diff --git a/core/src/main/java/io/undertow/UndertowLogger.java b/core/src/main/java/io/undertow/UndertowLogger.java
index cdc66549e9..705062eb76 100644
--- a/core/src/main/java/io/undertow/UndertowLogger.java
+++ b/core/src/main/java/io/undertow/UndertowLogger.java
@@ -458,4 +458,8 @@ void nodeConfigCreated(URI connectionURI, String balancer, String domain, String
     @LogMessage(level = WARN)
     @Message(id = 5102, value = "Flushing waiting in a frame more than %s miliseconds. The framed channel will be forcibly closed.")
     void noFrameflushInTimeout(long timeoutMiliseconds);
+
+    @LogMessage(level = ERROR)
+    @Message(id = 5103, value = "SSL outstanding task loop detected in doWrap/doUnwrap calls. This is indicative of task thread exhaustion so consider investigating any slowness and thread ehxaustion concerns via thread dumps and increasing task-max-threads as needed. Current state %s")
+    void sslTaskLoopDetected(SslConduit sslConduit);
 }
diff --git a/core/src/main/java/io/undertow/protocols/ssl/SslConduit.java b/core/src/main/java/io/undertow/protocols/ssl/SslConduit.java
index 91b6c898d7..9507a4f039 100644
--- a/core/src/main/java/io/undertow/protocols/ssl/SslConduit.java
+++ b/core/src/main/java/io/undertow/protocols/ssl/SslConduit.java
@@ -170,6 +170,7 @@ public class SslConduit implements StreamSourceConduit, StreamSinkConduit {
     private SslWriteReadyHandler writeReadyHandler;
     private SslReadReadyHandler readReadyHandler;
     private int readListenerInvocationCount;
+    private int outstandingTaskWaitCount;
 
     private boolean invokingReadListenerHandshake = false;
 
@@ -710,7 +711,15 @@ private synchronized long doUnwrap(ByteBuffer[] userBuffers, int off, int len) t
             throw new ClosedChannelException();
         }
         if(outstandingTasks > 0) {
+            if(outstandingTaskWaitCount++ == MAX_READ_LISTENER_INVOCATIONS) {
+                UndertowLogger.REQUEST_LOGGER.sslTaskLoopDetected(this);
+                IoUtils.safeClose(connection, delegate);
+                close();
+                return -1;
+            }
             return 0;
+        } else {
+            outstandingTaskWaitCount = 0;
         }
         if(anyAreSet(state, FLAG_READ_REQUIRES_WRITE)) {
             doWrap(null, 0, 0);
@@ -919,7 +928,15 @@ private synchronized long doWrap(ByteBuffer[] userBuffers, int off, int len) thr
             throw new ClosedChannelException();
         }
         if(outstandingTasks > 0) {
+            if(outstandingTaskWaitCount++ == MAX_READ_LISTENER_INVOCATIONS) {
+                UndertowLogger.REQUEST_LOGGER.sslTaskLoopDetected(this);
+                IoUtils.safeClose(connection, delegate);
+                close();
+                return -1;
+            }
             return 0;
+        } else {
+            outstandingTaskWaitCount = 0;
         }
         if(anyAreSet(state, FLAG_WRITE_REQUIRES_READ)) {
             doUnwrap(null, 0, 0);