diff --git a/internal/cli/main.go b/internal/cli/main.go
index 3ec483e1e..57aa7020e 100644
--- a/internal/cli/main.go
+++ b/internal/cli/main.go
@@ -97,6 +97,10 @@ func Main(args []string) int {
 		Autocomplete:               true,
 		AutocompleteNoDefaultFlags: true,
 		HelpFunc:                   GroupedHelpFunc(cli.BasicHelpFunc(cliName)),
+		// Write help to stdout to match Ruby vagrant behavior
+		HelpWriter: os.Stdout,
+		// Need to set Version on the CLI to enable `-v` and `--version` handling
+		Version: vsn.FullVersionNumber(true),
 	}
 
 	// Run the CLI
@@ -253,22 +257,22 @@ func logger(args []string) ([]string, hclog.Logger, io.Writer, error) {
 		}
 
 		switch arg {
-		case "-v":
+		case "-V":
 			if level == hclog.NoLevel || level > hclog.Info {
 				level = hclog.Info
 				_ = os.Setenv("VAGRANT_LOG", "info")
 			}
-		case "-vv":
+		case "-VV":
 			if level == hclog.NoLevel || level > hclog.Debug {
 				level = hclog.Debug
 				_ = os.Setenv("VAGRANT_LOG", "debug")
 			}
-		case "-vvv":
+		case "-VVV":
 			if level == hclog.NoLevel || level > hclog.Trace {
 				level = hclog.Trace
 				_ = os.Setenv("VAGRANT_LOG", "trace")
 			}
-		case "-vvvv":
+		case "-VVVV":
 			if level == hclog.NoLevel || level > hclog.Trace {
 				level = hclog.Trace
 				_ = os.Setenv("VAGRANT_LOG", "trace")
diff --git a/internal/version/version.go b/internal/version/version.go
index 3a40bb73b..bfdc699ce 100644
--- a/internal/version/version.go
+++ b/internal/version/version.go
@@ -3,6 +3,7 @@ package version
 import (
 	"bytes"
 	"fmt"
+	"regexp"
 )
 
 var (
@@ -30,9 +31,13 @@ func GetVersion() *VersionInfo {
 	md := VersionMetadata
 	desc := GitDescribe
 	if desc != "" {
-		ver = desc
+		// git describe is based off tags which always start with v, but
+		// Vagrant has always reported its version number w/o a leading v in
+		// the CLI, so we'll remove it here
+		re := regexp.MustCompile(`^v`)
+		ver = re.ReplaceAllString(desc, "")
 	} else {
-		ver = fmt.Sprintf("v%s", ver)
+		ver = fmt.Sprintf("%s", ver)
 	}
 	if desc == "" && rel == "" && VersionPrerelease != "" {
 		rel = "dev"