diff --git a/client/src/main.rs b/client/src/main.rs
index 6488e82..2af9493 100644
--- a/client/src/main.rs
+++ b/client/src/main.rs
@@ -839,10 +839,11 @@ fn set_listen_port(
     interface: &InterfaceName,
     unset: bool,
     network: NetworkOpt,
-) -> Result<(), Error> {
+) -> Result<Option<u16>, Error> {
     let mut config = InterfaceConfig::from_interface(interface)?;
 
-    if let Some(listen_port) = prompts::set_listen_port(&config.interface, unset)? {
+    let listen_port = prompts::set_listen_port(&config.interface, unset)?;
+    if let Some(listen_port) = listen_port {
         wg::set_listen_port(interface, listen_port, network.backend)?;
         log::info!("the interface is updated");
 
@@ -853,7 +854,7 @@ fn set_listen_port(
         log::info!("exiting without updating the listen port.");
     }
 
-    Ok(())
+    Ok(listen_port.flatten())
 }
 
 fn override_endpoint(
@@ -862,20 +863,32 @@ fn override_endpoint(
     network: NetworkOpt,
 ) -> Result<(), Error> {
     let config = InterfaceConfig::from_interface(interface)?;
-    if !unset && config.interface.listen_port.is_none() {
-        println!(
-            "{}: you need to set a listen port for your interface first.",
-            "note".bold().yellow()
-        );
-        set_listen_port(interface, unset, network)?;
-    }
+    let endpoint_contents = if unset {
+        prompts::unset_override_endpoint()?.then(|| EndpointContents::Unset)
+    } else {
+        let listen_port = if let Some(listen_port) = config.interface.listen_port {
+            Some(listen_port)
+        } else {
+            println!(
+                "{}: you need to set a listen port for your interface first.",
+                "note".bold().yellow()
+            );
+            set_listen_port(interface, unset, network)?
+        };
+        let endpoint = if let Some(port) = listen_port {
+            prompts::override_endpoint(port)?
+        } else {
+            None
+        };
+        endpoint.map(|endpoint| EndpointContents::Set(endpoint))
+    };
 
-    if let Some(endpoint) = prompts::override_endpoint(unset)? {
+    if let Some(contents) = endpoint_contents {
         log::info!("Updating endpoint.");
         Api::new(&config.server).http_form(
             "PUT",
             "/user/endpoint",
-            EndpointContents::from(endpoint),
+            contents,
         )?;
     } else {
         log::info!("exiting without overriding endpoint.");
@@ -1119,10 +1132,10 @@ fn run(opt: Opts) -> Result<(), Error> {
         Command::DeleteAssociation { interface } => delete_association(&interface)?,
         Command::ListAssociations { interface } => list_associations(&interface)?,
         Command::SetListenPort { interface, unset } => {
-            set_listen_port(&interface, unset, opt.network)?
+            set_listen_port(&interface, unset, opt.network)?;
         },
         Command::OverrideEndpoint { interface, unset } => {
-            override_endpoint(&interface, unset, opt.network)?
+            override_endpoint(&interface, unset, opt.network)?;
         },
         Command::Completions { shell } => {
             Opts::clap().gen_completions_to("innernet", shell, &mut std::io::stdout());
diff --git a/server/src/initialize.rs b/server/src/initialize.rs
index 6c553d4..fd36ba3 100644
--- a/server/src/initialize.rs
+++ b/server/src/initialize.rs
@@ -139,16 +139,6 @@ pub fn init_wizard(conf: &ServerConfig, opts: InitializeOpts) -> Result<(), Erro
             .interact()?
     };
 
-    let endpoint: Endpoint = if let Some(endpoint) = opts.external_endpoint {
-        endpoint
-    } else if opts.auto_external_endpoint {
-        let ip = publicip::get_any(Preference::Ipv4)
-            .ok_or_else(|| anyhow!("couldn't get external IP"))?;
-        SocketAddr::new(ip, 51820).into()
-    } else {
-        prompts::ask_endpoint()?
-    };
-
     let listen_port: u16 = if let Some(listen_port) = opts.listen_port {
         listen_port
     } else {
@@ -159,6 +149,18 @@ pub fn init_wizard(conf: &ServerConfig, opts: InitializeOpts) -> Result<(), Erro
             .map_err(|_| anyhow!("failed to get listen port."))?
     };
 
+    log::info!("listen port: {}", listen_port);
+
+    let endpoint: Endpoint = if let Some(endpoint) = opts.external_endpoint {
+        endpoint
+    } else if opts.auto_external_endpoint {
+        let ip = publicip::get_any(Preference::Ipv4)
+            .ok_or_else(|| anyhow!("couldn't get external IP"))?;
+        SocketAddr::new(ip, listen_port).into()
+    } else {
+        prompts::ask_endpoint(listen_port)?
+    };
+
     let our_ip = root_cidr
         .iter()
         .find(|ip| root_cidr.is_assignable(*ip))
diff --git a/shared/src/prompts.rs b/shared/src/prompts.rs
index bfcb635..5ee98ca 100644
--- a/shared/src/prompts.rs
+++ b/shared/src/prompts.rs
@@ -459,7 +459,7 @@ pub fn set_listen_port(
     }
 }
 
-pub fn ask_endpoint() -> Result<Endpoint, Error> {
+pub fn ask_endpoint(listen_port: u16) -> Result<Endpoint, Error> {
     println!("getting external IP address.");
 
     let external_ip = if Confirm::with_theme(&*THEME)
@@ -475,26 +475,23 @@ pub fn ask_endpoint() -> Result<Endpoint, Error> {
     Ok(input(
         "External endpoint",
         match external_ip {
-            Some(ip) => Prefill::Editable(SocketAddr::new(ip, 51820).to_string()),
+            Some(ip) => Prefill::Editable(SocketAddr::new(ip, listen_port).to_string()),
             None => Prefill::None,
         },
     )?)
 }
 
-pub fn override_endpoint(unset: bool) -> Result<Option<Option<Endpoint>>, Error> {
-    let endpoint = if !unset { Some(ask_endpoint()?) } else { None };
-
-    Ok(
-        if confirm(
-            &(if let Some(endpoint) = &endpoint {
-                format!("Set external endpoint to {}?", endpoint)
-            } else {
-                "Unset external endpoint to enable automatic endpoint discovery?".to_string()
-            }),
-        )? {
-            Some(endpoint)
-        } else {
-            None
-        },
-    )
+pub fn override_endpoint(listen_port: u16) -> Result<Option<Endpoint>, Error> {
+    let endpoint = ask_endpoint(listen_port)?;
+    if confirm(&format!("Set external endpoint to {}?", endpoint))? {
+        Ok(Some(endpoint))
+    } else {
+        Ok(None)
+    }
+}
+
+pub fn unset_override_endpoint() -> Result<bool, Error> {
+    Ok(confirm(
+        "Unset external endpoint to enable automatic endpoint discovery?",
+    )?)
 }