diff --git a/stream/src/main/scala/org/apache/pekko/stream/impl/io/TLSActor.scala b/stream/src/main/scala/org/apache/pekko/stream/impl/io/TLSActor.scala
index 6fd961ff65..0cb49f31f1 100644
--- a/stream/src/main/scala/org/apache/pekko/stream/impl/io/TLSActor.scala
+++ b/stream/src/main/scala/org/apache/pekko/stream/impl/io/TLSActor.scala
@@ -71,6 +71,8 @@ import pekko.util.ByteString
 
   import TLSActor._
 
+  private val maxTLSIterations = 1000
+  private var unwrapPutBackCounter: Int = 0
   protected val outputBunch = new OutputBunch(outputCount = 2, self, this)
   outputBunch.markAllOutputs()
 
@@ -364,6 +366,7 @@ import pekko.util.ByteString
 
   def flushToUser(): Unit = {
     if (tracing) log.debug("flushToUser")
+    if (unwrapPutBackCounter > 0) unwrapPutBackCounter = 0
     userOutBuffer.flip()
     if (userOutBuffer.hasRemaining) {
       val bs = ByteString(userOutBuffer)
@@ -419,6 +422,17 @@ import pekko.util.ByteString
         result.getHandshakeStatus match {
           case NEED_WRAP =>
             flushToUser()
+            // https://github.com/apache/incubator-pekko/issues/442
+            // A second workaround for an infinite loop we have not been able to reproduce/isolate,
+            // if you see this, and can reproduce consistently, please report back to the Apache Pekko team
+            // with a reproducer or details about the client causing it
+            unwrapPutBackCounter += 1
+            if (unwrapPutBackCounter > maxTLSIterations) {
+              throw new IllegalStateException(
+                s"Stuck in unwrap loop, bailing out, last handshake status [$lastHandshakeStatus], " +
+                s"remaining=${transportInBuffer.remaining}, out=${userOutBuffer.position()}, " +
+                "(https://github.com/apache/incubator-pekko/issues/442)")
+            }
             transportInChoppingBlock.putBack(transportInBuffer)
           case FINISHED =>
             flushToUser()