diff --git a/main-command/src/main/scala/sbt/internal/client/NetworkClient.scala b/main-command/src/main/scala/sbt/internal/client/NetworkClient.scala
index 4c3fc0613..170d661a9 100644
--- a/main-command/src/main/scala/sbt/internal/client/NetworkClient.scala
+++ b/main-command/src/main/scala/sbt/internal/client/NetworkClient.scala
@@ -156,13 +156,42 @@ class NetworkClient(
 
   private def mkSocket(file: File): (Socket, Option[String]) = ClientSocket.socket(file, useJNI)
 
+  @tailrec
+  private def connect(file: File, attempt: Int = 0): (Socket, Option[String]) = {
+    val res =
+      try Some(mkSocket(file))
+      catch {
+        case e: IOException
+            if Option(e.getMessage).exists(_.contains("Couldn't open")) && attempt < 10 =>
+          if (
+            Option(e.getMessage).exists(m => m.contains("Access is denied") || m.contains("(5)"))
+          ) {
+            errorStream.println(s"Access denied for portfile $file")
+            throw new NetworkClient.AccessDeniedException
+          }
+          None
+        case e: IOException => throw new ConnectionRefusedException(e)
+      }
+    res match {
+      case Some(r) => r
+      case None =>
+        Thread.sleep(new java.util.Random().nextInt(20).toLong)
+        connect(file, attempt + 1)
+    }
+  }
+
   private def portfile = arguments.baseDirectory / "project" / "target" / "active.json"
 
   def connection: ServerSession = connectionHolder.synchronized {
-    connectionHolder.get match {
-      case null => init(promptCompleteUsers = false, retry = true)
-      case c    => c
-    }
+    @tailrec def getConnection(): ServerSession =
+      connectionHolder.get match {
+        case null if rebooting.get && running.get =>
+          connectionHolder.wait(20)
+          getConnection()
+        case null => init(promptCompleteUsers = false, retry = true)
+        case c    => c
+      }
+    getConnection()
   }
 
   private val stdinBytes = new LinkedBlockingQueue[Integer]
@@ -215,29 +244,7 @@ class NetworkClient(
           waitForServer(portfile, log = true, startServer = true)
         }
       }
-      @tailrec def connect(attempt: Int): (Socket, Option[String]) = {
-        val res =
-          try Some(mkSocket(portfile))
-          catch {
-            // This catches a pipe busy exception which can happen if two windows clients
-            // attempt to connect in rapid succession
-            case e: IOException if e.getMessage.contains("Couldn't open") && attempt < 10 =>
-              if (e.getMessage.contains("Access is denied") || e.getMessage.contains("(5)")) {
-                errorStream.println(s"Access denied for portfile $portfile")
-                throw new NetworkClient.AccessDeniedException
-              }
-              None
-            case e: IOException => throw new ConnectionRefusedException(e)
-          }
-        res match {
-          case Some(r) => r
-          case None    =>
-            // Use a random sleep to spread out the competing processes
-            Thread.sleep(new java.util.Random().nextInt(20).toLong)
-            connect(attempt + 1)
-        }
-      }
-      connect(0)
+      connect(portfile)
     } catch {
       case e: ConnectionRefusedException if retry =>
         if (Files.deleteIfExists(portfile.toPath))
@@ -245,9 +252,35 @@ class NetworkClient(
         else throw e
     }
 
+  private def connectToRebootedServer(): (Socket, Option[String]) = {
+    val deadline = 10.seconds.fromNow
+    @tailrec def loop(lastError: Option[Throwable]): (Socket, Option[String]) =
+      if (deadline.isOverdue()) {
+        lastError match {
+          case Some(e) => throw e
+          case _ =>
+            throw new TimeoutException(
+              s"timed out reconnecting to rebooted sbt server via $portfile"
+            )
+        }
+      } else if (portfile.exists) {
+        try connect(portfile)
+        catch {
+          case e: NetworkClient.AccessDeniedException => throw e
+          case NonFatal(e) =>
+            Thread.sleep(20)
+            loop(Some(e))
+        }
+      } else {
+        Thread.sleep(20)
+        loop(lastError)
+      }
+    loop(None)
+  }
+
   // Open server connection based on the portfile
-  def init(promptCompleteUsers: Boolean, retry: Boolean): ServerSession = {
-    val (sk, tkn) = connectOrStartServerAndConnect(promptCompleteUsers, retry)
+  private def init(connectionInfo: => (Socket, Option[String])): ServerSession = {
+    val (sk, tkn) = connectionInfo
     val conn = new ServerSessionImpl(sk, s"sbt-serverconnection-${sk.getPort}") {
       override protected def onNotification(msg: JsonRpcNotificationMessage): Unit = {
         msg.method match {
@@ -267,7 +300,7 @@ class NetworkClient(
                 case c    => c.close()
               }
               waitForServer(portfile, true, false)
-              init(promptCompleteUsers = false, retry = false)
+              init(connectToRebootedServer())
               attachUUID.set(sendJson(attach, s"""{"interactive": ${!batchMode.get}}"""))
               rebooting.set(false)
               rebootCommands match {
@@ -333,10 +366,16 @@ class NetworkClient(
       initializationOptions = Some(opts),
     )
     conn.sendCommand(initCommand)
-    connectionHolder.set(conn)
+    connectionHolder.synchronized {
+      connectionHolder.set(conn)
+      connectionHolder.notifyAll()
+    }
     conn
   }
 
+  def init(promptCompleteUsers: Boolean, retry: Boolean): ServerSession =
+    init(connectOrStartServerAndConnect(promptCompleteUsers, retry))
+
   /**
    * Forks another instance of sbt in the background.
    * This instance must be shutdown explicitly via `sbt -client shutdown`
diff --git a/main/src/main/scala/sbt/internal/CommandExchange.scala b/main/src/main/scala/sbt/internal/CommandExchange.scala
index 8a542fb8c..9c3088eb2 100644
--- a/main/src/main/scala/sbt/internal/CommandExchange.scala
+++ b/main/src/main/scala/sbt/internal/CommandExchange.scala
@@ -479,7 +479,7 @@ private[sbt] final class CommandExchange {
             case e if e.commandLine.startsWith(CompleteExec) =>
               e.commandLine.split(CompleteExec).last.trim
           }
-          nc.shutdown(true, execId.map(_ -> remainingCommands))
+          nc.shutdown(true, Some(execId.getOrElse("") -> remainingCommands))
         case nc: NetworkChannel => nc.shutdown(true, Some(("", "")))
         case _                  =>
       }