diff --git a/main/src/main/scala/sbt/Main.scala b/main/src/main/scala/sbt/Main.scala
index 99e37e963..f2e7a2e9e 100644
--- a/main/src/main/scala/sbt/Main.scala
+++ b/main/src/main/scala/sbt/Main.scala
@@ -1003,10 +1003,12 @@ object BuiltinCommands {
 
           val s1 = exchange.run(s0)
           val exec: Exec = getExec(s1, Duration.Inf)
-          val remaining: List[Exec] =
-            Exec(FailureWall, None) :: Exec(s"${ContinuousCommands.waitWatch} $channel", None) ::
-              s1.remainingCommands
-          val newState = s1.copy(remainingCommands = exec +: remaining)
+          val wait = s"${ContinuousCommands.waitWatch} $channel"
+          val onFailure =
+            s1.onFailure.map(of => if (of.commandLine == Shell) of.withCommandLine(wait) else of)
+          val waitExec = Exec(wait, None)
+          val remaining: List[Exec] = Exec(FailureWall, None) :: waitExec :: s1.remainingCommands
+          val newState = s1.copy(remainingCommands = exec +: remaining, onFailure = onFailure)
           if (exec.commandLine.trim.isEmpty) newState
           else newState.clearGlobalLog
         case _ => s0
diff --git a/main/src/main/scala/sbt/internal/Continuous.scala b/main/src/main/scala/sbt/internal/Continuous.scala
index c5ba2aec9..92801f32b 100644
--- a/main/src/main/scala/sbt/internal/Continuous.scala
+++ b/main/src/main/scala/sbt/internal/Continuous.scala
@@ -116,7 +116,7 @@ private[sbt] object Continuous extends DeprecatedContinuous {
           case None    => StandardMain.exchange.run(s) -> ConsoleChannel.defaultName
         }
         val ws = ContinuousCommands.setupWatchState(channel, initialCount, commands, s1)
-        s"${ContinuousCommands.runWatch} $channel" :: ws
+        s"${ContinuousCommands.runWatch} $channel" :: s"${ContinuousCommands.waitWatch} $channel" :: ws
     }
 
   @deprecated("The input task version of watch is no longer available", "1.4.0")
@@ -1279,7 +1279,7 @@ private[sbt] object ContinuousCommands {
       case None => state
       case Some(cs) =>
         val pre = StashOnFailure :: s"$preWatch $channel" :: Nil
-        val post = FailureWall :: PopOnFailure :: s"$postWatch $channel" :: s"$waitWatch $channel" :: Nil
+        val post = FailureWall :: PopOnFailure :: s"$postWatch $channel" :: Nil
         pre ::: cs.commands.toList ::: post ::: state
     }
   }