diff --git a/cli/cliui/prompt.go b/cli/cliui/prompt.go
index ac39404e27d3f..16f0c438f4007 100644
--- a/cli/cliui/prompt.go
+++ b/cli/cliui/prompt.go
@@ -24,8 +24,21 @@ type PromptOptions struct {
 	Validate  func(string) error
 }
 
+func AllowSkipPrompt(cmd *cobra.Command) {
+	cmd.Flags().BoolP("yes", "y", false, "Bypass prompts")
+}
+
 // 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
+		}
+	}
+
 	_, _ = fmt.Fprint(cmd.OutOrStdout(), Styles.FocusedPrompt.String()+opts.Text+" ")
 	if opts.IsConfirm {
 		opts.Default = "yes"
diff --git a/cli/cliui/prompt_test.go b/cli/cliui/prompt_test.go
index 1926349c2d1fc..9c9167ad09708 100644
--- a/cli/cliui/prompt_test.go
+++ b/cli/cliui/prompt_test.go
@@ -1,7 +1,9 @@
 package cliui_test
 
 import (
+	"bytes"
 	"context"
+	"io"
 	"os"
 	"os/exec"
 	"testing"
@@ -24,7 +26,7 @@ func TestPrompt(t *testing.T) {
 		go func() {
 			resp, err := newPrompt(ptty, cliui.PromptOptions{
 				Text: "Example",
-			})
+			}, nil)
 			require.NoError(t, err)
 			msgChan <- resp
 		}()
@@ -41,7 +43,7 @@ func TestPrompt(t *testing.T) {
 			resp, err := newPrompt(ptty, cliui.PromptOptions{
 				Text:      "Example",
 				IsConfirm: true,
-			})
+			}, nil)
 			require.NoError(t, err)
 			doneChan <- resp
 		}()
@@ -50,6 +52,47 @@ func TestPrompt(t *testing.T) {
 		require.Equal(t, "yes", <-doneChan)
 	})
 
+	t.Run("Skip", func(t *testing.T) {
+		t.Parallel()
+		ptty := ptytest.New(t)
+		var buf bytes.Buffer
+
+		// Copy all data written out to a buffer. When we close the ptty, we can
+		// no longer read from the ptty.Output(), but we can read what was
+		// written to the buffer.
+		dataRead, doneReading := context.WithTimeout(context.Background(), time.Second*2)
+		go func() {
+			// This will throw an error sometimes. The underlying ptty
+			// has its own cleanup routines in t.Cleanup. Instead of
+			// trying to control the close perfectly, just let the ptty
+			// double close. This error isn't important, we just
+			// want to know the ptty is done sending output.
+			_, _ = io.Copy(&buf, ptty.Output())
+			doneReading()
+		}()
+
+		doneChan := make(chan string)
+		go func() {
+			resp, err := newPrompt(ptty, cliui.PromptOptions{
+				Text:      "ShouldNotSeeThis",
+				IsConfirm: true,
+			}, func(cmd *cobra.Command) {
+				cliui.AllowSkipPrompt(cmd)
+				cmd.SetArgs([]string{"-y"})
+			})
+			require.NoError(t, err)
+			doneChan <- resp
+		}()
+
+		require.Equal(t, "yes", <-doneChan)
+		// Close the reader to end the io.Copy
+		require.NoError(t, ptty.Close(), "close eof reader")
+		// Wait for the IO copy to finish
+		<-dataRead.Done()
+		// Timeout error means the output was hanging
+		require.ErrorIs(t, dataRead.Err(), context.Canceled, "should be canceled")
+		require.Len(t, buf.Bytes(), 0, "expect no output")
+	})
 	t.Run("JSON", func(t *testing.T) {
 		t.Parallel()
 		ptty := ptytest.New(t)
@@ -57,7 +100,7 @@ func TestPrompt(t *testing.T) {
 		go func() {
 			resp, err := newPrompt(ptty, cliui.PromptOptions{
 				Text: "Example",
-			})
+			}, nil)
 			require.NoError(t, err)
 			doneChan <- resp
 		}()
@@ -73,7 +116,7 @@ func TestPrompt(t *testing.T) {
 		go func() {
 			resp, err := newPrompt(ptty, cliui.PromptOptions{
 				Text: "Example",
-			})
+			}, nil)
 			require.NoError(t, err)
 			doneChan <- resp
 		}()
@@ -89,7 +132,7 @@ func TestPrompt(t *testing.T) {
 		go func() {
 			resp, err := newPrompt(ptty, cliui.PromptOptions{
 				Text: "Example",
-			})
+			}, nil)
 			require.NoError(t, err)
 			doneChan <- resp
 		}()
@@ -101,7 +144,7 @@ func TestPrompt(t *testing.T) {
 	})
 }
 
-func newPrompt(ptty *ptytest.PTY, opts cliui.PromptOptions) (string, error) {
+func newPrompt(ptty *ptytest.PTY, opts cliui.PromptOptions, cmdOpt func(cmd *cobra.Command)) (string, error) {
 	value := ""
 	cmd := &cobra.Command{
 		RunE: func(cmd *cobra.Command, args []string) error {
@@ -110,7 +153,12 @@ func newPrompt(ptty *ptytest.PTY, opts cliui.PromptOptions) (string, error) {
 			return err
 		},
 	}
-	cmd.SetOutput(ptty.Output())
+	// Optionally modify the cmd
+	if cmdOpt != nil {
+		cmdOpt(cmd)
+	}
+	cmd.SetOut(ptty.Output())
+	cmd.SetErr(ptty.Output())
 	cmd.SetIn(ptty.Input())
 	return value, cmd.ExecuteContext(context.Background())
 }
diff --git a/cli/create.go b/cli/create.go
index 4f09f71bc7eb3..1f762a55cca45 100644
--- a/cli/create.go
+++ b/cli/create.go
@@ -204,6 +204,7 @@ func create() *cobra.Command {
 		},
 	}
 
+	cliui.AllowSkipPrompt(cmd)
 	cliflag.StringVarP(cmd.Flags(), &templateName, "template", "t", "CODER_TEMPLATE_NAME", "", "Specify a template name.")
 	cliflag.StringVarP(cmd.Flags(), &parameterFile, "parameter-file", "", "CODER_PARAMETER_FILE", "", "Specify a file path with parameter values.")
 	return cmd
diff --git a/cli/create_test.go b/cli/create_test.go
index 955a001fa1245..3e29e3bdabad7 100644
--- a/cli/create_test.go
+++ b/cli/create_test.go
@@ -1,9 +1,11 @@
 package cli_test
 
 import (
+	"context"
 	"fmt"
 	"os"
 	"testing"
+	"time"
 
 	"github.com/stretchr/testify/require"
 
@@ -46,34 +48,24 @@ func TestCreate(t *testing.T) {
 		<-doneChan
 	})
 
-	t.Run("CreateFromList", func(t *testing.T) {
+	t.Run("CreateFromListWithSkip", func(t *testing.T) {
 		t.Parallel()
 		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
 		user := coderdtest.CreateFirstUser(t, client)
 		version := coderdtest.CreateTemplateVersion(t, client, user.OrganizationID, nil)
 		coderdtest.AwaitTemplateVersionJob(t, client, version.ID)
 		_ = coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID)
-		cmd, root := clitest.New(t, "create", "my-workspace")
+		cmd, root := clitest.New(t, "create", "my-workspace", "-y")
 		clitest.SetupConfig(t, client, root)
-		doneChan := make(chan struct{})
-		pty := ptytest.New(t)
-		cmd.SetIn(pty.Input())
-		cmd.SetOut(pty.Output())
+		cmdCtx, done := context.WithTimeout(context.Background(), time.Second*3)
 		go func() {
-			defer close(doneChan)
-			err := cmd.Execute()
+			defer done()
+			err := cmd.ExecuteContext(cmdCtx)
 			require.NoError(t, err)
 		}()
-		matches := []string{
-			"Confirm create", "yes",
-		}
-		for i := 0; i < len(matches); i += 2 {
-			match := matches[i]
-			value := matches[i+1]
-			pty.ExpectMatch(match)
-			pty.WriteLine(value)
-		}
-		<-doneChan
+		// No pty interaction needed since we use the -y skip prompt flag
+		<-cmdCtx.Done()
+		require.ErrorIs(t, cmdCtx.Err(), context.Canceled)
 	})
 
 	t.Run("FromNothing", func(t *testing.T) {
diff --git a/cli/delete.go b/cli/delete.go
index 8d1de59c2e653..42be08965fed4 100644
--- a/cli/delete.go
+++ b/cli/delete.go
@@ -11,13 +11,21 @@ import (
 
 // nolint
 func delete() *cobra.Command {
-	return &cobra.Command{
+	cmd := &cobra.Command{
 		Annotations: workspaceCommand,
 		Use:         "delete <workspace>",
 		Short:       "Delete a workspace",
 		Aliases:     []string{"rm"},
 		Args:        cobra.ExactArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
+			_, err := cliui.Prompt(cmd, cliui.PromptOptions{
+				Text:      "Confirm delete workspace?",
+				IsConfirm: true,
+			})
+			if err != nil {
+				return err
+			}
+
 			client, err := createClient(cmd)
 			if err != nil {
 				return err
@@ -40,4 +48,6 @@ func delete() *cobra.Command {
 			return cliui.WorkspaceBuild(cmd.Context(), cmd.OutOrStdout(), client, build.ID, before)
 		},
 	}
+	cliui.AllowSkipPrompt(cmd)
+	return cmd
 }
diff --git a/cli/delete_test.go b/cli/delete_test.go
index f9e1102a0eb39..e7af61b40cd82 100644
--- a/cli/delete_test.go
+++ b/cli/delete_test.go
@@ -20,7 +20,7 @@ func TestDelete(t *testing.T) {
 		template := coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID)
 		workspace := coderdtest.CreateWorkspace(t, client, user.OrganizationID, template.ID)
 		coderdtest.AwaitWorkspaceBuildJob(t, client, workspace.LatestBuild.ID)
-		cmd, root := clitest.New(t, "delete", workspace.Name)
+		cmd, root := clitest.New(t, "delete", workspace.Name, "-y")
 		clitest.SetupConfig(t, client, root)
 		doneChan := make(chan struct{})
 		pty := ptytest.New(t)
diff --git a/cli/start.go b/cli/start.go
index 1c562ddd9d093..7e35b22aa915a 100644
--- a/cli/start.go
+++ b/cli/start.go
@@ -10,12 +10,20 @@ import (
 )
 
 func start() *cobra.Command {
-	return &cobra.Command{
+	cmd := &cobra.Command{
 		Annotations: workspaceCommand,
 		Use:         "start <workspace>",
 		Short:       "Build a workspace with the start state",
 		Args:        cobra.ExactArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
+			_, err := cliui.Prompt(cmd, cliui.PromptOptions{
+				Text:      "Confirm start workspace?",
+				IsConfirm: true,
+			})
+			if err != nil {
+				return err
+			}
+
 			client, err := createClient(cmd)
 			if err != nil {
 				return err
@@ -38,4 +46,6 @@ func start() *cobra.Command {
 			return cliui.WorkspaceBuild(cmd.Context(), cmd.OutOrStdout(), client, build.ID, before)
 		},
 	}
+	cliui.AllowSkipPrompt(cmd)
+	return cmd
 }
diff --git a/cli/stop.go b/cli/stop.go
index af1f44da58af0..f2455458bd1f7 100644
--- a/cli/stop.go
+++ b/cli/stop.go
@@ -10,12 +10,20 @@ import (
 )
 
 func stop() *cobra.Command {
-	return &cobra.Command{
+	cmd := &cobra.Command{
 		Annotations: workspaceCommand,
 		Use:         "stop <workspace>",
 		Short:       "Build a workspace with the stop state",
 		Args:        cobra.ExactArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
+			_, err := cliui.Prompt(cmd, cliui.PromptOptions{
+				Text:      "Confirm stop workspace?",
+				IsConfirm: true,
+			})
+			if err != nil {
+				return err
+			}
+
 			client, err := createClient(cmd)
 			if err != nil {
 				return err
@@ -38,4 +46,6 @@ func stop() *cobra.Command {
 			return cliui.WorkspaceBuild(cmd.Context(), cmd.OutOrStdout(), client, build.ID, before)
 		},
 	}
+	cliui.AllowSkipPrompt(cmd)
+	return cmd
 }
diff --git a/cli/templatecreate.go b/cli/templatecreate.go
index 6c98afd66cfc8..06205aa008eb2 100644
--- a/cli/templatecreate.go
+++ b/cli/templatecreate.go
@@ -21,7 +21,6 @@ import (
 
 func templateCreate() *cobra.Command {
 	var (
-		yes           bool
 		directory     string
 		provisioner   string
 		parameterFile string
@@ -85,14 +84,12 @@ func templateCreate() *cobra.Command {
 				return err
 			}
 
-			if !yes {
-				_, err = cliui.Prompt(cmd, cliui.PromptOptions{
-					Text:      "Confirm create?",
-					IsConfirm: true,
-				})
-				if err != nil {
-					return err
-				}
+			_, err = cliui.Prompt(cmd, cliui.PromptOptions{
+				Text:      "Confirm create?",
+				IsConfirm: true,
+			})
+			if err != nil {
+				return err
 			}
 
 			_, err = client.CreateTemplate(cmd.Context(), organization.ID, codersdk.CreateTemplateRequest{
@@ -123,7 +120,7 @@ func templateCreate() *cobra.Command {
 	if err != nil {
 		panic(err)
 	}
-	cmd.Flags().BoolVarP(&yes, "yes", "y", false, "Bypass prompts")
+	cliui.AllowSkipPrompt(cmd)
 	return cmd
 }
 
diff --git a/cli/templateupdate.go b/cli/templateupdate.go
index 70c2611cea687..32902aab3b518 100644
--- a/cli/templateupdate.go
+++ b/cli/templateupdate.go
@@ -108,6 +108,7 @@ func templateUpdate() *cobra.Command {
 	currentDirectory, _ := os.Getwd()
 	cmd.Flags().StringVarP(&directory, "directory", "d", currentDirectory, "Specify the directory to create from")
 	cmd.Flags().StringVarP(&provisioner, "test.provisioner", "", "terraform", "Customize the provisioner backend")
+	cliui.AllowSkipPrompt(cmd)
 	// This is for testing!
 	err := cmd.Flags().MarkHidden("test.provisioner")
 	if err != nil {