diff --git a/cli/root.go b/cli/root.go
index 97e5e5620f674..a7c1b90ad751f 100644
--- a/cli/root.go
+++ b/cli/root.go
@@ -6,6 +6,7 @@ import (
 	"os"
 	"strconv"
 	"strings"
+	"text/template"
 	"time"
 
 	"golang.org/x/xerrors"
@@ -28,7 +29,7 @@ var (
 	// Applied as annotations to workspace commands
 	// so they display in a separated "help" section.
 	workspaceCommand = map[string]string{
-		"workspaces": " ",
+		"workspaces": "",
 	}
 )
 
@@ -52,12 +53,8 @@ var (
 )
 
 func init() {
-	// Customizes the color of headings to make subcommands more visually
-	// appealing.
-	header := cliui.Styles.Placeholder
-	cobra.AddTemplateFunc("usageHeader", func(s string) string {
-		return header.Render(s)
-	})
+	// Set cobra template functions in init to avoid conflicts in tests.
+	cobra.AddTemplateFuncs(templateFunctions)
 }
 
 func Root() *cobra.Command {
@@ -311,6 +308,30 @@ func isTTYOut(cmd *cobra.Command) bool {
 	return isatty.IsTerminal(file.Fd())
 }
 
+var templateFunctions = template.FuncMap{
+	"usageHeader":        usageHeader,
+	"isWorkspaceCommand": isWorkspaceCommand,
+}
+
+func usageHeader(s string) string {
+	// Customizes the color of headings to make subcommands more visually
+	// appealing.
+	return cliui.Styles.Placeholder.Render(s)
+}
+
+func isWorkspaceCommand(cmd *cobra.Command) bool {
+	if _, ok := cmd.Annotations["workspaces"]; ok {
+		return true
+	}
+	var ws bool
+	cmd.VisitParents(func(cmd *cobra.Command) {
+		if _, ok := cmd.Annotations["workspaces"]; ok {
+			ws = true
+		}
+	})
+	return ws
+}
+
 func usageTemplate() string {
 	// usageHeader is defined in init().
 	return `{{usageHeader "Usage:"}}
@@ -331,19 +352,21 @@ func usageTemplate() string {
 {{.Example}}
 {{end}}
 
+{{- $isRootHelp := (not .HasParent)}}
 {{- if .HasAvailableSubCommands}}
 {{usageHeader "Commands:"}}
   {{- range .Commands}}
-    {{- if (or (and .IsAvailableCommand (eq (len .Annotations) 0)) (eq .Name "help"))}}
+    {{- $isRootWorkspaceCommand := (and $isRootHelp (isWorkspaceCommand .))}}
+    {{- if (or (and .IsAvailableCommand (not $isRootWorkspaceCommand)) (eq .Name "help"))}}
   {{rpad .Name .NamePadding }} {{.Short}}
     {{- end}}
   {{- end}}
 {{end}}
 
-{{- if and (not .HasParent) .HasAvailableSubCommands}}
+{{- if (and $isRootHelp .HasAvailableSubCommands)}}
 {{usageHeader "Workspace Commands:"}}
   {{- range .Commands}}
-    {{- if (and .IsAvailableCommand (ne (index .Annotations "workspaces") ""))}}
+    {{- if (and .IsAvailableCommand (isWorkspaceCommand .))}}
   {{rpad .Name .NamePadding }} {{.Short}}
     {{- end}}
   {{- end}}
@@ -351,12 +374,12 @@ func usageTemplate() string {
 
 {{- if .HasAvailableLocalFlags}}
 {{usageHeader "Flags:"}}
-{{.LocalFlags.FlagUsagesWrapped 100}}
+{{.LocalFlags.FlagUsagesWrapped 100 | trimTrailingWhitespaces}}
 {{end}}
 
 {{- if .HasAvailableInheritedFlags}}
 {{usageHeader "Global Flags:"}}
-{{.InheritedFlags.FlagUsagesWrapped 100}}
+{{.InheritedFlags.FlagUsagesWrapped 100 | trimTrailingWhitespaces}}
 {{end}}
 
 {{- if .HasHelpSubCommands}}
diff --git a/cli/schedule.go b/cli/schedule.go
index 1cd7cc65edca9..b583915baf7f7 100644
--- a/cli/schedule.go
+++ b/cli/schedule.go
@@ -17,12 +17,6 @@ import (
 )
 
 const (
-	scheduleDescriptionLong = `Modify scheduled stop and start times for your workspace:
-  * schedule show: show workspace schedule
-  * schedule start: edit workspace start schedule
-  * schedule stop: edit workspace stop schedule
-  * schedule override-stop: edit stop time of active workspace
-`
 	scheduleShowDescriptionLong = `Shows the following information for the given workspace:
   * The automatic start schedule
   * The next scheduled start time
@@ -64,24 +58,24 @@ func schedules() *cobra.Command {
 		Annotations: workspaceCommand,
 		Use:         "schedule { show | start | stop | override } <workspace>",
 		Short:       "Modify scheduled stop and start times for your workspace",
-		Long:        scheduleDescriptionLong,
 	}
 
-	scheduleCmd.AddCommand(scheduleShow())
-	scheduleCmd.AddCommand(scheduleStart())
-	scheduleCmd.AddCommand(scheduleStop())
-	scheduleCmd.AddCommand(scheduleOverride())
+	scheduleCmd.AddCommand(
+		scheduleShow(),
+		scheduleStart(),
+		scheduleStop(),
+		scheduleOverride(),
+	)
 
 	return scheduleCmd
 }
 
 func scheduleShow() *cobra.Command {
 	showCmd := &cobra.Command{
-		Annotations: workspaceCommand,
-		Use:         "show <workspace-name>",
-		Short:       "Show workspace schedule",
-		Long:        scheduleShowDescriptionLong,
-		Args:        cobra.ExactArgs(1),
+		Use:   "show <workspace-name>",
+		Short: "Show workspace schedule",
+		Long:  scheduleShowDescriptionLong,
+		Args:  cobra.ExactArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
 			client, err := createClient(cmd)
 			if err != nil {
@@ -101,8 +95,7 @@ func scheduleShow() *cobra.Command {
 
 func scheduleStart() *cobra.Command {
 	cmd := &cobra.Command{
-		Annotations: workspaceCommand,
-		Use:         "start <workspace-name> { <start-time> [day-of-week] [location] | manual }",
+		Use: "start <workspace-name> { <start-time> [day-of-week] [location] | manual }",
 		Example: formatExamples(
 			example{
 				Description: "Set the workspace to start at 9:30am (in Dublin) from Monday to Friday",
@@ -153,9 +146,8 @@ func scheduleStart() *cobra.Command {
 
 func scheduleStop() *cobra.Command {
 	return &cobra.Command{
-		Annotations: workspaceCommand,
-		Args:        cobra.ExactArgs(2),
-		Use:         "stop <workspace-name> { <duration> | manual }",
+		Args: cobra.ExactArgs(2),
+		Use:  "stop <workspace-name> { <duration> | manual }",
 		Example: formatExamples(
 			example{
 				Command: "coder schedule stop my-workspace 2h30m",
@@ -200,9 +192,8 @@ func scheduleStop() *cobra.Command {
 
 func scheduleOverride() *cobra.Command {
 	overrideCmd := &cobra.Command{
-		Args:        cobra.ExactArgs(2),
-		Annotations: workspaceCommand,
-		Use:         "override-stop <workspace-name> <duration from now>",
+		Args: cobra.ExactArgs(2),
+		Use:  "override-stop <workspace-name> <duration from now>",
 		Example: formatExamples(
 			example{
 				Command: "coder schedule override-stop my-workspace 90m",