diff --git a/cmd/setup.go b/cmd/setup.go
index 73bedab..3a62664 100644
--- a/cmd/setup.go
+++ b/cmd/setup.go
@@ -5,6 +5,7 @@ import (
 
 	"github.com/dpastoor/wbi/internal/authentication"
 	"github.com/dpastoor/wbi/internal/config"
+	"github.com/dpastoor/wbi/internal/connect"
 	"github.com/dpastoor/wbi/internal/jupyter"
 	"github.com/dpastoor/wbi/internal/languages"
 	"github.com/dpastoor/wbi/internal/license"
@@ -149,6 +150,22 @@ func newSetup(setupOpts setupOpts) error {
 		return fmt.Errorf("issue handling authentication: %w", AuthErr)
 	}
 
+	// Connect URL
+	connectChoice, err := connect.PromptConnectChoice()
+	if err != nil {
+		return fmt.Errorf("issue in prompt for Connect URL choice: %w", err)
+	}
+	if connectChoice {
+		rawConnectURL, err := connect.PromptConnectURL()
+		if err != nil {
+			return fmt.Errorf("issue entering Connect URL: %w", err)
+		}
+		WBConfig.ConnectURL, err = connect.VerifyConnectURL(rawConnectURL)
+		if err != nil {
+			return fmt.Errorf("issue with checking the Connect URL: %w", err)
+		}
+	}
+
 	// Write config to console
 	WBConfig.ConfigStructToText()
 
diff --git a/internal/config/config.go b/internal/config/config.go
index 69e3a09..92f5edd 100644
--- a/internal/config/config.go
+++ b/internal/config/config.go
@@ -31,6 +31,7 @@ type WBConfig struct {
 	RConfig      RConfig
 	PythonConfig PythonConfig
 	AuthConfig   AuthConfig
+	ConnectURL   string
 }
 
 type AuthConfig struct {
diff --git a/internal/config/print.go b/internal/config/print.go
index 8d9b26d..ffea16e 100644
--- a/internal/config/print.go
+++ b/internal/config/print.go
@@ -7,6 +7,7 @@ func (WBConfig *WBConfig) ConfigStructToText() {
 	WBConfig.PythonConfig.PythonStructToText()
 	WBConfig.SSLConfig.SSLStructToText()
 	WBConfig.AuthConfig.AuthStructToText()
+	WBConfig.ConnectStringToText()
 	fmt.Println("\n=== Please restart Workbench after making these changes")
 }
 
@@ -55,3 +56,9 @@ func (OIDCConfig *OIDCConfig) AuthOIDCStructToText() {
 	fmt.Println("client-id=" + OIDCConfig.ClientID)
 	fmt.Println("client-secret=" + OIDCConfig.ClientSecret)
 }
+
+// Prints the ConnectURL configuration string information to the console
+func (WBConfig *WBConfig) ConnectStringToText() {
+	fmt.Println("\n=== Add to config file: /etc/rstudio/rsession.conf:")
+	fmt.Println("default-rsconnect-server=" + WBConfig.ConnectURL)
+}
diff --git a/internal/connect/prompt.go b/internal/connect/prompt.go
new file mode 100644
index 0000000..315de81
--- /dev/null
+++ b/internal/connect/prompt.go
@@ -0,0 +1,34 @@
+package connect
+
+import (
+	"errors"
+	"fmt"
+
+	"github.com/AlecAivazis/survey/v2"
+)
+
+// Prompt users if they wish to add a default Connect URL to Workbench
+func PromptConnectChoice() (bool, error) {
+	name := true
+	prompt := &survey.Confirm{
+		Message: "Would you like to provide a default Connect URL for Workbench?",
+	}
+	err := survey.AskOne(prompt, &name)
+	if err != nil {
+		return false, errors.New("there was an issue with the Connect URL prompt")
+	}
+	return name, nil
+}
+
+// Prompt users for a default Connect URL
+func PromptConnectURL() (string, error) {
+	target := ""
+	prompt := &survey.Input{
+		Message: "Connect URL:",
+	}
+	err := survey.AskOne(prompt, &target)
+	if err != nil {
+		return "", fmt.Errorf("issue prompting for a Connect URL: %w", err)
+	}
+	return target, nil
+}
diff --git a/internal/connect/verify.go b/internal/connect/verify.go
new file mode 100644
index 0000000..322d588
--- /dev/null
+++ b/internal/connect/verify.go
@@ -0,0 +1,44 @@
+package connect
+
+import (
+	"context"
+	"errors"
+	"fmt"
+	"net/http"
+	"time"
+)
+
+func cleanConnectURL(connectURL string) string {
+	// remove trailing slash if present
+	if connectURL[len(connectURL)-1] == '/' {
+		connectURL = connectURL[:len(connectURL)-1]
+	}
+	return connectURL
+}
+
+// VerifyConnectURL checks if the Connect URL is valid
+func VerifyConnectURL(connectURL string) (string, error) {
+
+	cleanConnectURL := cleanConnectURL(connectURL)
+	fullTestURL := cleanConnectURL + "/__ping__"
+
+	client := &http.Client{
+		Timeout: 30 * time.Second,
+	}
+	req, err := http.NewRequestWithContext(context.Background(),
+		http.MethodGet, fullTestURL, nil)
+	if err != nil {
+		return "", errors.New("error creating request")
+	}
+	res, err := client.Do(req)
+	if err != nil {
+		return "", errors.New("error retrieving JSON data")
+	}
+	defer res.Body.Close()
+	if res.StatusCode != http.StatusOK {
+		return "", errors.New("error in HTTP status code")
+	}
+
+	fmt.Println("\nConnect URL has been successfull validated.\n")
+	return cleanConnectURL, nil
+}