diff --git a/examples/src/cli.rs b/examples/src/cli.rs
index 90af3497..5dc7018f 100644
--- a/examples/src/cli.rs
+++ b/examples/src/cli.rs
@@ -165,6 +165,11 @@ enum Commands {
             help = "parent VID of the sender, used to listen for a response"
         )]
         parent_vid: Option<String>,
+        #[arg(
+            long,
+            help = "Ask for confirmation before interacting with unknown end-points"
+        )]
+        ask: bool,
         #[arg(long, help = "wait for a response")]
         wait: bool,
     },
@@ -253,6 +258,31 @@ async fn read_wallet(
     }
 }
 
+async fn ensure_vid_verified(
+    vid_wallet: &mut AsyncSecureStore,
+    receiver_vid: &str,
+    wallet_name: &str,
+    ask: bool,
+) -> Result<(), Error> {
+    if !vid_wallet.has_verified_vid(receiver_vid)? {
+        if !ask
+            || prompt(format!(
+                "Do you want to verify receiver DID {}",
+                receiver_vid
+            ))
+        {
+            vid_wallet.verify_vid(receiver_vid, None).await?;
+            info!("{receiver_vid} is verified and added to the wallet {wallet_name}");
+        } else {
+            tracing::error!("Message cannot be sent without verifying the receiver's DID.");
+            return Err(Error::UnverifiedVid(
+                "Message cannot be sent without verifying the receiver's DID.".to_string(),
+            ));
+        }
+    }
+    Ok(())
+}
+
 fn prompt(message: String) -> bool {
     use std::io::{self, BufRead, Write};
     print!("{message}? [y/n]");
@@ -568,18 +598,8 @@ async fn run() -> Result<(), Error> {
         } => {
             let non_confidential_data = non_confidential_data.as_deref().map(|s| s.as_bytes());
 
-            if !vid_wallet.has_verified_vid(&receiver_vid)? {
-                if !ask || prompt(format!("Do you want to verify receiver DID {receiver_vid}")) {
-                    vid_wallet.verify_vid(&receiver_vid, None).await?;
-                    info!(
-                        "{receiver_vid} is verified and added to the wallet {}",
-                        &args.wallet
-                    );
-                } else {
-                    tracing::error!("Message cannot be sent without verifying the receiver's DID.");
-                    return Ok(());
-                }
-            }
+            dbg!(ask);
+            ensure_vid_verified(&mut vid_wallet, &receiver_vid, &args.wallet, ask).await?;
 
             let mut message = Vec::new();
             tokio::io::stdin()
@@ -823,8 +843,11 @@ async fn run() -> Result<(), Error> {
             receiver_vid,
             nested,
             parent_vid,
+            ask,
             wait,
         } => {
+            ensure_vid_verified(&mut vid_wallet, &receiver_vid, &args.wallet, ask).await?;
+
             // Setup receive stream before sending the request
             let listener_vid = parent_vid.unwrap_or(sender_vid.clone());
             let mut messages = vid_wallet.receive(&listener_vid).await?;
diff --git a/examples/tests/cli_tests.rs b/examples/tests/cli_tests.rs
index d67837e7..b3e13e0d 100644
--- a/examples/tests/cli_tests.rs
+++ b/examples/tests/cli_tests.rs
@@ -5,6 +5,7 @@ use rand::{Rng, thread_rng};
 use std::process::Command as StdCommand;
 use std::thread;
 use std::time::Duration;
+
 fn random_string(n: usize) -> String {
     thread_rng()
         .sample_iter(&Alphanumeric)
@@ -163,7 +164,7 @@ fn test_send_command_unverified_receiver_ask_flag() {
     .stderr(predicate::str::contains(
         "Message cannot be sent without verifying the receiver's DID",
     ))
-    .success();
+    .failure();
 
     // Send a message from Marlon to Marc with --ask flag, answer yes
     thread::scope(|s| {
@@ -207,6 +208,60 @@ fn test_send_command_unverified_receiver_ask_flag() {
     clean_wallet();
 }
 
+#[test]
+#[serial_test::serial(clean_wallet)]
+fn test_request_command_unverified_receiver_default() {
+    clean_wallet();
+
+    // create a new sender identity to send the request
+    let random_sender_name = create_wallet("alice", "web");
+
+    // create a new receiver identity
+    let random_receiver_name = create_wallet("bob", "web");
+
+    // print the sender's DID
+    let alice_did = print_did(&random_sender_name, "alice");
+
+    // print the receiver's DID
+    let bob_did = print_did(&random_receiver_name, "bob");
+
+    thread::scope(|s| {
+        s.spawn(|| {
+            // send a relationship request from alice to bob
+            let mut cmd: Command = Command::new(cargo_bin!("tsp"));
+            cmd.args([
+                "--wallet",
+                random_sender_name.as_str(),
+                "request",
+                "-s",
+                "alice",
+                "-r",
+                &bob_did,
+            ])
+            .assert()
+            .stderr(predicate::str::contains("sent relationship request"))
+            .success();
+        });
+        // s.spawn(|| {
+        //     // receive the relationship request
+        //     let mut cmd: Command = Command::new(cargo_bin!("tsp"));
+        //     cmd.args([
+        //         "--wallet",
+        //         random_receiver_name.as_str(),
+        //         "receive",
+        //         "--one",
+        //         &bob_did,
+        //     ])
+        //     .assert()
+        //     .stderr(predicate::str::contains("received relationship request"))
+        //     .stdout(predicate::str::contains(&alice_did))
+        //     .success();
+        // });
+    });
+
+    clean_wallet();
+}
+
 #[test]
 #[cfg(feature = "create-webvh")]
 #[serial_test::serial(clean_wallet)]