diff --git a/usage.go b/usage.go
index 23f7aa5..61f0ad6 100644
--- a/usage.go
+++ b/usage.go
@@ -9,6 +9,9 @@ import (
 	"strings"
 )
 
+// the width of the left column
+const colWidth = 25
+
 // Fail prints usage information to stderr and exits with non-zero status
 func (p *Parser) Fail(msg string) {
 	p.WriteUsage(os.Stderr)
@@ -73,7 +76,17 @@ func (p *Parser) WriteHelp(w io.Writer) {
 	if len(positionals) > 0 {
 		fmt.Fprint(w, "\npositional arguments:\n")
 		for _, spec := range positionals {
-			fmt.Fprintf(w, "  %s\n", spec.long)
+			left := "  " + spec.long
+			fmt.Fprint(w, left)
+			if spec.help != "" {
+				if len(left)+2 < colWidth {
+					fmt.Fprint(w, strings.Repeat(" ", colWidth-len(left)))
+				} else {
+					fmt.Fprint(w, "\n"+strings.Repeat(" ", colWidth))
+				}
+				fmt.Fprint(w, spec.help)
+			}
+			fmt.Fprint(w, "\n")
 		}
 	}
 
@@ -88,7 +101,6 @@ func (p *Parser) WriteHelp(w io.Writer) {
 }
 
 func printOption(w io.Writer, spec *spec) {
-	const colWidth = 25
 	left := "  " + synopsis(spec, "--"+spec.long)
 	if spec.short != "" {
 		left += ", " + synopsis(spec, "-"+spec.short)
diff --git a/usage_test.go b/usage_test.go
index 07edc18..2375e81 100644
--- a/usage_test.go
+++ b/usage_test.go
@@ -16,7 +16,7 @@ func TestWriteUsage(t *testing.T) {
 
 positional arguments:
   input
-  output
+  output                 list of outputs
 
 options:
   --name NAME            name to use [default: Foo Bar]
@@ -30,7 +30,7 @@ options:
 `
 	var args struct {
 		Input    string   `arg:"positional"`
-		Output   []string `arg:"positional"`
+		Output   []string `arg:"positional,help:list of outputs"`
 		Name     string   `arg:"help:name to use"`
 		Value    int      `arg:"help:secret value"`
 		Verbose  bool     `arg:"-v,help:verbosity level"`
@@ -53,3 +53,26 @@ options:
 	p.WriteHelp(&help)
 	assert.Equal(t, expectedHelp, help.String())
 }
+
+func TestUsageLongPositionalWithHelp(t *testing.T) {
+	expectedHelp := `usage: example VERYLONGPOSITIONALWITHHELP
+
+positional arguments:
+  verylongpositionalwithhelp
+                         this positional argument is very long
+
+options:
+  --help, -h             display this help and exit
+`
+	var args struct {
+		VeryLongPositionalWithHelp string `arg:"positional,help:this positional argument is very long"`
+	}
+
+	p, err := NewParser(&args)
+	require.NoError(t, err)
+
+	os.Args[0] = "example"
+	var help bytes.Buffer
+	p.WriteHelp(&help)
+	assert.Equal(t, expectedHelp, help.String())
+}