diff --git a/go.mod b/go.mod
index 2ea4e64f..47a2ce24 100644
--- a/go.mod
+++ b/go.mod
@@ -11,6 +11,7 @@ require (
 	github.com/creack/pty v1.1.18
 	github.com/cyberark/conjur-api-go v0.10.3-0.20230217154521-e01f713716d2 // Run "go get github.com/cyberark/conjur-api-go@main" to update
 	github.com/hinshun/vt10x v0.0.0-20220301184237-5011da428d02
+	github.com/mattn/go-isatty v0.0.8
 	github.com/pkg/browser v0.0.0-20210911075715-681adbf594b8
 	github.com/spf13/cobra v1.5.0
 	github.com/stretchr/testify v1.8.1
@@ -27,7 +28,6 @@ require (
 	github.com/kballard/go-shellquote v0.0.0-20180428030007-95032a82bc51 // indirect
 	github.com/kr/text v0.2.0 // indirect
 	github.com/mattn/go-colorable v0.1.2 // indirect
-	github.com/mattn/go-isatty v0.0.8 // indirect
 	github.com/mgutz/ansi v0.0.0-20170206155736-9520e82c474b // indirect
 	github.com/pmezard/go-difflib v1.0.0 // indirect
 	github.com/sirupsen/logrus v1.8.1 // indirect
diff --git a/pkg/cmd/init_test.go b/pkg/cmd/init_test.go
index dd9e001a..134f291d 100644
--- a/pkg/cmd/init_test.go
+++ b/pkg/cmd/init_test.go
@@ -16,8 +16,12 @@ var initCmdTestCases = []struct {
 	args            []string
 	out             string
 	promptResponses []promptResponse
-	beforeTest      func(t *testing.T, conjurrcInTmpDir string)
-	assert          func(t *testing.T, conjurrcInTmpDir string, stdout string)
+	// Being unable to pipe responses to prompts is a known shortcoming of Survey.
+	// https://github.com/go-survey/survey/issues/394
+	// This flag is used to enable Pipe-based, and not PTY-based, tests.
+	pipe       bool
+	beforeTest func(t *testing.T, conjurrcInTmpDir string)
+	assert     func(t *testing.T, conjurrcInTmpDir string, stdout string)
 }{
 	{
 		name: "help",
@@ -89,6 +93,7 @@ appliance_url: http://conjur
 				response: "N",
 			},
 		},
+		pipe: true,
 		beforeTest: func(t *testing.T, conjurrcInTmpDir string) {
 			os.WriteFile(conjurrcInTmpDir, []byte("something"), 0644)
 		},
@@ -107,6 +112,7 @@ appliance_url: http://conjur
 				response: "y",
 			},
 		},
+		pipe: true,
 		beforeTest: func(t *testing.T, conjurrcInTmpDir string) {
 			os.WriteFile(conjurrcInTmpDir, []byte("something"), 0644)
 		},
@@ -168,6 +174,7 @@ appliance_url: http://host
 				response: "y",
 			},
 		},
+		pipe: true,
 		assert: func(t *testing.T, conjurrcInTmpDir string, stdout string) {
 			assertCertWritten(t, conjurrcInTmpDir, stdout)
 		},
@@ -181,6 +188,7 @@ appliance_url: http://host
 				response: "N",
 			},
 		},
+		pipe: true,
 		assert: func(t *testing.T, conjurrcInTmpDir string, stdout string) {
 			fmt.Println(stdout)
 			assert.Contains(t, stdout, "You decided not to trust the certificate")
@@ -205,6 +213,7 @@ appliance_url: http://host
 		},
 	},
 	{
+		name: "succeeds for self-signed certificate with --self-signed flag",
 		args: []string{"init", "-u=https://self-signed.badssl.com", "-a=test-account", "--self-signed"},
 		promptResponses: []promptResponse{
 			{
@@ -212,6 +221,7 @@ appliance_url: http://host
 				response: "y",
 			},
 		},
+		pipe: true,
 		assert: func(t *testing.T, conjurrcInTmpDir string, stdout string) {
 			assert.Contains(t, stdout, "Warning: Using self-signed certificates is not recommended and could lead to exposure of sensitive data")
 			assertCertWritten(t, conjurrcInTmpDir, stdout)
@@ -313,7 +323,17 @@ func TestInitCmd(t *testing.T) {
 			rootCmd.AddCommand(cmd)
 			rootCmd.SetArgs(args)
 
-			out, _ := executeCommandForTestWithPromptResponses(t, rootCmd, tc.promptResponses)
+			var content string
+			for _, pr := range tc.promptResponses {
+				content = fmt.Sprintf("%s%s\n", content, pr.response)
+			}
+
+			var out string
+			if tc.pipe {
+				out, _ = executeCommandForTestWithPipeResponses(t, rootCmd, content)
+			} else {
+				out, _ = executeCommandForTestWithPromptResponses(t, rootCmd, tc.promptResponses)
+			}
 
 			if tc.assert != nil {
 				tc.assert(t, conjurrcInTmpDir, out)
diff --git a/pkg/cmd/utils_test.go b/pkg/cmd/utils_test.go
index 7a06e52f..63416f26 100644
--- a/pkg/cmd/utils_test.go
+++ b/pkg/cmd/utils_test.go
@@ -3,6 +3,7 @@ package cmd
 import (
 	"bytes"
 	"io"
+	"io/ioutil"
 	"os"
 	"regexp"
 	"testing"
@@ -49,6 +50,49 @@ func executeCommandForTest(t *testing.T, c *cobra.Command, args ...string) (stri
 	return stripAnsi(stdoutBuf.String()), stripAnsi(stderrBuf.String()), err
 }
 
+func executeCommandForTestWithPipeResponses(
+	t *testing.T, cmd *cobra.Command, content string,
+) (stdOut string, cmdErr error) {
+	t.Helper()
+
+	mockHelpText(cmd)
+
+	// Send CLI stdOut and stdErr to Pipes and consolidate
+	outR, outW, _ := os.Pipe()
+	errR, errW, _ := os.Pipe()
+	combinedOutReader := io.MultiReader(outR, errR)
+
+	defer func(origOut *os.File) { os.Stdout = origOut }(os.Stdout)
+	defer func(origErr *os.File) { os.Stderr = origErr }(os.Stderr)
+	os.Stdout = outW
+	os.Stderr = errW
+
+	// Receive CLI stdIn from Pipe
+	inR, inW, _ := os.Pipe()
+	_, err := inW.Write([]byte(content))
+	if err != nil {
+		t.Fatal(err)
+	}
+	inW.Close()
+
+	defer func(origIn *os.File) { os.Stdin = origIn }(os.Stdin)
+	os.Stdin = inR
+
+	// Run CLI cmd
+	err = cmd.Execute()
+
+	// Collect stdOut
+	outW.Close()
+	errW.Close()
+	out, outErr := ioutil.ReadAll(combinedOutReader)
+	if outErr != nil {
+		t.Fatal(outErr)
+	}
+
+	// strip ansi from stdout and stderr because we're using promptui
+	return stripAnsi(string(out)), err
+}
+
 func executeCommandForTestWithPromptResponses(
 	t *testing.T, cmd *cobra.Command, promptResponses []promptResponse,
 ) (stdOut string, cmdErr error) {
diff --git a/pkg/prompts/prompt.go b/pkg/prompts/prompt.go
index 264cabeb..055cf199 100644
--- a/pkg/prompts/prompt.go
+++ b/pkg/prompts/prompt.go
@@ -5,8 +5,10 @@ import (
 	"fmt"
 	"net/url"
 	"os"
+	"strings"
 
 	"github.com/AlecAivazis/survey/v2"
+	"github.com/mattn/go-isatty"
 	"github.com/spf13/cobra"
 )
 
@@ -32,46 +34,65 @@ func newAccountPrompt() *survey.Question {
 	}
 }
 
-func newFileExistsPrompt(filePath string) *survey.Question {
-	return &survey.Question{
-		Prompt:   &survey.Confirm{Message: fmt.Sprintf("File %s exists. Overwrite?", filePath)},
-		Validate: survey.Required,
+func stringToBool(s string) bool {
+	switch strings.ToLower(strings.TrimSpace(s)) {
+	case "y":
+		return true
+	case "yes":
+		return true
+	default:
+		return false
 	}
 }
 
-// AskToOverwriteFile presents a prompt to get confirmation from a user to overwrite a file
-func AskToOverwriteFile(filePath string) error {
-	var userInput bool
+func basicConfirm(message string) bool {
+	fmt.Fprintf(os.Stdout, "%s ", message)
+	var answer string
+	fmt.Scanln(&answer)
+	fmt.Fprintln(os.Stdout, "")
+	return stringToBool(answer)
+}
 
-	q := newFileExistsPrompt(filePath)
-	err := survey.AskOne(q.Prompt, &userInput, survey.WithValidator(q.Validate), survey.WithShowCursor(true))
+func confirm(message string) (bool, error) {
+	var err error
+	var userInput bool
 
-	if userInput == false {
-		return fmt.Errorf("Not overwriting %s", filePath)
+	// When handling Pipe-based Stdin, we can't use Survey to gather responses.
+	// https://github.com/go-survey/survey/issues/394
+	// Instead, use standard fmt funcs to prompt to Stdout and gather from Stdin.
+	if isatty.IsTerminal(os.Stdin.Fd()) {
+		q := &survey.Question{
+			Prompt:   &survey.Confirm{Message: message},
+			Validate: survey.Required,
+		}
+		err = survey.AskOne(q.Prompt, &userInput, survey.WithValidator(q.Validate), survey.WithShowCursor(true))
+	} else {
+		userInput = basicConfirm(message)
 	}
-	return err
+
+	return userInput, err
 }
 
-func newTrustCertPrompt() *survey.Question {
-	return &survey.Question{
-		Prompt:   &survey.Confirm{Message: "Trust this certificate?"},
-		Validate: survey.Required,
+// AskToOverwriteFile presents a prompt to get confirmation from a user to overwrite a file
+func AskToOverwriteFile(filePath string) error {
+	userInput, err := confirm(fmt.Sprintf("File %s exists. Overwrite?", filePath))
+
+	if !userInput {
+		return fmt.Errorf("Not overwriting %s", filePath)
 	}
+	return err
 }
 
 // AskToTrustCert presents a prompt to get confirmation from a user to trust a certificate
 func AskToTrustCert(fingerprint string) error {
-	var userInput bool
-
 	warning := fmt.Sprintf("\nThe server's certificate fingerprint is %s.\n", fingerprint) +
 		"Please verify this certificate on the appliance using command:\n" +
 		"openssl x509 -fingerprint -noout -in ~conjur/etc/ssl/conjur.pem\n\n"
 	os.Stdout.Write([]byte(warning))
 
-	q := newTrustCertPrompt()
-	err := survey.AskOne(q.Prompt, &userInput, survey.WithValidator(q.Validate), survey.WithShowCursor(true))
+	userInput, err := confirm("Trust this certificate?")
 
-	if userInput == false {
+	if !userInput {
 		return errors.New("You decided not to trust the certificate.")
 	}
 	return err