@@ -41,12 +41,6 @@ func (cli *DockerCli) CmdAttach(args ...string) error {

 		return err

 	}

-	if c.Config.Tty && cli.isTerminalOut {

-		if err := cli.monitorTtySize(cmd.Arg(0), false); err != nil {

-			logrus.Debugf("Error monitoring TTY size: %s", err)

-		}

-	}

-

 	if *detachKeys != "" {

 		cli.configFile.DetachKeys = *detachKeys

 	}

@@ -82,6 +76,21 @@ func (cli *DockerCli) CmdAttach(args ...string) error {

 		defer cli.restoreTerminal(in)

 	}

+	if c.Config.Tty && cli.isTerminalOut {

+		height, width := cli.getTtySize()

+		// To handle the case where a user repeatedly attaches/detaches without resizing their

+		// terminal, the only way to get the shell prompt to display for attaches 2+ is to artifically

+		// resize it, then go back to normal. Without this, every attach after the first will

+		// require the user to manually resize or hit enter.

+		cli.resizeTtyTo(cmd.Arg(0), height+1, width+1, false)

+

+		// After the above resizing occurs, the call to monitorTtySize below will handle resetting back

+		// to the actual size.

+		if err := cli.monitorTtySize(cmd.Arg(0), false); err != nil {

+			logrus.Debugf("Error monitoring TTY size: %s", err)

+		}

+	}

+

 	if err := cli.holdHijackedConnection(c.Config.Tty, in, cli.out, cli.err, resp); err != nil {

 		return err

 	}

@@ -59,6 +59,10 @@ func (cli *DockerCli) registryAuthenticationPrivilegedFunc(index *registrytypes.

 func (cli *DockerCli) resizeTty(id string, isExec bool) {

 	height, width := cli.getTtySize()

+	cli.resizeTtyTo(id, height, width, isExec)

+}

+

+func (cli *DockerCli) resizeTtyTo(id string, height, width int, isExec bool) {

 	if height == 0 && width == 0 {

 		return

 	}