diff --git a/pkg/cmd/auth/shared/login_flow.go b/pkg/cmd/auth/shared/login_flow.go
index 5888995cb..48b0c773c 100644
--- a/pkg/cmd/auth/shared/login_flow.go
+++ b/pkg/cmd/auth/shared/login_flow.go
@@ -106,7 +106,7 @@ func Login(opts *LoginOptions) error {
 			if sshChoice {
 				passphrase, err := promptForSshKeyPassphrase()
 				if err != nil {
-					return err
+					return fmt.Errorf("could not prompt for key passphrase: %w", err)
 				}
 
 				keyPair, err := opts.sshContext.GenerateSSHKey("id_ed25519", passphrase)
@@ -235,8 +235,9 @@ func promptForSshKeyPassphrase() (string, error) {
 	err := prompt.SurveyAskOne(&survey.Password{
 		Message: "Enter a passphrase for your new SSH key (Optional)",
 	}, &sshPassphrase)
+
 	if err != nil {
-		return "", fmt.Errorf("could not prompt: %w", err)
+		return "", err
 	}
 
 	return sshPassphrase, nil
diff --git a/pkg/cmd/codespace/ssh.go b/pkg/cmd/codespace/ssh.go
index e8b5d039c..2c3f1c93f 100644
--- a/pkg/cmd/codespace/ssh.go
+++ b/pkg/cmd/codespace/ssh.go
@@ -126,10 +126,8 @@ func (a *App) SSH(ctx context.Context, sshArgs []string, opts sshOptions) (err e
 
 	if shouldGenerateSSHKeys(args, opts) && sshContext.HasKeygen() {
 		keyPair, err := sshContext.GenerateSSHKey("codespaces", "")
-		if err != nil {
-			if _, ok := err.(*ssh.KeyAlreadyExistsError); !ok {
-				return fmt.Errorf("failed to generate ssh keys: %s", err)
-			}
+		if err != nil && !errors.Is(err, ssh.ErrKeyAlreadyExists) {
+			return fmt.Errorf("failed to generate ssh keys: %w", err)
 		}
 
 		startSSHOptions.UserPublicKeyFile = keyPair.PublicKeyPath
diff --git a/pkg/liveshare/session.go b/pkg/liveshare/session.go
index cd6c2e078..f912fa5ea 100644
--- a/pkg/liveshare/session.go
+++ b/pkg/liveshare/session.go
@@ -75,7 +75,7 @@ func (s *Session) StartSSHServerWithOptions(ctx context.Context, options StartSS
 	if options.UserPublicKeyFile != "" {
 		publicKeyBytes, err := os.ReadFile(options.UserPublicKeyFile)
 		if err != nil {
-			return 0, "", fmt.Errorf("failed to read public key file: %s", err)
+			return 0, "", fmt.Errorf("failed to read public key file: %w", err)
 		}
 
 		params.UserPublicKey = strings.TrimSpace(string(publicKeyBytes))
diff --git a/pkg/ssh/ssh_keys.go b/pkg/ssh/ssh_keys.go
index 7f4a1e9d9..4f7b4ef1d 100644
--- a/pkg/ssh/ssh_keys.go
+++ b/pkg/ssh/ssh_keys.go
@@ -1,7 +1,7 @@
 package ssh
 
 import (
-	"fmt"
+	"errors"
 	"os"
 	"os/exec"
 	"path/filepath"
@@ -22,11 +22,7 @@ type KeyPair struct {
 	PrivateKeyPath string
 }
 
-type KeyAlreadyExistsError struct {
-	keyPath string
-}
-
-func (err *KeyAlreadyExistsError) Error() string { return "SSH key already exists: " + err.keyPath }
+var ErrKeyAlreadyExists = errors.New("SSH key already exists")
 
 func (c *Context) LocalPublicKeys() ([]string, error) {
 	sshDir, err := c.sshDir()
@@ -45,7 +41,7 @@ func (c *Context) HasKeygen() bool {
 func (c *Context) GenerateSSHKey(keyName string, passphrase string) (*KeyPair, error) {
 	keygenExe, err := c.findKeygen()
 	if err != nil {
-		return nil, fmt.Errorf("could not find keygen executable")
+		return nil, err
 	}
 
 	sshDir, err := c.sshDir()
@@ -59,8 +55,8 @@ func (c *Context) GenerateSSHKey(keyName string, passphrase string) (*KeyPair, e
 	}
 
 	if _, err := os.Stat(keyFile); err == nil {
-		// Still return keyPair because the caller might be OK with they - they can check the error with
-		return &keyPair, &KeyAlreadyExistsError{keyFile}
+		// Still return keyPair because the caller might be OK with this - they can check the error with errors.Is(err, ErrKeyAlreadyExists)
+		return &keyPair, ErrKeyAlreadyExists
 	}
 
 	if err := os.MkdirAll(filepath.Dir(keyFile), 0711); err != nil {