diff --git a/Cargo.lock b/Cargo.lock
index c40426b..ea51143 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -1138,6 +1138,7 @@ dependencies = [
  "tokio",
  "toml",
  "ureq",
+ "url",
  "warp",
  "wgctrl",
 ]
@@ -1169,6 +1170,7 @@ dependencies = [
  "structopt",
  "toml",
  "ureq",
+ "url",
  "wgctrl",
 ]
 
diff --git a/client/src/main.rs b/client/src/main.rs
index 1ddc74b..15929bf 100644
--- a/client/src/main.rs
+++ b/client/src/main.rs
@@ -283,6 +283,7 @@ fn redeem_invite(
     target_conf: PathBuf,
 ) -> Result<(), Error> {
     println!("{} bringing up the interface.", "[*]".dimmed());
+    let resolved_endpoint = config.server.external_endpoint.resolve()?;
     wg::up(
         &iface,
         &config.interface.private_key,
@@ -291,7 +292,7 @@ fn redeem_invite(
         Some((
             &config.server.public_key,
             config.server.internal_endpoint.ip(),
-            config.server.external_endpoint,
+            resolved_endpoint,
         )),
     )?;
 
@@ -369,6 +370,7 @@ fn fetch(
         }
 
         println!("{} bringing up the interface.", "[*]".dimmed());
+        let resolved_endpoint = config.server.external_endpoint.resolve()?;
         wg::up(
             interface,
             &config.interface.private_key,
@@ -377,7 +379,7 @@ fn fetch(
             Some((
                 &config.server.public_key,
                 config.server.internal_endpoint.ip(),
-                config.server.external_endpoint,
+                resolved_endpoint,
             )),
         )?
     }
@@ -821,7 +823,7 @@ fn print_peer(our_peer: &Peer, peer: &PeerInfo, short: bool) -> Result<(), Error
             &our_peer.public_key[..10].yellow()
         );
         println!("  {}: {}", "ip".bold(), our_peer.ip);
-        if let Some(endpoint) = our_peer.endpoint {
+        if let Some(ref endpoint) = our_peer.endpoint {
             println!("  {}: {}", "endpoint".bold(), endpoint);
         }
         if let Some(last_handshake) = peer.stats.last_handshake_time {
diff --git a/server/Cargo.toml b/server/Cargo.toml
index fb261d7..5b45c42 100644
--- a/server/Cargo.toml
+++ b/server/Cargo.toml
@@ -34,6 +34,7 @@ subtle = "2"
 structopt = "0.3"
 thiserror = "1"
 ureq = { version = "2", default-features = false }
+url = "2"
 tokio = { version = "1", features = ["macros", "rt-multi-thread"] }
 toml = "0.5"
 warp = { git = "https://github.com/tonarino/warp", default-features = false } # pending https://github.com/seanmonstar/warp/issues/830
diff --git a/server/src/api/mod.rs b/server/src/api/mod.rs
index 144d68c..41b17c8 100644
--- a/server/src/api/mod.rs
+++ b/server/src/api/mod.rs
@@ -11,7 +11,7 @@ pub fn inject_endpoints(session: &Session, peers: &mut Vec<Peer>) {
     for mut peer in peers {
         if peer.contents.endpoint.is_none() {
             if let Some(endpoint) = session.context.endpoints.get(&peer.public_key) {
-                peer.contents.endpoint = Some(endpoint.to_owned());
+                peer.contents.endpoint = Some(endpoint.to_owned().into());
             }
         }
     }
diff --git a/server/src/api/user.rs b/server/src/api/user.rs
index b7c5929..dd296f2 100644
--- a/server/src/api/user.rs
+++ b/server/src/api/user.rs
@@ -200,7 +200,7 @@ mod tests {
                 .put_request_from_ip(test::DEVELOPER1_PEER_IP)
                 .path("/v1/user/endpoint")
                 .body(serde_json::to_string(&EndpointContents::Set(
-                    "1.1.1.1:51820".parse()?
+                    "1.1.1.1:51820".parse().unwrap()
                 ))?)
                 .reply(&filter)
                 .await
diff --git a/server/src/db/peer.rs b/server/src/db/peer.rs
index 1d695ca..517282c 100644
--- a/server/src/db/peer.rs
+++ b/server/src/db/peer.rs
@@ -95,7 +95,7 @@ impl DatabasePeer {
                 ip.to_string(),
                 cidr_id,
                 &public_key,
-                endpoint.map(|endpoint| endpoint.to_string()),
+                endpoint.as_ref().map(|endpoint| endpoint.to_string()),
                 is_admin,
                 is_disabled,
                 is_redeemed,
@@ -138,7 +138,10 @@ impl DatabasePeer {
             WHERE id = ?5",
             params![
                 new_contents.name,
-                new_contents.endpoint.map(|endpoint| endpoint.to_string()),
+                new_contents
+                    .endpoint
+                    .as_ref()
+                    .map(|endpoint| endpoint.to_string()),
                 new_contents.is_admin,
                 new_contents.is_disabled,
                 self.id,
diff --git a/server/src/initialize.rs b/server/src/initialize.rs
index 24c6b80..8f71797 100644
--- a/server/src/initialize.rs
+++ b/server/src/initialize.rs
@@ -5,7 +5,7 @@ use indoc::printdoc;
 use rusqlite::{params, Connection};
 use shared::{
     prompts::{self, hostname_validator},
-    CidrContents, PeerContents, PERSISTENT_KEEPALIVE_INTERVAL_SECS,
+    CidrContents, Endpoint, PeerContents, PERSISTENT_KEEPALIVE_INTERVAL_SECS,
 };
 use wgctrl::KeyPair;
 
@@ -32,7 +32,7 @@ pub struct InitializeOpts {
 
     /// This server's external endpoint (ex: 100.100.100.100:51820)
     #[structopt(long, conflicts_with = "auto-external-endpoint")]
-    pub external_endpoint: Option<SocketAddr>,
+    pub external_endpoint: Option<Endpoint>,
 
     /// Auto-resolve external endpoint
     #[structopt(long = "auto-external-endpoint")]
@@ -49,7 +49,7 @@ struct DbInitData {
     server_cidr: IpNetwork,
     our_ip: IpAddr,
     public_key_base64: String,
-    endpoint: SocketAddr,
+    endpoint: Endpoint,
 }
 
 fn populate_database(conn: &Connection, db_init_data: DbInitData) -> Result<(), Error> {
@@ -126,7 +126,7 @@ pub fn init_wizard(conf: &ServerConfig, opts: InitializeOpts) -> Result<(), Erro
     // This probably won't error because of the `hostname_validator` regex.
     let name = name.parse()?;
 
-    let endpoint: SocketAddr = if let Some(endpoint) = opts.external_endpoint {
+    let endpoint: Endpoint = if let Some(endpoint) = opts.external_endpoint {
         endpoint.clone()
     } else {
         let external_ip: Option<IpAddr> = ureq::get("http://4.icanhazip.com")
@@ -139,7 +139,7 @@ pub fn init_wizard(conf: &ServerConfig, opts: InitializeOpts) -> Result<(), Erro
 
         if opts.auto_external_endpoint {
             let ip = external_ip.ok_or("couldn't get external IP")?;
-            (ip, 51820).into()
+            SocketAddr::new(ip, 51820).into()
         } else {
             prompts::ask_endpoint(external_ip)?
         }
diff --git a/server/src/test.rs b/server/src/test.rs
index 62430dd..88948e4 100644
--- a/server/src/test.rs
+++ b/server/src/test.rs
@@ -69,7 +69,7 @@ impl Server {
         let opts = InitializeOpts {
             network_name: Some(interface.clone()),
             network_cidr: Some(ROOT_CIDR.parse()?),
-            external_endpoint: Some("155.155.155.155:54321".parse()?),
+            external_endpoint: Some("155.155.155.155:54321".parse().unwrap()),
             listen_port: Some(54321),
             auto_external_endpoint: false,
         };
diff --git a/shared/Cargo.toml b/shared/Cargo.toml
index 1a7a5a4..0d943cd 100644
--- a/shared/Cargo.toml
+++ b/shared/Cargo.toml
@@ -17,4 +17,5 @@ serde = { version = "1", features = ["derive"] }
 structopt = "0.3"
 toml = "0.5"
 ureq = { version = "2", default-features = false }
+url = "2"
 wgctrl = { path = "../wgctrl-rs" }
diff --git a/shared/src/interface_config.rs b/shared/src/interface_config.rs
index dd5b23c..10febaa 100644
--- a/shared/src/interface_config.rs
+++ b/shared/src/interface_config.rs
@@ -1,4 +1,4 @@
-use crate::{ensure_dirs_exist, Error, IoErrorContext, CLIENT_CONFIG_PATH};
+use crate::{ensure_dirs_exist, Endpoint, Error, IoErrorContext, CLIENT_CONFIG_PATH};
 use colored::*;
 use indoc::writedoc;
 use ipnetwork::IpNetwork;
@@ -46,7 +46,7 @@ pub struct ServerInfo {
     pub public_key: String,
 
     /// The external internet endpoint to reach the server.
-    pub external_endpoint: SocketAddr,
+    pub external_endpoint: Endpoint,
 
     /// An internal endpoint in the WireGuard network that hosts the coordination API.
     pub internal_endpoint: SocketAddr,
diff --git a/shared/src/prompts.rs b/shared/src/prompts.rs
index e95f854..924f194 100644
--- a/shared/src/prompts.rs
+++ b/shared/src/prompts.rs
@@ -1,7 +1,7 @@
 use crate::{
     interface_config::{InterfaceConfig, InterfaceInfo, ServerInfo},
-    AddCidrOpts, AddPeerOpts, Association, Cidr, CidrContents, CidrTree, Error, Peer, PeerContents,
-    PERSISTENT_KEEPALIVE_INTERVAL_SECS,
+    AddCidrOpts, AddPeerOpts, Association, Cidr, CidrContents, CidrTree, Endpoint, Error, Peer,
+    PeerContents, PERSISTENT_KEEPALIVE_INTERVAL_SECS,
 };
 use colored::*;
 use dialoguer::{theme::ColorfulTheme, Confirm, Input, Select};
@@ -299,6 +299,7 @@ pub fn save_peer_invitation(
         server: ServerInfo {
             external_endpoint: server_peer
                 .endpoint
+                .clone()
                 .expect("The innernet server should have a WireGuard endpoint"),
             internal_endpoint: *server_api_addr,
             public_key: server_peer.public_key.clone(),
@@ -362,7 +363,7 @@ pub fn set_listen_port(
     }
 }
 
-pub fn ask_endpoint(external_ip: Option<IpAddr>) -> Result<SocketAddr, Error> {
+pub fn ask_endpoint(external_ip: Option<IpAddr>) -> Result<Endpoint, Error> {
     println!("getting external IP address.");
 
     let external_ip = if external_ip.is_some() {
@@ -379,7 +380,7 @@ pub fn ask_endpoint(external_ip: Option<IpAddr>) -> Result<SocketAddr, Error> {
 
     let mut endpoint_builder = Input::with_theme(&*THEME);
     if let Some(ip) = external_ip {
-        endpoint_builder.default(SocketAddr::new(ip, 51820));
+        endpoint_builder.default(SocketAddr::new(ip, 51820).into());
     } else {
         println!("failed to get external IP.");
     }
@@ -389,7 +390,7 @@ pub fn ask_endpoint(external_ip: Option<IpAddr>) -> Result<SocketAddr, Error> {
         .map_err(|e| Error::from(e))
 }
 
-pub fn override_endpoint(unset: bool) -> Result<Option<Option<SocketAddr>>, Error> {
+pub fn override_endpoint(unset: bool) -> Result<Option<Option<Endpoint>>, Error> {
     let endpoint = if !unset {
         Some(ask_endpoint(None)?)
     } else {
diff --git a/shared/src/types.rs b/shared/src/types.rs
index 3e6c952..4d2f146 100644
--- a/shared/src/types.rs
+++ b/shared/src/types.rs
@@ -2,13 +2,15 @@ use crate::prompts::hostname_validator;
 use ipnetwork::IpNetwork;
 use serde::{Deserialize, Serialize};
 use std::{
-    fmt::{Display, Formatter},
-    net::{IpAddr, SocketAddr},
+    fmt::{self, Display, Formatter},
+    net::{IpAddr, SocketAddr, ToSocketAddrs},
     ops::Deref,
     path::Path,
     str::FromStr,
+    vec,
 };
 use structopt::StructOpt;
+use url::Host;
 use wgctrl::{InterfaceName, InvalidInterfaceName, Key, PeerConfig, PeerConfigBuilder};
 
 #[derive(Debug, Clone)]
@@ -37,15 +39,105 @@ impl Deref for Interface {
     }
 }
 
+#[derive(Clone, Debug, PartialEq)]
+/// An external endpoint that supports both IP and domain name hosts.
+pub struct Endpoint {
+    host: Host,
+    port: u16,
+}
+
+impl From<SocketAddr> for Endpoint {
+    fn from(addr: SocketAddr) -> Self {
+        match addr {
+            SocketAddr::V4(v4addr) => Self {
+                host: Host::Ipv4(*v4addr.ip()),
+                port: v4addr.port(),
+            },
+            SocketAddr::V6(v6addr) => Self {
+                host: Host::Ipv6(*v6addr.ip()),
+                port: v6addr.port(),
+            },
+        }
+    }
+}
+
+impl FromStr for Endpoint {
+    type Err = &'static str;
+
+    fn from_str(s: &str) -> Result<Self, Self::Err> {
+        match s.rsplitn(2, ':').collect::<Vec<&str>>().as_slice() {
+            [port, host] => {
+                let port = port.parse().map_err(|_| "couldn't parse port")?;
+                let host = Host::parse(host).map_err(|_| "couldn't parse host")?;
+                Ok(Endpoint { host, port })
+            },
+            _ => Err("couldn't parse in form of 'host:port'"),
+        }
+    }
+}
+
+impl Serialize for Endpoint {
+    fn serialize<S>(&self, serializer: S) -> Result<S::Ok, S::Error>
+    where
+        S: serde::Serializer,
+    {
+        serializer.serialize_str(&self.to_string())
+    }
+}
+
+impl<'de> Deserialize<'de> for Endpoint {
+    fn deserialize<D>(deserializer: D) -> Result<Self, D::Error>
+    where
+        D: serde::Deserializer<'de>,
+    {
+        struct EndpointVisitor;
+        impl<'de> serde::de::Visitor<'de> for EndpointVisitor {
+            type Value = Endpoint;
+
+            fn expecting(&self, formatter: &mut fmt::Formatter) -> fmt::Result {
+                formatter.write_str("a valid host:port endpoint")
+            }
+
+            fn visit_str<E>(self, s: &str) -> Result<Self::Value, E>
+            where
+                E: serde::de::Error,
+            {
+                s.parse().map_err(serde::de::Error::custom)
+            }
+        }
+        deserializer.deserialize_str(EndpointVisitor)
+    }
+}
+
+impl fmt::Display for Endpoint {
+    fn fmt(&self, f: &mut Formatter<'_>) -> fmt::Result {
+        self.host.fmt(f)?;
+        f.write_str(":")?;
+        self.port.fmt(f)
+    }
+}
+
+impl Endpoint {
+    pub fn resolve(&self) -> Result<SocketAddr, String> {
+        let mut addrs = self
+            .to_string()
+            .to_socket_addrs()
+            .map_err(|e| e.to_string())?;
+        addrs
+            .next()
+            .ok_or_else(|| "failed to resolve address".to_string())
+    }
+}
+
 #[derive(Deserialize, Serialize, Debug)]
 #[serde(tag = "option", content = "content")]
 pub enum EndpointContents {
-    Set(SocketAddr),
+    Set(Endpoint),
     Unset,
 }
 
-impl Into<Option<SocketAddr>> for EndpointContents {
-    fn into(self) -> Option<SocketAddr> {
+impl Into<Option<Endpoint>> for EndpointContents {
+    fn into(self) -> Option<Endpoint> {
         match self {
             Self::Set(addr) => Some(addr),
             Self::Unset => None,
@@ -53,8 +145,8 @@ impl Into<Option<SocketAddr>> for EndpointContents {
     }
 }
 
-impl From<Option<SocketAddr>> for EndpointContents {
-    fn from(option: Option<SocketAddr>) -> Self {
+impl From<Option<Endpoint>> for EndpointContents {
+    fn from(option: Option<Endpoint>) -> Self {
         match option {
             Some(addr) => Self::Set(addr),
             None => Self::Unset,
@@ -246,7 +338,7 @@ pub struct PeerContents {
     pub ip: IpAddr,
     pub cidr_id: i64,
     pub public_key: String,
-    pub endpoint: Option<SocketAddr>,
+    pub endpoint: Option<Endpoint>,
     pub persistent_keepalive_interval: Option<u16>,
     pub is_admin: bool,
     pub is_disabled: bool,
@@ -287,8 +379,11 @@ impl Peer {
     pub fn diff(&self, peer: &PeerConfig) -> Option<PeerDiff> {
         assert_eq!(self.public_key, peer.public_key.to_base64());
 
-        let endpoint_diff = if peer.endpoint != self.endpoint {
-            self.endpoint
+        let endpoint_diff = if let Some(ref endpoint) = self.endpoint {
+            match endpoint.resolve() {
+                Ok(resolved) if Some(resolved) != peer.endpoint => Some(resolved),
+                _ => None,
+            }
         } else {
             None
         };
@@ -331,7 +426,9 @@ impl<'a> From<&'a Peer> for PeerConfigBuilder {
             builder
         };
 
-        if let Some(endpoint) = peer.endpoint {
+        let resolved = peer.endpoint.as_ref().map(|e| e.resolve().ok()).flatten();
+
+        if let Some(endpoint) = resolved {
             builder.set_endpoint(endpoint)
         } else {
             builder