diff --git a/src/commands.rs b/src/commands.rs
index 0791890ef..6620d2e7d 100644
--- a/src/commands.rs
+++ b/src/commands.rs
@@ -282,6 +282,9 @@ fn connect_or_start_server(port: u16) -> Result<ServerConnection> {
                         );
                     }
                 }
+                ServerStartup::AddrInUse => {
+                    debug!("AddrInUse: possible parallel server bootstraps, retrying..")
+                }
                 ServerStartup::TimedOut => bail!("Timed out waiting for server startup"),
                 ServerStartup::Err { reason } => bail!("Server startup failed: {}", reason),
             }
@@ -587,6 +590,7 @@ pub fn run_command(cmd: Command) -> Result<i32> {
                     }
                 }
                 ServerStartup::TimedOut => bail!("Timed out waiting for server startup"),
+                ServerStartup::AddrInUse => bail!("Server startup failed: Address in use"),
                 ServerStartup::Err { reason } => bail!("Server startup failed: {}", reason),
             }
         }
diff --git a/src/server.rs b/src/server.rs
index 30c5660bc..39a5f1663 100644
--- a/src/server.rs
+++ b/src/server.rs
@@ -79,6 +79,8 @@ const DIST_CLIENT_RECREATE_TIMEOUT: Duration = Duration::from_secs(30);
 pub enum ServerStartup {
     /// Server started successfully on `port`.
     Ok { port: u16 },
+    /// Server Addr already in suse
+    AddrInUse,
     /// Timed out waiting for server startup.
     TimedOut,
     /// Server encountered an error.
@@ -412,8 +414,15 @@ pub fn start_server(config: &Config, port: u16) -> Result<()> {
         }
         Err(e) => {
             error!("failed to start server: {}", e);
-            let reason = e.to_string();
-            notify_server_startup(&notify, ServerStartup::Err { reason })?;
+            match e.downcast_ref::<io::Error>() {
+                Some(io_err) if io::ErrorKind::AddrInUse == io_err.kind() => {
+                    notify_server_startup(&notify, ServerStartup::AddrInUse)?;
+                }
+                _ => {
+                    let reason = e.to_string();
+                    notify_server_startup(&notify, ServerStartup::Err { reason })?;
+                }
+            };
             Err(e)
         }
     }