diff --git a/cli/cliui/prompt.go b/cli/cliui/prompt.go
index 16f0c438f4..86c2aa0e50 100644
--- a/cli/cliui/prompt.go
+++ b/cli/cliui/prompt.go
@@ -24,25 +24,41 @@ type PromptOptions struct {
 	Validate  func(string) error
 }
 
+const skipPromptFlag = "yes"
+
 func AllowSkipPrompt(cmd *cobra.Command) {
-	cmd.Flags().BoolP("yes", "y", false, "Bypass prompts")
+	cmd.Flags().BoolP(skipPromptFlag, "y", false, "Bypass prompts")
 }
 
+const (
+	ConfirmYes = "yes"
+	ConfirmNo  = "no"
+)
+
 // Prompt asks the user for input.
 func Prompt(cmd *cobra.Command, opts PromptOptions) (string, error) {
 	// If the cmd has a "yes" flag for skipping confirm prompts, honor it.
 	// If it's not a "Confirm" prompt, then don't skip. As the default value of
 	// "yes" makes no sense.
-	if opts.IsConfirm && cmd.Flags().Lookup("yes") != nil {
-		if skip, _ := cmd.Flags().GetBool("yes"); skip {
-			return "yes", nil
+	if opts.IsConfirm && cmd.Flags().Lookup(skipPromptFlag) != nil {
+		if skip, _ := cmd.Flags().GetBool(skipPromptFlag); skip {
+			return ConfirmYes, nil
 		}
 	}
 
 	_, _ = fmt.Fprint(cmd.OutOrStdout(), Styles.FocusedPrompt.String()+opts.Text+" ")
 	if opts.IsConfirm {
-		opts.Default = "yes"
-		_, _ = fmt.Fprint(cmd.OutOrStdout(), Styles.Placeholder.Render("("+Styles.Bold.Render("yes")+Styles.Placeholder.Render("/no) ")))
+		if len(opts.Default) == 0 {
+			opts.Default = ConfirmYes
+		}
+		renderedYes := Styles.Placeholder.Render(ConfirmYes)
+		renderedNo := Styles.Placeholder.Render(ConfirmNo)
+		if opts.Default == ConfirmYes {
+			renderedYes = Styles.Bold.Render(ConfirmYes)
+		} else {
+			renderedNo = Styles.Bold.Render(ConfirmNo)
+		}
+		_, _ = fmt.Fprint(cmd.OutOrStdout(), Styles.Placeholder.Render("("+renderedYes+Styles.Placeholder.Render("/"+renderedNo+Styles.Placeholder.Render(") "))))
 	} else if opts.Default != "" {
 		_, _ = fmt.Fprint(cmd.OutOrStdout(), Styles.Placeholder.Render("("+opts.Default+") "))
 	}
diff --git a/cli/delete.go b/cli/delete.go
index ea4ef0ac2a..5950a7b034 100644
--- a/cli/delete.go
+++ b/cli/delete.go
@@ -22,6 +22,7 @@ func deleteWorkspace() *cobra.Command {
 			_, err := cliui.Prompt(cmd, cliui.PromptOptions{
 				Text:      "Confirm delete workspace?",
 				IsConfirm: true,
+				Default:   cliui.ConfirmNo,
 			})
 			if err != nil {
 				return err
diff --git a/cli/login.go b/cli/login.go
index 8543e5747a..9f26a2e30e 100644
--- a/cli/login.go
+++ b/cli/login.go
@@ -89,7 +89,7 @@ func login() *cobra.Command {
 					}
 					_, err := cliui.Prompt(cmd, cliui.PromptOptions{
 						Text:      "Would you like to create the first user?",
-						Default:   "yes",
+						Default:   cliui.ConfirmYes,
 						IsConfirm: true,
 					})
 					if errors.Is(err, cliui.Canceled) {
diff --git a/cli/logout.go b/cli/logout.go
index 1860d97673..cab5f46203 100644
--- a/cli/logout.go
+++ b/cli/logout.go
@@ -28,7 +28,7 @@ func logout() *cobra.Command {
 			_, err = cliui.Prompt(cmd, cliui.PromptOptions{
 				Text:      "Are you sure you want to log out?",
 				IsConfirm: true,
-				Default:   "yes",
+				Default:   cliui.ConfirmYes,
 			})
 			if err != nil {
 				return err
diff --git a/cli/templatecreate.go b/cli/templatecreate.go
index 759bee277b..e3ba05e9cb 100644
--- a/cli/templatecreate.go
+++ b/cli/templatecreate.go
@@ -60,7 +60,7 @@ func templateCreate() *cobra.Command {
 			_, err = cliui.Prompt(cmd, cliui.PromptOptions{
 				Text:      fmt.Sprintf("Create and upload %q?", prettyDir),
 				IsConfirm: true,
-				Default:   "yes",
+				Default:   cliui.ConfirmYes,
 			})
 			if err != nil {
 				return err
diff --git a/cli/templatedelete.go b/cli/templatedelete.go
index 9eecda2b29..aa4f5d6dda 100644
--- a/cli/templatedelete.go
+++ b/cli/templatedelete.go
@@ -76,7 +76,7 @@ func templateDelete() *cobra.Command {
 			_, err = cliui.Prompt(cmd, cliui.PromptOptions{
 				Text:      fmt.Sprintf("Delete these templates: %s?", cliui.Styles.Code.Render(strings.Join(templateNames, ", "))),
 				IsConfirm: true,
-				Default:   "no",
+				Default:   cliui.ConfirmNo,
 			})
 			if err != nil {
 				return err
diff --git a/cli/templateupdate.go b/cli/templateupdate.go
index d283788939..3922c8492e 100644
--- a/cli/templateupdate.go
+++ b/cli/templateupdate.go
@@ -53,7 +53,7 @@ func templateUpdate() *cobra.Command {
 			_, err = cliui.Prompt(cmd, cliui.PromptOptions{
 				Text:      fmt.Sprintf("Upload %q?", prettyDir),
 				IsConfirm: true,
-				Default:   "yes",
+				Default:   cliui.ConfirmYes,
 			})
 			if err != nil {
 				return err
diff --git a/cli/userstatus.go b/cli/userstatus.go
index 4596053a14..2eed093607 100644
--- a/cli/userstatus.go
+++ b/cli/userstatus.go
@@ -71,7 +71,7 @@ func createUserStatusCommand(sdkStatus codersdk.UserStatus) *cobra.Command {
 			_, err = cliui.Prompt(cmd, cliui.PromptOptions{
 				Text:      fmt.Sprintf("Are you sure you want to %s this user?", verb),
 				IsConfirm: true,
-				Default:   "yes",
+				Default:   cliui.ConfirmYes,
 			})
 			if err != nil {
 				return err
diff --git a/cmd/cliui/main.go b/cmd/cliui/main.go
index 52203893f2..45cdb6cb7f 100644
--- a/cmd/cliui/main.go
+++ b/cmd/cliui/main.go
@@ -43,7 +43,7 @@ func main() {
 			}
 			_, err = cliui.Prompt(cmd, cliui.PromptOptions{
 				Text:      "Do you want to accept?",
-				Default:   "yes",
+				Default:   cliui.ConfirmYes,
 				IsConfirm: true,
 			})
 			if errors.Is(err, cliui.Canceled) {