diff --git a/cli/server/add.go b/cli/server/add.go
index 24788dc1..2a99b650 100644
--- a/cli/server/add.go
+++ b/cli/server/add.go
@@ -88,10 +88,6 @@ developer machine. The domain is then set to "default".`,
 			return
 		}
 
-		if _, err := dns.EnsureIPv4(name); err != nil {
-			log.Warn(err)
-		}
-
 		_, err := createServerDir(name)
 		if err != nil {
 			log.Fatal(err)
@@ -100,21 +96,28 @@ developer machine. The domain is then set to "default".`,
 		created, err := newContext(name)
 		if err != nil {
 			cleanUp(name)
-			log.Fatal(err)
+			log.Fatalf("unable to create local context: %s", err)
 		}
 
 		log.Debugf("attempting to create client for %s", name)
 
 		if _, err := client.New(name, timeout); err != nil {
 			cleanUp(name)
-			log.Fatal(sshPkg.Fatal(name, err))
+			log.Debugf("ssh %s error: %s", name, sshPkg.Fatal(name, err))
+			log.Fatalf("can't ssh to %s, make sure \"ssh %s\" works", name, name)
 		}
 
 		if created {
 			log.Infof("%s successfully added", name)
-		} else {
-			log.Warnf("%s already exists", name)
+
+			if _, err := dns.EnsureIPv4(name); err != nil {
+				log.Warnf("unable to resolve IPv4 for %s", name)
+			}
+
+			return
 		}
+
+		log.Warnf("%s already exists", name)
 	},
 }
 
diff --git a/pkg/dns/dns.go b/pkg/dns/dns.go
index 62a6f588..40497d66 100644
--- a/pkg/dns/dns.go
+++ b/pkg/dns/dns.go
@@ -9,12 +9,11 @@ import (
 func EnsureIPv4(domainName string) (string, error) {
 	ipv4, err := net.ResolveIPAddr("ip4", domainName)
 	if err != nil {
-		return "", fmt.Errorf("unable to resolve ipv4 address for %s, %s", domainName, err)
+		return "", fmt.Errorf("%s: unable to resolve IPv4 address: %s", domainName, err)
 	}
 
-	// NOTE(d1): e.g. when there is only an ipv6 record available
 	if ipv4 == nil {
-		return "", fmt.Errorf("unable to resolve ipv4 address for %s", domainName)
+		return "", fmt.Errorf("%s: no IPv4 available", domainName)
 	}
 
 	return ipv4.String(), nil