diff --git a/scripts/enter-host.ps1 b/scripts/enter-host.ps1
index 4c6a7e26..0d308458 100755
--- a/scripts/enter-host.ps1
+++ b/scripts/enter-host.ps1
@@ -31,7 +31,10 @@ try {
 	}
 
 	& "$PSScriptRoot/ping-host.ps1" $remoteHost
-	if ($lastExitCode -ne "0") { exit 1 }
+	if ($lastExitCode -ne "0") {
+		Write-Host "Let's try to wake '$remoteHost' up..."
+		& "$PSScriptRoot/wake-up-host.ps1" 
+	}
 
 	Write-Host "⏳ Connecting as user '$remoteUser' using " -noNewline
 	& ssh -V
diff --git a/scripts/ping-host.ps1 b/scripts/ping-host.ps1
index b5f841da..e0373295 100755
--- a/scripts/ping-host.ps1
+++ b/scripts/ping-host.ps1
@@ -27,7 +27,7 @@ function GetPingLatency([string]$hostname) {
 try {
 	[int]$latency = GetPingLatency($hostname)
 	if ($latency -eq 1500) {
-		Write-Host "⚠️ Host '$hostname' doesn't respond - check the connection or wake the host up."
+		Write-Host "⚠️ Host '$hostname' doesn't respond - check the connection or maybe the host is down."
 		exit 1
 	} 
 	Write-Host "✅ $hostname is up and running ($($latency)ms latency)."