diff --git a/cli/internal/error.go b/cli/internal/error.go
new file mode 100644
index 00000000..ca1a24bf
--- /dev/null
+++ b/cli/internal/error.go
@@ -0,0 +1,64 @@
+package internal
+
+import (
+	"fmt"
+	"runtime"
+
+	"github.com/charmbracelet/log"
+)
+
+func Error(msg string) HelpError {
+	caller := ""
+	if Debug {
+		_, file, line, _ := runtime.Caller(1)
+		caller = log.ShortCallerFormatter(file, line, "")
+
+	}
+	return HelpError{err: msg, caller: caller}
+}
+
+func Errorf(format string, a ...any) HelpError {
+	caller := ""
+	if Debug {
+		_, file, line, _ := runtime.Caller(1)
+		caller = log.ShortCallerFormatter(file, line, "")
+
+	}
+	return HelpError{err: fmt.Sprintf(format, a...), caller: caller}
+}
+
+type HelpError struct {
+	err    string
+	caller string
+	help   string
+}
+
+func (e HelpError) Help(help string) HelpError {
+	e.help = help
+	return e
+}
+
+func (e HelpError) Helpf(format string, a ...any) HelpError {
+	e.help = fmt.Sprintf(format, a...)
+	return e
+}
+
+func (e HelpError) Error() string {
+	return e.format()
+}
+
+func (e HelpError) format() string {
+	msg := ""
+	if e.caller != "" {
+		msg += fmt.Sprintf("<%s> ", e.caller)
+	}
+
+	msg += e.err
+	if e.help == "" {
+		return msg
+	}
+
+	return fmt.Sprintf(`%s
+
+Help: %s `, msg, e.help)
+}
diff --git a/cli/run.go b/cli/run.go
index 104b3bf2..5c09a602 100644
--- a/cli/run.go
+++ b/cli/run.go
@@ -66,6 +66,8 @@ func Run(version, commit string) {
 	}
 
 	rootCmd.CompletionOptions.DisableDefaultCmd = true
+	// This prevents displaying usage for errors returned from RunE
+	rootCmd.SilenceUsage = true
 
 	manCommand := &cobra.Command{
 		Use:     "man [flags]",
diff --git a/cli/server/add.go b/cli/server/add.go
index 2a99b650..75c846fa 100644
--- a/cli/server/add.go
+++ b/cli/server/add.go
@@ -1,6 +1,8 @@
 package server
 
 import (
+	"errors"
+	"fmt"
 	"os"
 	"path/filepath"
 
@@ -41,19 +43,20 @@ developer machine. The domain is then set to "default".`,
 	ValidArgsFunction: func(
 		cmd *cobra.Command,
 		args []string,
-		toComplete string) ([]string, cobra.ShellCompDirective) {
+		toComplete string,
+	) ([]string, cobra.ShellCompDirective) {
 		if !local {
 			return autocomplete.ServerNameComplete()
 		}
 		return nil, cobra.ShellCompDirectiveDefault
 	},
-	Run: func(cmd *cobra.Command, args []string) {
+	RunE: func(cmd *cobra.Command, args []string) error {
 		if len(args) > 0 && local {
-			log.Fatal("cannot use [server] and --local together")
+			return errors.New("cannot use [server] and --local together")
 		}
 
 		if len(args) == 0 && !local {
-			log.Fatal("missing argument or --local/-l flag")
+			return errors.New("missing argument or --local/-l flag")
 		}
 
 		name := "default"
@@ -69,14 +72,14 @@ developer machine. The domain is then set to "default".`,
 		if local {
 			created, err := createServerDir(name)
 			if err != nil {
-				log.Fatal(err)
+				return err
 			}
 
 			log.Debugf("attempting to create client for %s", name)
 
 			if _, err := client.New(name, timeout); err != nil {
 				cleanUp(name)
-				log.Fatal(err)
+				return err
 			}
 
 			if created {
@@ -85,18 +88,18 @@ developer machine. The domain is then set to "default".`,
 				log.Warn("local server already exists")
 			}
 
-			return
+			return nil
 		}
 
 		_, err := createServerDir(name)
 		if err != nil {
-			log.Fatal(err)
+			return err
 		}
 
 		created, err := newContext(name)
 		if err != nil {
 			cleanUp(name)
-			log.Fatalf("unable to create local context: %s", err)
+			return fmt.Errorf("unable to create local context: %s", err)
 		}
 
 		log.Debugf("attempting to create client for %s", name)
@@ -104,7 +107,7 @@ developer machine. The domain is then set to "default".`,
 		if _, err := client.New(name, timeout); err != nil {
 			cleanUp(name)
 			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)
+			return internal.Errorf("can't ssh to %s", name).Helpf("make sure \"ssh %s\" works", name)
 		}
 
 		if created {
@@ -114,10 +117,11 @@ developer machine. The domain is then set to "default".`,
 				log.Warnf("unable to resolve IPv4 for %s", name)
 			}
 
-			return
+			return nil
 		}
 
 		log.Warnf("%s already exists", name)
+		return nil
 	},
 }
 
@@ -189,9 +193,7 @@ func createServerDir(name string) (bool, error) {
 	return true, nil
 }
 
-var (
-	local bool
-)
+var local bool
 
 func init() {
 	ServerAddCommand.Flags().BoolVarP(