreadId);
+                Assert.Equal(allowSynchronousContinuations && !cancelable, expectedId == Environment.CurrentManagedThreadId);
             }, CancellationToken.None, TaskContinuationOptions.ExecuteSynchronously, TaskScheduler.Default);
 
             Assert.True(c.Writer.WriteAsync(42).IsCompletedSuccessfully);
diff --git a/src/libraries/System.Threading.Channels/tests/ChannelTestBase.cs b/src/libraries/System.Threading.Channels/tests/ChannelTestBase.cs
index 42721f12c4bea..ed88b1bed9fcc 100644
--- a/src/libraries/System.Threading.Channels/tests/ChannelTestBase.cs
+++ b/src/libraries/System.Threading.Channels/tests/ChannelTestBase.cs
@@ -24,6 +24,12 @@ public abstract partial class ChannelTestBase : TestBase
         protected virtual bool RequiresSingleWriter => false;
         protected virtual bool BuffersItems => true;
 
+        public static IEnumerable<object[]> ThreeBools =>
+            from b1 in new[] { false, true }
+            from b2 in new[] { false, true }
+            from b3 in new[] { false, true }
+            select new object[] { b1, b2, b3 };
+
         [Fact]
         public void ValidateDebuggerAttributes()
         {